What happens when you save an old building from the wrecking ball? First and foremost, you get the moral superiority. You can brag on the Gram or if you’re that kind of guy, LinkedIn, or if you’re that kind of guy, Substack, that you wrestled a near perfect example of Victorian era Chicago architecture out of the grubby mitts of the unsentimental builder who planned to tear it down and build a hospital-white, hardie board farmhouse with vinyl siding on the side walls.

But as my Dad likes to say: “Don’t pat yourself on the back too hard, you’ll fall over.”

After all you’re not a hero, you’re a developer. You’re here to turn a buck.

And for what you paid for the building, you’re not exactly going to be providing affordable housing.

Here’s the thing about that price. When a building is in this rough of shape, it sells at land value, and no matter if you’re going to “save” the existing structure or tear it down, your basis in the project is the same.

It’s a helluva lot easier to start completely over and create a project with a predictable workflow like a farmhouse that has dozens of comparable builds with comparable back end sales projections in the neighborhood. It’s a whole other thing to work within the confines of a tiny obliterated building shell from the 1880s and expect to sell it for the same price.

Highest and Best Use

Commercial real estate is full of jargon and acronym soup. IRR, ROE, DSCR, NPV. But before you start hitting F9 on the spreadsheet, you need to answer a much simpler question: what is the most valuable thing you’re legally allowed to build on this piece of land?

In our case, the calculation is pretty straightforward:

• Lot size: 3,125 SF

• Zoning: RS-3

• Maximum units Per Lot Size: 1

• Maximum above grade footage: ~2,800 SF

• Potential basement: ~1,400 SF

• Maximum total finished space: ~4,200 SF

• Highest and best use: One ~4,200 SF single-family home

That last number is the important one.

There are plenty of recently built houses around here of roughly this size, which means there are plenty of comparable sales or “comps” telling a developer what a new 4,200 SF house is likely to sell for.

From there, the math works backwards.

Expected sale price of a 4,200 SF house
– Cost to build it
– Required developer profit
= What a developer can afford to pay for the property

That’s roughly how the land gets priced.

The problem for us is that there’s already a house sitting on it. And it’s nowhere near 4,200 square feet.

It’s closer to 2,600 sf.

And there’s nothing stopping us from tearing it down.

The building has no landmark designation or other historic protection guidelines on it. Even though its facade may be one of only a few dozen true brownstones (and maybe the only with a wedding cake cornice and a cupola) left in Chicago, behind it are 140 years of building components, alterations and repairs.

Working with those conditions is almost the opposite of building new.

With new construction, you have a predictable order of operations. Foundation, framing, mechanicals, drywall, finishes. With a building from the 1880s, you can draw beautiful architectural plans, but portions of them inevitably become more an abstract than an instruction manual. Problems that would have been solved on paper in new construction instead have to be solved standing inside the building.

More surprises mean more supervision. More supervision means less scalability.

And developers need economies of scale to maximize profitability. There’s no scalability without predictability.

Building variations of the same new house means tighter construction schedules, fewer change orders, less supervision and, most importantly, the ability to repeat the process across multiple projects. A builder who develops ten nearly identical houses isn’t really building ten houses independently. They’re refining one house ten times.

A 140-year-old renovation gives you almost none of those advantages. You solve a problem here that you may never encounter again.

But even if we accept all of that, we still have a more fundamental problem.

We can’t just leave the house at 2,600 square feet.

Remember the highest-and-best-use calculation. We paid for a piece of land capable of supporting roughly 4,200 square feet of house. Restoring the existing building and selling it as a charming little 2,600-square-foot brownstone sounds nice, but the economics don’t work.

Part of the reason is that construction costs don’t decline neatly with square footage. Every house needs an electrical service, a water service, HVAC equipment, plumbing, a kitchen, bathrooms, windows, roof, appliances, architectural drawings, permits and utility connections. A smaller house saves you lumber, drywall and flooring, but it doesn’t save you proportionally on the expensive systems that make a house function.

You don’t get to buy 57 percent of a water service.

So the smaller the finished house, the harder it becomes to spread both the land cost and those fixed construction costs across enough sellable square footage.

Which means that in order to save this house, we’re also going to have to make it substantially bigger.

There’s something slightly absurd about that.

We’re preserving the building because we believe the existing building has value, while simultaneously having to perform major surgery on it because the economics of the land won’t allow us to leave it alone.

The financially easiest thing to do would be to clear the lot and build roughly 4,200 square feet from scratch. Instead, we’re going to take a 2,600-square-foot, 140-year-old shell, preserve the parts that make it worth saving, and then figure out how to graft enough new footage onto it to make the entire project financially viable.

That’s the real preservation penalty.

It isn’t simply that old buildings cost more or are harder to work on. It’s that the developer trying to save one is competing against a development model that can efficiently capture virtually every square foot of value the zoning allows. We have to make the old house bigger in order to make saving the old house possible.

What We’re Building

Since zoning on this site does not allow us to build upward, we’re adding our footage to the back of the building.

The inspiration was drawn from a bunch of contemporary rear additions to terraced houses on tight, narrow lots in older European cities. Particularly the idea that the rear addition doesn’t have to be referential to the facade, but complementary to it.

We wanted an L-shaped addition to give the patio some privacy and a sense of encapsulation, but also to allow for a rear entryway with a buffer of mudroom storage between the yard and the main family room in the existing structure.

The curved glass block wall is take pretty directly from two of my favorite Chicago buildings. The Florsheim Mansion and the Frank Fisher Studios.

Glass block is having a moment now in the design world but in Chicago it’s always been ubiquitous. Practically every bungalow basement, alley facing coach house window or light industrial building is adorned with glass block and the way they filter natural light or emit glowing interior light makes it one of our favorite materials to work with.

The upstairs window above the family room is the primary bath shower. We're using cross-ribbed reeded privacy glass there, which gives us another translucent surface and loosely echoes the glass block below.

Above are my initial SketchUp drawings of the rear addition. Our architect Ross Renjilian from Chicago Common made these coherent and buildable with the existing structure and compliant with setback requirements through thoughtful interior and exterior grading.

Originally, the addition was only going to extend the first floor, with a roof garden above it. I preferred it that way. But once we started laying out the second floor, we realized we couldn’t fit a primary suite that could compete with the 4,200-square-foot new-build behemoths we’re eventually going to be sitting next to on Zillow.

So the bathroom got pushed out over the addition.

Even before construction started, the economics were already making the house bigger.

Below is the final rear elevation:

The floorplan for the addition. Main floor:

Second Floor:

Below is the floor plan of the whole house:

I will write a separate post on the plan for the interior

We’re adding enough to bring the finished house from roughly 2,600 square feet to around 3,500–3,600. That’s still well short of the 4,200 square feet we could build if we started over.

We aren’t going to beat new construction on square footage. Instead, we’re making the same bet we’ve made on our last few projects: that design can make up some of the difference.

This is admittedly a dangerous thing for a developer to believe. “Buyers will appreciate the design” is probably written somewhere on the tombstone of every developer who lost their shirt.

Real estate gets reduced to square footage, bedrooms, bathrooms and lot size because those things are easy to measure. They matter, obviously. But anyone who has shown enough houses knows buyers don’t experience them as spreadsheets. Two houses with identical stats can feel radically different, and I have yet to meet the dweeb who pulls out a laser at a showing to calculate his enjoyment on a price-per-square-foot basis.

It’s easy to write off other builders’ homes as lazy, cynical farmhouse, huge-for-the-sake-of-being-huge trash. But the fact of the matter is that people buy them, and they’re everywhere. These types of homes set the standard for pricing in the areas where we build. If we’re going to give up 600 or 700 square feet to preserve this original building, the remaining square footage has to work harder.

The materials and layout need to be more considered. Better relationship to light and palette. There need to be a few things about it that stick in your head after you’ve walked through six other houses that weekend.

We’re making a pretty enormous financial wager on this. But if we’re right, preserving the old building isn’t simply a constraint on the value of the property. The thing we saved and the new architecture we build around it become part of the value themselves.

To me, Kate Wagner may be the only interesting architecture critic in the country. Unlike the current state of architecture writing which tends to either cover the stars and the spectacles they design, or the look-how-unique-this-house-is, photo-heavy Dezeen world, Kate writes about architecture with an eye to the media, political and cultural landscape from which it is born.

Kate has contributed to countless periodicals. She still writes the blog, Mcmansion Hell for which she went viral for in 2016. After a stint at the New Republic, she is currently the architecture critic at The Nation.

We spoke about music school, Chicago, Helmut Jahn, HGTV Farmhouses, The Body Tea-Architecture Content Pipeline and of course…Mcmansions.

This interview was edited and condensed from a longer conversation.

Everything Starts with Steve Reich

Charlie Cohen:
Okay, so first of all, I read that you were a (music) composition major.

Kate Wagner:
Yeah. In a previous life.

Charlie Cohen:
Same. I was too.

Kate Wagner:
That’s funny.

Charlie Cohen:

It’s really exciting for me because I never talk to anyone who studied composition. Even running into another music major is rare enough, especially someone who’s in another field.

Kate Wagner:
For sure.

Charlie Cohen:
What’s your story? Who were your people? What did you write? What did you play?

Kate Wagner:
At first I was working in tonal music, kind of in the Benjamin Britten mode. I came from an interest in minimalism and sort of moved toward that. Then, during the last two years of undergrad, I decided to focus on electroacoustic music.

I did a lot with synthesizers, a lot of improvised music, and a lot of Pauline Oliveros–style Deep Listening work.

Charlie Cohen:
For sure.

Kate Wagner:
That rounded out my degree. At the time I was also working in a recording studio. I had an internship with a speaker company, and I wanted to go into acoustics—but I wanted to work on buildings because I was already into architecture. So I went to graduate school for that.

And then my blog went viral while all of that was happening.

Charlie Cohen:
I actually remember that from the Tumblr days.

McMansion Hell was like kleenex. It almost became shorthand for a way of describing neighborhoods.

I’ve always wondered whether you found a connection between music and architecture world. Personally I always felt like people stayed inside their own artistic silos.

In music school I felt completely alone in being interested with architecture.

Kate:
Yeah, I think a lot of people who are into architecture and into music end up going into building science. Architectural acoustics is an obvious overlap. A lot of people who studied classical music or recording engineering end up finding a niche there. And of course there’s stage design.

Charlie:
Right.

Kate:
And minimalism—that’s kind of how I got into it.

Charlie:
Yeah. I think we all got there through Philip Glass and Steve Reich.

Kate:
For sure.

Charlie:
That was exactly it for me. My audition portfolio was basically just a Steve Reich ripoff. I was as Steve Reich-pilled as somebody could possibly be.

Kate:
Right. I still love Steve Reich.

I was doing minimalist stuff in high school, just kind of testing the waters. Being self-taught, it seemed like the easiest thing to do.

But when you’re older, you realize that music comes out of a tradition that’s decidedly not easy to understand or pull off.

Charlie:
Yeah. When you’re in high school you think, “Wow, this is great. You just shift everything over an eighth note.”

Kate:
I was always really into early twentieth-century American music.
And British composers too—Samuel Barber, Benjamin Britten—that whole world.

My tastes have changed now only because I’ve just worn that music out. I can still put on Music for 18 Musicians any time of day, but I’ve probably listened to Barber’s Violin Concerto four hundred times.

Charlie:

For Reich, that era is really the peak. Everything from Different Trains onward has this sort of busy Richard Scarry world vibe to me. It’s almost unintentionally silly.

Philip Glass is kind of the same. We’re actually going to talk about that era today across all the arts.

Steve Reich Ensemble during a performance of “Drumming.”

Kate:

For me, Reich peaks as a theorist with Drumming. That’s where he completely figured out phase music as an acoustic form. Then it feels like he ran out of places to take it and started doing this sort of post-phase music.

I still love Different Trains, Music for 18 Musicians, and Electric Counterpoint. after that I don’t really, yeah so i’m in the same boat.

Charlie:
It almost feels like the opening credits to a TV show my eighteen-month-old son would watch. Around 1980 to 1984 is where that whole scene starts to turn for me.

What’s interesting is that architecturally, that’s probably the era I’m most interested in too. That late-modern, early-postmodern period.

Kate:
Same. That’s where I’ve basically spent my entire thinking life.

Charlie:
To the extent that I went into music school hoping it would feel like downtown New York in 1981 instead of... a bunch of band dorks.

Where did you go?

Kate:
UNC Greensboro.

Charlie:
I went to DePaul.

Kate:
Then I definitely sympathize with the band-dork experience.

We had a little electroacoustic music scene, though.

Charlie:
Yeah, we did too. There was a professor there I studied with a bit. He came out of that Glenn Branca, No Wave-adjacent world, while still being rooted in classical music.

Kate:

That’s really the kind of music I love.

Really all experimental music, musique concrète, serialism, spectralism...

My husband and I actually bonded over Robert Ashley. We’re both still huge fans.

We’re even planning on getting Robert Ashley tattoos.

Chicago

Charlie:
How did you end up in Chicago?

Kate:
I moved during the pandemic. I had been living in D.C., and I finally decided to move because I’d always wanted to live here.

Charlie:
Was it mainly an architecture thing?

Kate:
Yeah.

I fell in love with Chicago after I ran off with a guy I probably shouldn’t have run off with during my junior year of college. We went out to Oak Park and did all the Frank Lloyd Wright stuff.

I remember thinking, this is the most beautiful place in the world.

And I loved, I don’t know, I love Chicago.

I think yes, the architecture is part of it.

Although I think I’ve become so spoiled by Chicago architecture that I’ve developed almost an architectural ennui.

When I go back to my hometown now, or even the suburbs, I’ll suddenly notice buildings again because I’m not surrounded by beautiful architecture all the time.It makes me indolent and sad.

I used to have a post office box at the Mies post office downtown.

I remember thinking, this is peak living.

I just love Chicago broadly. I love the whole Chicagoland area.

I even love the suburbs. Which are like the apotheosis of the suburbs to me.

I grew up in a small town, not the suburbs, so my perspective is a little different. I was always jealous of my friends who grew up in suburbs because they had shopping centers and all this other stuff nearby.

Now I live in Rogers Park, and honestly Rogers Park is paradise.

Charlie:
That’s funny. I grew up in the Chicago suburbs.

My family’s been in Chicago for eternity. I’m the first Cohen that actually grew up outside the city.

I vividly remember coming to Rogers Park to see a play when I was about eight years old and thinking, this is how life should be from the car window

I think it was around Glenwood and Pratt.

Kate:
Yeah. I run near Glenwood and Devon.

It’s pretty great.

Charlie:
Do you have an aspirational Chicago building?

Somewhere you’ve always imagined yourself living?

Kate:
I’ve always wanted a three-bedroom condo in one of those kind of ugly mid-century buildings along Sheridan.

Or one of those grand 1920s Tudor Revival condo buildings around South Shore.

Basically any historic Chicago condo.

Financially, I think that possibility is probably foreclosed for me.

I like where I live now, though. It’s a 1924 two-flat.

The outside is kind of dowdy, but the inside has all the original built-ins and details.

Before that I lived in a workers cottage.

That was tough living.

Those are the narrowest houses.

Kate’s dream Chicago building

Charlie:
I’m literally sitting in one right now.

That’s my house.

Kate:
Then you know.

I understand why people deconvert workers cottages into single-family homes.

I don’t think they should. I think it ought to be banned citywide because we need to preserve that missing-middle housing.

But they’re really hard apartments to live in. Our living room was maybe ten feet wide.

Your knees were basically touching the coffee table.

Helmut Jahn, Late Modernism and PoMo

Charlie:
So I read that piece you wrote about Helmut Jahn, and I thought it was really interesting because I love that period.

Him, the whole Chicago Seven crowd—Stanley Tigerman, Larry Booth, all those guys.

I’m kind of a late Helmut Jahn adopter. He got a lot of hate in his career.

Do you think our generation has developed a sort of rosy retrospection for postmodern architecture?

Or do you think those buildings will actually end up in the canon when people inevitably start timeline-ifying that era?

Kate:
How old are you?

Charlie:
Thirty-seven.

Kate:
I’m thirty-two.

So basically the same generation.

I think nostalgia for our generation tends to be about interiors more than buildings.

Graphic design, industrial design, interiors—that’s where nostalgia culture really lives.

People still tend to be nostalgic about houses in a very vernacular way. Colonial Revival houses, split-levels, wood-paneled family rooms...

People remember the house they grew up in.

They remember wood-grain televisions.

That kind of thing.

Kate:
When it comes to postmodernism, people love looking at interiors.

Mall photographs are a perfect example.

Most of the time they’re not even looking at the outside of the mall—they’re looking at the atriums, the food courts, the escalators.

I think postmodern architecture itself already had its big revival maybe ten years ago, when there were all those retrospectives on Venturi, Tigerman, and everyone else.

Now we’re in this weird period where nostalgia itself has become flattened.

We’re nostalgic for things that aren’t even real anymore.

And I think that’s changed the way people look at architecture.

People love looking at pictures of postmodernism—again, mostly interiors. People love mall pictures, for example. Rarely are the outsides of the malls included in those pictures.

So this is all very interesting to me. I think postmodern architecture, except for the most Walt Disney–looking examples—the Gehry building in California that’s now Google, with the binoculars—people love that kind of thing. Or the K2* (**M2) Building in Japan. People call it the “vaporwave building.”

Binoculars Building, Frank Gehry 1991

That kind of work is popular.

But I also think postmodernism itself had its big revival maybe ten years ago. I remember there being all these retrospectives on Venturi, Tigerman, and all those architects. That felt like where postmodern fever peaked.

What’s interesting now is that we’re living in a kind of slopification of nostalgia. We’re not actually nostalgic for things that are real anymore, and I think that changes the dynamic with architecture.

Helmut Jahn is an interesting case because he always had one foot in late modernism and one foot in postmodernism. He applied all that high-tech language to postmodern forms, so he’s always been a little difficult to categorize.

He’s also a bit less immediately delightful to people. He’s an acquired taste.

The Accenture Building is a good example. In photographs it looks incredibly impressive, but when you actually experience it from the street it mostly feels like the entrance to a train station.

Then there’s 3-something-something Wacker...with the pixelated windows

Charlie:
One South Wacker.

One South Wacker, Murphy/Jahn 1982

Kate:
Exactly. That building is insane. I don’t think it’s a good building, but I love it.

Charlie:
Stanley Tigerman used to say about Helmut Jahn that “He needs to take a Great Books course.”

Kate:
That’s funny, I never heard that before. Tigerman was always the wittier of the two.

Jahn was really a businessman.

In my article I talked about how he was basically the first neoliberal architect. He was incredibly shrewd about marketing and about how he ran his firm.

He drove everyone into the ground. He kept the staff as lean as possible and expected an enormous amount out of them.

Even the Accenture Building being shaped like a cash register because it was originally intended as the Chicago Board of Trade addition... that’s such an arch-capitalist gesture.

Charlie:

He was on the cover of GQ.

Kate:

He also had a predilection for doing dangerous things. He had sports cars, motorcycles, rode his bicycle aggressively. When people say he died in a bike accident, they imagine someone leisurely riding a bike, but he rode his bike in the most insane way possible. That wasn’t really Helmut Jahn. He lived fast. Up until the last.

My favorite Jahn buildings are actually his early ones, most of which aren’t around anymore.

He did that technical school in Indiana—

Charlie:
The yellow one? I love that one. Had kind of a Richard Rogers…

Ivy Tech Community College, Murphy/Jahn 1981

Kate:
Yeah. That’s my favorite.

The post office near O’Hare is still there too.

I also wish the old gymnasium was still around—the one with the red structural supports. Then there’s the library in…

Charlie:
Michigan City.

Kate:
Yeah, the Michigan City Public Library. It’s still standing, but unfortunately it’s in pretty rough shape now.

Michigan City Public Library Murphy/Jahn 1977

Charlie:
He also designed the Rust-Oleum headquarters.

When I was in high school we used to go behind there and smoke cigarettes on weekends.

Kate:
That’s wild. That’s some real Chicago shit.

I actually like the Accenture Building too.

I don’t really like O’Hare, though.

Charlie:
Really? You don’t like the United Terminal with the glass-block tunnel and the neon lights?

O’Hare Terminal 1 and CTA Rapid Transit Station, Murhpy/Jahn 1988

Kate:
I like that part.

I don’t like the part where I have to sit and wait for the plane.

Kate:
My opinion of O’Hare actually changed because there was a period where I couldn’t really walk.

I had to use wheelchair assistance from the entrance all the way to the gate.

Helmut Jahn was the master of circulation as a parti—but then you get to the elevators and you’re sitting in some fucking corner that smells like piss.

It’s like... where’s the glamour? Where’s the glory?

Charlie:
So let me ask you this.

Architecture moves incredibly slowly. For years—sometimes decades—you get variations on the form du jour.

In Chicago especially, after that generation of architects, it doesn’t really feel like we’ve had another major movement.

Maybe that’s just my own bias.

Do you think there’s been a period of creative stagnation in Chicago architecture, whether large-scale or small-scale?

Or is this just what we were talking about earlier—rosy retrospection?

Kate:
I mean, there are a number of things going on there that aren’t necessarily unique to Chicago. “Where are the new architectural movements?” has been a question since the 2000s—really since the 2010s, when parametricism sort of ran its course.

I think the answer is a combination of things. First, we live in the age of the internet, which is extremely diffuse. The idea that you can have consolidated, concentrated architectural movements requires a number of institutions to function—one of which is slower journalism, and the ability to have serious public discourse instead of broad, polemical discourse.

Second, you need a thriving academia that isn’t just careerist for some people and a trade school for others, which is largely what architecture has become. To have serious bodies of thought, you need healthy academic and professional settings that are relatively concentrated in cities. You need people who actually want to work together, who are coming together around similar political or theoretical ideas.

Everything about the way architecture as a business works now is inimical to that.

Once you have the diffusion of ideas, the Instagrammable mode of architectural image generation, the fake theory people have to produce, the coffee table books nobody buys—it’s very hard to get serious work done because no one is organized within the field. I don’t just mean in a labor sense, although that helps. I mean in any sense. There isn’t much desire to organize oneself into a theoretical or stylistic movement.

Everyone wants to be unique.

And then there’s the client problem. Clients are not particularly interested in experimental architecture the way they were in the twentieth century.

I think that’s reflected in the McMansion. The people who had the money to build a custom house used to hire an architect. Now they see themselves as the architect.

Architecture itself has become just another house style.

That’s not a good place to be.

The most interesting architecture in the world isn’t happening in the West anymore. Part of that is for material reasons that I don’t want to get into that are a little inside baseball, but another part is that people in other parts of the world are living in more collectivized cultures or are at different stages of economic development—similar to where the United States was in the 1960s or ‘70s.

Those economic conditions are much more conducive to producing interesting architecture.

You see it in Mexico. Broadly across South America. In China, massively. And increasingly in parts of Eastern Europe and Southern Europe.

A lot of it comes down to the economic stage of development and the lack of a social safety net. It also comes down to architecture schools. Is architecture treated as a trade, or as a craft?

There are so many reasons.

But the reality is that we live in a dog-eat-dog, every-man-for-himself society, and that isn’t conducive to producing large, collective bodies of intellectual and artistic thought.

What if my house was the mall?

From Kate’s Mcmansion Hell Blog

Charlie:
There’s so much there that I want to get into, but I’m going to try to pick what I think we have time for.

One thing is this idea of the custom house—where someone hires an architect and their own general contractor to build a house. I don’t think that’s really possible anymore.

Kate:
Yeah, I agree.

Charlie:

It was always a minority of housing, even in the last 150 years of urban construction in America.

But the amount of time, money-the form of money and coordination it takes now—to build a custom house, or even to do a substantial addition on your own house—it’s just become incredibly difficult for almost anyone.

Everything is developer-built now.

If you looked at permits pulled in Chicago this year for true custom homes, I bet there are fewer than a dozen. And they’re basically all in Lincoln Park.

I guess this is where we get into McMansions and how that form evolved, which is what I originally wanted to talk to you about.

It seems to me that the general ethos behind suburban sprawl and McMansion development has really been a hundred-year trend.

My own family literally lived through that model.

My grandfather grew up in an apartment in South Shore.

My dad grew up in a bungalow in South Shore—part of the bungalow belt—which you could argue was basically the 1920s version of suburban tract housing and I grew up in the suburbs in a quasi-Mcmansion.

Kate:
Exactly.

That’s the thing.

Since about 1860 or 1870, everything has been mass-produced.

Even the charming bungalows, foursquares, minimal traditional houses, ranch houses—they were all mass-produced.

There wasn’t some mystical period where every house was individually handcrafted.

That’s simply not how you house millions of people.

Once builders developed the technology to mass-produce houses—originally for factory owners who needed to house workers—the cat was out of the bag.

Everything since then has basically been refinements to that technology.

Charlie:
The thing that’s always interested me is how that form evolved.

It feels like the trajectory is always toward people living farther apart, in smaller households, but in larger houses.

In Chicago, that really begins with the bungalow.

Before that, the dominant new housing types were the two-flat, the three-flat, and in some neighborhoods the workers cottage. Less dense than tenements but still multifamily.

The bungalow was the first really major move outward. These were all built on what was basically prairie at the time.

Then after World War II you get the near suburbs where I grew up—the ranch houses.

They’re all basically the same house, painted different colors.

Then our generation pushes even farther out, almost into farmland, and you arrive at what we now call the McMansion.

I guess what I’ve always wondered is: what is it about human nature that keeps pushing us in that direction?

Is that actually what people wanted?

Or was it a market construct—vacant, cheap land, development opportunities?

Why do people keep wanting to move farther away from each other, have more space, and occupy bigger houses?

Aerial View Bungalow Belt

Aerial View Mcmansion Development

Kate:
I think that’s a complicated question because it falls across a number of different axis.

One is that there’s a trend in home design, basically since the postwar period. Obviously, houses got smaller before they got bigger.

The common suburban house—the foursquare, the bungalow, all of those—shrank before World War II into these little minimal traditional houses.

For middle-class people, that’s the important caveat.

For working-class people, your living situation only got bigger after about 1870. You went from tenements into little houses, which was a massive increase in space per person.

But if you were a middle-class family living in a Victorian house, then yes, your house actually shrank.

So there are these two different processes happening simultaneously from the late nineteenth century through World War II.

After World War II, obviously, you have white flight and suburbanization. There was also genuine discomfort in those little FHA minimal traditional houses.

I have a friend who bought one recently. They’re tiny. Eight hundred to a thousand square feet. Today we’d probably call them tiny houses.

Charlie:
You’re talking about the Park Forest ranches?

Kate:
Exactly.

Then, as development moves farther out into farmland—with the interstate highway system making that possible—you suddenly have much more space per lot.

There were all kinds of marketing ideas around ranch living. Not having to go upstairs was presented as a labor-saving device for mommy, things like that.

But the reality is that the farther you moved from the urban center, the stronger the desire became to internalize parts of urban life inside the house.

That’s not a new idea.

Henri Lefebvre noticed something similar in Parisian apartments in the 1970s.

At the same time, you also get this idea of zoning—(not municipal zoning, but zoning within the house itself)

That was revolutionary.

A lot of what they were zoning was actually sound.

You designed houses with open spaces for entertaining while children’s spaces were completely separated.

You created different zones for entertaining, for relaxing, for family life.

There’s always been some separation between public and private space in houses, but beginning in the 1960s it became much more about leisure and convenience.

So you see the average floor plan expanding along two different axes.

But the reality is, is that like the further you went out from the urban center, the more the desire grew for you to interiorize elements of urban life into the house.

The second is the interiorization and privatization of amenities.

The more amenities you could accumulate inside the house—a wet bar, a lounge, a great room, whatever—the larger the house became.

The great room, as we know it today, is really a 1960s invention.

It’s funny because Victorian houses were also highly zoned.

Victorian houses had parlors, libraries, sitting rooms—all these specialized spaces.

Layout of a turn of the century Victiorian house

But those reflected nineteenth-century ideas about formal social life.

By the 1960s, when that fragmentation returns, it’s reflecting something completely different.

It’s based on a highly developed capitalist consumer culture.

It’s also highly technologized.

Air conditioning is a huge part of that story.

People forget how important central air was.

It existed much earlier, but it was mostly used in office buildings.

It wasn’t until the late 1950s that air conditioning started becoming common in houses, and really the 1960s before central air became widespread.

Once you didn’t have to worry about heating and cooling every separate room, you could open up the floor plan dramatically.

That allowed more and more amenities to be absorbed into the house.

The attached garage, for example, really doesn’t become standard until the 1970s.

Developers were constantly marketing some new feature every year.

If you look at house plans from about 1950 through 1980, you can literally watch these features being added one after another.

The cycle just keeps repeating.

By the time you reach the McMansion, you’ve really reached the peak of a certain kind of suburban thinking—the edge city, then the exurb.

Everything is decentralized.

At that point there actually is a social necessity for those huge gathering spaces inside the house.

A “High Mcmansion” Floorplan

The basement game room.

The home theater.

All of those things.

They’re luxury goods, obviously, but the fact that they need to exist inside the house at all says something about how isolated everyday life has become.

That alienation really reaches its high point there.

And when people ask why there were so many McMansions after the 1970s, I think the simplest answer is income inequality.

Income inequality basically doubled.

There were simply more rich people.

Why did rich people build giant houses?

Because there were more rich people.

More than anything else, that’s what explains the proliferation of the McMansion.

I remember seeing a statistic that the number of millionaires doubled—or maybe tripled—between the early 1980s and 2000.

Well, that’s who’s building those houses.

There just weren’t as many people capable of building them in the 1960s and ‘70s.

Charlie:
Do you think there was sort of a Platonic ideal that people were aspiring to? Like the country houses in Lake Forest—the Benjamin Marshall estates.

Was that always the ideal? That wealthy people lived in these large, somewhat isolated estates, and McMansions became the Temu version of that?

Kate:
That’s funny.

I’m not sure.

I think, to some extent, in places like Chicago—where you have neighborhoods like Lake Forest, Evanston, places with that old stock of wealthy housing from the early twentieth century—there is definitely an impulse to imitate those houses.

They’re beautiful. Colonial Revival, Tudor Revival, all those old-money styles.

But then you get somewhere like Barrington, and it becomes a fascinating situation.

To me it’s almost like a prion disease.

That’s probably a mean way of putting it.

There’s some feature that becomes popular, and then every new house has to evolve around that feature.

Those houses don’t really have a natural architectural lineage.

They’re kind of incestuous.

You can’t really look at one of those huge Barrington McMansions—and Barrington is absolutely the Frank Lloyd Wright of McMansions; it’s the Oak Park of McMansions—and say, “That comes from Colonial Revival,” or, “That comes from Mediterranean Revival.”

Sometimes you can see traces of Tudor or Colonial forms. They look like inflated versions of those houses.

But there are plenty of McMansions that take on forms that are completely alien to architectural history.

Those forms come almost entirely from builders and developers.

Their architectural references are mostly themselves.

South Barrington, IL

Charlie:
Yeah.

Kate:
The other place they borrow heavily from is commercial architecture.

The big atria.

The marble floors.

Those come from banks, office buildings, malls.

From Kate’s Mcmansion Hell Blog

Charlie:
The two-story foyer.

Kate:
Exactly.

That’s straight out of banks or malls.

There’s a lot of McMansion architecture that’s really trying to simulate being inside a shopping mall.

The oversized walk-in closet is almost like microdosing the feeling of shopping.

Charlie:
God, that’s sad.

Kate:
Or the home theater.

It’s almost like asking, “What if my house were the mall?”

That’s really one of the organizing desires behind what I’d call high McMansionism.

We’re past that now.

We still build what people call McMansions—large developer-built houses with open floor plans—but they’re not the same thing.

The McMansion survives now in a kind of crippled form.

Even the McMansions of the 1970s weren’t the same as the ones from the ‘80s, ‘90s, and early 2000s.

There really was a peak.

I’d say peak or “High Mcmansion” was roughly 1993 through 2008.

The Farmhouse and the Financialization of Domestic Architecture

Charlie:
That’s actually what I wanted to ask you about.

It’s not like they disappeared.

Especially in Chicago, there was a huge shift after 2008.

The Chicago housing market got hit incredibly hard by the recession.

It took years for prices to recover.

It took years before a lot of mortgages in the hardest-hit areas weren’t underwater anymore.

One thing that happened was that those really far-flung areas—the places where peak McMansionism happened—lost a huge amount of value. Some of them lost thirty percent or more.

At the same time, the city started seeing a lot more development.

There was a multifamily rental housing boom, but there was also this new kind of McMansion.

Not the old suburban version. I guess you call it the urban farmhouse.

You see it all over Chicago now, and to some extent in the suburbs too.

Kate:
Yeah.

The hospital-white houses.

They’re, like, ninety percent of Logan Square now.

Charlie:
Exactly.

Kate:
They’re so bad.

I hate them.

Really, I don’t hate most architecture.

I love McMansions—that’s why I’ve written about them for ten years.

But I hate those fucking houses.

Charlie:
Same.

I’ve always wondered what the derivation of those houses is

Where does that look actually come from? Is there a patient 0 of the white farmhouse?

Kate:
The look is borrowed from a style that hasn’t really settled on a definitive name.

You can’t call it Minimal Traditional, because that’s already a style from the 1930s, even though it really is the same basic idea.

“Modern farmhouse” is one name people use.

I actually wish we could call it Minimal Traditional because it is minimal and it is traditional—but we already used that term for those little postwar houses.

Sometimes I call it rustic modernism, because not all of them are actually farmhouses.

Some of them are barndominiums. Some borrow from Craftsman houses. Others borrow from foursquares or bungalows.

Really they’re all borrowing from vernacular American housing.

Politically it’s pretty conservative lots of rural America type larping going on.

This style started coming to the forefront right after the Great Recession.

At first you didn’t see the final hospital-white version—that came later.

Initially you saw these small revivals of Craftsman houses and OG vernacular farmhouses. Just really ordinary American houses you’d find in a field guide to American architecture as vernacular.

Charlie:
For sure.

Kate:
These became popular like in 2010-2011. And a new sort of generation of HGTV starts.

And you hate to blame media..but this really was a media phenomenon

People were watching old houses get renovated constantly.

Eventually they ran out of old houses to gentrify, so to speak, and started building entirely new houses that tried to capture that feeling.

It’s almost like selective breeding.

You have a daisy.

Then you have a genetically engineered daisy that’s somehow even more daisy than the original daisy.

That’s basically what happened with the farmhouse.

They just kept pushing the farmhouse button over and over until eventually all you had left was this abstracted image.

Board-and-batten siding.

Black windows.

White walls.

Charlie:
Exactly.

Kate:
But I actually think the white ones come from another typology that developed at the same time.

The flipper aesthetic.

Flip or Flop and Fixer Upper premiered within about a year of each other.

Fixer Upper went in one direction.

Whether or not you like it, it was at least asking, “What do we want to do with this old house?”

Flip or Flop was basically, “How do I flip this house for profit?”

That aesthetic—the one people call “millennial gray,” even though it’s not our fault—became, in a really warped way, a signifier of wealth.

So the aesthetic communicate that what’s being communicated in those houses is that i made a smart investment that it’s not actually about architecture. We’ve reached the financialization of the market to a zenith that that is what new houses try to convey with their architecture it’s it’s interesting

That way of thinking was reinforced even more by Zillow becoming completely hegemonic during the 2010s.

HGTV Flip or Flop Aesthetic

Charlie:

So there’s two things that I think about it based on what you just said.

I know guys that actually build those houses. And their idea behind it.

The need to speak to a common denominator here, the most broad common denominator as possible, because they are signing a loan to build this that’s based on a personal guarantee of their entire net worth to build these houses.

Kate:

Exactly yeah and that’s an interesting component

Charlie:

That’s why they get built and why people build them. But why do people buy them? They’re so out of place here. I always thought it was an interesting thing, like you said there’s an aspect of being a media construct from those shows, but for me it’s also kind of this show pony for the new economy of the sunbelt.

Modern “Farmhouse” Ashville, NC

Kate:

No, I agree.

I just never think about it that way because I know, intrinsically, that it doesn’t come from New York, and it doesn’t come from Chicago.

You’re totally right about that.

I spend so much time thinking about these houses in Chicago that I forget they’re really imports.

I also think this aesthetic is tied to geography.

A lot of it comes out of Texas, Santa Fe, and Southern Living magazine. For a long time, the South—or really the lower half of the country—has been the driving cultural force in interior design, at least for as long as I’ve been alive.

Charlie:
And I think that connects to the strength of those cities’ economies.

If you look at where people have been moving from Chicago over the last twenty years, so much of that migration is toward the Sun Belt.

Those places become culturally influential because they keep growing.

Kate:
Yeah.

When I go back home it’s insane.

It looks different every single time I go back.

Charlie:
Right.

Kate:
That’s why I don’t go home.

It makes me upset.

Someone else talked to me about the Mormonization of the US, and it’s like, that’s also true.

Charlie:

Yeah there’s like a Mormon to Farmhouse, that aesthetic pipeline too. Like the look of seven kids named, versions of Taylee or something.

Kate:

Yeah, RIP Taylee.

Money first. Body second. Clothing third. House fourth.

Charlie:
I want to talk a little bit more about this idea—and we touched on it a little with the media effect on housing—but if you scroll Instagram, at least maybe it’s just my algorithm because of what I do, it’s nonstop content of hot people in amazing modernist buildings.

Kate:
Yeah.

I hate this shit, actually. I’m like, get out of here.

Charlie:
It’s every component of that, right? From real estate agents whoring for clicks, to influencers who just go around being hot in interesting buildings, and everything in between.

The engagement is enormous. It’s a huge part of what I see day to day. Instagram knows me better than I know myself.

Does that actually have an effect on the built environment? Because we’re talking about realities of urban farmhouses, and then I’m watching a video of a hot instagram girl in a Luis Barragán house in Mexico City.

Kate:
I feel like this is really part of the travel sphere.

People ask me about this a lot—whether it’s an architecture thing—and I always say, “No, dog. This is travel influencer culture.”

The houses aren’t really about the architecture. They’re destinations.

They’re tourist destinations.

This isn’t an architecture phenomenon as much as it’s a lifestyle, Dubai, travel-blogger, influencer phenomenon.

The fact that architecture is involved is almost tangential to what that content wants to do.

That’s honestly how I feel about it.

It’s certainly not educational.

Charlie:

Do you think it’s competitive or aspirational? Like, “I’m now in this interesting house. Where are you?”

Kate:
I’m going to be so mean here and say it’s about the body.

It’s not about the house.

Charlie:
So it’s body first, house second.

Maybe I’m clicking because it’s body first, and then I stay for the Oscar Niemeyer civic building.

Kate:
Well, let’s be clear.

It’s money first.

Body second.

Clothing third.

House fourth.

Charlie:
Got it.

Interesting.

But even still—if you set aside travel blogging and click-farming for body engagement, and you set aside interesting locales—I do think we’re in a time where people are more aware of architecture than they used to be.

The other day I met someone I never would have expected to know anything about architecture, and they started talking to me about Adolf Loos.

I asked, “Where did you hear about Adolf Loos?”

They’d watched a video on Instagram.

So I wonder whether broader education—even if it’s just based on whatever slop your algorithm feeds you—is ultimately a net positive for architecture.

Given that we both kind of agree there’s a bit of a stagnation right now, doesn’t public interest have to come first if we’re ever going to get more interesting architecture in the built environment?

Kate:
I mean, I think that’s true.

However, I watch a lot of this content on YouTube and TikTok, and it’s extremely wrong.

It’s factually wrong.

Or it’s interpretively wrong in really basic ways.

I don’t think the public being miseducated about architecture is a good thing.

I actually think architectural interest peaked about ten years ago.

What we have now is something different.

I don’t think it’s really about learning architecture anymore.

I think it’s about signifying a certain kind of erudition.

This is very tech-adjacent too.

It’s the whole Palantir Chore Coat aesthetic.

It’s taste slop.

It’s not actually about knowing architecture in a way that matters.

I mean, I only say this because I make content that is for everybody—that’s for education, that’s for the people.

So it bothers me when people do that in a way that’s disingenuous, or where it becomes entangled with being a hot girl.

That’s vulgar.

That’s vile to me.

Charlie:
Yeah.

Kate:
It’s not actually about knowing architecture in a way that matters.

It’s about knowing just enough about architecture that you can talk about it at a party in San Francisco while sitting in a Wassily Chair.

Charlie:

Damn. That’s dark.

Kate:
It is, though.

The content isn’t good.

Just Walk Around, Bro

Kate:
But, yeah...

I don’t think...

Architectural education is kind of fucked because we don’t actually teach it in schools. and so you’re really at the mercy of whatever idiot you find online.

The best thing you can do, Is like, buy a field guide and walk around.

Charlie:

Especially here.

Kate Wagner:

Especially in CHI-CA-GO.

Charlie:
One thing I notice in Chicago is that there are still a lot of incredibly talented architects and designers here.

It just feels like that talent isn’t really being deployed in ways that you and I, walking around the city, actually get to appreciate anymore.

Kate:

Yeah, I agree. It’s kind of shameful that we are not like the best architectural city in the world anymore.

Charlie:

That’s the entireity of our cultural exports to me. Food and architecture.

Kate:

But it’s also—in our defense—it’s not like New York is doing that much better.

Charlie:

No, thank God.

Kate:

The United States is just in a period of extreme stagnation when it comes to architectural innovation.

We don’t have public funding.

That’s where adventure comes from.

We’re also in a period of economic stagnation. Billings are down.

The era of the star architect—and entirely cultural buildings that cost hundreds of millions of dollars—is over.

Everyone asks, “Why aren’t we doing architecture anymore?”

Well, we ran out of money to do that.

And it’s over.

That was a low-interest-rate phenomenon.

Charlie:

Right.

Kate:

People say, “Well, what about other countries?”

They’re building social housing.

That’s where the innovation is.

We’re not doing that.

So there’s no innovation.

I don’t know what to tell you!

We’re not building cultural centers.

We’re not building public libraries.

We can still make great little buildings.

Look at Jeanne Gang‘s small projects.

I don’t like her big buildings at all.

WMS Boathouse, Studio Gang

Kate:
The boathouse is great.

The little library she just did in New York is great.

We can make some great little buildings.

But in terms of like things that are innovative and form pushing is like what would that even mean

What would that even mean anymore?

And I’m not quite sure technological innovation has the same spirit that it did a hundred years ago.

Now it just feels like a gimmick.

Charlie:

Look, I’d settle for great little buildings.

Kate:
Honestly, I kind of love every building...

...except those fucking houses in Logan Square. I’m serious.

That’s the only type of building I genuinely don’t like.

That’s the only type of building I don’t like.

They have really negative...

Charlie:
Negative aura.

Kate Wagner:

Yeah.

Future Nostalgia

Charlie:
So here’s what I’ll end on with you today.

You’ve written about the McMansion. There are bungalow heads in Chicago. There are workers’ cottage heads in Chicago.

Maybe there are even raised-ranch, ugly postwar housing heads in Chicago.

Kate:
Oh, I love a raised ranch.

Charlie:
So, will my kid, in twenty-five years, be posting on his... whatever the Tumblr equivalent is... about the Logan Square farmhouses?

Kate:
That’s a funny question.

I feel like... no.

Only because, in all those other typologies, there’s something new in them.

You know what I mean?

The raised ranch is a great example. Those houses are fucking goofy to me.

Charlie:
Yeah. I can’t stand them personally.

Kate:

Yeah. They really look like a fucking double-wide made out of brick.

Charlie:

Yeah, for sure.

Kate:

But I like them because they’re unlike anything I’d ever seen before.

I feel like you can’t say that about those houses (the urban farmhouse)

They’re actually retrograde. They’re based on something you’ve seen before.

A Barrington McMansion is something no one had ever seen before.

Whereas these houses... they’re sort of a slurry of what people have seen before.

Charlie:

They’re rootless.

Kate:

The pieces are recognizable enough that profit can be extracted from them.

They’re all over the country.

If you dropped one into almost any metropolitan area in America, nobody would think twice about it.

They don’t belong to Chicago.

They don’t belong to Texas.

They don’t belong anywhere.

That’s part of what bothers me.

A raised ranch belongs to a very specific moment in American history.

A McMansion belongs to a very specific moment too.

Even if I think it’s ugly, it tells me something about the culture that produced it.

These houses don’t really tell me anything except that somebody looked at Pinterest.

But even beyond that, it depends hugely on what the social and architectural context is in those twenty-five years.

If there are only a handful of them, then they do become interesting. If they’re the majority of the housing stock, then no, they don’t.

Or maybe people paint them, or redecorate them, or whatever. They’re not fixed in perpetuity.

Charlie:

Right.

Kate:

I find them interesting, for sure. Would I post fan cams of them? No.

But they say everything that needs to be said about the way we live in contemporary society.

Most of it is negative, and very conservative, and very craven.

But it’s honest.

That’s what I like about buildings.

I think buildings are honest, even when they’re being dishonest.

Like, those are not real columns...

...but they’re still being honest.

Kate Wagner by Tomaž Černej

X

Substack

Mcmansion Hell

In the last few years, Chicago has enacted more pro-housing legislation than at any point in my two decades living here. Affordable housing requirements have expanded. Parking requirements have been relaxed. Transit-oriented development has been strengthened. Entire commercial corridors have been upzoned. The common thread has been making large multifamily rental projects faster, easier, more equitable.

Yet despite having no physical shortage of land, Chicago remains one of the country's most supply-constrained housing markets. Rents continue to climb far faster than the national average, and the city's most desirable neighborhoods have become increasingly unattainable for would-be homeowners.

Worse yet, In the effort to make large-scale projects more equitable and efficient, I fear we’ve overlooked some of the most straightforward planning changes that can make the most profound effect on the whole of the built environment.

To me, the blanket removal and right sizing a 70 year old zoning construct in our beloved neighborhoods should be a priority. Instead it feels like policy has been focused toward adding stand-on-your-head-while-patting-your-stomach-and-whistling-dixie zoning loopholes buried in ultra-dense ordinances to add bulk to huge apartment projects that only the biggest developers with the baddest in house counsel can take advantage of.

I don't think that's because these policies failed. I think it's because they've focused on making exceptions to our zoning code instead of questioning the code itself.

While so much of Chicago’s housing woes are defined by metrics units added or not added, it may be unclear to some that these days, this almost exclusively means rental units.

After the Great Recession, Chicago entered an apartment boom. By the mid-2010s, thousands of rental units were being built annually, almost all in large multifamily projects that required zoning changes. The city used those approvals to pursue broader policy goals through programs like ARO and Connected Communities.

At the same time, demand for homeownership shifted toward Chicago’s outer neighborhood districts. While the city became better at producing large rental housing projects, it remains remarkably bad at producing larger, family sized units and homes for people to buy.

As counterintuitive as it may seem, adding small scale for sale housing for families in these areas may be more complex than erecting a huge rental tower downtown.

Chicago's modern zoning code largely dates to the 1957 iteration, when residential districts were assigned density classifications from R1 through R8. By far the most common designation is R3.

Despite being applied to neighborhoods filled with two-flats, three-flats, courtyard buildings, and even former mixed-use structures that predate the ordinance, R3 generally permits only a single-family home by right. Existing multifamily buildings can remain, but if they are demolished, the zoning often requires that they be replaced with just one house.

You can watch this happen all over Chicago. An aging apartment building falls into disrepair, is purchased for its land value, torn down, and a $2 million single-family home goes up in its place. The market didn’t demand fewer homes on that lot. The zoning code did.

R3 was born out of a postwar vision of low-density residential living, with detached homes and offsite parking in city limits. Some think it was created to keep “undesirable” renters out of middle class bungalow belt neighborhoods. It was a poorly wielded and blunt tool. Spraying high density city neighborhoods with this code may have made sense 70 years ago when city planners were terrified of both suburban exodus and the expected five million city residents by the year 2000.

Today’s Chicago looks very different. The average household size has been shrinking for decades, housing demand has become concentrated in a handful of walkable, amenity-rich neighborhoods, and parking requirements have largely disappeared near transit. Yet the central premise of R3, that one household should occupy one lot, remains largely intact.

That single assumption has enormous consequences. On some of the most valuable residential land in the city, the zoning code often determines how many families can live there long before an architect ever draws a floor plan.

R3 Lots In Practice

This is a diagram of a standard Chicago R3 25’x125’ lot. You will find this lot size and designation from Rogers Park to Burnside.

R3 Zoned lot. Required setbacks and max bulk allowed on a standard 25’x125’ lot.

Lots in the high demand, residential neighborhoods mentioned above, it is not uncommon for land prices to run between $600-700k. This means the maximum you’re able to build on this lot is a 4200 SF single family home. With construction costs running around $225/SF this leaves a builder with a construction cost of $945,000 and an all in cost of $1,545,000. With a 20% markup to sell the house this house would sell for $1,854,000. This is 20x the median income for peak family aged buyers between 22-44. With land values this high, building a smaller house on a lot this expensive while incurring the same fixed cost dictated by the building code just doesn’t make sense.

R5 Zoned lot. Required setbacks and max bulk allowed on a standard 25’x125’ lot.

But what if these R3 lots were changed to the more generous R5 code?

On the same size lot eight 400 SF units are allowed by code. If we wanted to go for larger units: four 1,260 SF units. If we wanted enough space for a family to live comfortably we could build three 1,680 SF units.

Using the same pricing metrics as above these 1,680 SF units could sell at market for $693,000 or just 7.5x the median 25-44 y/o household income in Chicago.

Notice anything else from the diagram? We have 41’ of the lot dedicated to front and rear setback space. Why? Chicago removed the requirement for onsite parking for the vast majority of R zoned properties in 2025. So if we don’t want to add off street parking why are we required to have these giant setbacks? And the front setback? Why do we need that at all?

We could add 960 SF to our R5 building if we dropped the front setback. Even if we just cut the rear setback in half, we’d get a whole other unit and have another family living on the lot! That’s four families living in the space that by zoning only one is able to currently live in.

Four families getting to reap the benefits of our highest performing schools, best neighborhood resources and infrastructure for less than half of what a single family home would cost. The developer would make a higher yield on their investment and the city would take in more tax revenue from 4 units vs 1.

Part of the heavily publicized Illinois BUILD initiative was, at the statewide level, to allow four units by right on any lot greater in size than 2500 SF. Due to pushback from the suburbs and voices outside of Chicagoland, the bill did not gather enough steam to even make it to a vote in the Spring session. But where this bill did have broad support was in the City of Chicago.

We could achieve the goals of this bill locally. With some setback rules to reflect new parking standards and a by-right change of all R3 and R4 lots to R5.

R5 and The Power of “By Right”

Perhaps the biggest advantage of broader by-right zoning isn’t that it allows more homes. It’s that it removes the need to ask permission in the first place.

Today, if a developer wants to build anything more substantial than what the underlying zoning allows, they’re often forced into Chicago’s lengthy rezoning process. That means months of uncertainty, attorneys, zoning consultants, community meetings, aldermanic negotiations, and carrying costs before a shovel ever touches the ground. It’s an expensive gamble that only the largest and best-capitalized developers can realistically afford to take.

By-right zoning changes that equation entirely.

If a lot is already zoned to allow three or four homes, there is no community meeting, no political negotiation, and no waiting to find out whether a project lives or dies at City Hall. A small local builder, an architect, or even a homeowner suddenly has the same legal certainty as a national development firm.

Ironically, many of Chicago’s beloved neighborhoods weren’t built through megaprojects at all. They emerged lot by lot, as thousands of independent builders made incremental investments over decades. By requiring discretionary approvals for even modest increases in density, we’ve made it easier to build a 300-unit apartment tower than a three-flat.

That’s the real promise of by-right zoning. It allows housing to be created incrementally, predictably, and by far more people than the handful of firms capable of navigating Chicago’s entitlement process today.

So what would actually happen if City Hall changed every R3 lot to R5 overnight?

Mass upzoning could accelerate demolition

The most common objection to broad upzoning is also one of the most legitimate: demolition.

If land suddenly becomes more valuable because it can accommodate more homes, won’t more historic buildings be torn down?

The answer is yes—at least in some cases. Any honest discussion about increasing development rights has to acknowledge that higher land values create stronger incentives to redevelop older buildings. Chicago has already lost countless workers' cottages, greystones, two-flats and neighborhood commercial buildings to redevelopment over the last several decades. Thoughtless upzoning could accelerate that trend.

For a city known for its architecture, surprisingly few buildings are totally protected from demolition. Under current R3 zoning, many aging multifamily buildings are already torn down every year. The difference is that they are often replaced by a single luxury home. We lose an older building and reduce the number of households living on the site at the same time.

If demolition is going to occur regardless, is replacing four apartments with one $2 million house really a better outcome than replacing them with three or four homes that more families can actually afford to buy?

There’s another irony worth considering from a preservation standpoint. When redevelopment opportunities are artificially scarce, competition for those opportunities becomes intense. Developers are forced to bid aggressively on the relatively small number of large-zoned parcels that can produce a viable return, regardless of what currently occupies them.

A broader by-right upzoning could actually diffuse some of that pressure. Instead of concentrating redevelopment on a limited pool of sites—including architecturally significant buildings that happen to sit on valuable land, developers would suddenly have thousands of additional options. Vacant lots, obsolete commercial buildings, aging single-family homes, and underutilized parcels would all become economically competitive alternatives.

The goal shouldn't be to encourage indiscriminate demolition. Chicago already has landmark protections, historic districts, and conservation tools that can identify buildings with genuine architectural or cultural significance. Those protections for certain districts and buildings should be bolstered and made more robust but with an understanding that preserving every existing structure, regardless of its significance, comes with a cost of its own. When redevelopment is effectively limited to one expensive single-family home, the city isn't simply preserving buildings, it is preserving a pattern of land use that makes some of Chicago's most in demand neighborhoods accessible to fewer and fewer people.

Displacement Of Naturally Affordable Housing

Another reason mass upzoning hasn’t been rolled out is that nonconforming status can be seen as an accidental affordability preservation tool.

One could make the argument that Chicago’s patchwork of legally nonconforming apartment buildings has become an unintended form of tenant protection. Because many of these buildings sit on R3 lots where only a single-family home could be rebuilt by right, their redevelopment potential is limited. In many cases, that makes demolition financially unattractive and allows existing tenants, and naturally affordable rents to persist.

There’s truth to that argument. Restricting what can be built after demolition can discourage redevelopment and, in doing so, reduce displacement.

But it also raises a broader question. Should Chicago’s strategy for preserving affordable housing be to make redevelopment economically impossible?

Using blanket downzoning as a preservation tool treats every parcel as if it carries the same displacement risk. It protects occupied apartment buildings, but it also prevents additional housing on thousands of sites where no tenants would be displaced at all. In the process, it drives up the value of the limited housing that remains and makes those same neighborhoods increasingly inaccessible to future residents.

“Developers Will Just Build Luxury Houses Anyway”

Another criticism of broad upzoning is that changing R3 to R5 wouldn’t suddenly fill Chicago with family-sized condominiums or apartments. After all, R5 doesn’t require a minimum number of dwelling units per lot. A developer could still choose to build one large single-family home if they believed that was the most profitable use of the site.

That’s absolutely true. Upzoning doesn’t mandate density. It merely allows it.

Some lots would almost certainly continue to become large luxury homes. On blocks where demand for large single-family residences remains exceptionally strong, that may still be the highest and best economic use of the land for the developer.

But the important difference is that it would no longer be the only legal outcome.

Today, on thousands of lots across Chicago, the zoning code has already made the decision before the market ever gets involved. If a builder buys an R3 parcel, the default answer is a single-family home. Under a more permissive zoning district, builders, architects, lenders, and buyers could instead weigh multiple possibilities: one house, three large condominiums, four smaller ownership units, townhomes, or even rental apartments. Even if only 30–40% of eligible lots are eventually redeveloped into three or four-unit buildings over several decades, that would still represent tens of thousands of additional homes.

The goal of upzoning isn’t to guarantee that every lot becomes four homes. The goal is to stop guaranteeing that nearly every lot becomes just one.

For the better part of a decade, Chicago’s housing debate has focused on exceptions.

Should this development receive a density bonus? Should that project qualify for affordable housing incentives? Should parking be reduced here? Should this corridor be upzoned? Should that building receive a zoning change?

These have unquestionably yielded results, but slowly and for one asset class and for one type of builder.

The neighborhoods we celebrate today weren’t master-planned through megaprojects negotiated at City Hall. They evolved incrementally: One lot became a two-flat. Another became a courtyard building. A corner store appeared. A three-flat replaced a cottage.

Today, we’ve largely made that kind of evolution illegal and we’ve concentrated nearly all meaningful housing production into massive apartment projects that require years of political negotiation while making it remarkably difficult to add even a handful of homes to neighborhoods with the most demand.

Chicago doesn’t have a shortage of land. It has a shortage of legal opportunities to use that land more efficiently.

Changing R3 to R5 won’t solve the housing crisis overnight. It won’t stop every teardown, eliminate displacement, or suddenly make every neighborhood affordable.

But over time, the expected outcome changes. Instead of guaranteeing that nearly every redevelopment produces one expensive house, we allow thousands of independent decisions to gradually reshape the city’s housing stock the way Chicago has always grown: incrementally, predictably, and one lot at a time.

When I was putting together the plan for our new townhouse project, I knew exactly where to start. Look at designers who had worked on the same projects, in the same city, under the same constraints with light and an excess of verticality. I started by scouring the websites of architects’ work from the mid 1970s to the mid 90s, my favorite era of residential construction in Chicago, and I was surprised at how hard it was to find anything.

I was on page 13 of Google results. Downloading jumbled, twenty-letter-and-number-long scanned PDFs from CONNECTION NOT SECURE sites just to figure out who designed an I guess unremarkable townhouse on Burling St.

Many of the architects of these projects have since died and left only an obituary and a couple of sentences on Wikipedia as a digital footprint. If you’re lucky, some museum somewhere has a few of their elevation drawings archived. Those living and still working seem to omit any project older than 20 years from their CV.

Jim Nagle, one of my favorite and, I thought, most well-known designers to come out of Chicago during this period, seemed to be erased from the internet. His practice was sold to a firm that just builds data centers after he died. The new owners subsequently removed all traces of their namesake’s 50-year body of work from their marketing material. The old firm’s URL is now a GoDaddy landing page.

Nagle was part of the Chicago Seven. Not to be confused with Abbie Hoffman and that whole thing, this Chicago Seven was a group of architects in the 70s who publicly eschewed the oppressive dominance of Miesian-influenced, rigid glass-and-steel towers in America’s architectural landscape. Nagle summed up their ethos best: “You’d get off an airplane in any American city and not know where you were.” There had to be a way to design buildings other than just ripping off the mid-century’s most famous architect. There had to be a better method of urban planning than tearing down century-old historic neighborhoods and plopping some austere steel and glass tower in the middle of an empty field. Both Mies and his biggest acolytes at Skidmore, Owings and Merrill called Chicago home, so what better place to throw up a big middle finger at the old guard?

The Titanic, Stanley Tigerman.

The group was ambitious and intentionally provocative. One of their best-known images by de facto group leader Stanley Tigerman had Crown Hall, Mies’ most famous Chicago building, in a Titanic pose sinking into Lake Michigan. The Seven’s The Exquisite Corpse at Walter Kelly Gallery was groundbreaking. The show's dictum had each of the seven architects tasked with making a model of a townhouse designed to fit on a standard Chicago lot. The designs were totally wild. Minimal facades adorned with oddly placed Corinthian pillars, detached facades with MC Escher-esque staircases to nowhere. Crazy, bold colors. Some consider this show to be the starter pistol of what would eventually be known as Post-Modern Architecture. The Seven eventually became Eleven and fanned out to not only national acclaim but left long lasting legacy through the next generation of architects in Chicago.

Townhouse Models From Exquisite Corpse, 1978. From left to right: Tom Beeby, Larry Booth, Stuart Cohen, James Freed, Helmut Jahn, Jim Nagle, Stanley Tigerman, Ben Weese.

The Dolphin Hotel, Orlando Florida, Michael Graves, 1990

But not everything changed overnight. It would be another 10 years until the Michael Graves-Memphis-Saved By the Bell-Opening-Credits pipeline emerged and 80’s postmodernism infected design everywhere. There was a slow burn that started in Chicago to take all of the great that came with 50 years of modernist design and loosen the rules a bit. Make things less rigid and boxy and more pluralistic. Reference periods other than the immediate past, but not LARPing with facsimiles of bygone eras. Infuse some fun and warmth, but still be subtle and restrained. THIS is the time that most interests me.

Article cont’d after photos

Schiller St Townhouses, Old Town, Nagle Hartray 1988

Nagle’s Own House, Lincoln Park 1970s

Shedd Coach Houses, Old Town Booth and Nagle 1970s

Booth and Nagle, Vashon Island, Washington, 1976

Chicago Ave Arby’s, Stanley Tigerman 1977. Now Demolished

David Hovey, Winnetka House 1982. Now Demolished

310 W Willow, Old Town, Bruce Graham, 1972

Fullerton Parkway, Lincoln Park, and Lapoint, SW Michigan Wheeler Kearns Architects, 1989

Steel and Glass House, Lincoln Park, Krueck Sexton 1981

Brick and Glass House, Krueck Sexton, Lincoln Park, 1996

Manilow House, Lincoln Park, John Vinci 1989

I know I’m not the only one who loves this stuff. I feel like daily, I will see some fantastic late 70s/early 80s kitchen or living room on some hypenated-last-name beautiful coastal person’s beige-hued Instagram grid. Sandwiched between some perfectly messy al fresco post-dining pic carousel and some “unintentional” body tea.

This could be written off as millennial “wow, look how crazy this looks” nostalgia poisoning for a time that we idealize because we weren’t there. Or something about the patina of a glossy scanned photo from some thrifted 1983 book about kitchens feels more human than our 4k world. I think people like it because it’s just chic and great. Because this period of design between the loosening of modernist dogma and silly postmodern pastiche was just a high-water mark in residential architecture.

Yet despite its social media popularity, I don’t see even a vestige of its influence in contemporary builds in Chicago. I don’t know what the point of reference is anymore on new construction. It feels completely rootless and out of context. Outside, everything is a farmhouse or retirement-community-red utility brick facades. Inside, everything looks out of a Bravo franchise from 10 years ago, with MAYBE, best case some “color-drenching,” ribbed white oak millwork, or some excessively veiny luxuriating natural stone that looks like 10 spritzes of Armani Code.

To be sure, bad taste definitely doesn’t even come close to the top of the list of problems in Chicago’s housing landscape, but when the entry point to this product is $2m for a single-family home, it is easy to punch down on it. All that money, all that access, and you’re still just a chud. Buying a house at 5x Chicago’s median sale price that will blemish our streetscape and, like the McMansion, inevitably elicit groans from next generation’s homebuyers.

I’m not advocating that we should just start building replicas of this era’s architecture. We live much differently and contemporary aesthetics should reflect that. What I wish we saw was the passion behind these designs, both from the architect and from the homeowner. After my rabbit hole of research on this era what struck me most was how much this generation of both had it in droves, and today that feels like the missing ingredient. Not nostalgia or some forced revival. Just a willingness to make a house feel specific. To make something that suggests the person who designed it cared, and the person who bought it had interests beyond the appliance package.

But I’m done kvetching about it, and I’m putting my money where my mouth is. Our newest project, Project Townhouse, is directly inspired and dedicated to that wonderful period in Chicago Architecture and to all of the incredible creativity of its designers.

We took an abandoned four-story townhouse, the vernacular product du jour of this generation, and tried to imbibe the attention to nuance, volume and cohesion as you’d see in one of these fantastic aforementioned builds. Albeit in our normal dilletante, Temu-ified, budget-constrained way.

The goal of our project was to create a single-family alternative that could cost half of what a new construction house of the same bed/bath count in Wicker Park would, while making no compromises on design. I think we succeeded. Finished product coming in a post next week!

If you’d like to read more about the designer, the projects, and this period in Chicago’s and beyond’s architectural history:

Larry Booth Profile in NewCity Design

Margaret McCurry in MAS Context

Houses, The Architecture of Nagle Hartray

Stanley Tigerman Buildings and Projects 1966-1989

The Language of Postmodern Architecture, Charles Jencks

Ten Houses: Wheeler Kearns Architects

FIVE ARCHITECTS: EISENMAN, GRAVES, GWATHMEY, HEJDUK, MEIER By Peter Eisenman

Modern in the Middle: Chicago Houses 1929-75 Benjamin/Sabatino

The Nature of Dwellings: The Architecture of David Hovey

Krueck Sexton: Works in Progress

Total Performance Architecture: The Work of Booth Hansen

Harry Weese Houses, Kitty Baldwin

“Shunned here, Helmut Jahn is out to prove he’s more than flashy” Chicago Tribune 1998

John Hejduk: Mask of Medusa - Works 1947-1983

SOM: Architecture of Skidmore, Owings & Merrill, 1973-1983, Albert Bush-Brown

Oral History of James Lee Nagle, Annemarie van Roessel, 1998

Oral History of Laurence O. Booth Annemarie Van Roessel, 2000

John Vinci: Life and Landmarks Sharoff/Zbaren

Stanley Tigerman-designed Arby’s in Streeterville is long gone but not forgotten,Lee Bey, Chicago Sun-Times

You want to buy a condo in Chicago. You’ve been browsing Zillow for months; you’re practically an expert at this point.

You finally found a listing that isn’t marked “TEMP” or “CTG.” You don’t love it, but you figure it’s time to get your feet wet and actually see something in person. You send the listing to your broker to set up a showing. They respond by telling you there’s only one time slot this week to see it: Saturday between 11 and 1.

It’s supposed to be 70 degrees on Saturday. In March. You made plans in anticipation of this. You ask your broker if there are any other times you can see the place. They respond by screenshotting the publicly hidden broker remarks section of the listing:

“NO SHOWINGS UNTIL THE OPEN HOUSE. NO EXCEPTIONS. DO NOT ASK TO SHOW BEFORE THE OPEN HOUSE. ANY OFFERS SUBMITTED WILL BE CONSIDERED BY MONDAY MORNING. DO NOT TEXT OR CALL THE LISTING AGENT.”

You figure the showing will only take a couple of minutes, and there hasn’t been much else to see, so you decide to change your plans and go to the open house.

You notice a big group of people loitering on the block. You get a bit closer, and you realize there is a line to the front door of the building you’re trying to see. For a condo.

The atmosphere is tense in the line. The line moves as other prospective buyers leave the house with a thousand-yard stare. They chatter quietly with a pathologically overdressed character on the sidewalk that could only be a Realtor.

You enter the unit. There is an OCEAN of shoes strewn about the entryway. You make your way into the living room. Another pathologically overdressed person clears their throat and points to a piece of paper scotch-taped to the coat rack.

“Sorry, we ran out of booties. Please remove your shoes before entering.”

The sign is, of course, branded with the listing realtor’s logo and face at the bottom.

Your broker tells you that if you’re interested in what you just saw, you need to offer $100,000 over the listing price, waive your financing contingency, take the place as-is, and let the owner remain in the unit after you close as your tenant until they find a new place to buy.

How did we get here?

Over the last two years, I put together a series of write-ups on the history and economics of condos in Chicago from their legalization in the 60s to the boom and bust of the 2000s to 2023. When I was researching this, the condo market had just begun to gather steam after a somewhat flat early 2020s and an even slower 2010s. Today, it is reaching a level of inaccessibility I didn’t think was previously possible

Most of Chicago’s condo stock, by and large, comes from two major construction booms in this asset class. First was the 1970s. Fresh off the 1963 Illinois Condominium Act legalizing condos, landlords used the law to reap higher sale returns by reparceling their vintage apartment buildings or towers and selling the units individually.

This second condo boom in the 2000s was vast in product type and funded by easy access to debt from both builders and buyers alike. Condo deliveries peaked in 2005 with nearly 4,000 new units coming to market. In January 2008, just prior to the crash and subsequent recession, there were about 3,100 available new-construction condos and townhouses in the entire City of Chicago on the market; in March 2026, there were 101.

What little stock we’ve added in the last 17 years tends to be exclusively at the very top of the market.

Above is the market data on all new construction, attached housing units pulled from local MLS data. In Q1 2008, during the peak of available new construction condo units on the market, the sales price was $369,000; today it is $899,000. Considering that until a few years ago, many 2000s-era condos were still underwater from their pre 2008 sale prices, this gain is remarkable. This cannot simply be chalked up to inflation (3ish% average over 10 years) or our nominal population inflow. So what happened?

Unit Size and the Single-Family Alternative

In the 2000s, the condo market was varied and vast. Units of all shapes and sizes, marketed to all segments of buyers, were built.

In 2008, new-construction one-bedroom units accounted for about 15% of the new-construction condo pool. Today, they make up less than 3%. Two-bedroom units accounted for almost half of the inventory. Today, they are less than 18% of the pie.

What’s dominating the new-construction condo markets today are large, expensive, three-plus-bedroom units in amenity-rich, high-income areas with strong infrastructure. 80% of the current new-build condos on the market in Chicago have 3 or more bedrooms. 26% have at least 4 bedrooms, a radical departure from the 3% of new four-bedroom units listed in 2008.

Four Bedroom New Construction Condos For Sale, 2008-Q1 2026. Source: MRED.

The driving force behind this is the lack of single-family affordability. In Lincoln Park, the epicenter of the 2026 condo frenzy, the median sale price for a single-family home reached a staggering $2.46m in March 2026. That is a massive jump from even one year ago. How? Market inventory is below even the historic low of the last five years, with only 28 houses on the market in a neighborhood of around 70,000 residents. That’s half of what was available in March 2025. What little new stock is being added is even more out of reach. The range of new-construction SFHs on the market in Lincoln Park right now runs from $3-7 million.

While single-family homes may be unattainable to everyone but the ultra-wealthy in amenity and resource-rich neighborhoods like Lincoln Park, large family-friendly condos are slightly more attainable. A median-priced 3bed/2bath condo in Lincoln Park runs around $850-900k. Lincoln Park is as rich in cosmopolitan amenities as it is in excellent educational options. General enrollment schools from kindergarten all the way through 12th grade are among the highest performing in the state. Something few other neighborhoods in Chicago can claim. When single-family homes become out of reach in areas like Lincoln Park, families of means looking for detached housing commonly start to consider the suburbs. But what happens when even that’s no longer plausible?

One of the by-products of the COVID-era housing market was a boom in suburban housing values. The desire for more space, remote work, or just a change of scenery that so many wished for in the early 2020s were some of the drivers. Some suburbs saw as much as a 70% jump in values pre-COVID to 2024. Common suburban exit markets from city neighborhoods like Lincoln Park, Wilmette, or Glenview are up almost 60% from ten years ago. A dramatic shift in these markets from the 2010s, where growth was marginal, if not flat. Suburban affordability can still be found but in further-flung locales. That’s a bitter pill for commuters in a metro with reportedly the worst traffic in the country. These single-family home alternative condos have started to fill in that gap, but even the prices for these have risen dramatically in the last two years, commonly surpassing the $1m mark.

What about other neighborhoods in the city that have dramatically less competition, lower prices and similarly sized units?

Institute of Housing Studies, DePaul University

The Great Schools Market Effect

One of Chicago’s most onerous legacies is that of segregation. Chicago is a city where demographics, resources, and landscapes are starkly contrasted in different neighborhoods. These disparities aren’t just spread to different quadrants or “sides” of the city, but can be hyperlocal. Sometimes neighborhoods with almost identical landscapes can have dramatic differences in property values.

I chalk this up in large measure to a website called Great Schools. Great Schools is a non-for-profit company that compiles data from hundreds of thousands of schools nationwide and provides a summary score out of 10 points, which is prominently featured at the top of the page. The site is now so popular with potential homebuyers that it is even plugged into listing aggregators like Zillow or Homes.com, which show the school ranking prominently below the property photos.

In a 2020 issue, Mother Jones featured an article of biases in Great Schools’ data. In it, they highlight a 2018 study that found that the gap between average home prices near schools with better ratings increased by more than $16,300 after three years compared to those near average-rated schools. In Chicago, the difference can feel far more stark.

Take these two properties in Old Town and in South Lincoln Park. They are only 3 blocks apart. You can walk between them in a few minutes. The areas are virtually identical in amenities, both sharing North Ave as a main commercial corridor. Both are easily accessible to transit and highly walkable. Both properties are under 5 years old, have about the same square footage (Hudson is actually a bit bigger), bedroom/bathroom count, and same outdoor space size and parking amenities, but when they each sold last fall, Orchard sold for $1.599m. Hudson only $1.09m.

1646 Orchard 1S Sold for $1.599m Fall 2025

1501 Hudson 1 Sold for $1.091m in Fall 2025

Distance between the two

Why? North Avenue is the cutoff between Lincoln Elementary, which serves residents north of North Ave, and Manierre School, which serves residents south of North Ave.

Lincoln Elementary is rated a 9/10 on Great Schools, and Manierre is ranked 2/10.

You can see these differences in almost all of Chicago’s highest demand markets: Northeast Lakeview has Greeley School (5/10), Southeast has Nettelhorst (9/10). East Wicker Park has Pritzker (7/10), and West has De Diego (3/10). North Roscoe Village has Audubon (10/10), South has Jahn (6/10). For each of these disparities in school ranking, you can find a similar case study of differences in property values and demand.

There is no question that a quality education cannot be quantified by a website. Great Schools is a blunt assessment of a far more nuanced issue. However, when suburban exit markets with their famously exceptional schools are less accessible than before, and buyers are paying record high prices for these family-sized condos, who would want to take this risk of being in a worse school district? If not for the sake of their children’s future, then for that of resale value in their home. The net effect is more upward pricing pressure on fewer neighborhoods.

What about DINK Condos?

It’s not just the large, single-family substitute units that’re flying off the shelves in these neighborhoods, but the entry-level housing stock, the two-bedroom, two-bathroom units that dominated the 2000s building landscape as well.

These units were never designed to be long-term homes for families. The concept of DINKS or Yuppies or what have you raising a family in the city, much less in a condo, was still novel in the 90s and 2000s. These condos more closely resemble new construction rental product. Small, open concept living spaces, large allocations to primary bedrooms and unfriendly in layout to the concept of work-from-home.

Yet these units in neighborhoods like Lincoln Park, West Town, Logan Square, Lakeview, and along the northern lakefront have the strongest sale metrics (shortest market time, highest percentage of list price achieved) in the city.

Condos in these neighborhoods may dominate the conversation and move the market data, but they are anomalies vs the city at large.

Neighborhoods like Grand Boulevard and East Garfield Park, areas that are about equidistant to downtown as the aforementioned, saw huge property value gains in the 2010s and early days of low-interest COVID times, but have experienced relatively flat growth since 2023. Market times in these neighborhoods are currently nearly 10x that of Lincoln Park and West Town. Price attained at sale vs list price is also 5-6% lower than Lincoln Park and Lakeview and 2-3% below Chicago as a whole.

But the buyers driving this market don’t branch out into areas like Garfield Park. Even at a relative bargain. They’re often renters in high-amenity/high-cost neighborhoods and are seeking a similar lifestyle and resources in their more permanent home. Movers tend to relocate into census tracts of the same income classification as their original neighborhood, particularly when moving within Chicago.

High-cost neighborhood condo buyers usually reflect the in-migration demographic trends to Chicago, not the outward. High income, high education, small household size. They have less interest-rate sensitivity than buyers in traditionally lower-income, lower resource areas do. They also have high liquidity, or at least parents that do. 31% of condo transactions in Lincoln Park over the last year were cash, as were 29% of Lakeview and 12% of West Town.

But what happens when that still won’t get you a home in one of these superstar neighborhoods? Do you give up the amenities? Do you buy in an area hoping for an amenity transformation toward where you’re renting, or do you leave Chicago altogether?

Many of these buyers represent a professional class that was formerly city-fluid but now is forced to become more sedentary, as hiring numbers have contracted and the economy has settled into a low-hire/low-fire equilibrium.

Some of the exit markets that this sect of the population gravitated toward (Denver, Austin, Florida) have overbuilt and are now seeing a glut of housing for the first time in years. The problem is that with new job opportunities stalling out, these buyers can’t take advantage of the newfound affordability in these cities. With remote work numbers contracting since 2022, lifestyle arbitrage options for the remote nomad have also been drawing down.

Help on the Way?

So you can’t afford a house in Chicago. You can’t afford one in the suburbs. You can’t own and send your kids to a good neighborhood school. You can’t afford a condo in an area that you want to live in, and you’re unwilling to move to where you can. You want to leave the city? Good luck getting a job elsewhere. Keep renting? Enjoy record rent price inflation locally. Chicago is leading the nation in year-over-year rent growth.

The good news is that help may be on the way. Attitudes around housing have begun to shift in the last decade. This is manifesting in an amazingly comprehensive set of housing bills in Springfield that are set to be voted on next month, called the BUILD initiative. The plan would legalize 4 units by right on almost any land parcel, expedite the permitting process, eliminate antiquated and redundant building practices, and limit local municipalities’ ability to override the allowances outlined in this state-level law. In short, a tonic for almost all of the legislative ills keeping us from adding new housing.

However, those looking for short-term relief may be left holding their shoes at a packed open house for the next few years. If the bills pass, they will take effect on January 1, 2027. This means that even if these extraordinarily ambitious bills manage to make it through the house without carve-outs for suburban NIMBYs and parking-obsessed lame-os, we’re still at least 18 months away from seeing the effects of these new laws and years away from filling in the 150,000ish housing units we’re short of.

In the meantime, the math doesn’t change. A limited number of homes in a limited number of neighborhoods, competing for a concentrated pool of buyers with the means to act. Until that equation shifts in a meaningful way, the experience of buying in Chicago will continue to look much the same.

About eight months ago, when we were midway through our project at 1934 Superior, a broker we know called about another house down the street that might be coming on the market. It was exactly the kind of house we had always hoped to restore, and exactly the kind of house that rarely survives Chicago’s teardown economy.

The house was right up our alley. A turn-of-the-century “Worker’s Cottage” with some unusual quirks. The Worker’s Cottage was the dominant form of single-family home in Chicago until around the turn of the century. The forms of these types of houses varied from neighborhood to neighborhood and from era to era, but most are very similar, with a few aesthetic variations. This house had a very short front setback and a huge 3-panel bay window in front, both rare features on a cottage that gave us both precious extra interior footage and more light infiltration into the living space than an average Worker’s Cottage allows.

The Cottage on Erie st.

It wasn’t just the facade that attracted us to this project. Houses like this carry a particular piece of Chicago’s architectural DNA. Worker’s cottages were small, practical homes. They appear modest individually, but taken together, they give entire neighborhoods their texture.

On this block, that texture had mostly disappeared. New construction from the last twenty years lined both sides of the street, boxy houses with awkward proportions and materials that already looked tired. The cottage felt like the last reminder that we were in Chicago and not on any anonymous residential street in a mid-sized American city. Bringing a house like this into the 21st century and letting it see another 150 years was too exciting to pass up.

We were sold. We put in an offer sight unseen. It would be 6 months later that we actually got to see the inside of the house.

The property hadn’t sold in generations, and after the death of the family matriarch, the beneficiaries became locked in a probate dispute. Someone’s cousin’s friend’s boyfriend’s son ended up living there and completely destroyed the place. He wanted $50k from the sale because he just decided he should get $50k from the sale. The rest disagreed. Eventually, the dispute was settled. We got in touch with the attorney handling the estate and agreed on a number they would sell the property for: $600k.

Probate finally cleared, and we got to see the house. It was destroyed. You couldn’t even move in there, there was so much garbage. Not only that, but what was there couldn’t be salvaged at a price that could ever see a return on investment.

Basement Ceiling at The Workers Cottage

The basement had 6ft ceilings and would require adding at least another 3ft of height to make the space functional as living space. This meant digging down under the foundation walls and pouring 3 feet of new foundation.

The top floor was under 7ft high, which would require at least a dormer running the whole length of the building on each side, if not a raising of the entire second floor.

The house was also less than 40ft long, and the whole back section was collapsing. A whole new rear extension would have to be built as well.

I could go on.

We put the budget together later that day. $1.1m in just construction costs alone for a house expected to sell for $1.75m. After adding debt service, architectural fees, and other “soft” costs, we were cooked. The budget exceeded the sale price.

What about just building a smaller house? No matter the size of a house, certain components of a gut rehab are fixed. The house needed new water service, new electrical service and wiring, all new plumbing, all new windows, a new roof, a new garage, and architectural plans/permitsets. Just those items alone, on top of the $600k purchase price, would exceed the sale price for a smaller house by an even wider margin than the larger renovation we had originally planned.

We still wanted to figure something out, so we went back to the estate with a request for them to drop the price. We needed a price of $400k to make the project make sense, but we offered $450k as a show of good faith.

No dice. This is what happens when raw land value exceeds the value of the structure that sits on it. Comparable sales in this section of West Town over the last year show land sales, or teardowns, commanding a price between $550-600k and new construction homes built on those lots selling for around $2mil. In short, a developer can pay more and make more than we could because they aren’t going to keep the existing house.

Heirs to this estate weren’t sentimental. They didn’t care that their house was a spectacular example of turn-of-the-century vernacular architecture or that it was the last vestige of quintessential Chicago housing on an otherwise completely uninspired block. They want their money. A pair of hipster developers offering to save the house for less money was a non-starter.

We found out last week that the house sold to a different builder, and they will indeed be tearing it down. We didn’t even need to ask what would replace it. On teardown blocks across Chicago, the answer has become predictable. A white façade. Black windows. Tall gables. Another modern farmhouse. The style has become so dominant in new construction that it almost feels inevitable. But its rise is actually a very recent phenomenon.

Of the seemingly endless upheavals in housing over the last 20 years, the Sun Belt boomtown and its lure to the laptop class fleeing coastal and northern metros, and the subsequent effect it had on the landscape of the country, surprised me most.

Since the early 2010s, cities like Austin, Denver, and Nashville have grown from regional curios to places that have big blue-state cities quavering as more and more of their populations, especially of the professional classes, have tended to outflow here. The reasons people give for leaving are familiar: cost of living in bigger coastal cities becoming inaccessible, COVID unlocking remote work as a permanent possibility, local politics becoming more extreme, and the excitement of the growth itself. Yes, there has to be something refreshing about living somewhere that is constantly changing so rapidly, somewhere where daily life is filled with optimism instead of constant news of more decay, more crime, more financial insolvency.

I have visited each of these cities over the last ten years. Most recently, in Austin, I tried to walk as much of the city as I possibly could to help understand this phenomenon. Everywhere we walked, someone was wearing that big, suede-brimmed hat, and on every corner there was a black and white “modern farmhouse.” The two began to feel related. The hat is the portable version of the house: a stylized nod to land and frontier, worn by someone who likely hasn’t worked either. The farmhouse does the same work at scale. It distantly references agrarian permanence while housing every rote prosperity signifier a wealthy boomtown millennial so voraciously covets, while maintaining an image of groundedness.

It wasn’t just the hat and the house but the unbelievable coherence of everything in these cities. The hat, the house, the branding of cafés, the palette of interiors — all aligned. That alignment is easier in a city that is still consolidating its identity. Or trampling on the old identity, now just a novelty. The modern farmhouse thrives in that environment because it carries no visible tension. It does not argue with its surroundings; it defines them. In a boomtown, optimism compresses contradiction. The aesthetic follows.

Chicago, on the other hand, is a city full of these contradictions. Bars embedded in residential blocks. Old tool-and-die factories sit next to Victorian mansions. Our leadership was self-conscious of it. Especially as the population began to flow outward. In the mid 20th century, Chicago was a city that tore down enormous swaths of existing homes and buildings for the sake of modernity. For the sake of contemporary housing ideals that now often feel out of place, austere, and unloved.

A great city is always straddling the line between continuity and change, but when the dominant new-build aesthetic becomes interchangeable, cities compete on amenities rather than identity. A far less potent metric for liveability. I think to a certain extent, the housing stock in a city should be reflective of the city’s own distinct cultural landscape, and that when you live somewhere, you should feel that experience both internally and externally. In the 200 year old year old city, radiant heat is OK. Formal rooms are OK. Narrow stairwells are OK.

The problem is that residential development is all about squaring the circle on any potential gotcha that could impact resale velocity. Architectural purity is just too big a risk. If one builder spent an excess of money rehabbing this cottage, quirks and all, and another builder put up a farmhouse on the next block at the same price, what does the buyer go for when there are 10 years of market data showing successful farmhouse sales?

But why the farmhouse of all designs? Foremost is cost. Specifically, labor costs. Farmhouses are stick-framed, siding-clad houses. Wrapping a house entirely in Chicago’s native material, brick, requires skilled tradesmen. This doesn’t come close in cost to wrapping a building in easy-to-install EIFS or large panel Hardie board.

But that doesn’t fully answer the question. There are a million different ways to design a simple frame house that doesn’t look so out of place in Chicago’s earth-tone landscape. The farmhouse aesthetic is defined by competition. There are more American cities today competing for the same cohort than a generation ago. College-educated professionals, remote-capable workers, dual-income households with high property-tax tolerance, but only in exchange for amenities. Farmhouse cities like Austin, Nashville, and Denver aggressively marketed themselves as optimistic and ascendant, while Chicago has spent the last half-century fending off negative narratives.

Before the developer even has stakes in the ground, they’re trying to quantify this audience scrolling listings in other cities: “Does this place feel contemporary?”
“Does it feel like where people like me live now?” The modern farmhouse answers in a nationally recognizable dialect. White façade. Black windows. Open concept.
Quartz island. That familiarity lowers psychological friction: you can relocate here without cultural whiplash.

Developers operate almost entirely on precedent. Once the first farmhouse sells, it becomes data. Lenders finance what has worked before. Builders replicate what lenders will finance. One farmhouse sells, and suddenly there are three. Then six. Not because architects discovered a deep new love for rural vernacular, but because the market validated a product. Within a few years, the farmhouse stops being a design decision and becomes the default setting for new construction.

Two of my friends moved to Austin a few years back. Before they moved, I bought them both big suede hats as a gag gift. When I asked them if they ever wore the hats out in Austin, they said, “Yeah, and it wasn’t weird. Everyone was wearing them.”

Whether native or a facsimile for the protein class, the big hat in cities like Austin is ambient. In Chicago, it feels imported, out of place. It isn’t reflective of the local climate or the culture that formed around it. The same goes for the modern farmhouse.

Our cottage saga is not unique. All over the city, builders are making the same calculation on prospective projects: renovate or wreck. Renovations carry uncertainty, while years of strong sales data have shown the farmhouse to be a reliable and valued housing commodity. In the math of development, reliability usually wins.

Over time, that math reshapes the city. The housing that once gave Chicago its particular texture will slowly thin out. Worker’s cottages, two-flats, and bungalows will survive here and there, but no longer as the dominant form of the city. Instead, they will appear as isolated artifacts surrounded by houses designed for a different market and a different moment.

Cities are defined not just by their skylines and their amenities but by the ordinary buildings that fill the blocks between them. When those buildings begin to disappear, the city’s identity changes with them.

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Get them in the fucking car.

That’s the credo a friend and ex-Zillow Flex operator drilled into his team of brokers during their weekly meeting. The “them” in this mantra is usually an unwitting prospective homebuyer who clicked the prominent blue “Contact an Agent” or “Request a Tour” button displayed on the Zillow listing of a property they were interested in. Instead of being connected to the broker listing the property in question, the prospect is rerouted to one of the agents on his Zillow Flex team, who then sets up a showing with the listing agent of the subject property.

At the showing, there are two brokers. This other broker is identifying as the listing agent. What? It becomes clear that the Zillow broker you spoke to isn’t the one listing the property. If they aren’t the listing broker, who are they and why are they here?

Getting this wary prospect into the car or to the curb in front of the house for some “curb chat” was this Zillow team’s way of diffusing an awkward and confusing initial showing experience. Ideally, the Zillow agent’s chatter is so good that it convinces this prospect to work with them, sign a legally binding Buyer Broker Representation Agreement that day, and become a client.

Over the last decade, the seemingly inert mechanism behind browsing online listings has transformed into a multi-billion-dollar enterprise for Zillow and has upended how real estate brokers do business. Even as lawsuits put a microscope on Zillow’s controversial tactics, buy-in remains strong amongst local brokers. Nearly a third of the 15 highest-grossing real estate teams in Chicago are members of Zillow’s Flex program, and dozens of other brokers pay thousands of dollars a month for its pay-for-lead program called Premier Agent.

Through Zillow’s dominance as the American real estate “super app,” the company has created far-reaching implications that extend beyond just the bait-and-switch tactics of the Zillow Flex program. Zillow can dictate who sells you a house, who gives you a mortgage, and even decide the app that you sign the contract on. They get a 40% commission kickback. What do you get?

Zillow’s twenty-year history is another case study in the 2000s disruptor app-turned-household-name trajectory. Born out of the founder’s goal of democratizing access to real estate listings and modernizing the interface of what had come to feel like an antiquated, lethargic industry. By startup standards, it was a near-immediate success. Four years after its launch, it was already profitable.

Browsing on the app was and still is an awesome experience of convenience. The integrated map feature, which lets you look across different markets and asset classes on your phone, was totally revolutionary. “Zillowing” something became shorthand.

Requisite acquisitions followed promptly. Trulia, Streeteasy, Hotpads, and other Multiple Listing Service (MLS) aggregators were first. Then came the riskier plays, first with Zillow Mortgage, then with Zillow Offers.

Zillow Offers was a program where Zillow would buy your house, flip it, and resell it at a profit. The initiative was a money-where-your-mouth-is play to back up their famed property valuation tech, otherwise known as “Zestimates.” One problem. The ebb and flow of hyper-specific local real estate markets and construction pricing couldn’t be accurately calculated by a computer. Zillow overpaid for thousands of homes until the program was shuttered in 2021. Zillow took a $420m write-down and subsequently laid off 25% of its workforce.

After restructuring, Zillow refocused on its core competency: monetizing transactions without owning the asset. Liquidity and scalability became key. Zillow Flex. Premier Agent. Zillow Home Loans.

To the consumer, it’s just a big blue button below photos of a pretty house. In the residential brokerage world, Zillow Flex is the golden goose, the fatted calf, and the manna from heaven. My last brokerage had the less desirable Premier Agent account and never-ending questions. When are we getting Flex? Why aren’t we getting Flex? What do we have to do to get Flex?

Premier Agent had us paying over $100k/year for only a handful of leads a month, and to quote Mamet, The leads are weak. A guy clicks “request a showing” at 11 pm and you miss the call; you’re paying for that lead. A guy doesn’t have enough money for cab fare to the listing; you’re paying for that lead. A guy already has a broker but wants to see the place anyway. You’re paying for that lead.

Premier Agent is priced tiered based on zipcode. Exposure in far suburbs and submedian income areas can be had for a few hundred bucks a month. Wealthy areas like Lincoln Park and Winnetka can set brokers back tens of thousands per month.

The leadflow is tiered, too. You can pay top dollar and be the first name, first call, or, for a lower monthly payment, you can show up further down the list and receive only a handful of leads per month.

Flex is different. It requires no upfront cost; Zillow instead takes a flat 40% of the buy-side commission at closing. The Flex calls are also “warmed up” or more heavily vetted by a call center before being connected to the broker on the Flex team. And the leads flow. By the dozens. The average American realtor does around 10 transactions per year. It’s not uncommon for Zillow flex teams in large metropolitan areas to close 20x that number.

At the helm of Flex is your regional Zillow Rep. They have metrics for everything. Answer Rate, ALM, pCVR. Don’t forget to plug Zillow Home Loans. They want 60% of your leads minimum to reach out to a lender in-house at Zillow. Reps are constantly evaluating the Flex brokers, listening to their phone calls with potential buyers, and if they fall below guidelines, brokers are constantly under threat of having their Flex account yanked, or if you’re a lowly Premier Agent team, never getting tapped to move up. With a Zillow program leadflow allowing for 20x the average yearly transaction volume, this is a terrifying proposition.

What this creates is a frenzied, high-stakes game of close-at-all-costs. Real estate brokerage, which on paper at least was intended to be an advisory role in the professional services sector, becomes a high-stakes game of beguiling inquisitive Zillow scrollers, getting them to a showing, and whether they know they’re being surreptitiously represented or not, getting them in the fucking car and closing them.

Forget that cloth wiring in the electrical panel, the basement seepage. A Flex agent cannot afford to let many deals “die.” Their standing with Zillow depends on conversion rates, lender referrals, and closed ratios. If a buyer hesitates because of inspection issues, financing questions, or simple second thoughts, that hesitation isn’t just a moment of caution; it’s a metric.

So what kind of broker is willing to work in a gridiron like Flex? After all, the Zillow referral fee is just the beginning. After Zillow’s 40% cut, then the brokerage split, then the team split, a Flex agent can earn 50% less than they would on a self-generated client. While there are exceptions, many Flex agents are newer and less experienced, willing to trade margin for volume and access.

I asked some of my friends who have worked on Flex teams (off the record) about how buyers felt being represented in such a big transaction by a random broker summoned by a hasty button click.

“Buyers don’t give a shit. It’s Uber Eats. They want to click a button and have someone show them the place as fast as possible.”

Maybe that’s true. Reducing service-based interactions to the singularity of a click has become a generational norm. But in a city with one of the most complex housing landscapes in the country, buying real estate is not a burrito bowl or a ride to the airport. It’s difficult to imagine that, if the mechanics were fully transparent, many buyers would choose an agent with less experience, no direct connection to the listing, and a 40% referral obligation to the platform that routed them there.

But measured experience and knowledge aren’t in the Zillow rep’s metrics. Zillow doesn’t sell real estate anymore. It sells proximity to you, the buyer. After the big swing and miss of Offers, Zillow retreated from owning the real estate and transitioned to owning the funnel. The houses are bait. The map is bait. The Zestimate is bait. The true commodity is the moment a consumer raises their hand and says, “I’m interested.” That moment, or click, is what’s being monetized and what matters. Not an experienced agent globbing up the KPIs by oversharing with the buyer.

The genius, or the danger, depending on your perspective, is that Zillow operates without owning inventory and without technically employing most of the people doing the work. It sits above the marketplace, extracting tolls while remaining structurally separate from the fiduciary obligations brokers carry. Brokers are no longer competing only on service or reputation. They are competing on platform compliance. The regional rep becomes less a vendor partner and more a performance supervisor.

And because the consumer experience is clean and convenient, the underlying economics are almost invisible. The interface feels neutral. The algorithm feels objective. But the routing of your inquiry is not neutral. It is optimized for yield.

Twenty-first century platforms always begin by democratizing access. They end by concentrating control. The taxi medallion gave way to Uber’s pricing. The independent innkeeper gave way to Airbnb’s algorithm. Real estate, long insulated by local relationships and private MLS systems, was always going to face its version of this. Zillow’s big blue button is simply the most polite expression of that shift.

Whether this arrangement is clever or corrosive is almost beside the point. What matters is consumer clarity in an existing system that currently runs on obfuscation. When you click “request a showing,” you are not simply touring a property. You are entering a referral marketplace in which your inquiry has already been routed according to a set of economic incentives invisible to you, the professionals around you being quietly arranged. The agent who responds may be capable and diligent. But they were selected by proximity to the platform, not by proximity to the property or depth of expertise.

What is a townhouse? I suppose at some point it was a city house for the restless rakes of the landed class in England to fritter away their time in the city during “social season” until pa-pa takes to bed and lays down the mantle of running the family country estate upon his firstborn.

Fast forward three centuries. The townhouse is a stick-built, DINK-forward, vinyl-clad mass off a 4-lane road in a sidewalk-free portmanteau Denver neighborhood.

In the London townhouse, there was the drawing room where men gambled, smoked, and drank themselves into some Hogarthian stupor. Wiling away the time until a man of superior title or property to suck up to produced himself. In Denver, there is the den where a dual monitor belches Microsoft Teams alerts and a group of kettle bells gathers dust in a corner.

Somewhere between these two eras, the idea of a city house, one where lot size constraints necessitated vertical living, became the standard of the city family home. Of course, size and degrees of opulence varied, but up until the end of the 19th century, most American and European single-family housing in large urban centers came in the form of attached and semi-attached houses.

Even after a century of technological leaps in vertical urban multi-family building to solve for the lack of light and narrow rooms of the townhouses, something about living in your own house in your own parcel is what most Chicago families seem to want eventually. No matter what I or any urbanist tells you.

Rowhouse/Townhouse

I should start by clearing up some nomenclature. In Chicago, at least, rowhouse and townhouse denote different things. Today, a rowhouse is a single-family home with all of its own utilities, on its own parcel of land, with a shared party wall separating the house from its neighbors. Other than the fact that the exterior walls are touching each other, these houses have no shared common interests in property.

1880s Built Townhouses (or rowhouses depending on who you ask) Bronzeville c. 1941

Today’s townhouse is usually part of a homeowner’s association. While the innards of the house itself are usually the responsibility of the respective owner, the HOA typically has governing powers over each parcel, and owners share in responsibility for basic utilities like water, sewer, and trash.

1990s built Wicker Park townhouse complex where our project is

Developers in the mid-century started calling their new attached multi-level products “townhouses” to give prospective buyers the sense that they were buying something exclusive and urbane. Before this, townhouse was the term du jour for Chicago’s semi-attached, fee-simple owned single-family homes (what we know as rowhomes now) in the 19th and most of the 20th century. And the 19th-century Chicago townhouses that the term referred to were very townhousy indeed. In the traditional sense. Greystones, rusticated brownstones, or immaculate 1/8 inch spaced brickwork facades. Some had turrets, multi-story bays, peaks with decorative stone relief work. Simply some of the best urban housing that’s ever been built in this country.

1880s townhouses in Douglas, Chicago now demolished

After the turn of the century, attached single-family homes became much rarer in Chicago. The city, with its sprawling expanse of prairieland at city limits, was faster to embrace fully detached housing as its population boomed outward again in the 1910s and 20s.

It wasn’t until after World War II that attached housing began to re-emerge. At this point, much of Chicago as we know it was almost fully built out. What was left were old sagging Victorians or disused manufacturing facilities on far too big of parcels to be economically viable for average single-family buyers. Especially as the city began to lose its middle-class homebuyers to the suburbs. Developers saw an opportunity: give buyers vertical space for less than a detached house, and make the numbers work by stacking units.

Modernist townhouses from the early 50s in East Lakeview. Design by Homer Rissman.

The townhouse held a place as a housing mainstay for the next 50 years in Chicago. First with hip modernist projects in Hyde Park and Lakeview. Then came the clunky mid-century builds in the NW side and the inner ring suburbs. Then the vinyl-clad “transitional” messes and the even clunkier Playmobil-looking brick builds of the 1990s. The original builders of the South Loop wanted a sure thing for their monumental investment, so they chose to stack the 600-acre parcel in the shadow of the Loop’s towers with townhouses.

Aerial of sprawling townhouse development in the South Loop. Mid 1980s.

Our Townhouse

Our next project is a 90s build that falls in the Playmobil-brick era of townhouse design. Green windows and orange and red-orange brick banding dot the facade. It’s the type of color palette that can’t even be made cool through a claim of 90s nostalgia. Because it’s a townhouse that’s part of a homeowners’ association, we cannot change the way the exterior looks.

Still, there is some sauce to this house. Huge window openings frame the front and rear sides of the living room. There is a half bath on the main level, a family room on the first, three beds on the third, and a loft on the top floor with a peaked ceiling and skylights. Four-level townhouses are essentially extinct today due to egress and fire code requirements.

The houses in the development surround a charmingly landscaped courtyard, which is situated just off North and Milwaukee avenues. It feels shockingly serene for a townhouse development from this era.

Most importantly, the house gives us a unique opportunity that we seldom get a chance at: to deliver a new construction 4-bed/3-bath product that costs 40% less than a new single-family home in the area with the same bed/bath count. As single-family home pricing continues to spiral further out of reach, projects like this allow us to reach a far broader pool of buyers. If attached housing is to become the primary form of urban homeownership for all but the wealthiest families in neighborhoods like Wicker Park, it’s time to make them as thoughtful and considered as any high-end single-family home.

The Unbearable Lightness of Maple

The biggest issue with townhouses from any era is the lack of light in the middle of the house due to the party walls. The only light openings are in the front and back of the building. Old Chicago detached buildings aren’t much better with their tiny side setbacks. We solved for this with a light well above our switchback stairwell in the middle of the house for our last project on Superior St. Because of the uniformity required in roof lines and facades of the townhouse complex, this scheme won’t be possible here. We plan to optimize the quality of the existing light through our material palette.

Maple is going to cover all the floors, windows, window returns, moldings, and railings. I love Charles Gwathmey’s apartment projects. He and Richard Meier started the great Maple-ing wave of the 80s and 90s that eventually filtered into what I call the “Pick-Up-Your-Basketball-Shorts-and-Start-Working-on-Your-Torah-Portion” McMansions of the North Shore. Toshiaki Ishida was another maple king. This house from 1997 in Tokyo is an inspiration for the main living room:

Aboev: Nearly Seamless Maple floors by Gwathmey Siegel, Central Park South Apartment

I love the way these pine window returns looked at the Superior house. Want to try this again with the same wood species as the floor.

We’re going to use a water-based clear coat and no stain on the floors. This will keep the yellowing resins out of the floors and keep our limited sunlight as radiant as possible.

Renwick St Loft by Solveig Fernlund

Another Fernlund project in NYC

Brushed stainless steel, off-white, and concrete tones will round out the rest of the colorway. The first level will have polished concrete floors. Stainless steel fixtures will be featured throughout the project.

The loft ledge sits at the top of the 15ft ceilings in the bedrooms and is filled with light. Perfect for a row of hanging plants.

We’re gonna have a big Noguchi globe like this in the master.

Off-white cabinets with stainless countertops. These Petit Tatu lights will be wall-mounted in the master.

Bathroom spaces will be smaller and windowless in this project. I like this use of a tight space by Durand Courchesne in Montreal.

Demo starts in two weeks with a targeted May 2026 delivery date. Stay tuned for the rest!

William and Katie are buying an apartment. A three-bed, two-bath in East Lakeview on North Lake Shore Drive. It’s the type of high 1920s building that in the face of its austere glass-and-steel neighbors, almost gives credence to the redpilled Twitter hoard’s grumblings about the soullessness of modern architecture and the endless bounty of that which was built before World War II.

Indeed, the apartment is everything you’d expect from some impossible Nora Ephronian-Tri-Star-Pictures-Three-and-a-Half-Star-Shag-Bob urban lifestyle porn. A rambling 1800 square foot layout, high ceilings adorned with 6 inches of crown molding, a 7 by 15 foot entry gallery that would be an unthinkable waste of precious living space in modern construction. It’s the type of apartment where, in the provided floorplan, the bedrooms are still notated as chambers.

As dreamy and romantic as these apartments are, they are far from the condo product du jour in Lakeview. No, for the last several decades, newer construction walkup condos with their low HOAs, on-site parking, and HVAC systems have won the day. Even at far higher sticker prices.

The median-priced 3-bed/2-bath condo in a building under 4 stories in Chicago this year hovered right around $735k. In a high-rise building, a 3/2 unit of about the same footage is going for around $525k.

Not only that, but a huge number of these middle-priced Lakeview 3/2 walkup units sold for well above their asking prices in multiple offers. This year, particularly in the spring, it wasn’t uncommon for these types of condos to sell for 10% over their list price, with winning bids often in cash or with financed buyers daringly waiving their entire financing contingency. The 3/2s in buildings 7 stories or over? Only one this year sold above its list price in all of Lakeview.

The reasons William and Katie chose Lakeview for their new home are in line with what I imagine most other buyers this year were looking for: an amenity and infrastructure-rich area that is highly walkable and has excellent public schools. As massive and expansive as Chicago can seem, there are really only a handful of neighborhoods that can claim all of this criteria in the entire city.

Like most young families in Chicago, William and Katie cannot drop $800k in cash to competitively secure a coveted 3/2 walk-up unit in Lakeview. William works in the Loop, and choosing a suburban house in a similarly ranked school district in their budget would give him a drastically longer commute. What they could handily afford, even with a home sale contingency on their current house, is a large pre-war apartment in a high-rise for $495k.

With soaring prices and demand for more “conventional” condos in Lakeview, is it time for a reappraisal of the neighborhood’s oft-overlooked high-rise units as a viable and even affordable option for young families?

Families In Chicago Apartments

Although family living in multi-story buildings dates back to Roman Insulae and before, in the formative years of pre-fire Chicago and other mid-19th-century American cities, this was something of a rarity. Families, no matter what their social strata, by and large lived in single-family dwellings. Clapboard cottages for the working man, handsome brick row houses for the professional class, limestone and copper peaked palaces for the gentry.

Owning your own house on your own land was then, as it is now a core tenet of the American experience for many. Even today, about two thirds of Americans live in single-family homes. The middle class balked when multi-story housing began to dot Chicago’s landscape in the late 1870s and 1880. Rickety frame two-flats and squalid tenement houses were seen as housing last resorts for down-and-outers. The problem was, the massive jump in Chicago’s population at the turn of the century made single-family homes the golden goose that fewer and fewer Chicagoans could afford. Neighborhoods evolved rapidly, and for developers targeting middle-class clientele, higher land costs meant too much exposure to build just one dwelling unit per lot. From this was born a novel solution.

A 1918 ad for an apartment hotel at Surf and Pine Grove St

The first middle-class apartment houses were something between a hotel and an apartment building. There were buildings with small units with kitchenettes, a billiard hall, a full-service valet and restaurant marketed to bachelors, and then there were sprawling eight-room palaces with libraries, parlors, and servants’ quarters for well-heeled families. By packing the buildings with all kinds of luxurious amenities, builders thought they could assuage potential residents’ fears of being seen as lesser than by their single-family home-dwelling contemporaries. The experiment was a success. Apartment buildings became the dominant form of middle-class construction along the lakefront for the next 30 years.

Multi-Unit Living in Lakeview

East Lakeview began as a resort community. The western section of the then-independent city of Lakeview was dotted with inns, lumber yards, and truck farms by the 1850s. The section between Halsted and Lake Michigan was a barren but beautiful collection of swampy marshlands, low dunes, and gnarled oaks. The turning point was an 1854-built hotel called “Lake View House” that catered to summertime tourists from Chicago looking to catch lake breezes from the hotel’s veranda.

Lakeview House Hotel at Grace St and Lake Shore Drive, c 1880

Eventually, wealthy Chicagoans followed suit with first summer cottages and then permanent homesteads. Large multi-lot Victorian houses began to pop up in the 1870s and 80s. Lakeview was annexed by the City of Chicago in 1889. By the turn of the century, these large multi-acre estates became less economically viable amidst record population growth. First, the land parcels were sold off, then the houses themselves began to be demolished to make way for the apartment houses we still see today.

441 W Surf. One of the last of the original big lot Victorian houses in SE Lakeview. Now apartments.

The Great Depression put a pause on high-rise construction in East Lakeview for 20 years. In that time, the idea of who lives in these towers radically changed. The biggest difference was the unit footprints. Big, sprawling layouts became open living spaces, formal dining rooms became dining areas, and servants’ quarters disappeared, as the custom of live-in help began to fade. No longer were these units marketed to families but to proto-DINKS in silk suits who spent two paychecks on a coffin-sized hi-fi.

339 Barry. Common postwar floorplan design in Lakeview high rises

In the 1960s-70s, city leaders tried with all their might but failed to stem the tide of mass middle-class suburban exodus. So what happens to the gleaming lakefront towers of the haute 20s? Conversions from rental buildings to condos in the late 70s and 80s of many of these buildings saw a new class of square-jawed, nylon-swishing yuppie that legendary Chicago writer Mike Royko dubbed “Condo Man” trickle in, but by and large, these buildings began to get a growing reputation as mausoleums. Heaven’s waiting room for those too gruff to make the move to Florida. Octogenarians who looked to spend their last days kibbitzing in the lobbies or banging on their ceiling with a broom handle every time their neighbors sneezed.

This reputation persists today. No question that the lakefront high-rise set is getting long in the tooth. In Streeterville alone, 40% of residents are over 45 years old. 20% of those are over 65. Streeterville and its Loop adjacent counterparts are some of the only inner-ring housing markets to not see double-digit growth in sale price in the last 5 years. Tower-heavy South Loop hasn’t seen a meaningful change in median sale price in 10 years! The drying of the downtown-bound empty-nester pipeline and the rise of remote work have dramatically cut down on interest in Loop-adjacent post-war glass box living. I get it. High taxes, high HOA fees, and increasingly uninspiring local amenities are a bitter pill when all the action is in the neighborhoods. But what about high rises in areas with the commercial infrastructure, with the green space, with the schools?

The Numbers

I think at the top of the list of why so many buyers shy away from high-rise living would be the high maintenance (HOAs) cost. “They cost more than the mortgage!” “It’s sunk cost, not going to my home equity!” “You’re better off renting!” Except for the latter (3-bed/2-bath rentals down the street at Optima Lakeview are commanding $7420/month before utilities), these are fair points. That, coupled with the 21st-century conveniences that walkup condos offer like dedicated off-street parking and central AC being sine qua non for Chicago buyers these days, it becomes all but impossible to view high rise units as anything but a novelty to be lived out in some late 90s romcom.

BUT. With the differences in purchase price for the same square footage between walkup and high/mid-rise unit, is it too soon to write these off? Let’s break it down:

William and Katie’s Place:

William and Katie’s apartment is a 3-bed/2-bath 1800 SF with a purchase price of $495,000. The monthly HOA fee is $1504/month. This fee includes just about everything (gym, cable/internet, gas, heat, common insurance) outside of the electricity bill. Because of the lower sale price, the taxes are considerably lower than a similarly sized, higher-priced walk-up unit. Let’s see what the monthly carrying cost is between William and Katie’s apartment and a recent sale in a 1800 SF walk-up on Burling St.

• $495,000 purchase price

• 30-year fixed conventional mortgage with a 6.75% interest rate

• 20% down payment

• $1,504 monthly HOA

• $7224 yearly taxes

• $1000 yearly insurance

= $4757.79/month all in cost

The Walkup

This 3/2 walkup on Burling Street sold for $770k in July. It is marketed as the same square footage, it’s in the same school district, with the same neighborhood amenities. It has onsite parking and central AC. The HOA only includes the water/trash bill and this unit’s share in the common building insurance.

• $770,000 purchase price

• 30-year fixed conventional mortgage with a 6.75% interest rate

• 20% down payment

• $242 monthly HOA

• $12,237 yearly taxes

• $1000 yearly insurance

=$5340.45

We then have to factor in the costs of building amenities every month that are included in William and Katie’s HOA fees and not in the walkup:

• $120/month average gas cost/month (based on averages from 2025 in Chicago)

• $150/month for a mid-tier cable and internet package

• $75/month gym membership for a basic local gym

• $40/month security system

=$5725/month

That’s $1000 more a month (or $800 if William and Katie decide to rent an off-street parking space) in just total monthly carrying costs for the same square footage between the walkup and high-rise.

With the additional monthly costs in the walkup that’re included in the high rise, it brings the walkup’s net effective monthly HOA to $627. When you take into account the additional $417.75/month in higher taxes in the walkup, the high-rise unit only has a $460/month premium in monthly non-equity carrying costs.

If we factor in the difference in down payments ($154,000 walkup vs $99,000 high rise) and we put that $55k saved into an S&P Index Fund with an annualized return of 10%, the gains from the money saved in down payment cancel out this extra $460 premium completely.

Did I crack the code on this? Does it actually make more sense to buy a cheaper high-rise unit than a more expensive walk-up, or is this just a giant cope of mine to coerce people into buying something that I deem to be superior in aesthetic value and liveability?

One could easily point to the last five years of explosive growth in the Lakeview walkup condo sector and what that means for people’s wealth via their gains in home equity. They could also remind you of the high degree of lip service around the efficiency of Chicago’s transit system and that car ownership, especially with children, is essential in Chicago. That circling the block for 30 minutes with a whining toddler looking for parking east of Clark just won’t work and is worth paying the large premium for a walk up with dedicated off-street parking.

While walk-ups may win on appreciation because they’re scarcity plays, High-rises win on use-value per dollar right now. Walkup affordability is showing no signs of improving in Chicago’s highest-performing school districts. No major signs walkup inventory will loosen up and paltry new for sale construction numbers don’t look to ease pricing for these existing homes anytime soon. For the $400k buyer, the choice to either sacrifice some creature comforts or to move an hour outside of the city to provide their kids with the same educational opportunities is a no-brainer.

This is the fourth and final part of my series on this construction project. You can find the other parts here:

Part 1

Part 2

Part 3

If the last 15% of a building project are hard, the last 5% are excruciating. Especially when you’re on a deadline.

For every builder, there exists a delicate yin and yang between trying to deliver a thoughtful, holistically designed product and throwing in whatever crap is lying around Home Depot at the end to fill in all the things you either forgot about or didn’t account for in your meticulous designboarding process.

The last 5% is when your idea-execution pipeline begins to suffer from what I call $1000 Syndrome. This malady is when your original plan not only does not work the way you intended, but its fallout spins out into multiple avenues that somehow each cost $1000 to remedy. Some examples:

Trimgate

After tile and cabinets get installed, it’s time to trim out your plumbing, lighting and hardware fixtures. When we called our supplier two weeks ago to request our trim kits, we found not only that they had forgotten to order these parts when we placed our initial order in the spring, but also that the pieces we need are made to order and will take 6-8 weeks to arrive. We were closing on the house in 3. Not only that, but in a new construction project, the bank does a second appraisal to make sure the house is complete before they agree to lend the money for the mortgage at closing. With no fixtures, we couldn’t close on the house and our construction loan was about to mature. We had to cobble together a frankenstein of random plumbing pieces that worked with our rough fittings to get around this. Of course, these fittings are only compatible with one brand of faucet. A luxury brand. This cost $2000 for something that would be hanging on the wall for 3 weeks.

Sprinklers

If you recall from these earlier posts, Chicago building code dictates that any single-stair home with two or more stories above grade requires a fire suppression system. We thought a second stairwell would ruin the layout of our house so we opted to sprinkle it. Problem is neither of us nor our subcontractors had much experience with sprinkler systems. On Tuesday of last week (one week before closing) we found out from the sprinkler company that we had failed to install an automatic shut-off from the sprinkler system in the basement to the furnace on the top floor. This is something we should have done before the drywall was even in and fixing this retroactively meant ripping out a bunch of walls to run the conduit up 3 stories. This was 3 extra days of work for our electrical crew all while both the painters, carpenters and electricians were also working in the house. The painters threw up their hands at the chaos, and Morsch and I were left to paint the entire second floor in 24 hours over the course of a weekend ourselves.

“In Stock”

This was a big insight into why new construction homes in Chicago look the way they do. The fixtures we placed in this house were designed to complement the layouts, the way light interacts with each room and the tile/paint/floor colors. Getting this specific meant having to traverse almost two dozen different e-commerce sites to find everything we were looking for. One site for the towel bars in one bathroom, one site for the toilet paper holder, one for the bathroom faucet one for the lighting. It was like this for every room in the house.

The shipping and the definition of what a product being “in stock” varied on every one of these websites. In stock could mean it’s down the street in a fulfillment center or its sitting around a warehouse in Sweden. Getting the timing of these to arrive while still having the guys on site to install the parts at once before they move to another project was really hard. I have been spending hours over the last few weeks on hold with call centers. To make matters worse, a week out from delivery we had fixtures stolen, arrive with European wiring, or be a busted dropship version of what the picture on the page looked like. Same thing happened with our exterior cladding. We had to go through three orders and three returns of different siding before we settled on this for our garage cladding.

Garage cladding in corrugated steel

It would have been 5000x easier and simpler if we had just gone to a big box local store and picked up what was on the shelves or ordered the same fixtures for every room. It gives a lot of color to the finishes in most new construction houses in this price point being so shit. It would be almost impossible to scale our method without a designer or a dedicated project manager.

ICE Comes to Superior

Worst of all, ICE agents made a surprise visit to our jobsite a few weeks ago. They were down the street from the job and accosted our countertop fabricator on this project, Soledad as part of their illegal non-warrant “investigations”. They hassled him for papers for the grave danger to national security he posed as a Mexican-American guy standing on the street with a countertop. They then tried to enter our site. They were unsuccessful. Everyone was pretty shook up. If you aren’t already aware, these “non-warrant” interactions have become a common sight at construction projects all over Chicago and serve as an enduring reminder of the federal government’s whole-hearted embrace of turning the darkest of human impulses into policy. Our workforce at Superior is about 60% Latino and nearly 100% immigrant. Among them, I count some of the most competent and skilled people I’ve ever met. This project would have been completely impossible without tradesmen of their skill level working it. To threaten to disrupt their lives as a political chess move from Washington is nothing short of disgusting.

The House

The house turned out beautifully. Rare instance of both being exactly what we hoped and exactly what we expected it to look like. It’s almost impossible to remember the old building. A broken-down, eyesore with satellite dishes hanging all over the facade, a partially collapsed old storefront, weeds growing through the chassis of a decades-old abandoned 525i. We were the only group of builders who didn’t want to tear the building and start over. I’m so happy, even in the darkest days of the demolition work we elected to keep (at least parts of) the original structure. Here’s a look back from the beginning to the final project.

Before:

Front facade November 2024

The back of the building when we bought it

The front room

Demo:

Framing:

Front and Rear Elevations:

Finish Work:

The Finished Product:

Catch you on the next one.

In 1923, there was a convention at the Chicago Coliseum. Plopped in the middle of the room was a full-sized bungalow, completely furnished. The design was by architect R.C. Spencer and was the winner of the “best small home planning ideas.” The event was the culmination of the growing “Own Your Own Home” movement of the 1910s and early 1920s, where, amongst a booming population, rent prices in Chicago had doubled in a five-year span. Looking to capitalize on these renters’ frustrations and a post-WWI frenzy for new housing, the event was put on by the Chicago Board of Realtors. 150,000 spectators turned out. What followed was the biggest mass building boom in Chicago’s history, where the city’s underutilized borderlands were transformed into thousands of homes for middle-income earners seemingly overnight.

Sound familiar? Today, we are experiencing a housing shortage nationally of 4.5 million units, and it is felt locally. Housing inventory in Illinois is 67% lower than pre-pandemic levels. Even amidst decades high interest rates, buyer demand in Chicago remains incredibly strong.

As housing affordability reaches its nadir, I’m seeing more and more think pieces about Chicago bungalows — and how to build a 21st-century counterpart to these famed starter homes. Between 1910 and 1930, tens of thousands of these homes went up. At the time, the median cost of a bungalow in Chicago was roughly 1.5 to 3 times the average household income in 1925. Today, the ratio for all single-family homes has climbed to about 4.5 times the median household income — and for new construction, 17 times. Yet these century-old bungalows aren’t just still standing; they’re still coveted by buyers. Maybe it’s time to go back to the well and ask what it would take to replicate this beloved form today.

**There is no comprehensive dataset on household median income from the 1920s. The US census did not begin asking about income until 1940, and the concept of “household income” wasn’t even formalized until a decade later. The best we can get is average, and most of that data comes from retroactive reconstructions.

I’ve written about the Chicago housing paradox: the eroding of entry-level housing affordability despite the city being dotted with thousands of vacant lots. Will we ever be able to build middle-income attainable single-family homes again, or are bungalows a relic of a time and place where the stars aligned and the average Chicagoan could afford well built, attractive, and modern home?

The Bungalow Belt

The Bungalow Belt Illustrated, from Chicago Bungalow Association, an outstanding resource for information regarding these homes

What we now know as the Bungalow Belt was once seen as far-flung prairie hinterlands to Chicagoans of the 1920s. As generations matriculated from first the crowded inner ring ports of call and eventually through the adjacent two flat belt, Chicago began to add infrastructure and transit to the surrounding farm and low-density prairie land it had annexed in the late 19th and early 20th century. The need to live close to work began to take a backseat to the want of a single-family dwelling for its burgeoning middle class. The city’s extensive streetcar system (fully retired in the late 1950s) now provided access to areas that previously seemed unimaginably far from the cramped industry-adjacent tenements of the previous generations.

The lack of density in the new, then fringe bungalow communities must have felt like the pinnacle of luxury to prospective home buyers. Prior to the 1910s, most Chicago residents had been accustomed to hyper-dense 40 units per acre living standards. These new farmland-turned-neighborhoods often had a density of only 10 units per acre.

Form and Function

While there’s no direct roadmap for what informed the design of the Chicago Bungalow, it seems to have taken form over a generation through the trickling down of Arts and Crafts aesthetic principles of the late 19th century, adapted to the narrow constraints of the standard Chicago lot size. This period coincided with a new phase of American industrialization that standardized, among other things, the components of a home.

The early mass production building methods seen in the 1910s exploded in the 20s when Fordist manufacturing techniques began to reach all kinds of American industries. Plumbing, lighting, windows, and lumber mills also adopted mass production techniques to supply this burgeoning middle-class home market with modestly priced, attractive, and well-made fixtures.

Evolution of the Form

Worker’s Cottages, the first iteration of entry-level single-family homes built in Chicago

A First-Generation Bungalow in Albany Park Built 1914

A 1910 California Bungalow in Berkeley, CA

The first generation of these homes to be built in Chicago borrowed heavily from two earlier counterparts. Functionally, from the 1 and 1/2 story Worker’s Cottage, which was designed for the standardized 25x125 lot sizes, and aesthetically, it drew inspiration from the California Arts and Crafts homes, characterized by frame construction with stucco or clapboard siding exteriors. Small footprints set back from the street, short, very tight basements with wooden main beams and posts. Frame bungalows were almost always the least expensive and least practical, given the drastic difference in climate between the West Coast, where these houses originated, and Chicago. Unlike their successors, first-generation bungalows are less commonly found today, and their building techniques and quality can vary wildly.

A second-generation flat-front bungalow in Portage Park built 1927

Bungalow construction hit its peak between 1918 and 1928, and as more were built, their forms began to become more and more standardized. These houses were some of the first in America to rely almost wholly on mass production techniques in their construction. Sometimes, only two or three architects were responsible for the plans of hundreds of homes in these new megadevelopments, giving somewhat of a copy/paste feel to these bungalow belt blocks.

In these second-generation bungalows, brick exteriors began to replace wood cladding, and basement and attic spaces were expanded to factor in future use in their design. All of this was aided by the ease of attaining new factory-built windows, plumbing fixtures, standardized pipe fitting systems, hardwood floors, and millwork. Mass production techniques, as well as the expanding scale of bungalow development tracts, kept affordability still within reach of middle-income buyers.

1927 Kohler ad for matching bathroom fixture set

Block of Bungalows Under Construction, Far South Side

The third and final generation of bungalows are some of the most coveted by buyers today. These were built on what was considered the fringe of the fringe of Chicago in the 1920s. These homes date from around 1927-1930, and in a way, they reflect the lavishness of the late 1920s pre-crash of ‘29. Middle-class buyers now began to have an appetite for stylings and exoticism outside the quotidian, and builders responded in kind. When these parcels were subdivided, developers often gave more generous allowances on lot size than to parcels closer into the city. They also began experimenting with the form and layout of these homes. 30-35’ wide lots became common, as did the ornament of the interior finishes. Think leaded glass windows, decorative tile work, complex millwork, and plaster curves in living spaces. These houses were often built much deeper into the lot with less backyard space than first and second-generation bungalows.

Living room in a West Ridge Jumbo Bungalow

There was a giant leap forward in livability considerations between the bungalow and the previous generation single-family housing design in Chicago. In contrast to the often cramped, squat, and dark worker’s cottage, bungalow designs were cognizant of the desire for ample light through large window bays and expanded living space for families. Almost all bungalows had separate living and dining spaces, wider bedrooms (by 1920s standards), and ample closet space. Setbacks became important too. In contrast to buildings in inner ring neighborhoods, most bungalows have a relatively sprawling front lawn and are set back between 7-10 feet from the sidewalk.

Most importantly, these houses included unfinished basements and attics with reasonable ceiling height, giving the homeowner a fair-priced home with the opportunity to expand into the other levels as their needs grew.

Chicago saw a few more waves of entry-level housing stock built after WWII. Raised Ranches and Cape Cods took over where the bungalows left off, providing housing still within the reach of middle-income families. Problem is the last generation of these mass-produced entry-level city homes is well over 60 years old. What happened and what would it take today to build market-rate housing for middle-income families?

What Does a Middle-Income Home Mean in 2025?

As of August 2025, the median sale price of all MLS-recorded single-family homes (resale and new construction) in the City of Chicago is $340,000. New ground-up construction SFHs are currently at a median of $1,342,000. From the latest census data, the median household income for all households in Chicago is $75,134. This gives a gross income multiplier to home cost of about 4.5x for all homes and 17x for new construction.

Yes, you’re reading that right. A median-priced new construction home currently costs around 17x median household income in Chicago

**Data caveats: first is that new construction sales data from MLS is dependent wholly on somewhat loose guidelines that the realtor enters upon closing. This can cause issues when it comes to gathering hyperlocal housing data. Square footage can be fluffed or completely made up with few guardrails, and corresponding property type boxes aren’t checked. This makes aggregation on things like price per/SF really difficult in Chicago’s MLS. New construction homes can easily sell and be recorded with brokers refusing to check the box, clicking “rebuilt” or “rehab” accidentally, or skipping this protocol. Although MLS isn’t completely reflective of the housing market as a whole, the vast majority of home sales use this system. According to a 2023 study, 84% of home sales nationally are marketed and recorded on an MLS.

I was so shocked by this number that I manually reviewed all the aggregate data to see if this was possible. It is. I even went through all the listing photos (over 2500 in total) to make sure these were all ground-up houses. There are a handful of rehab/rebuilt data entry errors at the low end of the spectrum, but if anything, they’re pulling the median sales price downward. Indeed, out of the currently 103 single-family homes with a year built of 2024 or 2025 active or contingent on the market in Chicago right now, the median price is right around $1.35m.

How? A million reasons I will dedicate another write-up to. Bottom line is that what is currently profitable in the for-sale space for builders are large single-family homes and condos at the very top of the luxury market. Very different from our target bungalow audience.

Still, median is median. There are dozens of ground-up homes below this number that can theoretically command a sales price within reach of the same middle-income earning households relative to those that bought bungalows 100 years ago. Right?

Our Bungalow Buyer

Let’s break down who entry-level single-family housing like bungalows were originally designed for and marketed to, and bring it to 2025: households within both child-rearing years (29-34) and within the median age of a first-time homebuyer (38) and peak workforce participation age. The 2023 median income for a Chicago household in this 25-44 bracket is $92,347/year.

Although Fannie/Freddie loans succeeded the bungalow boom by decades, these conventional mortgages are the most common loan product in the US today, and we’re going to assume our buyer will be using this to purchase our bungalow.

We’re going to apply a generous 6% interest rate on a 30-year fixed-rate conventional loan with 20% down to these examples. Going to assume taxes are around 1.5% of a property’s value per year, and insurance for a small house will run around $1500/year. The standard maximum debt-to-income (DTI) ratios that Fannie Mae and Freddie Mac allow for a loan to be warrantable are around 45%. Sometimes borrowers can be given some forbearance to push DTI up to 50% depending on mitigating factors.

This leaves our median 25-44 year old buyers with a maximum purchase price of $615,000 with these loan terms, with no upward wiggle room. And $615k is tight. $3843/month all in. That leaves our buyer’s annual housing cost about 49% of their total income. Just snaking by Fannie/Freddie absolute maximum guidelines.

Rebuilding the Bungalow

First, let’s look at the hard construction costs to build a Chicago bungalow today. We’re going to build the most common, middle-period bungalow. Current market expectations aside, that means an all-brick 1 and 1/2 story house with an unfinished basement and 1/2 story attic, left to the owner to finish later if necessary. Each floor of a bungalow tends to run between 900-1200 SF per floor, depending on lot size and construction era. Let's split the different and assume each floor is about 1050 SF, with the attic having half of that as liveable space due to footage being lost under the roof eaves.

This gives us a 2650 SF structure to build. I went through all the line items of my last several projects, both ground-up and retrofits, and I’ve landed on a VERY liberal, near-miracle number of around $220/square foot.

This does not factor in “soft costs” outside of insurance and architectural plans and permit sets, which I have also very conservatively estimated at $15k. No debt in this scenario. That means the builder in this hypothetical project is buying both the land and funding the construction in cash.

I’m also not including “they don’t build them like that anymore” features. We’re losing the 2 courses of common brick that these houses were built with. We will pour a concrete foundation, and concrete block will sub for brick the interior walls. Instead of common brick on the exterior sides of the house like a traditional bungalow, we’re going to use larger utility brick to save on labor and material costs. We’re going to use the same window size and count, but you can forget leaded and stained glass windows and solid oak doors and trim. This budget is for vinyl windows and MDF moldings.

Almost unheard of for ground-up builds in Chicago today, we’re going to have just 5 major plumbing runs, of which only 3 (Kitchen, Laundry+Utility, Bathroom) will be finished at the time of sale. We’ll put auxiliary plumbing roughs in the basement and attic for future expansion.

Basement height is going to be brought up to 8ft from the shorter bungalow-era basements so it can be finished later and remain code-compliant. I’m also including a flood control system and an ejector pit for below-grade plumbing, things that are often skipped in bungalow retrofits but are required by the city today.

This gives us a grand total of: $583,000 to rebuild the bungalow.

Just the Tip of the Iceberg

Notice anything missing there? LAND COST.

5323 S Wolcott

Now, Chicago’s 30,000 vacant lots would be the logical place to start to build our bungalow. Many of both the 20,000 privately owned lots and 10,000 city-owned lots are readily available to purchase at any given time and for bargain basement prices. Let’s try it here at 53rd and Wolcott in Back of the Yards. This lot has appropriate zoning and dimensions for our bungalow and is priced at only $7500.

Great! Say we’re somehow able to negotiate the land seller to pay closing costs, that leaves our all in cost at $591,000. Well within our buyer’s $615,000 max. But what about the developer’s cut? Yes, like the vast majority of 1920s bungalows and ground-up builds today, this is not going to be a homeowner-built project, so we need to factor in a profit margin for the builder.

Builders don’t tend to spend a year on a construction project for any paltry return that can be seen from investing in a simple S&P-weighted ETF. 10% or under (the annualized average growth in the S&P) is considered a wash, so let’s figure a 20% gross profit margin for our one-off bungalow would make this a worthwhile project.

Even that’s not so great for the builder’s real net and really not good for our buyer. That gives us a market price of $709,200. Say we find another buyer who pays full price, we need to shell out 6% in broker fees and transaction costs at the closing table. This leaves a profit to the builder of barely $75k when all is said and done. Remember, this is without borrowing costs. Interest on construction debt is currently hovering somewhere around 9-10%.

The Appraisal Paradox

Even if there was just a $75k profit here, I feel pretty confident there would be some developer out there who would build this project. So why don’t they?

Back of the Yards, especially the portion south of 51st between Ashland and Western, was an area heavily affected by the same problems of pre-bungalow belt Chicago neighborhoods: deindustrialization, deterioration, and haphazard city intervention via aggressive tear-downs. The population in Back of the Yards is about half of what it was in 1920.

The very eastern section of Back of the Yards has seen growth in home values of late, but the neighborhood as a whole still has a single-family home median sale price of just $232,000. The most expensive single-family home on record in this southwestern section of the neighborhood sold for just $311,000 last year.

Realistically, a builder who is likely to be OK with a $75k profit on a year-long process is one who most likely has lots of projects going on at once. Multiple projects going on at once means, for the vast majority of builders, using construction debt to build economies of scale as opposed to deploying one massive pile of cash. While some commercial banks are less stringent than others, appraisals of after-renovation value (ARV) play heavily into their due diligence on what and how much to lend. What bank is going to finance a construction project where the all-in project cost is nearly double the highest price sale on record in the area? Our developer could put more money down to assuage the bank’s concerns, but thin profit margins usually mean the goal is to put as little down per project as possible to maintain scale.

The same problems affect the buyer. First off, at $709k, we’ve pushed our median income $93k/year buyer way past the aforementioned conventional loan debt-to-income guidelines. Even if this buyer has an extra chunk of change to put down to qualify, they still have to worry about the bank’s appraiser agreeing with a market price 2.5x the most expensive recorded sale in the neighborhood.

So what if we tried this in an area with more tried and true ARVs for new construction homes?

830 N Fairfield

This house is located in Southeast Humboldt Park/Smith Park, an area that has seen a surge in new construction single-family product over the last decade. Most have sold well. This area has a median of 99.7% of listing price attained at sale and a lower average market time than the city as a whole. The house sold for $365k in 2022. A demolition permit was filed and stamped for this property in February. What if we built our bungalow here?

• $365k Land cost (closing costs seller assumed again)

• $583k Build cost + $20k to demo the existing structure

• Developer profit margin of 20%

This gives us a market price of $1.161m. For a bungalow.

That’s 12x our subject buyer’s income. Using the above-mentioned loan terms means a monthly mortgage payment of $7144/month or 93% of their total household income. Is it becoming easier to see how a median-price ground-up house can be 17x middle-income in Chicago?

So no more bungalows. No more leaded glass, no more built-in oak buffets, no more plaster, no more brick.

The good news is that the bungalows we have left aren’t going anywhere. Even at a critically low point in for-sale inventory, there are still several hundred on the market in Chicago at any given time, most well within reach of our subject buyer’s price range. The bad news is we can’t make more of them. If the spread between existing homes and new construction continues to narrow, we will be forced to confront a simple question: if we can’t build the next generation of affordable homes the way we built the last, what will take their place?.

In Part Two of this series, we’ll explore how middle-income single-family fell off — and what supplanted it in the 21st-century middle-end for-sale space. We’ll look at why you hate the way it looks, how the city tries to help, and how some of the most interesting solutions to rebuilding this essential middle-income house are happening right here in Chicago. On paper, at least

When is the last 15% of anything easy? Obamacare, weight loss, downloading Bawitaba on dial-up, the last steps of what seems to be a seemingly binary process devolves into a fire drill with a constant stream of tiny overlooked items eating you alive.

This house is no exception. Like any big retrofit project, there have been a series of calamities. Collapsing facades, psychotic neighbors, months-delayed windows, etc. But by and large, we sailed through framing, masonry, mechanical rough-ins, drywall. The last 15% is coming along about as smooth as sandpaper. Details/devils something like that?

The Moodboard vs Reality

This project is chock-full of inspiration and riffs on some of my favorite modernist design turns. Our original idea was that by incorporating a more refined aesthetic language into this house, we could create a better and more highly valued project than our competition.

Problem is the moodboard we used for inspiration is just that, a collection of pretty pictures. It’s so easy to forget that these buildings we love and took so many cues from aren’t spec homes in Chicago. They’re custom homes built for the global plutocrats who often have nary a care about the future economic viability of what they’re building, and it is executed by the best of skilled tradesmen and designers. These are projects where the smallest trim detail, pattern, or material has the luxury of time and money to be made perfect. So how do you build something like this on spec for the Chicago market?

Temu Modernism

Our answer was pretty simple. Find a big existing structure that’s totally destroyed. Pay chump change for it. Keep the shell. Get a good consulting architect. Shred design books. GC, design, market, and broker it yourselves. Use high-quality but simple and easy-to-find material executed elegantly. Temu Modernism, I like to call it.

Even with our temuified/simplified methods, we’re still not immune to the last 15% execution curse. Here’s what we’re slogging through:

Cool Door Cognitive Dissonance

A flush, frameless door. Getting the drywall around the jamb to be this clean is easier said than done.

Superior St doors after install

Superior St doors after the corrective drywall work.

One of my favorite features in the house is the frameless doors and our base molding-free living space. The simplicity of the way these make the rooms feel really adds to the serenity that all the natural light inherently brings to the house.

These things are an insane pain in the ass.

We’d never done either of these features before, and we realized we made some mistakes as soon as the carpenters started mounting the doors. Big gaping holes had to be cut in the passageways to shim in the doors level. We didn’t account for this extra space when we hung the drywall. The gaps are so large that what could initially have been an easy tape and bead job has, in some places, become cutting out awkward sizes of sheetrock, shoving them into these gaps, mudding them, and then running the drywall bead between the doorway and the door jamb. This adds another week of labor cost to our delivery timeline.

We also forgot to put the reveal piece on the bottom of the first floor sheetrock during the initial install. This means we now need the drywall crew to come back after the hardwood floors and all the finish carpentry and cabinets are installed to get this to look right.

How a baseboard-free wall with a bottom reveal should look

We did a lot of improvising for possible solutions to having another week of this very precise work pushing our already strained budget. The easiest thing this late in the game would just be to say fuck it and just put a baseboard in to cover up the uneven drywall cuts. But we really want the design of this project to be perfect. When we were working through the design and renderings, we decided on “Northern Italian Sex meets Dune II” as our aesthetic mantra, and clumsily throwing a baseboard over the walls in a project we put months of thought and prep into wouldn’t do. We ended up just having to suck it up and redo the bottom of all the walls on the first level.

Northern Italian Sex: Claudio Silvestrin Residence

La Grotta Rosa, Gae Aulenti

These latent problems were amplified by a trade bunch-up. Last week, the flooring crew, tile crew, drywall crew, and carpenters all overlapped on the site. We thought it could work. It ended up just being a mess. The finish carpentry order was wrong. People tripping over cords. The order of install operations got screwed up. All made worse by a disgustingly overused porta-potty in an Indian summer.

Draw Schedules

One of the reasons the developer built or improved home is so much more commonplace than the homeowner built is the complexities around financing the construction. Cash is king and those with enough of it to cover the entirety of the purchase and construction cost are often dominant in the small ground-up or flip space. Whether you’re buying a fixer via a FHA 203k loan or a developer like us using hard money debt, you’re at the whims of the bank’s draconian rules on when and how much of the construction funds they will release.

In theory, this is of course a safeguard against malfeasance. What bank is going to cut you a check for the entire construction budget as soon as you start a project? The reality is that the due diligence to get portions of the money released piecemeal derails your timeline and leaves you quibbling with someone at a call center who halves the amount of your draw request because the light bulbs aren’t in the fixtures yet.

The result is a constant cycle of having to pay out of pocket to satisfy the pace of your project and then reimburse yourself when the draw finally comes through. This makes the accounting difficult, and for those without cash on hand to frontload these costs, stuck between angry contractors and a protracted construction timeline, all the while still paying interest on the loan without adequate construction funds incoming.

The Good: A Slideshow

I was completely verklempt the day the windows went in. The front and rear glazing is the primary design element of the house, and I think they turned out perfectly.

Privacy glass effect with a passerby

These are the rear glass doors. Over 10ft tall and open out fully into the backyard.

Here’s how the tile and finish work is shaping up. Pretty thrilled with the result. We were really focused on having this gradient effect based on how the natural light interacted relative to each room.

Tile in the middle bathroom

Tile in top floor bathroom

Mudroom is this terrazzo. Abutts right up against the white oak in the rest of the living spaces

The top level from the landing. The wetbar cabinets are a stainless maple. Windows are cased in pine returns with no surrounds or trim. We extended the returns a bit out to make the window look like its at the bottom of a box. Cool effect.

The pattern got screwed up in the glass block wall initially and had to be rebuilt. Really happy with the way the master bath turned out.

Front living room and kitchen pre-cabinetry

Second floor landing. One of the problems we wanted to solve for with this big expanse was the lack of the light in the middle of the house on a standard Chicago lot.

We used extra bricks from the facade to build a matching parkway garden. That’s White Muhly grass in there.

The best news is that we found a buyer! The first group to see the house ended up writing an offer that we accepted a day later. We will be hosting a launch of the house prior to closing once the house is complete. Excited to share one last post on this year-long transformative project in a few weeks with the event details.

Maybe it’s the Real Estate broker. Pathologically overdressed with blinding veneers. Clogging up your instagram feed whoring for business. The two pages of badges and accolades in their email signature will definitely make you forget they were tending bar at Hubbard Inn this time last year.

If you’ve attended a community meeting lately or followed the saga of the Northwest Side Preservation Ordinance, you might think the answer is the developer. What could be worse? After all, over the last century, the role has shifted from first and second generation immigrants building entry-level and middle-class housing in their own communities to carpetbagging finance majors from non-targets who destroy our city’s historic building stock to displace anyone who isn’t a Late Stage Athleisure-clad corporate cog.

There’s some validity to the hate. I’ve written at length about how all we see going ground up in construction today are large-scale multi-family rental buildings or ultra-luxury small condo buildings or single-family homes. Worse yet, they’re all so ugly.

A New Ground Up Luxury Condo Build

The 2020s Multi-Family Rental Building. What do you call this style?

These days, if you aren’t a deep-pocketed potential home buyer, renter, or someone whose income isn’t low enough to qualify for an ARO unit in one of these new projects, you get the feeling that nothing being built is for you. I don’t just mean for you to live there, but for you, the resident of the city, to have a positive experience existing in the built environment of a neighborhood.

Differences in Douglas, Chicago before and after the Lake Meadows and Prairie Shores Development

I can’t afford a mansion on Astor st or handle the impracticalities of a loft in Printer’s Row or a glassy Mies condo. What I can do is experience these milestones of American design as a passerby as part of my daily life in Chicago which I consider a real inspiration and gift.

I think what is often forgotten by people outside of the RE world is that a developer was behind the vast majority of our favorite structures being erected. The architect’s plans are only as good as the capital, planning, and execution provided by the developer. Behind every building that broke the mold, set a new standard, or made a radical departure, someone decided to risk their own capital, time, energy, and reputation to see it through. It’s the exception, not the rule that a developer in Chicago understands or even cares about the impact their building’s existence has on the neighborhood or city, but to those who did, I think we owe some gratitude. Here are two examples from this week:

2400 Lakeview, Listing

Mies Van Der Rohe was Herbert Greenwald’s fourth choice for an architect for his first tower project. He tried Frank Lloyd Wright. Too expensive. Le Corbusier. Wouldn’t deign to design a building for American philistines. Walter Gropius. Couldn’t make the commute from Boston but asked “Why should you come to me, when ‘the master of us all’, Mies van der Rohe, is in Chicago?”

The pair’s first project, the sometimes forgotten Promontory Apartments was finished in the late 1940s. This was the first new residential tower in Chicago in years. It was a bold choice by the developer when FHA favored single-family homes at the edge of the city and suburbs were the product du jour.

Greenwald was not only personally enamored with Mies’ designs, but the units sold well, and it became Greenwald’s ambition to build Mies designs “coast to coast.” They went on to build seven more towers together in Chicago. Perhaps their most famous collaboration was 860-880 Lake Shore. The first of the Mies curtain wall buildings and arguably the most influential high-rise buildings of the last 80 years.

The above unit is in their last collaboration 2400 Lakeview. Greenwald died in a plane crash in 1959. 2400 Lakeview was the last Mies residential building built in Chicago.

This unit was part of two semi-combined neighboring apartments. This is the far cooler side. The decor is solidly in the camp of what I call the Charles and Susan Cohen Foundation: The type of apartment that would be lived in by octegenarian donors to WBEZ or The Newberry Library or the Center for Early American Whatever. This came to me when my wife took my last name, and when I looked at the Google results for Susan Cohen: 80% obituaries, 20% women in red glasses and big purple scarves.

It’s essentially a big 1bed with a den so $550k is a bit steep. Still nothing like a corner unit in a Mies/Greenwald building. Especially one facing southeast.

720 Dearborn, Listing

Without Duncan Henderson, there may never have been any residential lofts in Chicago. Henderson had come to Chicago via New York in the mid-1970s. He lived in a loft in SoHo right around the time that these famous disused industrial turned artist spaces started to become en vogue for the emerging yuppie set of the later 1970s/early 1980s. When he came to Chicago, Henderson, along with several now famous Chicago architects, was drawn to the empty hulking masses in Chicago’s former printing district: Printer’s Row.

Henderson, along with Harry Weese and a handful of ambitious builders and architects, turned the massive block long Donohue building on South Dearborn into the city’s first residential loft building in 1977.

While the project was underway and dragging, it was Henderson’s idea to get some cash flow from the building by leasing the unimproved space to artists and the like.

This first generation of residents moved in in 1978. They would carve out the amount of footage they wanted and finish the space themselves. Residents would add bathrooms, kitchens, showers, etc. A few years later the building went condo and many of the original tenants who built out their units became permanent residents.

Several more great industrial-loft conversions followed in the coming years. The Mergenthaler Building on Plymouth. The William Le Baron Jenney built Rowe Building on Dearborn. The last of the loft giants to be converted was this building 720 Dearborn otherwise known as the Franklin Building.

The market for lofts had changed a bit by the late 1980s. Buyers were looking for more finished spaces. 720 Dearborn was ready to accommodate. Less raw but still flexible, most floor plans were large open lofts but with a far more functional heating and cooling system and with kitchens and baths already installed. Residents could then decide how to carve up the space with temporary or permanent room dividers.

The above unit is the first penthouse I’ve seen in years in the building come to market. Because of the more rigorous second-generation conversion, the unit features stuff like private outdoor space and ductwork for hot and cold air paid for via monthly HOAs (which are quite low relative to the Donohue).

Even with the dated finishes, this is really an exceptional offering at $700k and despite Printer’s Row’s sleepy summer market, I think it will move fast.

A 23 minute yap sesh into what I think are the best houses on the market from 1870 to today and the historical context of each period that defined the way they were built and why.

Here are the listings for all the homes featured in the video:

1870s

1880s

1890s

1900s

1910s

1920s

1930s

1940s

1950s

1960s

1970s

1980s

1990s

2000s

2010s

2020s

BONUS

1100 n Lake Shore Drive Listing

You may not like it, but is this what peak performance looks like? Compared to the rest of Chicago’s condo market, maybe.

Perhaps the most overlooked type of residential units in Chicago are those in 1970s and 1980s high rise buildings. I understand it to a degree. The high energy costs of the era often meant lower ceilings and smaller windows. In a high-rise where the aerie effect is kind of the whole thing, this can really be a bummer.

The 1970s were a period in high rise construction between steam heat and two-pipe systems. This often meant heating and cooling in this era’s buildings were individually controlled via pass-through heat pumps, a cheap and inefficient way of temperature control and one step above lugging and installing your window-mounted AC unit up from your mildewed basement storage unit.

Of all the condos in the Near North Side, units in the 70s-80s buildings fare the worst at market. Long market times compound and often leave sale prices even below their post-2008 foreclosure or short sale prices. 1100 Lake Shore is no exception. The lowest sale prices in the last 15 years were recorded here in 2023 and 2024 . The lower priced of which had the same floor plan as the above-mentioned unit, sold for $325k, the price of a small 1bed unit without parking in Bucktown.

I think there is much to love here. The unit layouts at 1100 were thoughtfully designed by beloved Chicago architect Harry Weese in the late 1970s. The late 1970s and 80s were both a time of boomers making a more prosperous suburban sprawl than their post-war forebears while a new generation of yuppies firmly planted a flag in formerly run-down first-ring neighborhoods. While most city developers responded to this in kind with large towers appealing to transient DINK residents with small 1 and 2 bed units, Weese’s design called for family-friendly 3bed/2bath bi-level units and only 3 units per floor. Subsequent generations of builders followed the former trend. Large, two-level 3bed condos seldom exist in the Gold Coast outside of the very top of the luxury market.

Practicalities of this flexible layout aside, this unit has panache. That stairwell is straight out of the international school design playbook and I think deep-set unadorned window returns complement this simplicity beautifully. The problem with these late modernist units is that they don’t take kindly to design trends du jour, which most of the condos in this building have been subjected to. 2000s Tuscan Kitchens, 1990s mahoghany and dark granite, 2010s gray and white shaker nonsense don’t look right in spaces like this. Like all buildings, the footprint of the units suggests a certain way of life that I think subsequent design refreshes should be more cognizant of.

The problem, of course is the $600k price tag when the HOAs are $2100/month. The evergreen target of all downtown condo marketing, the former-city-resident-returned-pied-a-terre and empty nester buyer now have more options in the Near North Side than in any north side condo market. I can’t imagine a fixer in one of the area’s least coveted building types would be at the top of their lists.

Like the two most recent comps in the building suggest, a price point of between $400-500k hopefully could entice a buyer who sees the value in product, the neighborhood infrastructure and the comparable monthly carrying cost for a much more expensive(and more boring) walk-up of similar square footage in a further out neighborhood. For example, below is a duplex down condo in East Humboldt Park of the same footage listed at $880k:

Check out this 1980s re-fit by Stanley Tigerman at 1100 LSD:

5555 s Everett, Listing

5555 s Everett is one of about a dozen or so buildings in Chicago that feature these high 1920s, exorbitantly appointed double-height condos. The B tier at 5555 s Everett really leaned into the Golden Age of Hollywood Spanish Revival trend of the time. I have been in several of these apartments and they’re stunning. Requisite musty smell and all.

Even at its foreclosure price of $340k this unit may have difficulty trading. HOAs…..high. Parking……nay. When I posted this to my story the other day 24 of 27 dms I got about this building: “Yeah but those HOAs.” “Parking?” “HOAs..ouch” “Sick but we need parking” Bro chill. You think a 4bed/5bath condo on the lake that looks like this just costs $100k under the nationwide SFH median sale price and there’s no catch?

Let’s do a breakdown of what this would cost to carry this unit monthly with the current HOAs($2949/month):

Let’s assume 20% down on a 30y fixed note with an interest rate at today’s benchmark(6.5%):

-Principal and Interest: $1718/month

-Principal, Interest, Insurance, Taxes HOAs: $5299/month

Yes the HOAs are higher than the P/I. Substantially. Factoring in taxes, that’s $53,972 not going to your home equity to live here yearly. Is there a price point where aesthetics supersede this deep of a lack of practicality in Chicago? If so, what is it?

Lincoln Tavern on Wabansia St Closed in 2013. Storefront has been vacant since and Building is currently zoned R4

The B2 code is a relatively new zoning designation. It appears prominently in the 2004 Zoning Ordinance rewrite and was intended to combat the throngs of storefront vacancies on semi-major streets, a result of decades of population density loss and the growing consumer preference for big box retailers over mom and pop specialty stores.

The code permits living space in these first-floor former storefronts as of right, a potential game changer for owners struggling for years to find commercial tenants in the era of Amazon. Some call this the “artist designation,” as many old Chicago storefronts, with their high ceilings, lack of mid-room bearing walls, and huge windows, lend themselves nicely to live/work or creative uses.

17-3-0103-A “The purpose of the B2, Neighborhood Mixed-Use district is the same as the B1 district, but with the added objective of providing a greater range of development options for those streets where the market demand for retail and service uses is relatively low. By allowing ground-floor residential uses by-right, the B2 district is intended to help stimulate development along under-developed streets.”

B2 Designation as defined by Chicago 2004 Zoning Ordinance

The ordinance itself outlines “market demand” as a key driver for the flexibility of this code compared to other zoning designations. There is no doubt that the intent behind B2 at the time was to make parcels more attractive to builders and owners by making the first floor habitable and thus more easily rentable. This would be a net positive for the community by cutting back on now austere, once bustling commercial corridors and filling them in with housing. What I wonder is if there’s a world where having the flexibility of potential commercial use on the first floor of former mixed-use, now residential-zoned buildings off of major streets could be an enticement for owners and a net positive for the neighborhood?

New Chicago Stores Have a Size Problem

If there’s one trend I’ve written about to death, it’s the changing locational wants of Chicago’s home buyer over the last decade. Even before Covid, there was a growing stagnation of residential median sales price in and around downtown Chicago, while each year prices and demand grew for second and third ring neighborhoods with their low-rise, walk-up character and tree-lined streets.

I live in Bucktown, a perfect example of this, and one of the highest performing residential markets in Chicago in the last 10 years. Like many second-ring from downtown neighborhoods, most of the existing housing stock dates from around the turn of the century, decades before Chicago’s first zoning ordinance in 1923 forbade future uses of mid-block or residential corner businesses. While dozens have been converted or torn down, a handful of these old mixed-use buildings have remarkably retained active businesses through both the 1957 zoning fortification and the 1970s-90s urban flight era.

Today, what side street businesses still remain are seen as a blessing to the neighborhood, and I believe a major contributor to the immense demand to live here. Something about dining at Club Lucky or Antico, drinking at the Charleston, and shopping at Olivia’s Market lets people relive some of the ooh and ahhing they did on their European or even New York vacation. It’s not just the aesthetic TikTok fodder shoppy-shops that make an impact. Corner stores like Bucktown Market are vital. Who wants to have to drive or walk half a mile along the highway or a crazy 4-lane arterial street to a supermarket every time they need a household essential? Aren’t we ranked as having the worst traffic congestion in the country?

In neighborhoods like Bucktown, the problem isn’t the lack of commercial space, its that the active commercial storefronts themselves suck ass. Bucktown, like so many gentrifying areas in the early 2000s, saw waves of condo development. Developers liked building on major streets because the huge floor area ratios(FAR) zoning codes allotted on major streets allowed them to pack a parcel with a higher unit count and thus a higher net yield when the project sells out. The problem for the builders was what to do with the pesky requirement of first-floor retail space. Three lot developments (which are common here) would suddenly have 7500 square feet of retail space at the base of the building. To make the residential units above more marketable, builders commonly forbade certain uses of the commercial space, like restaurants, bars, cafes, pet stores, and stores that include liquor sales in the HOA bylaws. How many and what kind of businesses outside of this scope in a second-ring neighborhood can actually fill a 7500 SF space profitably? It is common for these types of storefronts to sit vacant for years between tenants.

Conversely, turn-of-the-century residential mixed-use buildings often feature storefronts as small as 800 SF. Turn-of-the-century businesses were smaller and more specialized than the big box retailers we’re comfortable with today.

Major street retail in Bucktown conservatively tends to rent around $35/SF/Y. If we applied this metric to an 800 SF residential corner storefront, we’d get a monthly rent pre-utility/tax/insurance of $2333/month. This is about $350 a month more than the median 800 SF 1-bed rent price in Bucktown from 1/1/2025-6/1/2025, according to MLS data.

This could be a boon to both the building owner and the commercial tenant. Let’s break down how:

For the Tenant:

• A cafe wants to open in an 800 SF residential storefront. Cafes are allowed in the ground floor of a building by right in the B2 zoning designation.

• Bucktown has a population density of about 21,000 per square mile. According to a report by the National Coffee Association in 2022, 66% of Americans aged 18 and over drink coffee daily. About 85% of Bucktown’s population is over 18.

• Assuming most customers live within a square mile of the business, that gives us 11,220 potential customers.

• Let’s assume the average cost of a coffee is $3.50, and that’s all one customer spends per visit.

• Even if 5% of those 11,220 potential customers in that square mile visited that cafe a day and only bought a $3.50 coffee, the gross revenue would be $1963 per day. Now I know nothing about running a small coffee shop or cafe, but that daily revenue margin against at $2400 base rent seems pretty damn good.

For The Building Owner

• The base rent price is higher than that of a mid-quality residential unit of the same footage.

• Commercial leases are usually drawn as triple net agreements in Chicago, meaning that the utilities, trash, share of taxes, and insurance would be paid on top of the base rent amount, bolstering the net return for the owner as commercial use. These leases are also generally much longer than residential leases. 10 years with baked-in annual increases in base rent is commonplace.

• Less maintenance and upkeep. Our company (which has about 14,000 residential rental units under management) has about a 40% annual rental turnover rate. Fair to assume that in a 10-year timeline, a residential unit will turn over several times at least. Residential leasing fees usually equate to one month’s rent, and deep cleaning, painting, and repairs can easily cost over $1000 each cycle.

• The B2 zoning the hypothetical building carries allows the unit owner to hedge: both living space and commercial space are allowed on the first floor. If retail demand is too slow, space can be rented out as living space.

• B2 also has a far higher floor area ratio by right than R3 or R4 lots, the most common zoning designation in inner-neighborhood Bucktown. In a time where the shortage of housing availbility is on seemingly everyone’s mind, This could mean the ability to make up for a residential unit lost to commercial use, stack a building with more units, build taller, or at the very least substantially add to a buildings value as land for a future, more robust development.

Sounds great, right? So why isn’t anyone talking about this?

Well, they kind of are. The focus of legislation on flexible storefront use still centers on converting to residential rather than the other way around. 43rd Ward Alderman Knudsen introduced a new ordinance this spring that allows qualifying buildings to convert their disused storefronts to apartments without going through the onerous zoning change process. Now, buildings carrying a B, R, and some D and C codes can apply for ground-level residential use with a much simpler request for administrative adjustment in a permit application.

Around the same time, the city launched the Commercial Corridor Storefront Activation Program. This is a program from the Department of Planning and Development that seeks to connect empty storefront owners with grant-fueled small business operators via nonprofit brokers.

In true Chicago form, these come as part of a long line of caveat-heavy amendments as opposed to a FAR retooling or repealing of existing hurdles to giving these buildings more flexibility from the get-go. In the Knudsen ordinance, storefronts can’t convert to residential unless at least 50% of ground floor spaces on the same side of the block are already being used as such. There’s also no flexibility in use after this administrative adjustment is enacted on the parcel. No live/work spaces and no future use as a storefront again.

Don’t get me wrong, I very much appreciate this ordinance and its spirit of cutting excess red tape to more quickly and efficiently optimize usage of these spaces, but wouldn’t it just be easier to more broadly roll out a Zoning code that allows for either use by right?

Everyone loves a corner store…right?

We have a saying at my company as a check against confirmation bias: “If he’s a good hitter, why doesn’t he hit good?” If these small residential businesses are so charming, so beloved, and a net positive to the neighborhood, then why aren’t they everywhere in the city?

Maybe the novelty of a business still existing on a residential corner in Chicago blinds us from the reality of living amongst them in the past. So many of these now-converted or boarded-up old storefront buildings were once taverns or liquor store/bar hybrids, sometimes referred to as “slashies.” Over 8000 taverns existed in Chicago around the turn of the 20th century. Today, there are fewer than 1000. Drunken stumbling, boorish behavior, and loitering around residential neighborhoods were a particular bugaboo for both Richie J and Richie M Daley. Both of the Daleys’ terms in office were during critical periods of population and reputation loss. Perhaps because of this, they were always sensitive to Chicago’s appearance to outsiders and had little sympathy for the role the neighborhood tavern played. “A bad liquor establishment can tear the fabric of a neighborhood and send it into decline,” Richard M touted when reminding Chicago precincts they could “Vote Dry” on the 1998 ballot. He was largely successful in his efforts: between 1990 and 2005, 1000 of Chicago’s remaining 3300 taverns were lost. One of Richie’s swan songs in office was taking this a step further, where anyone who lives within 500 SF of one of these businesses can petition to hold a hearing before the liquor board. Neighbors can get a hearing for ostensibly any reason, and the burden of proof is on the operator to prove they aren’t a nuisance. If the board isn’t satisfied with the operator’s case, they can pull their license.

Bad actors or not, once these neighborhood side street taverns are closed, our zoning code assures no future business can use the space. Businesses aren’t able to evolve to accommodate the neighborhood's needs, and residents are forced to arterial streets for any commercial activity.

There is no doubt we need more housing units in Chicago, but as a city with some of the worst traffic congestion in the country, it’s time for a heavy rethink on how we look at retail. What happens to carless residents when it’s 5 or 100 degrees out and you need some eggs? You have to walk a mile round trip to a busy street or to one of the massive strip mall developments Chicago seemed all too happy to welcome? Is it tacit acceptance that to live in most of Chicago, you need to own a car for basic subsistence because of a law we enacted 100 years ago?

When we have a zoning tool like B2 that allows for flexible, market-informed use of ground floor space while providing a large enough FAR to allow a higher unit count on a parcel, it seems incredible this code is not rolled out more.

Whether it be in Bucktown or Little Village, side street businesses have existed for generations because they serve an important function in urban life. While we may not need as many residential businesses as we once did, there is still a role for them today, and it should be up to the building operator to decide how to use their neighborhood retail space.

The new facade is up. Not without some setbacks. The already jacked-up face brick got worse once we tore out the original framing and put the trusses in. The top 10 feet of the building collapsed during demo….Thankfully, the scaffolding was up and no one was hurt. It also gave us an opportunity to ever so slightly tweak the decorative banding. The new brick is an orangey-peach we think complements the sandblasted rear facade beautifully.

Facade before

Rear of building pre-demo. Because we got rid of the exterior stairway, we were forced to install a sprinkler system in the house to bring it up to fire code.

Morsch and the rear elevation post masonry work

Rendering, rear elevation

Cleaning up the yellow paint off the brick took some doing. We’re thrilled with the result. The blasting brought up all the hues you love to see in common brick. We wanted to go with these huge asymmetrical window openings in every room. The light is really something to behold when standing inside the house. While the front facade will feature bronze windows, the rear will be stainless. John Pawson is a big influence on the design of this project. I love the contrast of the stainless windows against the yellow/pink brick in his Cotwolds project.

John Pawson Cotswolds House, UK

This is the Pawson House in London. The gradient color scheme of this project was also a huge influence on our interior design. Like this rowhouse, Superior gets most of its light from the huge front and rear windows. Over the course of a day, we think the sunlight will interact beautifully with the natural wood tones and soft white walls.

Rendering detail, Superior House

Living Room 2, Superior House

The kitchen, rendering

The reeded glass wall is the main feature of the house. It’s how passersby will identify the home and the interior glow in the front living space will be the first thing that catches your eye when you walk in. That’s Foerster grass in the parkway you see at waist height to provide some texture and visual buffer between the window and street.

Living room front detail, rendering

Rendering detail, Superior House

Claudio Silvestrin, Monte Carlo Penthouse

I love Claudio Silvestrin’s use of natural stone and plaster. Subtle and so beautiful. We tried to ape his style (and pull it wayyy back, this is a spec house in Chicago after all) a bit for the master bath. We’re opting for a large format, hardy porcelain floor with a waterproof plaster shower enclosure.

Top Floor Bathroom 3 Tile

Bathroom 3 Tile

We wanted something interesting but still subtle for the other bathrooms. Each bathroom is a different riff on these speckled large-format floor tiles tapering off into the matte 4x4 floor-to-ceiling wall tile.

The Deck

1761-63 Sedgwick 1909

Yes, Old Town spent the better part of a century at the cultural vanguard of Chicago. Some say the scene started in the 50s with the beatnik-passing-the-hat-fueled Second City and Old Town School of Folk realm, but it really started in the 1920s with Edgar Miller and his band of merry craftsmen.

Carl St Studios, One of the most interesting places I’ve had the privilege to sell.

By the 1920s, Old Town had already become a worn-down, sooty Victorian neighborhood. Miller, with the help of his high-born posse, started buying up these old houses and doing a number on them. These imposing just-post-fire houses were chopped up into dozens of small studios under the mantra of the “handmade home” for artists, by artists. Victorian bays and turrets were turned into stunning two-story stained glass showpieces, mahogany staircases were adorned with salvage tile and cold chiseled steel railings, heavy wood wainscotting replaced with curving gestural plasterwork.

Carl Street (now Burton Place ) was the center of the action in Old Town of the 20s with Miller and his great patron Sol Kogen hosting legendary parties for Chicago’s cultural elite and the bored progeny of the city’s plutocrats who hung around alike.

Red Star Inn, “La Clark” streetscape before Sandburg Village was built

In the early 60s, the area to the east of Wells Street, then known as “La Clark” from all the first wave Puerto Rican immigrants who called the neighborhood home, was in classic Daley era fashion unceremoniously seized, torn down and replaced by Sandburg Village. The sterile, 1-bed heavy, 2600 unit megadevelopment hastened the gentrification cycle in Old Town, giving a new generation of yuppies a place to comfortably rent outside of the ramshackle clapboard apartment buildings with their craggy-faced landladies that dotted the area.

Wells St, 1960s

Topper’s Restaurant, Wells/North Ave

Pipers Alley 60s, Groovy Baby

Old Town exploded in the 60s. While businesses and white middle-class Chicagoans were absconding to the suburbs, small businesses in Old Town dug in. Seedy porn peddlers eventually gave way clothing stores, the original Crate and Barrel, music venues and high concept restaurants. The Wells Street row was packed so tight it was said to take an hour to drive from North Ave to Division on a Saturday night.

By the 70s, gone were the Schlitz-signed sawdust joints in the northern section of Old Town. More bland, yuppie catering towers popped up on Wells, Clark, and Lasalle streets. Eventually, these new residents turned their eyes to the aging cottages in the Triangle to the west.

The Old Town Triangle itself is remarkable. One of the only areas in the entire city not to succumb to the post-fire grid restructuring, the streets ramble through blocks of hopa crabapple trees and paved brick sidewalks. The housing stock is phenomenal. The Triangle residents were quick to react to the callousness of city-sponsored teardowns in the mid-century. Even in the 1940s, there were efforts to form neighborhood revitalization groups. The neighborhood was officially landmarked in 1977 and added to the National Register several years later.

310 Willow, a great ground-up house designed by Bruce Graham in the 70s

425 Eugenie, Larry Booth

What makes the Triangle’s landmark designation so special is the robustness of its neighborhood association. For better and worse, if you want to make a change to a property within the historic district, you better come heavy. Although almost uniformly 19th century, there have been some cool 70s intrusions into the stock’s historic fabric over the years. These outliers are a fixed reminder of the period just before bohemian Old Town began to falter. An era when at least those with some money were willing to take a risk on the designs of their homes. When the directive to the architect was more than “bigger” and “chateau but with a garage roof deck.”

The Library Loft, Video

This is where the library loft comes in. The shell is that of a classic Old Town mixed use building. 1885 built, Cast iron facade for the old commercial space and adorned with Chicago red face brick and a dentilated cornice. The interior aesthetic shares more in common with the neighborhood outliers that went ground-up in the 70s like this Bruce Graham house on Willow, or this Larry Booth house on Eugenie.

The space itself was last in commercial use as a cigar store. Like so many great multi-family buildings in lakefront neighborhoods, 1761-1763 Sedgwick went condo in the late 1970s. The first owners of the former commercial space, a couple of sociology professors from University of Chicago were the first to move in. Their idea was to live amongst the thousands of books they collected. Books that we negotiated in my 2021 sale of the space to remain with the unit.

1761 Sedgwick, Listing

The library is oriented toward the back of the unit. It’s a two-story, multi-thousand volume collection boasting titles like “Jungian Archetypes in Pre-Columbian Mesoamerican Folklore.” The second story is an iron catwalk bolted to the ceiling framing adorned with maple shelves.

The front space has huge scale. The ceilings are about 14 ft high, the windows about 12. The view is looking west onto a perfectly preserved section of Sedgwick st. Slate floors run throughout and there is a maple floored sleeping loft and bathroom separating the two sections of the unit. The private outdoor spaces looks out into the ivy-filled landlocked courtyard.

THE LOOK, THE VIBE, THE FEEL of 70s Old Town in my mind

What makes this unit so special and important to me is how representative it is of a bygone era. Stepping foot in the apartment is like looking into the lives of characters seemingly plucked from 70s Woody Allen movie. You can imagine its heyday with Morrocan textiles on the walls, plants sitting in ceramics sourced from some Yucatan jungle excursion, dinner parties where the importance of Freud’s psychoanalytic legacy was disputed.

Not only is the culture of this Old Town gone, but so are the idiosyncratic interiors. While the Old Town Triangle Association is dedicated to preserving the exteriors of the homes in the neighborhood, the interiors have become cannon fodder for the new school of Lincoln Park buyers who simply refuse to live in a space that in any way doesn’t reflect the rote conveniences of today.

My client, the current owner of the space, is so dedicated to preserving this space that every year he turns down offers to purchase the unit. Some of the terms of these offers would make your head spin. Bless him. The shift from spaces being homeowner improved vs developer built has left a massive chasm in the market for unique spaces, especially for small-scale units. What we have left is so important to keep for the next generation of creatives or those that cherish these spaces, even if the Old Town of today is slouching toward a Solidcore DIML in a matching set.

When I was a kid, I imagined Bucktown as something like the edgier sister to granola Evanston. A place with a more fullhearted embrace of Bohemia than its suburban cousin. One who shirked the domestic embrace of the North Shore and lived somewhere described as “up and coming.”

Of course, like Lincoln Park a generation before, haught urbanity in Bucktown came at the expense of the previous generations of largely Eastern European, Mexican and Puerto Rican occupants of more modest means who gradually moved out over the span of several decades, giving way to more cobalt-blue wine glass drinking, black turtleneck wearing, CHANT scored dinner party attending, art history majors who settled in Bucktown in the 1980s-1990s.

This is the CD. There was an inexplicable yuppie resurgence of interest in Gregorian Chant in the 1990s. Maybe stemming from a sample in the 1990 hit Sadeness by Enigma.

This is the dinner party where it’s playing.

Regardless of the deleterious effect on affordability and density this new creative class had on Bucktown, there’s one contribution that they undeniably made: amazing restorations to historic buildings. Renovations so great that they are only accessible to the wealthiest of Chicagoans today.

1825 Wabansia, Listing

This building is the perfect example of this early Bucktown adaptive reuse. Once a tavern, a retroactive noncompliant zoning code made the building obsolete after the business had closed. By 1990 (the earliest listing of the property I could find), the building had been converted into a large loft-like house with a small apartment. It sold in 1991 for $267k. It has been renovated and refreshed again over the course of three owners since 2005.

The home is immaculately designed. Finding the balance of privacy and natural light for these old storefront conversions is tricky. This home executes it beautifully. I walk by this house every day and almost always see someone admiring the half-fogged privacy glass on the first floor. Living space is ample with large rooms on both first and second levels, but bedroom count is scant, and the layout separates sleeping spaces by two levels.

$2.575m is an eye-watering amount for a single-family home anywhere in Chicago. Nearly 7x the median sale price for a SFH citywide and almost unheard of for a house with only 3 bedrooms. The “____ Capital Partners” private equity performance fleece crowd who have supplanted Bucktown’s aging creative class of late tend to favor the double lot monstrosities where home size and living/sleeping practicality are regarded over forward-thinking design. So who is the end user? I’d be more skeptical of the asking price if this super unconventional Wheeler Kearns live/work house in Wicker Park didn’t just trade for $2.4m.

1266 Winwood, Listing

I gotta be honest. I’m not a big Mid Century Modern House guy. I can appreciate that wave of early 1950s ranch designs with the simple forms and big glass walls but I’m really not a 60-70s Mid Century Modern guy. I usually think these houses are dowdy and remind me of the Brady Bunch. There are some exceptions. This house being one of them.

Designed by Arnold Schaffner in 1965, this house sits adjacent to the Middlefork Nature preserve in Western Lake Forest. This is about as close as you can get to rural native prairie land in the North Shore. 5000 SF internally with the centerpiece of the home being this double-height living space. Maybe to appeal to some midwestern Imelda Marcos type, the listing description mentions that the closet fits 180 pairs of shoes. I’m more concerned with the quality of the landscape design. It blends perfectly with the rambling public land next door. This is notable as this area is dotted with lots of trugreen Mcmansioncore.

The owner has an impeccable eye for furniture design and placement. This is worth noting as this is the fourth time this house has been listed since 2007 in much the same condition, and each time it sat on the market for over a year. This time even with a $700k bump, it’s being primed to sell the first weekend with showing times already restricted to just one afternoon. Gotta love this market.

2345 Michigan, Listing

This is my dream project. This may very well be the dream project. The loft building stock in Motor Row is second to none. Shocking considering how woefully undertulitized this section of Michigan ave still is.

The first thing that comes to mind for me would be that this could be the perfect project to replicate the first generation loft conversion model. Carve up 6 or so huge raw loft spaces, get the MEP in place, and then work with a preferred lender to get an interest-only 12 month construction portfolio loan so the owners could customize the spaces themselves and refinance into conventional mortages when they’re finished.

I first heard of this while researching loft conversions at 2035 w Charleston. The developer followed this model when the building was converted in the 90s and the result was a resounding success.

Of course, this is a pipe dream on so many levels:

1. This in an auction, so the likelihood this building actually trades for $950k is low. The last time this was listed was in 2022 for $3.5 million. The condo vision does not work at the latter price point.

2. The call of the multi family rental players. Motor Row is in a TIF district, and contender for historic tax credits. The zoning code this building holds also has a gigantic floor-area-ratio which could allow for a far higher unit count than my vision for a space like this. “Stacking the parcel” is a way to hedge on viability, especially when you’re building something novel for the area.
   

If you find this project as exciting as I do, reach out. The auction is in early June.

415 N East Water, Listing

People’s faces contort like they’re smelling the bathroom at a Greyhound terminal when I tell them I love Streeterville.

Maybe it is the desolation of post-remote work downtown. Or that local businesses that cater exclusively to tourists or to the quarter of the neighborhood population that is over 65. Or that the new prevailing notion amongst homebuyers is that the pinnacle of Chicago urban living belongs to the leafy second ring neighborhoods. All this could help explain how this place went from a list price of $13mil to $3mil in the span of 10 years.

This is a penthouse in its most pure The Game era Michael Douglas form. 9000+ square feet. A basketball court, a squash court, a 500-gallon saltwater fish tank. Maybe the first time I’ve seen a property where the stonework alone amounts to 1/3 of the asking price.

The location, the $150k tax bill and the $9k HOAs doesn’t make this feel like a bargain but consider this is selling for both a fraction of replacement cost and for only 25% of the current mortgage amount!

Even if you don’t buy this, pick up squash. I play every week. It is better exercise than tennis and way easier to get a court.

431 Saint James, Listing

As of March 2025, the median sale price of a single-family home in Lincoln Park is $1.787m, the average is $2.25m. It is a market that feels completely beat except for the most well-heeled of the well-heeled. There is one notable exception where a relative bargain can still be had: the NE corner in the Arlington/Roslyn historic district.

Houses on these so-charming-it-hurts blocks can still be found for around $1mil.

How?

-These are rowhouses. The only interior light comes from the front, back or the sooty mid-house light wells.

-The lots are usually narrower than the average city lot. 18’-20’ is common here leaving room sizes to feel squat, especially when they are adjacent to a stairwell.

-THERE IS NO PARKING. This simply won’t do for the average Lincoln Park seeking-to-plop-the-accouterments-of-Glencoe-into-the-heart-of-the city single-family buyer. Maybe a tacit acceptance of the shortcomings of our transit system, off-street parking is a near-tantamount parameter for home buyers in Chicago. Not just the ultra-wealthy ones either.

Still, if you don’t mind walking a few blocks to a parking garage on Lakeview or Clark, I think this is a great alternative and an exceptional bargain compared to the new class of pushing-two-mil condos in Lincoln Park.

2732 Belmont, Listing

Covered land play? Private nightclub or studio? Bite the zoning change bullet and build out the parcel with mixed-use retail?

Obviously, from a traditional multi-family investment standpoint this makes no sense. Economics on small-scale multi-family are fraught enough these days, so no cash flowing this one. It also makes no sense at this price without a guarantee that talks with the 35th ward brass are in place on changing the zoning.

I like this for a creative current user who is confident about land value. Eventually, Chicago will start taking our housing shortage problem seriously. There will be a day that upzoning from M-1 on a nearly completely residential/retail strip won’t require months of slogging through opaque guidelines.