Grey Oaks Country Club has something few private golf communities can offer: 54 holes of golf without ever leaving the community.

But the three golf courses are only part of the Grey Oaks story.

Located in the heart of Naples, Grey Oaks combines championship golf, an extensive collection of club and wellness amenities, luxury real estate and a location that puts residents just minutes from many of the things that make Naples such a desirable place to live.

For buyers looking for a private golf community where the club lifestyle extends well beyond the golf course, Grey Oaks deserves to be near the top of the list.

Three Golf Courses, Three Different Experiences

For the serious golfer, this is where Grey Oaks immediately separates itself.

Members have access to three 18-hole courses—the Pine, Palm and Estuary—providing 54 holes of private golf within one club. The Pine and Palm courses are located on the main Grey Oaks campus, while the Estuary Course anchors the more secluded Estuary section of the community.

That variety matters.

One potential drawback of living in a private golf community is playing the same 18 holes over and over again. At Grey Oaks, you have three different courses and three different golf experiences.

For someone who expects golf to be a major part of their Naples lifestyle, having 54 holes available within your own club is a significant advantage.

Another feature many golfers appreciate: Grey Oaks lets members own their own golf carts and use them on the courses and within the community.

A Location That’s Hard to Replicate

One of Grey Oaks' biggest advantages has nothing to do with golf.

It’s the location.

Grey Oaks sits in central Naples, giving residents convenient access to 5th Avenue and downtown, the sandy white beaches of the Gulf, high-end shopping, world-class dining, and cultural activities such as Artis or Gulfshore Playhouse. That makes it particularly appealing to buyers who want the private country club lifestyle without feeling removed from everything else Naples has to offer.

You can spend the morning on the golf course, the afternoon at the beach and the evening dining downtown.

For many of our buyers, that matters.

Some Southwest Florida golf communities are destinations unto themselves. Grey Oaks offers that resort-style environment while still keeping you close to the rest of Naples.

The Lifestyle Goes Well Beyond Golf

Calling Grey Oaks simply a “golf community” doesn’t really capture the lifestyle.

The club has invested heavily in wellness, fitness, racquet sports, aquatics, dining and social programming. Grey Oaks currently highlights tennis, pickleball, bocce, aquatics, wellness facilities and multiple dining and social experiences as core components of club life. The Sports Center alone includes eight pickleball courts, while the pool includes three 32-meter lap lanes.

That’s important because even passionate golfers aren’t going to spend every waking hour on the golf course.

Maybe pickleball is just as important as the golf courses. We’ve had many clients say if the club doesn’t have pickleball, we’re not interested in the community. Or maybe fitness is a big part of your daily routine. And much of the social life within a private club develops through dining, events, and activities away from golf.

Grey Oaks gives residents plenty of ways to use the club and meet other members.

Understanding Grey Oaks Membership Is Critical

This is where I would encourage prospective buyers to slow down.

Don’t find the house first and figure out the membership later.

Full Golf membership has a $375,000 non-refundable initiation fee, and there is a multi-year waitlist.

However, Grey Oaks also offers other membership options, so understanding exactly which category fits your lifestyle—and what privileges come with it—should be part of the buying process from the beginning.

When we’re working with a buyer interested in Grey Oaks, membership is one of the first conversations we want to have.

Do you need year-round golf?

How frequently do you expect to play?

Is limited play an option?

Are the sports, fitness, and social amenities equally important?

And, most importantly, when can you actually obtain the membership you want?

With a six-figure initiation fee involved, this isn’t something you want to discover after you’ve fallen in love with a house.

The Property That Comes With More Than a House

This is where Grey Oaks real estate gets particularly interesting.

Some properties may offer a buyer the opportunity to obtain an immediate Full Golf membership when the seller relinquishes their membership at closing, allowing the buyer to bypass the normal golf waitlist, subject to club requirements and approval. The buyer still pays the applicable initiation fee.

These opportunities can be extremely valuable to the right buyer.

If your goal is to move to Naples and begin enjoying full golf privileges immediately, waiting several years for membership may not fit your plans.

A home that provides a path to immediate golf access can therefore have an advantage that isn’t apparent when you’re simply comparing bedrooms, square footage, finishes and price.

And these properties aren’t always easy to find.

That’s why, when we’re helping a serious golfer evaluate Grey Oaks, we’re looking at both the real estate and the membership situation attached to that real estate.

You need to evaluate the house and the golf membership together.

Limited Inventory Tells Part of the Story

Grey Oaks contains approximately 909 residences, including properties within Grey Oaks and the Estuary.

As of today, only 11 homes are for sale out of 909 residences, which represents roughly 1.2% of the community.

When you look at the current homes available, you may rule them out because they need renovations or don’t have your desired view. So, it shows just how little of the community is available for purchase.

That’s where understanding the community at a neighborhood-by-neighborhood and membership-by-membership level becomes important.

Who Should Consider Grey Oaks?

Grey Oaks won’t be the right fit for every Naples golf buyer—and no community is.

But I would put it high on the list for buyers who prioritize:

• Golf variety and want 54 holes within one private club

• A central Naples location

• Extensive fitness, racquet, dining and social amenities

• A high-end private club environment

• A variety of luxury residential options

• The ability to own and use a personal golf cart

• The possibility of securing immediate Full Golf membership through the right property

The biggest question may not be whether Grey Oaks checks enough boxes.

For many buyers, it will.

The bigger questions are whether the lifestyle feels right for you, which membership option fits your needs, and whether the right property is available when you’re ready to buy.

Experience Grey Oaks Before You Buy

As I discussed in my last Inside the Fairway article, I believe buyers should choose the community and lifestyle before choosing the house.

Grey Oaks is a perfect example.

You can look at photographs of a beautiful home online. You can study floor plans and compare price per square foot.

But that won’t tell you what it’s like to drive through Grey Oaks in your golf cart, play three different courses, spend an afternoon at the Sports Center, have dinner at the club, or become part of the community.

And when Full Golf membership requires a substantial financial commitment, understanding the club before purchasing the property becomes even more important.

If you’re considering Grey Oaks, we can help you evaluate both sides of the decision—the community and membership first, and then the properties that best fit the lifestyle you’re looking for.

That’s how you find more than a house in Naples.

You find the community you want to call home.

If you’re thinking about making Southwest Florida home, contact us and let’s start by finding the golf community that fits your lifestyle.

From Naples to Sarasota, we’ll help you find the community and home that fits your lifestyle.

When buyers begin searching for a home in a Southwest Florida golf community, they often start the same way: bedrooms, bathrooms, square footage, price range, pool, view, and finishes.

Those things matter. But after years of helping buyers navigate golf communities, I’ve found that the house is only half the decision.

The community and lifestyle may ultimately matter even more.

That’s why I encourage our clients to approach their search differently. Instead of finding the perfect house and then deciding whether they like the community, we work to identify the golf communities and lifestyles that fit them first.

Then we find the right home.

There’s an important reason for that approach: you can change a house. You can’t change the community around it.

Start With the Lifestyle, Not the Listing

It’s easy to fall in love with a house.

Maybe it has the perfect kitchen, a beautiful lanai, an incredible primary suite or exactly the floor plan you’ve been looking for.

But what happens after you move in?

That’s where the community becomes so important.

You’re not going to spend every minute inside your home. You’re going to drive through the neighborhood, play the golf course, visit the clubhouse, eat at the restaurants, use the fitness center, meet your neighbors and participate in the social life of the club.

In a SWFL golf community, you’re buying much more than real estate. You’re buying into a lifestyle.

And we’ve seen the importance of that firsthand with our clients.

When our buyers take the time to select the community and lifestyle first, something interesting often happens: they stay.

Even when their housing needs change, they frequently don’t want to leave the community. Instead, they sell their original property and move into a larger home—or simply a different type of property—within the same community.

Why?

As one client said to me, “I found my people”! They found their routine. They found the golf, amenities, and social environment they enjoy.

They can change houses without giving up the lifestyle they’ve come to love.

What Does It Feel Like When You Arrive?

One of the most valuable things you can do when evaluating a golf community is surprisingly simple:

Pay attention to how you feel when you’re there.

Don’t just tour the available homes.

Look around.

How well maintained is the community?

What condition are the landscaping and common areas in?

How does the clubhouse present itself?

Does the community feel active?

How are you treated when you arrive?

How does the staff interact with members and guests?

Do people acknowledge one another?

Do the members seem friendly?

Those details can tell you things that aren’t going to appear in an MLS listing.

You can learn about initiation fees, HOA fees and amenities on paper. Understanding the personality of a community requires spending some time there.

Two clubs can have similar homes, similar golf courses and comparable amenities but feel completely different once you walk through the door.

The question isn’t necessarily which community is “better.”

It’s which one feels better to you.

How Important Is the Golf?

For some buyers, golf is the first consideration. For others, it’s one part of a much larger lifestyle.

You need to know which camp you’re in.

If you’re an avid golfer who expects to play four or five times a week, you’ll probably evaluate a community differently than someone who plays occasionally and is equally interested in tennis, pickleball, fitness, dining and social activities.

Consider more than whether the community has a golf course.

What kind of golf experience do you want?

Is the course challenging enough to keep you interested?

Is it enjoyable for both golfers in the household if they have different handicaps?

How easy is it to get tee times?

Are there active men’s and women’s golf groups?

What is the practice facility like?

What’s the culture surrounding golf?

And don’t overlook the membership structure.

Our area offers bundled golf communities, private clubs, equity and non-equity memberships, optional memberships and a variety of other arrangements. Initiation fees, annual dues, waitlists and membership availability can vary significantly.

For buyers considering an equity golf community, I believe the club evaluation should happen before we ever start looking at homes. We encourage our clients to meet with the membership director, tour the club and amenities, ask questions about the membership, and get a genuine sense of the culture and personality of the community. When an initiation fee can reach well into six figures, the last thing we want is for a client to fall in love with a house, make that substantial financial commitment, and then discover that the club isn’t the right fit for them. The home can be remodeled or even replaced down the road. The club and lifestyle you’re joining are much harder to change—which is why getting the community decision right from the beginning is so important.

The right house paired with the wrong golf situation isn’t the right purchase.

Don’t Underestimate the Amenities

This is one area where buyers’ priorities have changed considerably.

Golf may bring you to the community, but the amenities often determine how you spend the rest of your week.

Fitness centers, resort-style pools, tennis, bocce, walking paths, dining options, spa services and social programming can all factor into the decision.

And then there’s pickleball.

We hear versions of this more often than you might expect:

“If it doesn’t have pickleball, cross it off the list.”

For that buyer, it doesn’t matter how beautiful the house is. If pickleball is an important part of their Southwest Florida lifestyle and the community doesn’t offer it, there’s no reason to try to convince them otherwise.

That’s exactly the point of putting lifestyle first.

Your must-have might not be pickleball. It could be a particular golf experience, an active tennis program, multiple dining venues, a great fitness center or a busy social calendar.

Whatever it is, identify it before you start falling in love with houses.

The Social Side Matters More Than Many Buyers Expect

One of the harder things to evaluate from a distance is the social environment of a community.

Yet it can become one of the most important aspects of living there.

Do you want an active social calendar or more privacy?

Are you looking forward to meeting people through golf leagues, dinners, clubs and community events?

Would you prefer a smaller club where you quickly recognize familiar faces, or do you like the variety offered by a larger membership?

There’s no universally correct answer.

I’ve found that buyers are happiest when the community’s personality fits their own.

The home might initially attract you to a property. The friendships and experiences you build within the community are often what make it feel like home.

Location Still Matters—Even When You’re Inside the Gates

It’s easy to think of golf communities as self-contained destinations, but you’re still going to leave the gates.

Think about how you expect to live.

How important is proximity to downtown Naples?

Do you want easy access to beaches?

What about shopping, restaurants, healthcare, or the airport?

Will you spend most of your time within the community, or do you expect to be out exploring several days a week?

A fantastic community in the wrong location can create friction you didn’t anticipate.

Again, the right answer depends entirely on the lifestyle you’re trying to create.

Pay Attention to What You Can’t Change

This may be the most important concept in the entire search.

When buyers walk through a house, they sometimes get hung up on things they don’t like.

The flooring is dated.

The kitchen isn’t their style.

The paint colors are terrible.

The bathrooms need updating.

Those issues deserve consideration because renovations cost money. But they’re also things you can change.

You can replace the flooring.

You can remodel the kitchen.

You can renovate the bathrooms.

You can repaint every room in the house.

What can’t you change?

You can’t move the golf course.

You can’t change the personality of the club.

You can’t replace your neighbors.

You can’t redesign the community’s amenity package.

You can’t move the community closer to downtown.

And you certainly can’t change the view outside your back door.

That’s why I would rather see a buyer find a home that needs some updating in a community they absolutely love than buy a beautifully renovated home in a community that doesn’t fit their lifestyle.

The countertops can be replaced. And we have reputable contractors who can assist even from afar.

The lifestyle can’t.

Build Your Community Shortlist Before Your Home Shortlist

If you’re considering buying in a Naples golf community, try reversing the traditional home-search process.

Before making a list of houses, make a list of communities.

Think about your priorities and separate them into must-haves and nice-to-haves.

Consider:

• Golf and membership structure

• Membership availability and potential waitlists

• Tennis and pickleball

• Fitness and wellness facilities

• Clubhouse and dining options

• Own my own golf cart

• Social activities

• Community size and atmosphere

• Location within Naples

• Home styles and price ranges

• HOA and club expenses

• Views and neighborhood setting

Then visit the communities that appear to be the best matches.

Spend enough time in each one to get beyond the real estate.

Tour the clubhouse. Look at the golf facilities. Walk through the fitness center. Check out the racquet facilities. Have lunch if possible. Watch how members and staff interact.

You’re trying to picture your life there—not just your furniture in a particular house.

Once you’ve narrowed the field to the communities where you can genuinely see yourself living, then focus on finding the right property.

The Best House Isn’t Always the Best Purchase

The Southwest Florida golf community market offers an extraordinary range of choices, and that’s both an advantage and a challenge.

There isn’t one “best” golf community for everyone. What might be right for one buyer may be completely wrong for another.

There is, however, likely to be a community that’s a much better fit for your version of the Southwest Florida lifestyle.

That’s what we work to uncover with our buyers.

The goal isn’t simply to find the house with the prettiest kitchen, biggest lanai, or most impressive photographs.

It’s to find the place where you’ll look forward to playing golf, meeting friends for dinner, heading to pickleball, spending time at the club and coming home at the end of the day.

Because years after you’ve forgotten what initially attracted you to a particular listing, you’ll still be living with the community you chose.

Choose the lifestyle first. Choose the community second. Then find the home that allows you to enjoy both.

That’s often the difference between buying a beautiful house in Southwest Florida and finding a place you truly don’t want to leave.

Ready to Find the Right Southwest Florida Golf Community?

If you’re considering a home in a golf community, don’t start with a list of properties. Start with a conversation about the lifestyle you’re looking for.

We help buyers compare golf communities from Naples to Sarasota based on the things that will matter long after closing—the golf experience, membership options, amenities, location, social environment and, ultimately, how well the community fits the way you want to live.

Once we’ve identified the communities that are the best fit, we can focus on finding the right home within them.

If you’re thinking about making Southwest Florida home, contact us and let’s start by finding the golf community that fits your lifestyle.

That closes the loop on the entire article and positions you as a golf-community advisor first and real estate

For decades, buyers in Southwest Florida have used the term equity golf community to describe a private golf community where membership requires a substantial upfront payment.

But as initiation fees at many clubs have climbed to $150,000, $250,000 or more, it is worth asking a simple question:

How much equity are you actually receiving?

In many cases, the answer is very little.

You may receive a nominal ownership interest—sometimes as little as $1—along with voting rights and the privileges associated with membership. However, most or all of the six-figure initiation fee itself may be non-refundable.

That does not necessarily make the membership a poor value. It simply means buyers need to understand that the word equity may not mean what they assume it means.

Today, many of Southwest Florida’s so-called equity golf communities operate more like private clubs with a one-time, non-refundable admission fee. The fee gives you access to the club, its golf courses, amenities and social lifestyle, but it should not automatically be viewed as an investment or an amount you will recover when you leave.

What Equity Traditionally Meant

Traditionally, an equity membership represented a meaningful ownership interest in the club.

A member paid an upfront amount, owned a share of the organization, and could potentially recover some or all of that equity after resigning or transferring the membership.

The refund was not always immediate. Some clubs paid departing members only after a new member joined, and others used formulas based on the amount originally paid or the club’s prevailing membership price.

Still, there was a tangible financial interest associated with the word equity.

That structure became challenging for some clubs, especially when the housing market crashed in 2008 and 2009, and there was an increase in resignations and fewer new members were joining. Over the past 20 years, many clubs moved away from large refundable equity obligations and adopted non-refundable initiation fees instead.

As a result, many clubs that are still casually categorized as equity clubs no longer provide meaningful refundable equity to new members. Most now require an upfront initiation fee that is not returned when the member resigns.

If You Pay $200,000, What Do You Own?

Suppose you purchase a home in a private golf community and pay a $200,000 initiation fee at closing.

Do you own $200,000 worth of the club?

Usually not.

Depending on the club’s documents, you may receive a nominal membership certificate, a small stated equity amount, and the right to vote for the club’s board of directors. The remainder of your payment may simply be the cost of admission.

In practical terms, you are paying for:

• Access to the golf course

• A lower ratio of golf members per hole than many bundled communities

• Clubhouse, dining and social privileges

• Fitness, racquet and wellness amenities

• The ability to participate in leagues, tournaments and member events

• The lifestyle and relationships that come with private-club membership

Those benefits can be extremely valuable.

But they are not the same as receiving a $200,000 asset that can later be sold or redeemed.

That distinction matters because buyers frequently hear the term equity community and assume that a significant portion of their initiation payment will come back to them when they sell their home or resign from the club.

At many clubs, it will not.

There Are Still Exceptions

Although meaningful refundable equity has become less common, it has not disappeared completely.

Tiburón Golf Club

Tiburón is one notable example.

Medallion Memberships are available to residents of Tiburón, and the membership structure has historically included a significant refundable component. Under the current structure provided to prospective members, 80% of a resident’s Medallion Membership initiation payment may be refundable, subject to the club’s governing documents, resignation provisions and membership terms.

That is materially different from paying a similarly sized initiation fee that is entirely non-refundable.

We always recommend you verify the current fee schedule and refund terms directly from the club.

The Estates at Bay Colony

The Estates at Bay Colony is another community where membership continues to include meaningful equity.

Based on the current membership information available to buyers, 25% of the $350,000 initiation payment is refundable. That would represent $87,500 in potential refundable equity, subject to the club’s membership documents and applicable resignation procedures.

Bay Colony Golf Club describes itself as being limited to 300 Equity Members, reinforcing that meaningful equity remains part of its membership structure.

The important lesson is not that every buyer should choose a club with refundable equity.

It is that two clubs can charge comparable initiation fees while offering very different financial arrangements.

At one club, most of the payment may eventually be refundable.

At another, the entire payment may be a sunk cost from the day you join.

What About Legacy Members?

The membership structure can become even more complicated in established communities.

At some clubs, original or legacy members may retain rights that are no longer offered to new members. These members may be entitled to receive a portion of their original equity after resigning, selling their home or transferring their membership.

The buyer purchasing that home, however, may be required to pay a new, entirely non-refundable initiation fee.

Shadow Wood Country Club is an example of a club where certain homes may have transferable golf opportunities and where membership rights can vary depending on the property and the existing member’s status. The club is member-owned, but new applicants should not assume that member ownership automatically means their initiation fee is refundable.

This creates two separate transactions:

The departing member may receive money based on an older membership agreement.

The incoming buyer pays according to the club’s current membership program.

That is why a listing that advertises an “equity membership,” “transferable membership” or “golf membership available” needs to be examined carefully. Those phrases do not necessarily tell you what the new buyer must pay, whether there is a waitlist or how much—if anything—will be refundable in the future.

Member-Owned Does Not Always Mean Refundable

Another common source of confusion is the distinction between a member-owned club and a refundable equity membership.

They are not necessarily the same thing.

A club may be governed by its members, with members electing a board of directors and voting on major decisions. Yet new members may still pay an initiation fee that is almost entirely non-refundable.

In that situation, the member has governance rights, but the initiation payment does not function like a conventional investment.

Similarly, a club may call its membership an equity membership because the member receives a nominal ownership certificate. That does not mean the member will receive a meaningful portion of the initiation fee upon resignation.

When evaluating a club, buyers should separate three questions:

Who owns and governs the club?

What voting or ownership rights does the membership provide?

How much of the initiation payment, if any, is refundable?

The answers may be very different.

Traditional Stand-Alone Clubs May Be Different

Many traditional private country clubs that are not connected to a residential development still offer more conventional equity structures.

These clubs may allow members to purchase a membership share that can be transferred, redeemed or refunded according to the club’s bylaws.

However, even here, the details matter.

A refund could be based on:

• The member’s original payment

• A fixed percentage of the current initiation fee

• A fixed dollar amount

• The sale of a membership to an incoming member

• A waiting list or turnover formula

• The financial condition of the club

The word refundable also does not necessarily mean immediately refundable. A departing member could wait months or years before receiving a payment.

Every club structures its membership differently.

Is a Non-Refundable Initiation Fee Bad?

Not necessarily.

A non-refundable initiation fee can still provide access to an exceptional club, less competition for tee times, and a lifestyle the buyer values for many years.

In fact, many of Southwest Florida’s premier golf communities now use this structure. The initiation payment helps clubs control demand, fund facilities and capital improvements, and maintain the exclusivity and service levels their members expect.

The key is to view the payment correctly.

It is generally not money you are investing with the expectation of a financial return.

It is the price of gaining access to a particular lifestyle.

A buyer who spends $200,000 to join the right club and enjoys ten or fifteen years of golf, friendships, dining and recreation may consider that money very well spent.

A buyer who pays the same amount and discovers a year later that the course, culture, or membership experience is a poor fit will see it very differently.

The Most Expensive Mistake Is Choosing the Wrong Club

When buyers begin searching for a golf home, it is natural to focus first on the property.

How many bedrooms does it have?

Is the kitchen updated?

Does it have a golf course view?

Is there a pool?

Those questions matter, but the home is only one part of the decision.

You are also choosing a club—and in many communities, that decision may require writing a six-figure check at closing.

Before making that commitment, buyers should consider:

• How frequently they want to play

• How easy it is to obtain tee times

• Whether there is a golf membership waiting list

• Whether purchasing a particular home provides immediate membership

• The number of golf members per 18 holes

• The club’s culture and level of formality

• Men’s, women’s and couples golf programs

• Dining, fitness, tennis, pickleball and social amenities

• Annual dues and expected assessments

• Planned capital improvement projects

• The initiation fee and payment schedule

• How much of the initiation fee is refundable, if any

• The process and timing for receiving any future refund

• Whether the membership is tied to the home, the individual or both

These questions should be answered before a buyer becomes emotionally committed to a property.

How We Help Buyers Navigate the Process

One of the most important parts of our role is helping clients identify the golf community that best fits their lifestyle before they write an offer and commit to a substantial initiation payment.

We begin by understanding how they actually want to live.

How often do they play golf?

Do they prefer a competitive golf environment or a more casual atmosphere?

Are they looking for an active social calendar?

How important are fitness, dining, pickleball, tennis or spa amenities?

Do they want a newer home, a condominium, a villa or a larger estate property?

What is their budget for the home, initiation fee, annual dues and other community expenses?

From there, we identify the clubs with homes in the appropriate price range and work directly with their membership directors to confirm current availability, fees, waitlists, privileges and membership terms.

Membership programs change frequently. Initiation fees increase. Waitlists expand or contract. Refund policies evolve. A property that provided immediate golf access last year may not provide the same opportunity today.

That is why current information and direct communication with the club are so important.

Our goal is not simply to help someone purchase a beautiful home.

It is to help them choose the golf community where they will be happy for years to come.

The last call we want to receive is from someone a year after closing saying:

“We bought in the wrong community.”

⛳Matt’s Take

The term equity golf community has become more of a real estate category than a precise description of what a new member owns.

In many cases, it now means a private golf community that charges a separate initiation fee, rather than a bundled community where golf membership is attached to the property.

That shorthand may be convenient, but it can also be misleading.

Before writing a $100,000, $200,000 or $350,000 check, buyers deserve to know exactly what they are purchasing.

How much of the payment represents actual equity?

How much is refundable?

When would it be refunded?

What voting rights come with the membership?

Is the membership available immediately?

And most importantly, is this the club where they truly want to spend their time?

The amount you may receive back one day is worth understanding.

But choosing the club that fits your lifestyle today is even more important.

Final Thoughts

A six-figure initiation fee should never be treated as a footnote in a real estate transaction.

Whether the fee is refundable, partially refundable or entirely non-refundable, it is a significant part of the buyer’s overall investment in the golf-community lifestyle.

The word equity alone does not provide the answer.

The club’s current membership documents do.

Before committing to a home and membership, buyers should obtain the latest written fee schedule, bylaws, refund provisions, waitlist information and capital obligations directly from the club.

Because the right home in the wrong golf community is still the wrong home.

And when a substantial initiation fee is non-refundable, making the right choice from the beginning matters more than ever.

Thinking About Buying in a Southwest Florida Golf Community?

Choosing the right golf community isn’t just about finding the right home. It’s about finding the club, membership structure, and lifestyle that best fit the way you want to live.

Every community is different. Golf availability, membership requirements, initiation fees, annual dues, amenities, and club culture can vary significantly from one community to the next. Taking the time to understand those differences before you buy can help you avoid costly mistakes—and ensure you’re happy with your decision for years to come.

If you’re considering a move to Southwest Florida, we’d be happy to help you compare communities, arrange club tours, connect you with membership directors, and identify the neighborhoods that best match your lifestyle and goals.

After all, our goal isn’t simply to help you buy a home. It’s to help you find the golf community where you’ll love living. Visit NaplesGolfGuy.com.

Membership fees, refund provisions, waitlists, and eligibility requirements are subject to change. Buyers should confirm all terms directly with the club and review the applicable membership documents before purchasing a home or submitting a membership application.

There are more than 200 golf communities across Southwest Florida.

Each has its own personality, amenities, membership structure, and lifestyle.

So why does Esplanade Golf & Country Club consistently rank among the communities I recommend most often?

Because it offers something many buyers are searching for but struggle to find—a true resort lifestyle where championship golf is just one part of the experience.

For more than 20 years, I’ve helped buyers navigate Southwest Florida golf communities. Esplanade attracts a different type of buyer than many traditional country clubs.

People certainly move here for the golf.

They stay because of the lifestyle.

A Community Designed Around Lifestyle

The amenities at Esplanade are unparalleled. Being one of the newest golf communities, everything feels new and fresh.

Neighbors are walking and biking throughout the community. Friends are meeting for lunch at the Bahama Bar. Pickleball courts are busy. The resort pool is active. Members are heading to fitness classes or gathering for dinner after a round of golf.

It’s a community that feels alive.

That isn’t by accident.

Esplanade was designed to be much more than a golf community. It’s a place where residents can stay active, socialize, and enjoy Florida living every day—not just when they have a tee time.

Residents enjoy:

• Championship golf

• Resort-style pool and cabanas

• The popular Bahama Bar

• The Culinary Center featuring wine tastings, cooking classes, and chef events

• Tennis and pickleball

• A modern fitness center

• Spa services

• Walking and biking trails

• An active social calendar throughout the year

The Culinary Center: More Than Just Dining

One of my favorite features at Esplanade is the Culinary Center because it’s something you simply don’t see in most golf communities.

While many clubs offer excellent restaurants, Esplanade has created a destination where members can gather for chef demonstrations, interactive cooking classes, wine tastings, themed dinners, and special culinary events throughout the year.

It reinforces what makes this community unique—golf may bring people together, but it’s the shared experiences and active social lifestyle that make them want to stay.

Investing in the Future

One characteristic I always look for when evaluating a golf community is whether the club continues to reinvest in itself. Maintaining and enhancing resident benefits helps property values continue to appreciate over the long run.

Esplanade is doing exactly that.

Several exciting improvements are currently underway, including:

• A fully renovated and expanded poolside Bahama Bar

• An expanded outdoor bar at the Barrel House

• An enlarged golf practice facility

• A new air-conditioned indoor pickleball complex with four indoor courts

These aren’t simply cosmetic upgrades.

They demonstrate a commitment to continually improving the member experience while helping maintain the community's long-term desirability.

The Golf Experience

The 18-hole championship course provides an enjoyable challenge for players of all skill levels. The course is forgiving off the tees with wider fairways for those, like me, who appreciate a little more room to swing away!

Practice facilities, leagues, tournaments, couples events, and an active golf calendar create an environment that’s welcoming whether you’re an accomplished player or simply enjoy getting out with friends.

One feature that often surprises buyers is Esplanade’s approach to private golf carts.

Homeowners are permitted to drive their own golf carts on the course—a benefit that’s becoming increasingly popular and isn’t allowed by many other bundled clubs.

You do have the option to pay an annual trail fee or a cart fee each time you play.

What to Expect During Season

Esplanade can be a very good fit for golfers who plan to play about twice a week during the busy winter season, with the possibility of adding a third round through leagues, organized events, or occasional openings.

However, buyers hoping to play four, five, or six days a week should understand that a bundled golf community may not provide the level of tee-time access they expect during peak season.

Setting realistic expectations about how often you want to play is an important part of choosing the right golf community.

What Buyers Often Miss

If there’s one misconception I hear more than any other, it’s this:

“Every home in Esplanade includes golf.”

It doesn’t.

Although Esplanade is considered a bundled golf community, not every property conveys a Golf Membership.

There are two distinct membership types.

Golf Membership Homes

These homes include:

• Full golf privileges year-round

• Practice facilities

• Clubhouse access

• Dining

• Fitness

• Tennis

• Pickleball

• Social activities

Social Membership Homes

These properties include access to nearly all of Esplanade’s outstanding lifestyle amenities, including:

• Resort pool

• Dining

• Bahama Bar

• Culinary Center

• Fitness center

• Tennis

• Pickleball

• Social events

However, they do not include golf privileges from November through April.

Just as importantly, Golf Memberships are tied to specific deeded properties.

A Social Membership home cannot later be converted into a Golf Membership home.

Understanding that distinction before beginning your search is incredibly important.

I’ve worked with buyers who fell in love with a particular home, only to discover later that it wasn’t a Golf Membership property.

Knowing that upfront helps ensure you’re looking at homes that truly fit your lifestyle.

Who Is Esplanade Best For?

In my experience, Esplanade is an excellent choice for buyers who want:

• An active social environment

• Resort-style amenities

• Championship golf without the traditional equity club structure

• Beautiful newer homes

• A full calendar of activities

• Flexibility to enjoy much more than golf

• A convenient North Naples location

It’s especially appealing for people who want their community to feel active every day of the week.

⛳Matt’s Take

One thing I’ve learned after touring hundreds of golf communities with clients is this:

People rarely remember the fifth hole.

They remember how a community made them feel.

That’s why I enjoy showing Esplanade.

The golf course is excellent.

The amenities are impressive.

But what really stands out is the atmosphere.

It feels welcoming.

It feels energetic.

It feels like people genuinely enjoy living there.

Every time I tour the community, I see neighbors stopping to talk, members gathering after golf, and residents taking advantage of everything the club has to offer.

That’s something you can’t appreciate from photos or listing descriptions.

You have to experience it.

And that’s exactly why I encourage buyers to look beyond square footage, golf course rankings, or amenity lists.

The right golf community isn’t simply where you’ll play.

It’s where you’ll live.

Final Thoughts

Esplanade Golf & Country Club has become one of Naples’ most desirable bundled golf communities because it offers far more than championship golf.

It delivers a lifestyle built around recreation, wellness, dining, and connection.

If you’re considering Esplanade—or comparing it with other golf communities throughout Southwest Florida—I’d be happy to help you understand the differences, explain the membership options, and identify homes that best align with your lifestyle and goals.

Finding the right golf community isn’t just about buying a home.

It’s about choosing where you’ll make memories for years to come.

—

Inside the Fairway is a recurring series where I share insights on Southwest Florida golf communities, market trends, membership structures, and the lifestyle that makes each community unique. My goal is to provide buyers with the information they need to make confident, informed decisions—well beyond what you’ll find in a listing description.

Construction fences.

Architectural renderings.

New pickleball courts.

Expanded outdoor dining.

Resort-style pools.

Lifestyle centers.

Clubhouses being completely reimagined.

This isn’t a coincidence.

Across Naples, Bonita Springs, Estero and Fort Myers, private clubs are investing hundreds of millions of dollars—not simply to improve their golf courses, but to redefine the member experience.

The modern private club is no longer just a place to play golf.

It’s becoming the center of everyday life.

And for buyers considering a golf community home, that’s changing what makes one club more attractive than another.

A Fundamental Shift

For decades, clubs competed primarily on golf.

Which architect designed the course?

How difficult was it?

What condition was it in?

Today those questions still matter.

But they aren’t enough.

Members increasingly expect clubs to deliver an experience that extends well beyond 18 holes.

That means:

• Multiple dining venues

• Outdoor social spaces

• Resort-style pools

• Fitness and wellness

• Pickleball

• Casual gathering spaces

• Flexible work areas

• Family-friendly programming

• Year-round social calendars

Golf is still the foundation.

Lifestyle has become the differentiator.

Communities Leading the Transformation

This isn’t happening at one club.

It’s happening across the region.

One of the region’s most ambitious projects is Bonita Bay Club’s proposed $110 million clubhouse redevelopment. The new 80,000-square-foot clubhouse would replace the existing 57,000-square-foot facility and include expanded indoor and outdoor dining, a dramatically enlarged 55th Hole gathering space, a sushi bar, the Sunset Lounge, larger event venues, and covered parking. The vision is to create the social heart of the club rather than simply replacing an older building.

Mediterra

Mediterra’s investment demonstrates that wellness has become just as important as golf.

The club is constructing a new 30,000+ square foot Sports & Lifestyle Center while simultaneously renovating its Tom Fazio-designed South Course. The new center will include:

• Expanded fitness center

• Dedicated Pilates, yoga, spin and functional fitness studios

• New spa

• Infrared saunas

• Hot and cold plunge pools

• Café and smoothie bar

• New social gathering spaces

• Additional bocce and racquet sport amenities

Importantly, the existing Sports Club remains open during construction, allowing members to continue enjoying amenities while the new facility is built. The investment follows recent renovations to both the clubhouse and private Beach Club, illustrating Mediterra’s long-term commitment to continually enhancing the member experience.

Shadow Wood

Shadow Wood’s new $22.5 million Lifestyle Center continues the industry’s shift toward wellness-focused amenities.

Highlights include:

• Resort-style pool

• Lap lanes

• Indoor pickleball

• Poolside bar

• Grab-and-go café

• Expanded wellness facilities

Rather than simply upgrading existing amenities, the project expands the ways members can spend an entire day at the club.

TwinEagles

TwinEagles continues investing in its outdoor lifestyle experience through renovations to its poolside cabana and outdoor dining area.

While the championship golf remains a major draw, the club recognizes that members increasingly value spaces to relax, dine, and socialize after their round.

Cypress Woods

Cypress Woods recently added pickleball courts while simultaneously renovating the golf course.

It’s another example of clubs investing equally in recreation and golf.

Olde Cypress

Olde Cypress recently completed a clubhouse renovation that refreshed its dining, gathering, and social spaces, giving members a more contemporary experience off the course.

Sarasota National

The trend extends north into Sarasota County as well.

Members at Sarasota National recently approved a multi-million-dollar master renovation plan designed by Fry/Straka Global Golf Course Design. The project includes:

• Complete reconstruction of all greens to USGA specifications

• Regrassing all fairways, tees and rough

• Complete bunker renovation

• New irrigation system

• Expanded practice facility

• 47,000-square-foot putting complex

• 1.75-acre short game area

According to the club, the renovation is designed to improve playability for golfers of every skill level while enhancing sustainability and preserving the community’s Audubon International Certified Signature Sanctuary environment. Construction is scheduled to begin in 2026.

Fiddlesticks

Fiddlesticks recently approved a $36.7 million capital improvement plan centered on the member experience. The project includes expanded covered outdoor dining, new indoor and outdoor bar areas, refreshed clubhouse spaces, an enlarged Cabana kitchen with grab-and-go service, and gatehouse improvements. Notably, the club’s planning process was driven by extensive member surveys, reinforcing that today’s investments are responding directly to evolving member expectations.

Why This Matters for Buyers

One of the biggest misconceptions I hear from prospective buyers is:

“I’m really only buying for the golf.”

Golf is certainly the foundation of every great private club. But after helping clients purchase homes in golf communities from Naples to Sarasota, I’ve found that the golf course is only part of what shapes the ownership experience.

Today’s members spend just as much time enjoying fitness centers, pickleball courts, resort-style pools, outdoor dining, wellness programs, and social events as they do on the fairways. For many couples, those amenities are what make the club an everyday destination rather than simply a place to play golf.

That’s why the clubs making significant investments today aren’t just renovating buildings—they’re enhancing the overall lifestyle their members enjoy.

What Smart Buyers Should Evaluate

When touring a golf community, don’t focus solely on the course.

Consider the club’s long-term vision by asking questions such as:

• What major capital improvements have been completed recently?

• Are additional renovations or amenity upgrades planned?

• How do the dining, wellness, and racquet sports facilities compare with competing clubs?

• Is the club continuing to invest in the member experience?

• Does the club’s vision align with how you and your family expect to use it?

A beautifully maintained golf course is important. But a club that continues to reinvest in its facilities, amenities, and member experience is often better positioned to remain desirable for years to come.

⛳Matt’s Take

After spending years touring golf communities throughout Southwest Florida, one thing has become increasingly clear.

Private clubs are no longer competing solely on the quality of their golf courses.

They’re competing on lifestyle.

Today’s buyers want championship golf—but they also expect exceptional dining, wellness facilities, pickleball, resort-style pools, outdoor gathering spaces, and vibrant year-round social calendars.

Whether you’re looking in Naples, Bonita Springs, Estero, Fort Myers, Venice, or Sarasota, the clubs making these investments understand that luxury living extends far beyond the 18th green.

For buyers, that’s an important consideration. A club’s willingness to reinvest in its facilities is often a reflection of its long-term vision, financial strength, and commitment to delivering an exceptional member experience.

And I don’t expect this trend to slow down anytime soon.

Bottom Line

The most successful private clubs in Southwest Florida aren’t standing still. They’re investing in the future by creating destinations that blend championship golf with exceptional dining, wellness, fitness, racquet sports, and social experiences.

For today’s buyers, choosing the right golf community isn’t simply about finding the best golf course—it’s about finding the lifestyle you’ll enjoy every day. As clubs continue making significant investments in their amenities, buyers should look beyond today’s facilities and consider each club’s long-term vision and commitment to its members.

Thinking about buying in a Southwest Florida golf community?

Every club has its own personality, membership structure, amenities, and long-term vision. The communities making the biggest investments today may not be the best fit for every buyer—and that’s why choosing the right golf community requires more than comparing golf courses.

If you’re considering a move to a golf community from Naples to Sarasota, I’d be happy to help you compare clubs, understand membership options, and find the community that best fits your lifestyle.

Until next time,

Here’s to living the good life in paradise.

Matt Klinowski

Naples Golf Guy

NaplesGolfGuy.com

That disconnect creates both challenges and opportunities for buyers and sellers.

The Headlines Don’t Tell the Whole Story

If you’ve been following the national real estate news, you’ve probably seen headlines about rising inventory and a more balanced housing market. While that’s generally true across much of Southwest Florida, it doesn’t accurately reflect what’s happening in many of the region’s premier golf communities.

In reality, buyers searching for a golf lifestyle often face a much smaller pool of homes than the raw inventory numbers suggest.

In some communities, single-family home inventory remains extremely limited, particularly during the summer months when many homeowners wait until fall to list their properties. In others, inventory may appear plentiful, but a closer look tells a different story. Communities such as Esplanade Golf & Country Club, Bonita National Golf & Country Club, and Treviso Bay may have dozens of active listings, yet many of those homes convey only a social membership, meaning buyers do not receive golf privileges during the season.

The same principle applies to many of Naples’ premier equity clubs. Grey Oaks is a great example. With more than 900 residences, there are currently just 14 homes on the market, including only 12 single-family homes. At first glance, that may seem like reasonable inventory. However, only three of those homes include a transferable Golf Membership, allowing a buyer to enjoy immediate golf privileges. The remaining homes require buyers to join the club’s golf membership waitlist, making the number of homes with immediate golf access far smaller than the MLS would suggest.

This is why simply counting active listings doesn’t tell the whole story.

The Reality Inside Golf Communities

Buying in a golf community isn’t just about purchasing a home—it’s about securing the lifestyle you want to enjoy.

For some buyers, that means waking up and playing golf the day after closing. For others, it’s having access to tennis, pickleball, fitness, dining, and an active social calendar. Every golf community offers a different combination of amenities, membership structures, and ownership costs, so simply finding a home you love isn’t enough.

That’s why inventory numbers can be misleading. Two homes with similar prices may offer completely different lifestyles. One may include immediate golf privileges, while another comes with only a social membership or requires joining a golf waitlist. In equity clubs, one home may include a transferable golf membership, while the home next door does not.

The right home isn’t just the one with the best floor plan or lake view—it’s the one that aligns with how you want to live. That’s why we encourage buyers to evaluate each opportunity through the lens of lifestyle first, then real estate.

In Southwest Florida, you're not just buying a home—you're buying a membership, a community, and a lifestyle. Understanding the difference is what separates a good purchase from the right one.

Why It Matters

For buyers, understanding the true golf community market can save both time and frustration.

It’s easy to assume that if a community has 20 homes for sale, there are 20 opportunities to choose from. In reality, the number of homes that match your lifestyle may be much smaller. Some homes don’t include golf privileges, others require joining a waitlist, and in many communities there may be only a handful of single-family homes available.

That’s why looking beyond the MLS is so important. Understanding a community’s membership structure, golf availability, and ownership requirements can be just as important as evaluating the home itself.

Whether you’re looking for immediate golf, a bundled golf community, or an equity club with long-term membership opportunities, knowing the differences before you begin your search helps you make more informed decisions—and often prevents costly surprises after closing.

The best buying decisions happen when you evaluate both the home and the lifestyle that comes with it.

The goal isn't simply to buy a home—it's to buy the right golf lifestyle.

Biggest Misconception: More Listings Mean More Choices

One of the biggest misconceptions I’m hearing today is that because inventory has increased across Southwest Florida, buyers have more options in golf communities.

From my perspective, that’s simply not what I’m seeing.

Yes, inventory has grown in many traditional neighborhoods and coastal communities. But inside golf communities, the story is much more nuanced. In many of the communities where my clients are looking, the supply of single-family homes remains limited. Even when there are active listings, many don’t include the golf privileges buyers expect. Some convey only a social membership, while others are located in clubs where buyers will still need to join a golf membership waitlist.

As a result, a community that appears to have a dozen homes available may only have a handful that truly meet the needs of someone looking for immediate golf and the full country club lifestyle.

That’s why I spend as much time discussing membership structures, waitlists, and lifestyle goals as I do touring homes. Finding the right golf community isn’t just about identifying the best house—it’s about finding the home that gives you the lifestyle you want from day one.

The MLS tells you what's for sale. It doesn't tell you what's actually available to live the golf lifestyle you're looking for. That's where local knowledge makes all the difference.

⛳Matt’s Take: What I’m Seeing

Every month, I spend time touring golf communities, showing properties, talking with club membership directors, and helping buyers compare communities across Southwest Florida. Here are a few trends I’m seeing right now:

Buyers are becoming more selective.
The urgency of the past few years has given way to a more thoughtful buying process. Buyers are taking the time to compare communities, evaluate memberships, and determine which lifestyle truly fits their needs before making an offer.

Well-priced homes continue to sell quickly.
While the market has become more balanced overall, desirable homes that are priced appropriately still attract strong interest. Sellers who price realistically from the beginning continue to have the best results.

Updated homes command a premium.
Move-in ready homes with renovated kitchens, modern finishes, updated outdoor living spaces, and newer mechanical systems remain the most sought-after. Many buyers prefer enjoying the Florida lifestyle immediately rather than taking on a renovation project.

Immediate golf remains one of the strongest selling points.
Whether it’s a bundled golf community or an equity club with a transferable membership, buyers consistently place a premium on homes that allow them to start playing golf right away. As waitlists continue at many private clubs, immediate golf has become one of the most valuable features a property can offer.

No two golf communities are the same.
One of the biggest misconceptions I encounter is the belief that all golf communities have similar inventory and membership opportunities. They don’t. Some communities have very limited single-family home inventory. Others have available homes but lengthy golf waitlists. And in bundled communities, a large percentage of active listings may include only social memberships. Understanding these differences is often the key to finding the right opportunity.

The biggest lesson?
Don’t judge a golf community by the number of active listings. Look at what those listings actually offer. That’s where the real story—and the best opportunities—are found.

Final Thoughts

The Southwest Florida golf market is unlike any other real estate market. Looking at inventory alone doesn’t tell you whether you can play golf next season, whether a membership transfers with the home, or whether a community is truly the right fit for your lifestyle.

That’s why I believe buying in a golf community starts long before you tour your first home. It starts with understanding the clubs, the memberships, and the lifestyle each community offers.

My goal with Inside the Fairway is simple: to help you look beyond the headlines and make more informed decisions—whether you’re buying this year, next year, or simply exploring what’s possible.

Until next time,

Here’s to living the good life in paradise.

Matt Klinowski
Naples Golf Guy

NaplesGolfGuy.com

If you’ve been searching for homes in Southwest Florida, you’ve probably come across the term “bundled golf community.” It’s one of the most common questions buyers ask me, and it’s also one of the most misunderstood.

Many people assume “bundled” means golf is free. Others believe every home in the community automatically includes golf privileges. Neither is necessarily true.

So, let’s start with the basics.

What Does “Bundled Golf” Mean?

A bundled golf community is one where golf membership is included with the purchase of a home. Instead of purchasing a separate golf membership after you buy your property, your membership is tied—or “bundled”—with the home itself.

That’s one of the biggest reasons bundled golf communities are so popular. Once you own the home, you immediately become part of the club and have access to much more than just golf.

Most bundled communities also include amenities such as:

• Championship golf

• Practice facilities

• Clubhouse dining

• Resort-style pools

• Fitness centers

• Tennis and pickleball

• Bocce ball

• Social clubs and events

• Walking and biking paths

You’re not just buying a home—you’re investing in a lifestyle.

Bundled Doesn’t Mean Free

One of the biggest misconceptions is that golf doesn’t cost anything because it’s “included.”

While there isn’t a separate membership to purchase, homeowners pay association dues that help support the golf course, clubhouse, amenities, and community operations.

Every community is different, so before purchasing, I always encourage buyers to understand the complete cost of ownership, including:

• HOA and condo fees

• Club operating fees

• Capital contributions

• Food and beverage minimums (if applicable)

• Special assessments

• Transfer fees

• Cart fees

The goal isn’t simply to find a home within your budget—it’s to find a community whose lifestyle fits both your budget and the way you want to live.

Not Every Home Includes Golf Membership

This surprises buyers more than almost anything else.

Some communities have neighborhoods or property types where homes include social memberships only, while others include full golf privileges.

Treviso Bay and Esplanade are good examples. Certain residences include golf membership, while others do not. During season (October through April), social members may have little or no access to the course.

Never assume that because you’re buying inside a bundled golf community, golf automatically comes with the property.

Always verify exactly what transfers with the home before making an offer.

How Easy Is It to Get Tee Times?

This is one of the smartest questions a buyer can ask.

During Southwest Florida’s peak season—from January through April—tee times become more competitive in many communities.

In most bundled golf communities, there are 800 properties per 18 holes, with potentially two members per home vying for tee times. Therefore, to manage the high density and heavy demand, the club uses a reservation system to ensure fairness in the allocation of tee times.

Some clubs use online reservations, while others rely on weighted lottery systems such as The Chelsea System or priority windows. The experience can vary significantly from one community to another.

If golf is one of the primary reasons you’re moving here, understanding how tee times work is every bit as important as understanding the home itself.

A good rule of thumb is you will be able to play the course 2 times per week and likely a 3rd time if you play in club golf leagues.

As you can imagine, it varies by course, and factors such as bringing guests will impact your ability to play.

If you plan to play more than 3 times a week or have guests regularly, a bundled golf community will likely not be a good fit.

Every Community Has Its Own Personality

One of my favorite parts of helping clients is matching them with the right community—not simply the right house.

Some bundled golf communities feel quiet and relaxed.

Others are incredibly active, with full calendars that include happy hours, wine dinners, trivia nights, fitness classes, live entertainment, card groups, and dozens of social clubs.

Some buyers want to play golf four days a week.

Others may only play once or twice a month but want outstanding dining, pickleball, and an active social scene.

There isn’t a “best” bundled golf community.

There’s only the one that’s best for you.

Think Beyond the Golf Course

The quality of the golf course matters, but so do the things you’ll use every day.

When touring communities, I encourage buyers to look beyond the fairways and ask questions such as:

• What other amenities are available?

• Is the clubhouse updated?

• How active is the social calendar?

• Are the fitness facilities modern?

• What’s planned for future improvements?

• What are the pet restrictions?

• What are the rental restrictions?

These details have a significant impact on both your lifestyle and your home’s long-term value.

⛳ Matt's Take

After helping buyers navigate Southwest Florida golf communities for more than two decades, I’ve learned that choosing the right community is often more important than choosing the right home.

You can remodel a kitchen.

You can update flooring.

You can’t change the culture of a community or the lifestyle it offers.

That’s why I spend as much time helping clients compare golf communities as I do showing homes. The goal isn’t simply to find a property—it’s to find a place you’ll love calling home for years to come.

Thinking About Buying in a Bundled Golf Community?

Southwest Florida is home to dozens of outstanding bundled golf communities, and each offers a unique combination of golf, amenities, lifestyle, and value.

If you’re trying to decide which community best fits your lifestyle, I’d be happy to help you narrow the options and identify the clubs that match your priorities before you begin touring homes.

Explore Southwest Florida bundled golf communities…

You can also explore community guides, current listings, market reports, and golf community resources at NaplesGolfGuy.com.

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If you’re considering a home in one of Naples’ premier private golf communities, chances are TwinEagles Golf & Country Club has already caught your attention—and for good reason.

Having helped buyers and sellers in TwinEagles for many years, I’ve had the opportunity to watch the community evolve into one of the best values in luxury golf living in Southwest Florida. From its two championship golf courses and recently renovated clubhouse to its expansive preserves and exceptional amenities, TwinEagles offers a lifestyle that’s increasingly difficult to find at its price point.

But what truly sets TwinEagles apart isn’t just the golf or the beautiful homes—it’s the overall experience of living here.

If we were touring the community together today, here’s what I’d want you to know before making a buying decision.

Why Buyers Love TwinEagles

In addition to 2 excellent golf courses designed by Jack Nicklaus and Steve Smyers, the club offers exceptional practice facilities. Additionally, there’s a beautiful renovated clubhouse offering formal and casual dining options.

Beyond golf, there are 2 Har-Tru Tennis Courts, 4 Pickleball Courts, 4 Bocce Courts, a resort-style swimming pool with outdoor cabana bar, and a fitness center.

The upfront initiation fee of $150,000 is among the lowest for clubs with 2 golf courses in Naples.

Notably, while the membership is an equity membership, the initiation fee is non-refundable. This is consistent with other high-quality clubs in Southwest Florida.

Additionally, homeowners may own their own golf cart to use within the community. However, personal carts are not permitted on the golf course.

Finally, TwinEagles offers a sense of space. Unlike many Southwest Florida communities, thousands of acres have been preserved, creating long views, abundant wildlife, and a quieter, more natural setting.

What Makes TwinEagles Different

Not every home includes an immediate golf membership. A golf, sports, or social membership is deeded to the property. Each of these memberships has a different upfront initiation fee, annual dues, and different amenity use.

Navigating the various options can be a challenge! The information doesn’t always appear on real estate websites such as Zillow.

Additionally, there are other fees a buyer incurs when purchasing a home in Twin Eagles beyond the annual membership dues, including a one-time resale fee and an annual food-and-beverage minimum.

Current Market Snapshot

As of this week:

• Active single-family homes - 15

• Average asking price - $1,507,053

• Price ranges - $674,900 to $3,897,000

• Average Days on market - 123 days

• Inventory trend - 18 percent decrease month-over-month

⛳ Matt's Take

If I were buying in TwinEagles today, I'd focus on homes that combine updated interiors with immediate access to a golf membership. Renovations can always be made over time, but bypassing a membership waitlist can dramatically enhance your enjoyment of the community from day one. Immediate golf privileges are one of the features buyers consistently tell me they value most.

Featured Home

11945 Heatherwoods Ct. Naples, FL 34120

This week's featured property showcases many of the qualities buyers are looking for today: a fully renovated interior, panoramic lake views, an oversized lanai, and immediate golf membership.

Learn More About TwinEagles

Looking for current listings, market reports, community videos, or a complete guide to TwinEagles Golf & Country Club? Visit our Twin Eagles Community Page for additional resources and the latest homes for sale.

👉 Twin Eagles...

What’s Next?

If you’re considering TwinEagles—or any golf community from Naples to Sarasota—my goal is to help you understand not just the homes, but the lifestyle each community offers.

Every week in Inside the Fairway, I’ll share market insights, community updates, and practical advice to help you make informed decisions.

Thanks for reading, and I’ll see you next week.