Inside Windermere, Florida: Why Celebrities and Luxury Buyers Love This Exclusive Community

Windermere, Florida, is more than just a lakeside town in Central Florida—it’s a magnet for celebrities, professional athletes, and high-net-worth individuals seeking privacy, luxury, and a peaceful community near Orlando. This exclusive enclave, nestled among the Butler Chain of Lakes, is widely recognized as one of Florida’s most prestigious places to live. From multi-million-dollar lakefront estates to private golf communities, Windermere has become a sanctuary for those who value space, security, and access to world-class amenities.

As local real estate advisors at ALIGN Real Estate, we’ve helped many buyers find their dream homes in Windermere. Whether you’re looking to live like a celebrity or just want a quiet, upscale neighborhood to call home, here’s everything you need to know about this sought-after community.

Why Celebrities Love Living in Windermere, Florida

Windermere, Florida, is known as one of the most exclusive and desirable places to live in Central Florida. This luxury town near Orlando has become a favorite among celebrities, professional athletes, and high-net-worth individuals thanks to its gated communities, privacy, and scenic lakefront properties. With access to top-rated golf courses, excellent schools, and quick connections to major attractions, it offers both comfort and convenience in a high-end setting.

What Makes Windermere, Florida So Appealing:

• Gated neighborhoods like Isleworth and Lake Butler Sound
  
  

• Waterfront estates with private docks and lake views
  
  

• Close to Disney, downtown Orlando, and Orlando International Airport
  
  

• Tax advantages, including no state income tax in the state of Florida 

At ALIGN Real Estate, we work with buyers who are looking for more than just a home—they’re looking for the lifestyle Windermere provides. Whether you're relocating, investing, or upgrading your home, this community offers a rare mix of luxury, privacy, and long-term value.

Why Windermere Attracts Celebrities and High-Profile Residents

Celebrities and high-net-worth individuals are drawn to Windermere for many reasons, including its tranquil ambiance, lakefront living, and proximity to Orlando’s best attractions. One of the main attractions is the sense of privacy and exclusivity. Windermere is home to some of the region’s most elite gated communities, including Isleworth, Lake Butler Sound, and Keene’s Pointe, each offering luxury amenities and controlled access that ensures security and discretion.

From waterfront estates with private docks to luxury homes with resort-style pools and lush landscaping, the properties in Windermere are tailored to a high-end lifestyle. The homes are grand in design and offer custom features such as wine cellars, home theaters, expansive outdoor kitchens, and private fitness centers. Many properties sit along the Butler Chain of Lakes, offering panoramic views and boating access that’s rare in Central Florida.

Yet, despite its luxury reputation, Windermere also embraces a strong sense of community. The Windermere Farmers Market, held weekly in the heart of downtown, is a local favorite. With fresh produce, handmade goods, and small business vendors, it’s a relaxing way to spend the morning, meet neighbors, and enjoy the local charm that makes Windermere feel like home.

Favorable Tax Benefits for Florida Residents

Florida is one of the few states with no state income tax, which makes it financially appealing for celebrities and high-income earners. For many who relocate from high-tax states like California and New York, the savings are significant. Combined with homestead exemptions and other local tax incentives, Windermere becomes a smart financial decision, not just a lifestyle one.

Who Lives in Windermere?

Windermere has long been a magnet for celebrities, professional athletes, and affluent families seeking privacy, luxury, and an upscale community close to Orlando. The list of past and present residents is impressive, a testament to the exclusivity and appeal of the area.

Notable residents have included:

• Shaquille O’Neal – NBA Hall of Famer who owned a 31,000-square-foot mansion in Isleworth, complete with a full indoor basketball court.

• Tiger Woods – Formerly lived in Isleworth during the peak of his golf career.

• Millie Bobby Brown – The Stranger Things star spent part of her upbringing in the Windermere area before rising to international fame.

• Johnny Damon – Two-time World Series Champion and MLB All-Star.

• Vince Carter – NBA legend and slam dunk icon.

• Joey Fatone – Singer and entertainer, best known from NSYNC.

• Wesley Snipes – Hollywood actor and producer.

• Mark Tremonti – Grammy-winning musician and guitarist for Creed and Alter Bridge.

• Ken Griffey Jr. – MLB Hall of Famer and one of the greatest baseball players of all time.

• David and Jackie Siegel – Owners of Westgate Resorts and stars of The Queen of Versailles.

• Charles Woodson – NFL Hall of Famer, formerly resided in Isleworth.

• Hideo Nomo – Former MLB pitcher, also known to have lived in the area.

• Chris Johnson – NFL Pro Bowl running back with ties to Windermere’s gated communities.

Many of these high-profile individuals are drawn to Windermere for its private, gated neighborhoods, lakefront properties on the Butler Chain of Lakes, world-class golf, and proximity to Downtown Orlando, top-rated schools, and Orlando International Airport. Whether it's celebrities seeking a quiet lifestyle or athletes looking for an elite retreat, Windermere offers a rare blend of discretion, luxury, and prestige.

Inside a Celebrity Estate: Shaquille O’Neal’s Former Home in Isleworth

For a closer look at the luxury lifestyle Windermere is known for, take a video tour inside one of its most iconic homes — the former estate of NBA legend Shaquille O’Neal. This 31,000-square-foot property features a full-size indoor basketball court, expansive lakefront views, and custom design details throughout. It’s a stunning example of the level of privacy, space, and exclusivity that defines life in Windermere.

Beyond the Gated Communities – The Lifestyle of Windermere

Despite its star-studded population, Windermere still maintains a charming, small-town feel. The downtown area features boutique shops, local cafes, parks, and a weekly farmers market. Community events like wine walks, food truck nights, and art festivals foster a warm and connected environment for families and residents of all backgrounds.

With top-rated Orange County schools and close proximity to private institutions, Windermere is also highly desirable for families. The town is surrounded by championship golf courses, including Isleworth Golf & Country Club and The Golden Bear Club, which offer members-only experiences and elite athletic facilities.

Accessibility and Location Advantages

Windermere’s location is another major draw. It’s just 20 minutes from Downtown Orlando and 25 minutes from Orlando International Airport. Disney, Universal, and SeaWorld are all a short drive away, making it an ideal location for entertainment lovers and frequent travelers. You’ll also find premium shopping at The Mall at Millenia and Restaurant Row in Dr. Phillips, just minutes away.

Real Estate in Windermere: What You Can Expect

As of early 2025, the average home value in Windermere, FL is $704,761, reflecting a 1.2% increase year-over-year, according to Zillow. Homes in this market typically go pending in around 48 days, signaling steady demand and a competitive environment. While many properties fall in the $600,000–$1 million range, Windermere’s luxury market includes exclusive lakefront estates and custom-built homes that can exceed $10 million—especially in prestigious neighborhoods like Isleworth and Lake Butler Sound. Whether you're searching for a family-friendly home or a private retreat, Windermere offers a wide spectrum of real estate options with long-term value.

Some of the most exclusive neighborhoods include:

• Isleworth – Known for its celebrity residents and private golf course

• Lake Butler Sound – Gated with custom estates and lush landscaping

• Keene’s Pointe – Family-oriented community with golf access and amenities

• Reserve at Lake Butler Sound – Ultra-luxury homes with architectural distinction

Ready to explore Windermere for yourself? Let us guide you through the neighborhoods, homes, and hidden gems that make it so special.

FAQs About Living in Windermere, Florida

Why is Windermere, Florida so popular with celebrities?
Many celebrities choose Windermere for its privacy, exclusivity, and scenic beauty. Gated communities like Isleworth and Lake Butler Sound offer the seclusion high-profile individuals need, along with luxury homes, lakefront access, and proximity to top golf courses—all just minutes from Orlando.

Is Windermere a good place to buy a luxury home?
Yes. Windermere is one of Central Florida’s most prestigious markets. Whether you're a luxury buyer or an investor, Windermere offers strong long-term value, limited inventory, and high demand—especially for waterfront and golf course properties.

Can I live in the same neighborhood as celebrities in Windermere?
Absolutely. Communities in Windermere, like Isleworth and Keene’s Pointe, are home to a mix of professional athletes, entertainers, executives, and families. While privacy is valued, these neighborhoods are known for their upscale, welcoming environments.

What kind of real estate is available in Windermere?
Windermere offers a wide range of luxury homes—from custom estates with lake views and private docks to newer builds in gated communities. You’ll also find smart homes, golf-front properties, and homes with premium outdoor living features.

Is Windermere a good area for families or just for celebrities?
Windermere is great for families, too. Alongside its high-end appeal, Windermere is known for top-rated public and private schools, safe neighborhoods, and a strong sense of community. It’s not just a celebrity retreat—it’s a place people truly call home.

Is Windermere Right for You?

Windermere is ideal for those seeking a combination of sophistication, natural beauty, and a strong sense of community. Whether you’re a buyer relocating from out of state, an investor looking for a high-end opportunity, or a family ready to upgrade, Windermere offers something truly special.

Whether you’re relocating from out of state, investing in a luxury property, or simply searching for a community that matches your lifestyle, Windermere offers rare quality and value in Central Florida. At ALIGN Real Estate, we’re local experts who specialize in high-end homes and lifestyle-focused real estate guidance. Let us help you explore the possibilities in Windermere and find the perfect place to call home.