If you’ve heard of Windermere, FL, chances are you’ve also heard that it’s home to the rich and famous! Many celebrities living in the Central Florida area have chosen the charming town of Windermere as their residence. The town offers a welcoming atmosphere, privacy, and luxurious living. In this article, we’re sharing which celebrities have called Windermere home—both past and present.
In fact, if you live in Windermere or nearby towns like Winter Garden, you might just spot a familiar face at the local Target or Publix!
Why Do Celebrities Find Windermere, FL So Appealing?
A Golfer’s Dream Location
With Florida’s beautiful year-round weather, it’s no surprise many professional athletes call this state home—especially golfers. Windermere is the ultimate dream for golf enthusiasts, offering world-class courses and a climate perfect for play any time of year.
Full Lake Life Experience
Many of Windermere’s celebrity residents enjoy waterfront living on the stunning Butler Chain of Lakes. This scenic chain includes 13 interconnected lakes connected by canals. Living on the water in a beautiful, private community within a quaint town is an alluring lifestyle that’s hard to resist.
Exceptional Privacy
Privacy is a huge draw for celebrities, and Windermere delivers. The large mansion-style homes are often gated and tucked away behind tall walls that offer complete seclusion. Communities like the prestigious Isleworth are world-renowned for their elite amenities and country club lifestyle. These secure neighborhoods provide a peaceful retreat where celebrities’ privacy is truly respected by locals.
Easy Access
Windermere is conveniently located:
- 20 minutes from Walt Disney World
- 15 minutes from Universal Studios
- 30 minutes from Downtown Orlando and Orlando International Airport
This ideal location offers quick access to entertainment, shopping, dining, and travel options.
No State Income Tax
Florida’s lack of state income tax is another reason why it’s such a desirable location for high-net-worth individuals.
Past & Current Celebrity Residents of Windermere
Celebrities Currently Living in Windermere:
Shaquille O’Neal
Shaq resides in Isleworth in the well-known home with the bright blue roof—easily visible from Chase Road. Although his home has been listed for sale, it’s uncertain where he’ll go next. If you’re in the market for a 31,000-square-foot mansion (with a 6,000-square-foot indoor basketball court) and have $19.5 million to spare, let us know—we’d be happy to schedule a tour!
Johnny Damon
The former MLB star grew up in nearby Dr. Phillips and currently lives in Windermere.
David Siegel
The Westgate Resorts founder and his wife Jackie have been longtime Windermere residents. They’ve been building their 85,000-square-foot “Versailles” mansion since 2004 in Lake Butler Sound. Jackie’s rumored walk-in closet alone is around 4,000 square feet!
Mark Tremonti
Creed and Alter Bridge’s lead guitarist, Mark Tremonti, also lives in Lake Butler Sound in a stunning 20,000-square-foot estate.
Vince Carter
NBA legend Vince Carter owns a Mediterranean-style home in Isleworth. Built on 10.5 acres, his 30,742-square-foot mansion includes nine bedrooms, 17 bathrooms, and an 82-foot pool!
Devon Hester
The NFL icon still owns his 9,400-square-foot Windermere home. With floor-to-ceiling windows, a custom man cave, and a chef’s kitchen with Wolf appliances, this home has it all.
Celebrities Who Used to Live in Windermere:
Shaquille O’Neil
Shaquille O’Neil lives in Isleworth. He lives in the one with the bright blue roof that can easily be spotted while traveling down Chase Road. Though his house is on the market, it is unclear where his next big move will be. If you want to upgrade your current digs to a gorgeous 31,000 square feet home, including a 6,000 square foot indoor basketball court, and have a measly $19.5 million to spend, this house is for you! Let us know, and we will be happy to arrange a tour.
Johnny Damon
Baseball star Johnny Damon grew up in the neighboring town of Dr Phillips and resides in Windermere.
David Siegal
Westgate founder David Siegal and his wife Jackie have been long-time residents of Windermere. They have been building the American version of the “Palace of Versailles” since 2004; clearly, it is a big undertaking. This home is located in the coveted Lake Butler Sound neighborhood on a 10-acre lot. Once fully completed, this home will be a staggering 85,000 square feet! Rumor has it that Jackie’s walk-in closet will be around 4,000 square feet!
Mark Tremonti
Neighbors to David and Jackie Siegal in Lake Butler Sound, Mark Tremonti also calls Windermere home. Known for being the lead guitarist in Creed and Alter Bridge, Mark’s home is a gorgeous 20,000-square-foot newly built home.
Vince Carter
NBA Star Vince Carter owns a home in Isleworth. In 2017, his house was the number one in Orange County and Central Florida. His Mediterranean-style home is simply breathtaking. Sitting on almost 10.5 acres, with nine bedrooms and 17 bathrooms, this 30,742-square-foot home boasts an 82-foot-long pool!
Devon Hester
The famous NFL Punt Returner and legend Devon Hester calls Windermere home. Though he listed his property for sale in 2018, it is still owned by the player. With floor-to-ceiling windows in the main living areas, a man cave sure to make every man envy, and fantastic outdoor views, this 9,400 square-foot home has room for the whole family. With spacious bedrooms and bathrooms and a fully loaded chef’s kitchen with Wolf Appliances, this house has everything you could possibly need!
Celebrities Who Used to Live in Windermere:
Arnold Palmer
Golf legend Arnold Palmer purchased the land that became Isleworth in 1984. He built his dream home overlooking the 17th hole and Lake Louise. Though he sold the land in 1993, his legacy lives on.
Tiger Woods
Tiger famously lived in Isleworth during his marriage to Elin Nordegren. He was often spotted around town and even had his own booth at a nearby Perkins. His property featured tennis and basketball courts, a natural putting green, and two pools—a 100-foot lap pool and a 60-foot diving pool.
Backstreet Boys & NSYNC
Both boy bands lived in Windermere during their early careers, alongside manager Lou Pearlman. Justin Timberlake sold his Windermere home in 2006, while Joey Fatone still lives in the area. He owns “Fat Ones,” a hot dog business, and occasionally makes surprise appearances around town—even on his food truck!
Professional Golfers
Other professional golfers who’ve lived in Windermere include:
- Mark O’Meara
- Stuart Appleby
- Robert Allenby
- Charles Howell III
- Lee Janzen
- Paula Creamer
Other Stars:
- Morgan Freeman (Actor, Director, Narrator)
- Ken Griffey Jr. (Baseball)
- Barry Larkin (Baseball Hall of Famer)
- Wesley Snipes (Actor)
- Grant Hill (NBA)
- Dwight Howard (NBA, formerly with the Orlando Magic)
- Hidayet “Hido” Türkoğlu (NBA)
- Bubba Watson (Golf) – He bought and remodeled Tiger’s former home, then later sold it.
- Derrick Mason (NFL) – Sold his Windermere home in 2016.
- Vince Carter: A former NBA player, he resides in Isleworth.
- Gloria Estefan: A Grammy-winning singer, she has a home in Windermere.
- Bill Gates and other notable individuals have homes in Windermere.
You Can Call Windermere Home, Too!
While Windermere may be known for celebrity residents, it also offers a wide range of homes—from townhouses to luxurious waterfront estates. Depending on your price point, you might even snag your own slice of lakefront living! It’s an ideal place to settle down, with excellent schools, low crime rates, and a strong sense of community.
Windermere hosts events year-round, like the Halloween Parade, Oktoberfest, and the beloved Golf Cart Christmas Parade—there’s always something bringing neighbors together.
Let the Erica Diaz Team Help You Find Your Dream Home
If Windermere sounds like the perfect place for you and your family, the Erica Diaz Team is ready to help. We know Windermere and its surrounding areas inside and out. Whether you’re buying your first home or upgrading to something new, we’ve got the experience and local knowledge to guide you every step of the way.
Thinking about joining the ranks of Windermere’s elite? Contact us today and let’s find your dream home in this beautiful, vibrant town.
If you’re inspired by Windermere’s charm and wondering what it takes to make this exclusive community your home, working with a knowledgeable Windermere real estate agent can make all the difference. From luxury estates on the Butler Chain of Lakes to private gated neighborhoods favored by celebrities, a trusted local expert will guide you through every step of the buying process.
