
The Exciting History of Clermont, Florida
March 15, 2021
Update on 29 Palms at City Center in Ocoee
March 21, 2021Discover Why Many Celebrities Call Windermere Home
If you’ve heard of Windermere, FL, chances are you’ve heard it’s home to the rich and famous! Many celebrities living in the Central Florida area, live in the town of Windermere, Florida. The town is very inviting and provides privacy along with luxury living. In this article we are sharing with you which celebrities once called Windermere their home and who currently still lives here today.
In fact, if you live in Windermere or a neighboring town like Winter Garden there’s a chance you’ve spotted one of these celebrities at the local Target or Publix.
Why do Celebrities Find Windermere, FL so Enticing?
A Golfers Dream Location
With beautiful weather all year round, who would’t want to live in Florida? Many professional athletes find themselves here for that reason alone. Golfers make up a very large number. With world class golf courses close by, and a fantastic climate all year long, Windermere is literally a golfer’s dream location to call home.
Lake Life to the Fullest
Most celebs living here in Windermere enjoy living on Butler Chain of Lakes for its natural beauty and serenity. The lake itself is a beautiful body of water consisting of 13 interconnects lakes through small canals. Living on the water in a beautiful, private community in a quaint town is very enticing.
Very Private
Windermere specifically is extremely enticing to celebrities. The large mansion homes here are gated and offer the upmost of privacy. Tall ivory walls encircling these coveted communities. Such as the prized Isle Worth which is world renowned for its country club accommodations. The walls which offers little to no glimpse of life behind the gates. As the town is home to many celebrities, locals really do seem to respect athlete’s and celebrity’s space.
Easy Access
Only 20 minutes to Walt Disney World, 15 minutes to Universal, 30 minutes to both downtown Orlando and roughly about the same time to the Orlando International Airport. The proximity to endless entertainment and easy travel options also plays a role of being an inviting place for many stars to call home.
No State Income Tax
Florida also does not have any state income tax which makes Florida a very desirable place to live for the rich and famous.
Past & Current Celebrity Residents of Windermere, Florida
Celebrities Currently Living 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 he currently has his house on the market, it is unclear where his next big move will be. If you are looking 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 would be happy to arrange a tour.
Johnny Damon
Baseball star Johnny Damon grew up in the neighboring town on Dr Phillips and currently 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, and clearly is a big under taking. This home is located in the very 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 newly built home of 20,000 square feet.
Vince Carter
NBA Star Vince Carter owns a home in Isleworth. In 2017, his house was the number one house in Orange County and Central Florida. His Mediterranean style home is simply breath taking. Sitting on almost 10.5 acres, with 9 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 has listed his property for sale in 2018, it is still currently owned by the player. With floor to ceiling windows in the main living areas, a man cave sure to make every man envy, amazing 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 Use to Call Windermere Home
Arnold Palmer
PGA Golf Legend Arnold Palmer actually purchased the land of what would become Isleworth with the dream of creating luxury real estate and a phenomenal golf course in 1984. Though he sold the 600-acre land in 1993, his dream really did become a reality. Living off Isleworth’s main drag, the famous golfer built his dream home for him and his wife to enjoy that overlooked the 17th hole of the golf course as well as Lake Louisa.
Tiger woods
World Renowned professional golfer and multi-award-winning Champion, Tiger Woods famously lived in Isleworth during his marriage to Elin Nordegren. After his marriage crumbled, he relocated to Jupiter Island. He was a staple around the town of Windermere and neighboring town of Dr Phillips, and even had his own booth at the nearby Perkins! His stunning home featured a putting green naturally, as well as a tennis court and basketball court. During his time in this home, he also enjoyed a 100-foot lap pool and a 60-foot diving pool.
Backstreet Boys & N’sync
Backstreet Boys and N’sync both famously called Windermere home in their early days along with their Manager Lou Perlman. Justin Timberlake sold his home here in 2006. Boy band member Joey Fatone still lives in the area. He can been spotted from time to time in Winter Garden. Joey grew up in Orlando, having attended Dr Phillips High and owns his own hot dog business called “Fat Ones.” They even have a food truck and if you are lucky, you may even get a surprise visit from Joey himself!
Professional Golfers
Professional golfers who have called Windermere home include Mark O’Meara, Stuart Appleby, Robert Allenby, Charles Howell III, Lee Janzen and Paula Creamer have all called Windermere home.
Other Stars
- Famous Actor, Director, and Narrator Morgan Freeman was once a resident
- Baseball star Ken Griffey Jr
- Baseball hall of famer Barry Larkin
- Actor Wesley Snipes
- Basketball stars Grant Hill and Dwight Howard, once an Orlando Magic player as well as former Magic player Hidayet “Hido” Turkoglu all lived in this famous zip code.
- Masters Tournament Champion Bubba Watson, who bought the residence from Tiger Woods completely remodeled the home. He has since sold his Windermere residence.
- Former NFL player and wide receiver Derrick Mason and his wife Marci sold their beautiful Windermere home in July of 2016.
You can Also Call Windermere Home!
While Windermere is home to many professional athletes and famous celebrities, there are many wonderful homes available throughout the town of Windermere at affordable prices. Depending on your price point, you may even be able to snag yourself a waterfront home! From town homes to mansions and everything in between, Windermere is a great place to settle in and call home. The area is beautiful and centrally located to Walt Disney World, Universal, movie theaters, restaurants, shopping, and all of your entertainment needs. Our team of real estate agents at the Erica Diaz Team, are ready and happy to assist you in the hunt for your very own dream home in Windermere, FL!
Windermere is a fantastic area for those looking for a great community. With great schools and high safety ratings and a plethora of fun to be had close by, it is no wonder why there are so many famous celebrities who have called Windermere home. There are great community events held throughout the year. Something fun to do is always around the corner. From the annual Halloween Parade for kids to the Oktoberfest and annual Windermere Golf Cart Christmas Parade, there is always something bringing neighbors together.

Erica Diaz Team – Discover Why Many Celebrities Call Windermere Home
If this sounds like a town for you and your family, let the Erica Diaz Team be of assistance to you, and contact us today! We have an amazing team that is knowledgeable of not just Windermere, but its surrounding areas and would be eager to help you in your search for the perfect home for you!
If you are ready to live among the rich and famous, the Erica Diaz Team can help! We are a team of experienced realtors who know the area well and can most definitely help you find your next home. If you have a current home you need to sell, we can also assist in that as well! Contact us today and let us find you your dream house in beautiful town of Windermere, Florida.