By Cassady Quintana
Located in the heart of Windermere, Florida, Isleworth Golf and Country Club continues to stand as one of the most luxurious and sought-after communities in Central Florida. Known for its exclusivity and stunning estates, Isleworth has attracted a who's who of celebrities, including Tiger Woods, Shaquille O'Neal, Wesley Snipes, and many others.
The combination of upscale living and stunning natural surroundings makes Isleworth the pinnacle of elite Florida real estate.
Read more below or check out our YouTube video!
A Rich History Rooted in Citrus
Isleworth’s story began in Florida's citrus industry. Brothers Sydney and Joshua Chase, pioneers in the 1880s, founded Chase and Co. and discovered the land that would eventually become Isleworth. While others abandoned Florida due to severe frosts, the Chase brothers expanded their holdings, demonstrating the foresight that shaped the region’s future. In the early 1900s, Sydney Chase built a bungalow on Lake Louise, and the family maintained a strong presence in the area for decades.
Arnold Palmer 1986 - Credit: Isleworth
In 1984, the legendary golfer Arnold Palmer envisioned something greater for the opportunistic land. He partnered with The Concord Corporation to design an 18-hole golf course that would later become the foundation and focal point of Isleworth’s community. By 1993, the land was sold to Aviva Land Holdings, which developed the exclusive estate homes that define Isleworth today.
Unparalleled Luxury and Amenities
Isleworth’s 600 acres are framed by lush cypress and oak trees, surrounded by freshwater lakes, creating an idyllic environment. The community is known for its iconic sculptures and renowned art pieces, including works by Philip Jackson, Henry Moore, and Salvador Dali. Most famously, the Wall Street Charging Bull is a centerpiece on the golf course, symbolizing the strength and prestige of the neighborhood.
Credit: Isleworth
At the heart of Isleworth is the Mediterranean-style Clubhouse, spanning 89,000 square feet. This top-tier facility offers a fitness center, spa, multiple restaurants, and event spaces. The club itself is ranked #14 in the U.S. and is undergoing a $10 million renovation to maintain its status. Members can enjoy the adult-only Windermere Room, the family-friendly Champions restaurant, and the newly refurbished pool area known as Shades.
Isleworth Clubhouse
The Real Estate of Isleworth
Isleworth is home to 380 estates, separated into three distinct areas: Isleworth, Isleworth West, and Butler Side. With Joe Lewis' development expertise, the estate lots have quadrupled in size since Arnold Palmer's original vision. Current listings sit at an average price of ~$5 million, with the most expensive property on the market listed at over $13 million.
Though the golf course is currently undergoing renovations, members have access to sister properties in the meantime. For those interested in joining the exclusive club, there is a four-year waiting list and a $200,000 initiation fee. Even non-residents can enjoy Isleworth’s world-class amenities, including its lakeside boat docks and butler service, if you are willing to pay the price.
A Gateway to the Best of Orlando
Situated just 50 minutes from Florida's world-renowned beaches and minutes away from Orlando's acclaimed restaurants, shopping, and entertainment, Isleworth is a prime location for those seeking the ultimate exclusive and luxurious lifestyle.
No matter if you're drawn by the allure of its celebrity residents, its rich history, or its unparalleled amenities, Isleworth remains the epitome of luxury in Central Florida—a neighborhood that truly offers "only the best."
Do you live in Orlando or want to live here? We'd love to chat if you're interested in buying or selling your home!
The Orlando Real is sponsored by The Pozek Group. If you’re thinking of buying or selling a home in Orlando, reach out and we would love to help!
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