Sean Spencer & Barbara Vance
Global Real Estate Advisors
Orlando & Central Florida Real Estate

Isleworth in Windermere, Florida stands as the crowning jewel of Orlando’s luxury communities, home to world-renowned estates, championship golf, and a legendary way of life surrounded by natural beauty and timeless prestige. Here, every detail is orchestrated for those seeking extraordinary living, and the emotional heartbeat of Isleworth is felt in moments of connection, serenity, and accomplishment.

​

Rooted in Rich History, Rising to Distinction

Isleworth’s story began in the late 19th century as the “Isle of Worth,” land chosen by the Chase brothers for its fertile soil in a time when Florida’s citrus industry dominated the local economy. Their vision turned citrus groves into a landscape of bounty, and decades later, golf legend Arnold Palmer saw potential for something even greater. In 1984, Palmer purchased the acreage, meticulously crafted a championship golf course, and set the foundation for one of America’s most elite residential clubs. By the 1990s, Isleworth’s reputation for luxury and exclusivity drew prominent families, business titans, and world-class athletes from around the globe, cementing it as a symbol of status and accomplishment in Central Florida.

​

The Isleworth Lifestyle: Pure Elegance and Emotional Connection

Through its guarded gates, Isleworth welcomes residents into a private paradise of 600 landscaped acres along the Butler Chain of Lakes, offering breathtaking views, lush cypress trees, and tranquil water vistas from every angle. The emotional impact of arriving home here is immediate: a sense of calm, privacy, and aspiration unfolds as you traverse winding drives and manicured gardens. With just 338 estate residences, the community ensures genuine exclusivity, harmonious living, and an environment where families and friends can gather and grow together.

The architectural masterpieces of Isleworth range from Mediterranean-inspired estates to innovative contemporary designs, set on expansive lots that allow for personal retreats and fabulous entertaining spaces. Many homes boast private lake frontage, infinity pools, wine cellars, home theaters, and outdoor kitchens perfectly designed for Florida’s climate and grand parties under the stars.

​

Championship Golf and World-Class Club Amenities

Isleworth Golf & Country Club is widely recognized as one of the finest private clubs in the world, consistently ranked among the “Top 100 Platinum Clubs of the World”. The 18-hole championship course, originally designed by Palmer, features lush fairways that meander past glistening lakes and mature oaks. Golfing at Isleworth is more than a pastime—it’s a celebration of excellence, tradition, and friendship, often accompanied by celebrity tournaments and exclusive member events.

The 89,000-square-foot clubhouse is a Mediterranean-style icon, hosting fine dining, wine tastings, social events, and family celebrations at the highest level of hospitality. Members enjoy state-of-the-art fitness centers, spa treatments, tennis centers with Har-Tru courts and a padel court, youth programs, and infinity-edge resort pools with poolside bar and grill—all cared for by a staff of over 200 providing personalized service each day.

​

Endless Recreation and Connection to Nature

Isleworth’s seven miles of shoreline invite residents to enjoy fishing, boating, paddleboarding, and waterskiing on the interconnected lakes. Private docks ensure seamless access to the sparkling waters of the Butler Chain, a paradise for water-lovers, families, and adventure-seekers alike. Lush parks and walking trails add opportunities for quiet reflection and energizing exercise, all set within an environment that feels untouched and timeless.

​

Fame and Notoriety: The Legendary Residents of Isleworth

The allure of Isleworth has drawn a dazzling array of celebrity residents, from NBA icons like Shaquille O’Neal to Major League Baseball stars such as Ken Griffey Jr. Business moguls, entertainers, and celebrated athletes have chosen Isleworth for the privacy, luxury, and enduring value it provides. Grand estates, some exceeding 30,000 square feet, reveal the possibilities of life at the top, but it’s the emotional connection—with neighbors, the land, and the spirit of accomplishment that truly sets Isleworth apart.

​

Community, Security, and Unrivaled Convenience

Isleworth’s commitment to 24-hour guarded access delivers peace of mind for residents and guests alike, enhancing the sense of sanctuary found within its gates. The community is minutes from Restaurant Row, luxury shopping at The Mall at Millenia, Walt Disney World, Universal Studios, and Orlando's elite schools, blending retreat-like privacy with direct access to urban excitement and business opportunities.

​

The Isleworth Promise: Living Legendary

To live in Isleworth is to embrace a lifestyle where every day is a new opportunity for joy, connection, and achievement. Step out onto your terrace, breathe in lake air, and feel the pulse of excellence that has defined this community for generations. From championship golf outings to spirited gatherings at the clubhouse, from quiet sunrise paddles on the lake to memories made poolside with loved ones, Isleworth offers the finest canvas on which to paint the story of your life.

This is Isleworth Windermere Florida, where the world’s elite gather, not just to live, but to feel truly alive. Welcome home to Central Florida’s most exclusive community, the apex of luxury living, and the promise of legendary living every day.

​

BACK TO TOP