Isleworth Homes with Pool Amenities

Welcome to Isleworth, one of Windermere’s most prestigious subdivisions, nestled in the heart of Orange County, Florida. This exclusive community is renowned for its luxurious lifestyle, stunning architecture, and breathtaking surroundings, making it a sought-after destination for discerning homebuyers.

Isleworth boasts a collection of exquisite homes, each designed with meticulous attention to detail and crafted to provide the ultimate in comfort and elegance. Many of these properties feature private pool amenities, allowing residents to bask in the Florida sun, unwind, and enjoy the serene ambiance of their own outdoor oasis. Imagine hosting summer barbecues or enjoying a quiet evening swim under the stars—these homes offer the perfect backdrop for both relaxation and entertainment.

The community itself is beautifully landscaped, with tree-lined streets and lush greenery that create a peaceful retreat from the hustle and bustle of everyday life. Residents of Isleworth enjoy access to a wealth of amenities, including a world-class golf course, fitness centers, and scenic walking trails, all contributing to a vibrant and active lifestyle.

Located just minutes from the charming shops and restaurants of downtown Windermere, as well as the sparkling shores of Lake Butler, Isleworth combines luxury living with convenience. Whether you’re looking to raise a family, retire in style, or find a vacation getaway, this subdivision offers a unique blend of tranquility and sophistication.

Discover your dream home in Isleworth, where every day feels like a vacation and the possibilities are endless. Experience the best of Florida living in a community that truly has it all!

Newest Isleworth Homes with Pool Amenities

$3,500,000

4 Beds ⋅ 6 Baths ⋅ Isleworth SubDv. ⋅ 34786 Zip Code

Welcome to the exclusive gates of Isleworth, golf front estate offers over 7,600 square feet of refined luxury living overlooking the fairway of the renowned Isleworth Golf & Country Club, one of the worlds most prestigious golf club communities, this championship course was designed by Arnold Palmer and set along the Butler Chain of Lakes. The neighborhood is defined by beautifully landscaped scenery, sweeping water views, and exceptional 24 hour guard gated privacy. This estate offers exceptional potential supporting four beds, six baths, a private office, inside gym, approached by a private driveway with ample guest parking and a 4 car garage. The two story residence opens with a regal marble foyer and fountain feature. Inside, vaulted ceilings, skylights, and wall to wall sliding glass doors fill the main living areas with natural light while framing views of the pool, sauna, golf views and rolling fairways beyond. A grand fireplace and wet bar create an inviting space for entertaining. The chef’s kitchen centers on a dramatic island and is highlighted by a striking copper range hood, warm cabinetry, and an open eat in layout designed for both everyday living and hosting. Above the garage, a private accessory dwelling unit provides flexible secondary living space or maids living. Each of the spacious bedrooms offers its own view and is finished with marble baths. A dedicated home gym adds further convenience. Exceptional amenities and sophisticated living in the world renowned community of Isleworth.

5524 Worsham Court, Windermere

$5,975,000

7 Beds ⋅ 7 Baths ⋅ Isleworth SubDv. ⋅ 34786 Zip Code

Newly renovated, this private Isleworth residence offers a rare balance of architectural authority, thoughtful design, and quiet indulgence. Spanning approximately 8,000 square feet, the home unfolds with intention. Rich walnut cabinetry and wood detailing create warmth and continuity throughout, while the fireplace and wine cellar anchor the living spaces with understated elegance. Every room feels deliberate, refined, and composed. The kitchen is a statement of both form and performance; finished with Taj Mahal quartzite countertops, a 60-inch Wolf gas cooktop, Dacor refrigerator and freezer, two warming drawers, a steam oven, and a discreet hidden pantry designed for seamless entertaining. Dual dishwashers and two laundry areas support effortless daily living behind the scenes. Designed for both privacy and flexibility, the home features six bedrooms, a dedicated office, a bonus room with a closet suitable as an additional bedroom, and an elevator for ease across levels. Bathrooms are equally considered, with five full and 2 half baths, all executed with a calm, modern sensibility. Outdoors, the residence enjoys full privacy and tranquil pond views, complemented by a gas-heated pool and jacuzzi, and summer kitchen; a serene backdrop for both quiet mornings and refined gatherings. Mechanically, the home has been comprehensively updated with four new A/C units (2025), two tankless water heaters, and recently replaced garage doors and motors, ensuring modern efficiency beneath the elegance. It is a residence restored with intention, where discretion, craftsmanship, and comfort converge. Some photos have been virtually staged. Private showings are easily accommodated, including same-day requests.

9725 Chestnut Ridge Drive, Windermere

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