Isleworth Homes with Pickleball Court(s) Amenities

Welcome to Isleworth, an exquisite subdivision nestled in the heart of Windermere, Florida, within the picturesque Orange County. This upscale community is renowned for its luxurious homes, lush landscapes, and a vibrant lifestyle that caters to both relaxation and recreation. Isleworth is not just a place to live; it’s a lifestyle choice that embodies elegance and sophistication.

One of the standout features of Isleworth is its commitment to providing residents with top-notch amenities, including the increasingly popular pickleball courts. This fast-paced sport combines elements of tennis, badminton, and ping-pong, making it a favorite among all ages. Whether you’re a seasoned player or new to the game, the pickleball courts in Isleworth offer an inviting atmosphere where neighbors become friends, and friendly matches foster a sense of community.

The homes in Isleworth are designed with luxury in mind, featuring spacious layouts, high-end finishes, and stunning outdoor spaces that are perfect for entertaining. Many properties boast private pools, expansive patios, and beautifully landscaped gardens, allowing residents to enjoy the Florida sunshine year-round.

Living in Isleworth means you’re just moments away from Windermere’s charming downtown, where you can explore boutique shops, delightful eateries, and scenic parks. With its serene environment and active lifestyle, Isleworth is the ideal place for families, retirees, and anyone looking to embrace the Florida lifestyle.

Discover your dream home in Isleworth, where luxury meets leisure, and every day feels like a vacation. Come and experience the vibrant community and exceptional amenities that make Isleworth a truly special place to call home.

Newest Isleworth Homes with Pickleball Court(s) 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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