Isleworth Homes with Pickleball Court(s) Amenities

Welcome to Isleworth, an exclusive and picturesque subdivision nestled in the heart of Windermere, Florida. Known for its stunning landscapes and luxurious living, Isleworth is a premier destination for those seeking a serene yet vibrant community. With its lush greenery, scenic lakes, and meticulously designed homes, this neighborhood offers an idyllic backdrop for a refined lifestyle.

One of the standout features of Isleworth is its commitment to providing residents with exceptional amenities, including the increasingly popular pickleball courts. As a sport that combines elements of tennis, badminton, and ping-pong, pickleball has taken the community by storm, fostering a spirit of camaraderie and active living among residents. Whether you’re a seasoned player or new to the game, the well-maintained courts provide the perfect setting for friendly matches and social gatherings.

The homes in Isleworth are not just residences; they are masterpieces of design and comfort. Many properties boast expansive layouts with luxurious finishes, private pools, and breathtaking views of the surrounding landscapes. Living here means enjoying the best of both worlds—tranquility and access to a vibrant community life.

In addition to pickleball, Isleworth offers a range of recreational opportunities, upscale dining, and boutique shopping just moments away. With its prime location in Orange County, residents can easily explore Orlando’s attractions while returning to the peaceful embrace of their neighborhood.

Discover the charm of Isleworth, where luxury meets leisure, and every day feels like a vacation. Embrace the lifestyle you deserve in this enchanting community!

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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