Isleworth Homes with Pickleball Court(s) Amenities

Welcome to Isleworth, a stunning subdivision nestled in the heart of Windermere, Florida, within the picturesque Orange County. This exclusive community is not just a place to live; it’s a lifestyle choice that seamlessly blends luxury with leisure. Isleworth is renowned for its beautiful homes, meticulously landscaped grounds, and a vibrant community atmosphere that makes it a sought-after destination for families and individuals alike.

One of the standout features of Isleworth is its commitment to an active lifestyle, highlighted by the availability of homes with private pickleball courts. This exciting sport has taken the world by storm, combining elements of tennis, badminton, and ping-pong, making it perfect for players of all ages and skill levels. Imagine stepping out of your elegantly designed home and onto your very own pickleball court—perfect for friendly matches with neighbors or family gatherings.

Beyond the courts, Isleworth offers residents an array of amenities that enhance the living experience. The community boasts beautifully designed parks, walking trails, and recreational facilities, catering to those who appreciate both relaxation and activity. With its close proximity to the vibrant downtown Windermere, residents can enjoy fine dining, boutique shopping, and cultural experiences, all while being surrounded by the natural beauty that Florida has to offer.

Isleworth isn’t just a neighborhood; it’s a community that fosters connections, encourages an active lifestyle, and provides a serene escape from the hustle and bustle of city life. Discover your dream home in Isleworth, where luxury meets leisure in perfect harmony.

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

$6,000,000

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. Private showings are easily accommodated, including same-day requests. Some photos (4 rooms on the second floor) have been virtually staged.

9725 Chestnut Ridge Drive, Windermere

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