Isleworth Homes with Pickleball Court(s) Amenities

Welcome to Isleworth, a prestigious subdivision nestled in the heart of Windermere, Florida, within the scenic Orange County. This exclusive community is renowned for its luxurious homes and resort-style amenities, making it a sought-after destination for discerning buyers seeking both elegance and an active lifestyle.

Isleworth boasts an impressive array of custom-built residences, each designed with meticulous attention to detail. These stunning homes feature expansive layouts, high-end finishes, and breathtaking views of lush landscapes and serene waterways. With a variety of architectural styles, from Mediterranean-inspired villas to contemporary masterpieces, Isleworth offers something for everyone.

One of the standout amenities that sets this community apart is the availability of homes with dedicated pickleball courts. As the popularity of this engaging sport continues to rise, residents of Isleworth can enjoy the convenience of having their own private courts right at their doorstep. Whether you are a seasoned player or a beginner looking to learn, the pickleball courts offer a fantastic way to stay active, socialize with neighbors, and embrace the vibrant community spirit.

In addition to pickleball, Isleworth residents enjoy access to a wealth of amenities, including a state-of-the-art fitness center, swimming pools, and beautifully landscaped walking trails. With its prime location near the enchanting lakes of Windermere and proximity to top-rated schools, shopping, and dining, Isleworth truly provides the perfect blend of luxury living and a laid-back lifestyle.

Discover your dream home in Isleworth, where elegance meets recreation, and every day feels like a vacation. Experience the charm of this exceptional community today!

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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