Isleworth Homes with Pool Amenities

Isleworth Homes with Pool Amenities

Welcome to Isleworth, an exquisite subdivision nestled in the heart of Windermere, Florida, within the picturesque Orange County. Renowned for its luxurious lifestyle and breathtaking surroundings, Isleworth offers an exclusive community that perfectly blends elegance with comfort.

As you enter this prestigious enclave, you'll be greeted by meticulously manicured landscapes and stunning architecture that reflects the sophistication of the area. Isleworth is not just a neighborhood; it’s a lifestyle choice, ideal for those who appreciate the finer things in life. The community boasts a variety of custom-built homes, each designed to cater to the unique tastes of its residents, ensuring that every family finds their perfect sanctuary.

One of the standout features of Isleworth is the abundance of homes equipped with pool amenities. Imagine stepping into your own private oasis, where a sparkling pool beckons on warm Florida days. These outdoor retreats are perfect for entertaining friends and family, enjoying a refreshing swim, or simply soaking up the sun in your serene backyard. Many homes also feature outdoor kitchens and spacious patios, enhancing the outdoor living experience.

In addition to the luxurious homes and pool amenities, Isleworth is conveniently located near top-rated schools, fine dining, and upscale shopping. With easy access to major highways, residents can enjoy the vibrant lifestyle of Orlando while returning to the tranquility of their beautiful community.

Discover the charm and elegance of Isleworth—where your dream home awaits in this idyllic Windermere paradise!

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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