Isleworth Homes with Pool View

Welcome to Isleworth, an exquisite subdivision nestled in the heart of Windermere, Florida, within the beautiful Orange County. This prestigious community is renowned for its stunning landscapes, luxurious homes, and a lifestyle that truly embodies the essence of Florida living.

Isleworth offers an array of magnificent residences, each designed with elegance and sophistication in mind. Many of these homes boast breathtaking pool views, allowing residents to enjoy serene outdoor spaces right from their backyards. Imagine waking up to the gentle sounds of water cascading from your private pool, surrounded by lush greenery and vibrant florals. Whether you’re entertaining guests or enjoying a quiet evening under the stars, these picturesque settings provide the perfect backdrop for unforgettable moments.

The community itself is a haven for those seeking a blend of tranquility and luxury. With meticulously manicured grounds, private security, and a range of amenities, Isleworth ensures that every resident feels safe and at home. Enjoy leisurely walks along the tree-lined streets, or take advantage of the nearby recreational opportunities, including golf courses, lakes, and parks.

Living in Isleworth means embracing a lifestyle of comfort and elegance, with easy access to the vibrant culture and entertainment options that Windermere has to offer. From fine dining to boutique shopping, you’ll find everything you need just a stone's throw away.

Discover the enchanting allure of Isleworth and experience the ultimate in Florida living, where luxury meets leisure, and every day feels like a vacation. Come find your dream home with a pool view in this idyllic community today!

Newest Isleworth Homes with Pool View

$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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