Isleworth Homes with Golf Course Amenities

Isleworth Homes with Golf Course Amenities

Welcome to Isleworth, an exquisite subdivision nestled in the heart of Windermere, Florida, within the picturesque Orange County. This prestigious community is renowned for its luxurious lifestyle, offering residents a harmonious blend of elegance and leisure, all set against the backdrop of stunning natural beauty.

Isleworth is not just a neighborhood; it’s a lifestyle. With its beautifully manicured landscapes and serene surroundings, this community is home to some of the most exquisite properties in Central Florida. Many of these homes boast breathtaking views of the golf course, providing a perfect setting for both relaxation and entertainment. The golf course amenities are a standout feature, catering to golf enthusiasts and socialites alike. Residents have exclusive access to a world-class golf course that challenges players of all skill levels, along with a clubhouse that serves as a vibrant hub for social gatherings and events.

The homes in Isleworth are designed with sophistication and comfort in mind, featuring spacious layouts, high-end finishes, and private outdoor spaces that invite you to soak in the Florida sunshine. Whether you’re hosting a summer barbecue or enjoying a quiet evening under the stars, your home in Isleworth will be your personal sanctuary.

Living in Isleworth means being part of a close-knit community that values luxury, leisure, and an active lifestyle. With its prime location near top-rated schools, shopping, and dining options, Isleworth is the perfect place to call home for those seeking an upscale living experience in Windermere. Come discover the charm and elegance of Isleworth, where every day feels like a vacation!

Newest Isleworth Homes with Golf Course Amenities

$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

$3,200,000
4 Beds 5 Baths Isleworth SubDv. 34786 Zip Code
Discover the effortless blend of luxury, privacy, and modern design in this lovely Gardens of Isleworth villa.  Featuring timeless elegance, this beautiful four-bedroom, four-bathroom custom villa, where every detail has been thoughtfully curated to create a refined sanctuary for everyday living and entertaining. Beyond the stately arched main entry door lies a secluded courtyard oasis—a private retreat centered around a sparkling pool, serene waterfall feature, and generous lounging areas. Whether basking in the sun or relaxing beneath the stars, this outdoor haven sets the tone for the extraordinary spaces within. Designed to embrace indoor-outdoor living, the oversized courtyard welcomes you with a seamless open-plan layout connecting the pool, summer kitchen, and a charming guest cabana. Perfect for hosting or escaping, the cabana offers a private retreat for guests or a peaceful haven for the homeowner. Inside the main residence, a sense of contemporary sophistication flows through the light-filled kitchen, elegant dining room—highlighted by a statement chandelier—and the spacious grand room. French doors throughout invite the outdoors in, offering lush views from nearly every space and extending the living area to multiple porches and verandas. The living room, centered around a calming fireplace, is the perfect spot to unwind after a long day, while the spa and cascading waterfall nearby add to the sensory appeal. Retreat to the expansive master suite, where a private porch overlooks vibrant greenery, offering a peaceful start and end to each day. Additional property highlights include a cozy morning room, a dedicated office with custom Burl wood built-ins, and a series of intimate outdoor and indoor spaces designed to inspire comfort and connection.

4819 Alexandra Garden Court, Windermere

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