Isleworth Homes with Pond Frontage

Welcome to Isleworth, a prestigious and scenic subdivision nestled in the heart of Windermere, Florida, within Orange County. This exclusive community is renowned for its luxurious homes, stunning landscapes, and unparalleled access to the beauty of Florida’s natural surroundings. Isleworth is not just a neighborhood; it’s a lifestyle, where every day feels like a vacation.

One of the standout features of Isleworth is its enchanting homes with pond frontage. Imagine waking up to the serene views of glistening waters right outside your window. These properties are designed to embrace the natural beauty of their surroundings, offering both tranquility and a perfect backdrop for entertaining. With spacious backyards that lead directly to the shimmering ponds, residents can enjoy peaceful mornings sipping coffee by the water, or lively afternoons hosting family gatherings against a picturesque setting.

The community itself is a haven for those who appreciate an active lifestyle, featuring beautifully landscaped walking trails, golf courses, and recreational facilities. Isleworth is also conveniently located near top-rated schools, upscale shopping, and gourmet dining, making it an ideal choice for families and professionals alike.

Whether you are seeking a serene retreat or a vibrant community, Isleworth offers the perfect blend of luxury and comfort. Discover the charm of pond-front living and make Isleworth your next home, where every moment is a chance to enjoy the beauty of Florida living. Come explore this enchanting community and find your dream home today!

Newest Isleworth Homes with Pond Frontage

$3,850,000

4 Beds ⋅ 6 Baths ⋅ Isleworth SubDv. ⋅ 34786 Zip Code

Welcome to an exceptional estate built in 2016 by Wyatt, nestled within the prestigious guarded gates of Isleworth. Ideally situated in the intimate Gardens of Isleworth, this beautifully appointed two-story residence offers approximately 6,600 square feet of refined living space, complemented by serene water views, lush landscaping, and a private walking trail. Elegant interiors showcase inlaid wood and travertine flooring, custom ceiling details, a beautiful fireplace, and expansive sliding glass pocket doors that effortlessly connect the interior living spaces to the spectacular outdoor retreat. The chef’s kitchen is designed for both everyday living and sophisticated entertaining, featuring Viking appliances, a striking copper hood, oversized center island, wet bar, butler’s pantry, breakfast nook, and hidden walk-in pantry. The luxurious primary suite offers a private lounge, dual-sided fireplace, cozy sitting area, dual walk-in closets, dressing area, and spa-inspired bath with dual vanities, soaking tub, and an impressive indoor-outdoor shower. Additional highlights include a private theater, balcony, bonus space, elevator, whole-house generator, and a smart-home system. Outdoor living is exceptional, featuring a sparkling pool and spa, fire pit, summer kitchen, outdoor shower, and expansive covered lanai with retractable screens, creating a comfortable year-round setting for relaxing and entertaining while overlooking the tranquil water. An extraordinary six-car garage setup includes four individual single-car garages, with two equipped with vehicle lifts. This exceptional residence seamlessly combines sophisticated design, modern technology, resort-style outdoor living, and privacy within one of Windermere’s most coveted guard-gated communities. Grounds maintenance is included through the HOA. Be sure to explore the virtual tour links for an immersive look at this remarkable Isleworth estate.

4906 Aviva Garden Court, Windermere

$5,975,000

7 Beds ⋅ 7 Baths ⋅ Isleworth SubDv. ⋅ 34786 Zip Code

Virtually Staged. 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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