Isleworth Homes with Fire Pit Exterior Features

Welcome to Isleworth, a premier subdivision nestled in the heart of Windermere, Florida, within the beautiful Orange County. Renowned for its luxurious lifestyle and stunning landscapes, Isleworth offers a unique blend of elegance and comfort, making it a coveted destination for families and individuals alike.

As you explore this enchanting community, you’ll find an array of exquisite homes that exemplify modern architectural design paired with timeless elegance. One of the standout features of many properties in Isleworth is the outdoor fire pit, perfect for cozy evenings under the stars. Imagine gathering with friends and family around the warm glow of a fire, sharing stories and laughter while enjoying the serene ambiance of your beautifully landscaped backyard.

Isleworth is not just about stunning homes; it’s also about a lifestyle. Residents enjoy access to world-class amenities, including golf courses, exclusive clubhouses, and picturesque walking trails. The community is designed to foster connections among neighbors, providing a friendly atmosphere where everyone feels at home.

Windermere itself is known for its charming small-town feel, top-rated schools, and proximity to the vibrant city of Orlando. Whether you’re seeking a peaceful retreat or an active lifestyle, Isleworth offers the perfect setting to create lasting memories.

If you're looking for a home that combines luxury with the warmth of community, Isleworth is the place to be. Come experience the magic of Florida living in this exceptional subdivision, where every sunset is a reminder of the beauty that surrounds you.

Newest Isleworth Homes with Fire Pit Exterior Features

$18,750,000

6 Beds ⋅ 9 Baths ⋅ Isleworth SubDv. ⋅ 34786 Zip Code

Virtually Staged. Pre-Construction. To be built. Poised on a remarkable .69-acre homesite along the shores of Lake Bessie, this exceptional new residence offers a rare opportunity to create a substantial private estate in one of Isleworth’s most coveted lakefront settings. Designed and to be built by Supreme International Construction, the residence will encompass approximately 15,337 square feet of living space across three levels, with six bedrooms, including two private primary suites, an elevator and a four-car garage accommodating up to eight vehicles with lifts. Created for both grand entertaining and effortless everyday living, the main level will feature a dramatic great hall, formal dining room, family room, expansive kitchen, private study and serene primary retreat. Soaring architectural spaces and multiple covered balconies create a natural connection to the lakefront setting. The lower level is envisioned as a private destination for leisure, with a beautifully appointed theater delivering an immersive viewing experience, complemented by a separate popcorn and snack room for added convenience and fun. A generous entertainment area, bar, summer kitchen, gym, yoga/Pilates studio, sauna and spa complete the level. The upper floor offers a second primary suite, additional bedroom suites, viewing lounge and PJ lounge. The outdoor living space is designed to maximize the breathtaking lakefront setting. Landlocked and private, Lake Bessie offers an intimate waterfront experience for boating, water sports and fishing, with no public access to the lake. This rare pre-construction opportunity offers the privilege of securing an extraordinary lakefront residence while personalizing select finishes as the residence takes shape. Within Isleworth’s 600-acre residential community, Isleworth Golf & Country Club, consistently recognized among the world’s finest private clubs, offers an exceptional lifestyle, with Membership offered separately and subject to application and approval.

5036 Latrobe Drive, 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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