Isleworth Homes with Three+ Story Property Description

Welcome to Isleworth, a prestigious subdivision nestled in the heart of Windermere, Florida, within the picturesque Orange County. Known for its luxurious lifestyle and stunning landscapes, Isleworth is a haven for those seeking an upscale living experience in a vibrant community.

Isleworth boasts an array of exquisite homes, and among its most captivating offerings are the remarkable three-plus story properties. These architectural masterpieces provide an unparalleled living experience, combining elegance with modern amenities. With spacious floor plans that often exceed 5,000 square feet, these homes are designed to accommodate both intimate family gatherings and grand entertaining.

As you step into one of these magnificent residences, you are greeted by soaring ceilings and expansive windows that fill the space with natural light while offering breathtaking views of the lush surroundings. Gourmet kitchens equipped with top-of-the-line appliances, luxurious master suites with spa-like bathrooms, and multiple outdoor living spaces are just a few of the standout features that define these homes.

Living in Isleworth means enjoying a lifestyle enriched by world-class amenities. Residents have access to a private golf course, tennis courts, and a state-of-the-art fitness center, all within the gated community. The tranquil lakes and scenic walking trails create an idyllic backdrop for relaxation and leisure, while the vibrant local culture of Windermere offers shopping, dining, and entertainment just minutes away.

Discover the charm and sophistication of Isleworth, where your dream home awaits amidst the beauty of Florida’s finest living. Experience the perfect blend of luxury and comfort in this extraordinary community.

Newest Isleworth Homes with Three+ Story Property Description

$11,750,000

6 Beds ⋅ 10 Baths ⋅ Isleworth SubDv. ⋅ 34786 Zip Code

Virtually Staged. A true Lake Butler trophy estate. Set within the world-famous gates of Isleworth and commanding panoramic western sunset water views of Lake Butler from virtually every room, 9832 Laurel Valley Drive offers over 11,000 square feet of luxury lakefront living, situated upon 150 feet of expanded sandy beachfront, thoughtfully enlarged by the current owners, in one of Florida’s most well known communities. This statement home features six bedrooms, seven full bathrooms, and three half bathrooms, a newly installed bespoke theater room with custom seating, an infrared sauna and dedicated wellness and fitness area, two full bars, a private pub and game room, an elegant pool and spa, a fully equipped summer kitchen, and multiple levels of outdoor living and lounge space overlooking the lake. Complemented by countless additional spaces designed for both grand-scale entertaining and everyday enjoyment, every room exudes elegance and has been meticulously designed and expertly executed down to the finest detail. Beyond its unmatched location and architecture, the home has benefited from several million dollars’ worth of enhancements and upgrades, further elevating an already impressive estate into something truly magnificent. The result is a residence that blends timeless luxury with modern comfort while offering one of the most desirable waterfront settings in Central Florida. Not all lakefront homes are created equal, and Laurel Valley is a shining example of that. More than a home, 9832 Laurel Valley Drive is a statement. A trophy estate befitting a legacy. A rare opportunity to own one of Florida’s most compelling waterfront properties ever. The home may be negotiated to include select furniture, a brand-new pontoon boat, two new Sea-Doo jet skis, and a golf cart.

9832 Laurel Valley Drive, 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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