Isleworth Homes with Three+ Story Property Description

Welcome to Isleworth, a prestigious and picturesque subdivision nestled in the heart of Windermere, Florida. Known for its stunning natural beauty and luxurious living, Isleworth offers a unique blend of tranquility and sophistication, making it one of the most sought-after communities in Orange County.

As you meander through the tree-lined streets of Isleworth, you’ll discover a variety of exquisite homes that embody the essence of upscale living. Among these, the three-plus story properties stand out as architectural masterpieces, designed to maximize both elegance and functionality. These spacious homes often feature soaring ceilings, expansive open floor plans, and an abundance of natural light, creating an inviting atmosphere perfect for both relaxation and entertaining.

The three-plus story homes in Isleworth typically boast multiple bedrooms and bathrooms, providing ample space for families of all sizes. Many of these residences come equipped with luxurious amenities, including gourmet kitchens, home theaters, and private outdoor retreats complete with pools and outdoor kitchens. Imagine hosting gatherings in your expansive backyard while enjoying breathtaking views of the lush surroundings.

Living in Isleworth means being part of a vibrant community that values privacy, security, and an active lifestyle. Residents enjoy access to world-class golf courses, fine dining, and boutique shopping, all just moments away. With its prime location and exceptional properties, Isleworth is not just a place to live; it’s a lifestyle choice that promises comfort, elegance, and a true sense of belonging. Come experience the charm of Isleworth, where your dream home awaits!

Newest Isleworth Homes with Three+ Story Property Description

$12,750,000

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

$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

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