Isleworth Homes with Three+ Story Property Description

Isleworth Homes with Three+ Story Property Description

Welcome to Isleworth, an exclusive and picturesque subdivision nestled in the heart of Windermere, Florida. Known for its stunning landscapes and luxurious living, Isleworth is a haven for those seeking a refined lifestyle amidst the beauty of Orange County. This prestigious community is renowned for its elegant homes, world-class amenities, and a vibrant sense of community.

Isleworth boasts a collection of exquisite properties, including a selection of stunning three-plus story homes that redefine luxury living. These spacious residences often feature breathtaking architectural designs, offering panoramic views of lush greenery and serene waterways. With ample square footage, these homes are perfect for families and individuals who appreciate both comfort and style. Imagine waking up to the gentle sounds of nature, enjoying your morning coffee on a private balcony, or hosting unforgettable gatherings in expansive living areas that seamlessly blend indoor and outdoor spaces.

Residents of Isleworth enjoy a lifestyle that is second to none. The community features top-notch amenities, including a private golf course, a state-of-the-art fitness center, and a lavish clubhouse, ensuring there is always something to do. Additionally, the proximity to Windermere's charming downtown area provides easy access to boutique shopping, gourmet dining, and recreational activities.

Isleworth is not just a place to live; it’s a vibrant community that offers a unique blend of luxury and tranquility. Discover your dream home in Isleworth, where every day feels like a vacation in paradise. Experience the epitome of Florida living in this enchanting subdivision!

Newest Isleworth Homes with Three+ Story Property Description

9725 Chestnut Ridge 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

Start Your Search

How much is your home worth?

Get instant property value now!