Isleworth Homes with Pickleball Court(s) Amenities

Isleworth Homes with Pickleball Court(s) Amenities

Welcome to Isleworth, the crown jewel of Windermere, Florida, where luxury meets leisure in a stunning lakeside community. Nestled in the heart of Orange County, Isleworth is renowned for its exquisite homes, lush landscapes, and a vibrant community atmosphere. This gated enclave is not just a place to live; it’s a lifestyle that offers an array of amenities designed to cater to your every need.

One of the standout features of Isleworth is its commitment to active living, exemplified by its exceptional pickleball courts. These state-of-the-art facilities provide residents with the perfect opportunity to engage in friendly competition or simply enjoy a game with neighbors. Whether you’re a seasoned player or new to the sport, the welcoming community spirit makes it easy to connect with others who share your passion for pickleball.

Isleworth’s homes are a blend of elegance and comfort, featuring spacious layouts, modern finishes, and breathtaking views of the surrounding natural beauty. Many properties boast private outdoor spaces, perfect for entertaining or unwinding after a busy day. The community’s meticulously maintained grounds, coupled with the serene ambiance of the nearby lakes, create an idyllic setting for families and individuals alike.

Living in Isleworth means more than just having a beautiful home; it’s about embracing a lifestyle filled with recreation, relaxation, and camaraderie. With its prime location in Windermere, you’ll find yourself just moments away from upscale shopping, dining, and top-rated schools. Discover your dream home in Isleworth, where every day feels like a vacation!

Newest Isleworth Homes with Pickleball Court(s) Amenities

$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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