Isleworth Homes with Pond Frontage

Isleworth Homes with Pond Frontage

Welcome to Isleworth, a prestigious subdivision nestled in the enchanting city of Windermere, Florida, within the heart of Orange County. This exclusive community is renowned for its luxurious homes, stunning landscapes, and picturesque surroundings, making it a sought-after destination for those who appreciate the finer things in life.

Isleworth boasts a unique charm, characterized by its beautifully designed residences that often feature pond frontage, offering residents breathtaking views and a serene atmosphere. Imagine waking up to the gentle sounds of water lapping at the shore, with the sun glistening off the surface of the pond right outside your window. These homes provide an idyllic setting for both relaxation and entertaining, with ample outdoor spaces that seamlessly blend with nature.

In addition to its stunning properties, Isleworth is home to a vibrant community that values privacy and exclusivity. Residents enjoy access to world-class amenities, including a championship golf course, a state-of-the-art fitness center, and a luxurious clubhouse that serves as the social hub of the neighborhood. The beautiful landscapes and meticulously maintained grounds create a tranquil retreat, perfect for leisurely strolls or enjoying a quiet afternoon by the water.

Located just minutes from the upscale shopping and dining options of Windermere, Isleworth combines the best of both worlds: a peaceful, suburban lifestyle with easy access to urban conveniences. Whether you’re looking for a family home or a luxurious retreat, Isleworth's pond-front properties offer an unparalleled living experience that is both charming and sophisticated. Discover the beauty and elegance of Isleworth today!

Newest Isleworth Homes with Pond Frontage

$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

Start Your Search