Listed at US$6 million, 9725 Chestnut Ridge Drive brings together the elements that continue to define Windermere’s luxury market: privacy, generous scale, renovated interiors, outdoor living, and a setting inside one of Central Florida’s most recognized private communities.
Located in Isleworth, this waterfront residence spans approximately 8,000 square feet and offers seven bedrooms, five full baths, two half baths, and a layout designed for both everyday comfort and elevated entertaining. Newly renovated, the home presents itself not only as a large estate, but as a property with a clear sense of lifestyle.
Listing Highlights
- PriceUS$6,000,000
- Address9725 Chestnut Ridge Drive, Windermere, FL 34786
- CommunityIsleworth
- SizeApproximately 8,000 sq ft
- Bedrooms7
- Bathrooms5 full baths + 2 half baths
- Price per square footUS$750
- StatusActive
- WaterfrontYes
- MLSO6370294
For buyers considering Windermere’s high-end residential market, Isleworth remains one of the area’s strongest addresses. Known for its privacy, security, golf community setting, and established luxury residences, the neighborhood offers a level of discretion that continues to appeal to those seeking a refined Florida lifestyle without sacrificing proximity to Orlando.
At 9725 Chestnut Ridge Drive, that sense of privacy is central to the experience of the home. The residence enjoys tranquil pond views, a gas-heated pool and jacuzzi, and a summer kitchen, creating an outdoor environment that feels calm, usable, and well suited for both quiet mornings and relaxed gatherings. The exterior spaces extend the home naturally, offering the kind of indoor-outdoor rhythm that is especially valuable in Florida living.
Inside, the renovation brings warmth and consistency to the property. Rich walnut cabinetry and wood detailing appear throughout the residence, giving the interiors a cohesive and inviting character. The living spaces feel generous, but not impersonal. A fireplace and wine cellar help anchor the main areas, adding atmosphere without making the home feel overly formal.
The kitchen is one of the residence’s strongest features. Designed for serious use as much as visual impact, it includes Taj Mahal quartzite countertops, a 60-inch Wolf gas cooktop, Dacor refrigerator and freezer, two warming drawers, a steam oven, dual dishwashers, and a hidden pantry. It is a kitchen built for people who entertain, but also for those who expect daily function to feel seamless.
The home’s layout adds another layer of flexibility. In addition to seven bedrooms, the residence includes a dedicated office, a bonus room with closet, an elevator, and two laundry areas. These details matter because they move the property beyond visual appeal. They support real life: guests, family, work, entertaining, privacy, storage, and ease of movement across levels.
This property also holds a particular connection to Home&Decor. Featured in our 10th edition, the residence was presented through the lens of design and real estate, with interiors connected to Artefacto’s elevated visual language under the leadership of Paulo Bacchi, design by Andria Tagliari, and representation by realtor Dianna Desboyaux. In that feature, the home illustrated how thoughtful presentation can strengthen the way a buyer understands a property.
That remains one of the most compelling aspects of this listing. The home has the numbers expected from a luxury estate — scale, location, bedroom count, outdoor amenities, and waterfront positioning — but it also has a finished point of view. It is not simply a large house waiting to be interpreted. It is a residence where the renovation, material choices, and spatial flow help make the lifestyle easy to imagine.
Behind the scenes, the home has also been updated with practical improvements, including four new A/C units installed in 2025, two tankless water heaters, and recently replaced garage doors and motors. In a property of this size, those upgrades are not secondary. They are part of the value, offering comfort and confidence beneath the polished presentation.
For buyers seeking a private Windermere estate with scale, renovation, outdoor living, and a strong design presence, view the full listing for 9725 Chestnut Ridge Drive. Private showings are available, including same-day requests, through Dianna Desboyaux.
