9731 CHESTNUT RIDGE DRIVE
WINDERMERE, FL, 34786
Price$3,400,000
Beds4
Baths4
SqFt4,877
Baths4
SqFt4,877
Status:Active
Property Type:Residential
School:
Property Type:Residential
School:
Nestled within the gates of the renowned Isleworth Golf & Country Club, this beautiful four-bedroom estate offers nearly 5,000 square feet and showcases an elegant transitional style. The main level welcomes you with gracious formal living and dining rooms, each crowned with sparkling chandeliers and framed by oversized windows that capture elevated views of the resort-style pool and spa below. Travertine floors flow seamlessly into the gourmet kitchen appointed with stainless steel appliances, a sunlit casual dining space, and direct access to both the intimate family room and an outdoor balcony for effortless indoor-outdoor living. Also on the primary level, the serene master suite offers a separate access to the terrace along with a luxuriously updated bath, and dual closets. Completing the primary level is a richly detailed wood-paneled office and a well-appointed laundry room, adding both warmth and function. The home’s thoughtful layout places the secondary bedrooms on the lower level, ensuring privacy and comfort for family or guests. Here, glass doors open to the multi-level terrace that gracefully surrounds the sparkling pool and spa, featuring generous deck space for year-round lounging and entertaining under the Florida sun. Offering an exceptional combination of timeless design, resort-inspired grounds, and a premier location within the gates, this remarkable residence is truly a sanctuary to call home.
| Price | $3,400,000 | |
| Bedrooms | 4 | |
| Full Baths | 4 | |
| Half Baths | 0 | |
| Total Baths | 4 | |
| Lot Size Area | 23624 | |
| Lot Size Area Units | Square Feet | |
| Acres | 0.54 | |
| Property Type | Residential | |
| Sub type | Single Family Residence | |
| MLS Sub type | Single Family Residence | |
| Features | Cathedral Ceiling(s), Ceiling Fan(s), Kitchen/Family Room Combo, Primary Bedroom Main Floor, Stone Counters, Thermostat, Walk-In Closet(s) | |
| Exterior Features | Balcony, Irrigation System, Outdoor Grill, Rain Gutters | |
| Year Built | 1986 | |
| Subdivision | ISLEWORTH | |
| View | Pool | |
| Roof | Tile | |
| Waterfront | LAKE BUTLER CHAIN OF LAKES | |
| Heating | Central, Electric, Natural Gas | |
| Foundation | Block, Slab | |
| Lot Description | Landscaped, Near Golf Course | |
| Laundry Features | Laundry Room | |
| Pool features | Heated, In Ground, Lighting, Self Cleaning | |
| Parking Description | Circular Driveway, Golf Cart Garage | |
| Garage spaces | 2 | |
| Association Name | Dan O’Connell | |
| Association Fee | 3672 | |
| Association Amenities | Cable TV, Playground, Security | |
| Directions | I-4 to Conroy Windermere Road west to Isleworth subdivision. Stay straight on Isleworth Country Club Drive. Turn right on Latrobe, turn right on Chestnut Ridge Drive. Estate will be on the Right. | |
| County | Orange | |
| Latitude | 28.492813 | |
| Longitude | -81.522664 | |
| Market Area | 34786 – Windermere | |
| Address | 9731 CHESTNUT RIDGE DRIVE, WINDERMERE, FL 34786 | |
| Postal Code | 34786 | |
| City | WINDERMERE | |
| State | FL | |
| Country | United States | |
| Listing Office | ISLEWORTH REALTY LLC | |
| Listing Office Phone | 407-909-9000 | |
| Listing Agent | Monica Lochmandy | |
| Listing Agent Phone | 407-230-6888 | |
| Special listing conditions | None | |
| Ownership | Fee Simple | |
| Terms | Cash, Conventional | |
| Elementary School | Windermere Elem | |
| Middle School | Chain of Lakes Middle | |
| High School | Olympia High | |
| Days on market | 187 | |
| MLS Status | Active | |
| Listing Date | Aug 16, 2025 | |
| Listing Last Modified | Feb 19, 2026 | |
| Tax ID | 162328389900070 | |
| Tax Year | 2024 | |
| Tax Annual Amount | 19866 | |
| MLS Area | 34786 – Windermere | |
| MLS # | O6336655 | |
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