Home in 9725 Chestnut Ridge Dr Windermere for sale with MLS# O6370294
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.
9725 Chestnut Ridge Dr, Windermere, FL 34786
- Price:
- $5,975,000.00
- Previous Asking Price:
- $6,000,000.00
- Original List Price:
- $6,950,000.00
- List Price per Sq Ft (Calculated, Approx.):
- $746.88
- Listing Type:
- For Sale
- Status:
- Active
- Listing Category:
- Residential
- Property Type:
- Single Family House
- MLS Number:
- O6370294
- Bedrooms:
- 7
- Bathrooms Total:
- 7
- Full Bath:
- 5
- Half Bath:
- 2
- Additional Rooms:
- Den/library/office, Media Room, Family Room, Formal Living Room Separate, Interior In-law Suite W/private Entry
- Living Area:
- 8,000 Sqft
- Built-Up Area:
- 11,952 Sqft
- Lot Area:
- 24,349 Sqft
- Building Area Source:
- Builder
- Living Area Source:
- Builder
- Lot Features:
- Paved, Near Golf Course, Landscaped
- Lot Size Acres:
- 0.56
- View from the Property:
- Pool, Garden, Water
- Waterfront:
- Yes
- Waterfront Features:
- Pond
- Private Pool
- Swimming Pool Features:
- Heated, Indoor, In Ground, Screen Enclosure, Outside Bath Access, Tile, Lap
- Spa
- Spa Features:
- Heated, In Ground
- Security:
- Smoke Detector(s), Gated Community
- Furnished:
- Furnished
- Appliances:
- Dryer, Dishwasher, Disposal, Microwave, Refrigerator, Washer, Freezer, Built-in Oven, Ice Maker, Exhaust Fan, Range, Range Hood, Bar Fridge
- Interior:
- High Ceilings, Walk-In Closet(s), Built-in Features, Wet Bar, Elevator, Ceiling Fans(s), Kitchen/family Room Combo, Living Room/dining Room Combo, Open Floorplan, Split Bedroom, Stone Counters, Thermostat, Primary Bedroom Main Floor
- Exterior:
- Outdoor Kitchen, Fire Pit
- Patio and Porch:
- Screened, Covered, Rear Porch, Enclosed
- Windows:
- Skylight(s), Energy Star Qualified Windows, Skylight(s)
- Laundry:
- Laundry Room
- Fireplace
- Fireplace:
- Gas, Living Room, Primary Bedroom
- Air Conditioning System:
- Zoned, Central Air
- Heating System:
- Central
- Vegetation and Trees:
- Trees/landscaped, Mature Landscaping
- Property Entrance Faces:
- West
- Other Equipment:
- Fire Pit
- Water Access
- Water Access Features:
- Lake - Chain Of Lakes, Pond
- Water View
- Water View Details:
- Pond
- Year Built:
- 1999
- Roof:
- Tile
- Levels:
- Three Or More
- Construction Materials:
- Block, Stucco
- Flooring:
- Tile, Wood, Travertine
- Number of stories:
- 2
- Foundation Details:
- Slab
- Flood Zone Code:
- X
- Tax Annual Amount:
- $29,046.23
- Tax Year:
- 2024
- Association Fee:
- $3,129.00
- Association Fee Frequency:
- Quarterly
- Total Annual Fees:
- $12,516.00
- Total Monthly Fees:
- $1,043.00
- Garage
- Garage Spaces:
- 3
- Attached Garage
- Parking Features:
- Driveway, Garage Faces Side
- Sewer:
- Septic Tank
- Utilities Available:
- Electricity Connected, Water Connected
- Water Source:
- Public
- Association
- Minimum Lease Term:
- 8-12 Months
- Pets Allowed?
- Amenities Provided by the Homeowner's Association (HOA):
- Pool, Sauna, Spa/hot Tub, Elevators, Clubhouse, Recreation facilities, Playground, Maintenance, Storage, Security, Fitness Center, Recreation Facilities, Tennis Court(s), Golf Course, Gated, Pickleball Court(s), Park, Racquetball
- Subdivision Name:
- ISLEWORTH
- Community Features:
- Clubhouse, Fitness Center, Pool, Tennis Court(s), Golf, Playground, Restaurant, Golf Carts Ok, Buyer Approval Required, No Truck/rv/motorcycle Parking, Racquetball, Gated Community - Guard
- Association Fee Includes:
- Maintenance Grounds, Security, Pool, Guard - 24 Hour, Management
- Senior Community:
- No
- Association Fee Required:
- Required
- Association Management:
- Dan O'Connell
- Association Phone:
- 407-909-2071
- Listing Terms Considered by Seller:
- Cash, Conventional
- Occupant Type:
- Vacant
- Lease Considered:
- Yes
- Tax Legal Description:
- ISLEWORTH 16/118 LOT 6 & BEG NW COR OF SAID LOT 6 TH S 63 DEG E 85 FT N 76 DEG E39.14 FT N 63 DEG W 113.43 FT S 30 DEGW 25.29 FT TO POB & BEG AT WLY MOST COROF LOT 4 TH N33-00-00E ALONG WLY LINE OFLOT 4 10.06 FT TH N63-04-56W 133.88 FTTH S30-16-40W 1 0.02 FT TO NELY LINE OF LANDS DESC IN 5925/4062 TH S63-04-56E 133.40 FT TO POB
- Real Estate Folio Number (Parcel Number):
- 16-23-28-3899-00-060
- Zoning:
- P-D
- Title to the property is held by owner as:
- Fee Simple
- High School:
- Olympia High
- Middle Or Junior School:
- Chain Of Lakes Middle
- Originally published on:
- January 2, 2026 5:14 am
- Active on the market since:
- January 2, 2026
- Listing Agreement executed on:
- January 2, 2026
- Price change occurred on:
- August 22, 2026 1:39 am
- Listing Status Last Changed On:
- January 2, 2026 5:14 am
- Photos updated on:
- June 29, 2026 9:11 pm
- Last Modified:
- August 26, 2026 8:23 pm
- Association Approval Required
- Courtesy of:
- DOUGLAS ELLIMAN
- Attribution:
- 305-695-6070
- Road Surface Type:
- Asphalt
- Street Name:
- CHESTNUT RIDGE
- Street Number:
- 9725
- City:
- WINDERMERE
- State:
- Florida
- Zip Code:
- 34786
- County:
- Orange
- Latitude:
- N28° 29' 33.4''
- Longitude:
- W82° 28' 39.9''
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Neighborhood Stats
Source: U.S. Census Bureau, ACS 5-Year Estimates
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