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Property for sale at 9725 CHESTNUT RIDGE DRIVE, WINDERMERE, FL, 34786
Property for sale at 9725 CHESTNUT RIDGE DRIVE, WINDERMERE, FL, 34786
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9725 Chestnut Ridge DriveWindermere, FL, 34786

7beds
7baths
8,000sqft
Single Family Residence
Built in 1999
$3,129 Quarterly HOA Fee
$5,975,000
For sale
$6,950,000−$975,000 (14%)
Price per sqft
$747
Days on market
279
Listed Jan 2, 2026
Last reduction
−$25,000
Aug 22, 2026
MLS #O6370294Updated Sep 22, 2026

About this property

Virtually Staged. 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. Some photos have been virtually staged. Private showings are easily accommodated, including same-day requests.

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Property details

Property type
Single Family Residence
Street address
9725 Chestnut Ridge Drive
City
Windermere
State
FL
ZIP code
34786
Year built
1999
New construction
No
Faces
West
Rooms
5
Building stories
2
Living area
8,000 sqft
Total building area
11,952 sqft
Levels
Three Or More

Stellar MLSThe data relating to real estate displayed on this website comes in part from the Internet Data Exchange (IDX) Program of Stellar MLS. All listing information is deemed reliable but not guaranteed and should be independently verified through personal inspection by appropriate professionals. Listings displayed on this website may be subject to prior sale or removal from sale; the availability of any listing should always be independently verified. Listing information is provided for consumers' personal, non-commercial use, solely to identify potential properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law.Stellar (MFR) data last updated at October 8, 2026 at 12:01 AM EDT

Price & sale history

Asking price reduced by $975,000 (14%) since first listed.

EventPrice
Price reducedMLS #O6370294$5,975,000Change: −14%−$975,000
Listed for saleMLS #O6370294$6,950,000
History may be incomplete.
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Property for sale at 9725 CHESTNUT RIDGE DRIVE, WINDERMERE, FL, 34786
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