9725 CHESTNUT RIDGE DRIVE, WINDERMERE, FL 34786

$6,000,0007 Beds7 Baths8,000 Sq. Ft.$750 / sq. ft.

WINDERMERE, FL 34786 · MLS# O6370294 · Active · ISLEWORTH

Status
Active
Type
Single Family Residence
Year Built
1999
Days on Market
178
Lot Size
24,349 sqft
MLS #
O6370294
County
Orange

Description of 9725 CHESTNUT RIDGE DRIVE, WINDERMERE, FL 34786

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.

Property Details for 9725 CHESTNUT RIDGE DRIVE, WINDERMERE, FL 34786

Bathrooms Full
5
Bathrooms Half
2
Interior Features
Built-in Features, Ceiling Fan(s), Elevator, High Ceilings, Kitchen/Family Room Combo, Living Room/Dining Room Combo, Open Floorplan, Primary Bedroom Main Floor, Skylight(s), Split Bedroom, Stone Counters, Thermostat, Walk-In Closet(s), Wet Bar
Appliances
Bar Fridge, Built-In Oven, Dishwasher, Disposal, Dryer, Exhaust Fan, Freezer, Ice Maker, Microwave, Range, Range Hood, Refrigerator, Washer
Flooring
Porcelain Tile, Travertine, Hardwood
Heating
Central
Cooling
Central Air, Zoned
Garage Spaces
3
Attached Garage
Yes
Parking Features
Driveway, Garage Faces Side
Pool Features
Heated, In Ground, Indoor, Lap, Outside Bath Access, Screen Enclosure, Tile
Pool Private
Yes
Direction Faces
West

Building Information for 9725 CHESTNUT RIDGE DRIVE, WINDERMERE, FL 34786

Building Area Total
11952
Building Area Units
Square Feet
Stories Total
2
Association
Yes
Association Fee
$3,129
Association Fee Frequency
Quarterly
Association Amenities
Clubhouse, Elevator(s), Fitness Center, Gated, Golf Course, Maintenance, Park, Pickleball Court(s), Playground, Pool, Racquetball, Recreation Facilities, Sauna, Security, Spa/Hot Tub, Storage, Tennis Court(s)
Pets Allowed
Yes
Security Features
Gated Community, Smoke Detector(s)

Property Information for 9725 CHESTNUT RIDGE DRIVE, WINDERMERE, FL 34786

Lot Features
Landscaped, Near Golf Course
Lot Size Square Feet
24,349
Waterfront
Yes
Waterfront Features
Waterfront, Pond
View
Garden, Pool, Water
Construction Materials
Block, Stucco
Roof
Tile
Exterior Features
Fire Pit, French Doors, Outdoor Kitchen
Sewer
Septic Tank
Water Source
Public
New Construction
No

Public Records for 9725 CHESTNUT RIDGE DRIVE, WINDERMERE, FL 34786

Parcel Number
162328389900060
Tax Annual Amount
$29,046
Tax Year
2024
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
Zoning
P-D
County Or Parish
Orange

Schools Near 9725 CHESTNUT RIDGE DRIVE, WINDERMERE, FL 34786

Elementary School
Windermere Elem
Middle School
Chain of Lakes Middle
High School
Olympia High

School assignments are provided by the listing and should be independently verified.

Payment Calculator

Estimated Payment
$36,803/mo
Principal & Interest
$30,339
Property Taxes
$2,421
Home Insurance
$3,000
HOA Dues
$1,043

Estimate only — actual rates, taxes and insurance vary. Not a loan offer or financial advice. Financing through Matthew Gromadzki, NMLS #2560919 · Innovative Mortgage Services, Inc., NMLS #250769.

Location

9725 CHESTNUT RIDGE DRIVE, WINDERMERE, FL 34786 · See all Windermere homes for sale

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More information about 9725 CHESTNUT RIDGE DRIVE, WINDERMERE, FL 34786

9725 CHESTNUT RIDGE DRIVE is a single family home for sale in WINDERMERE, FL 34786. This property was listed for sale on January 2, 2026 by DOUGLAS ELLIMAN, it's currently listed at $6,000,000. This listing's school district is Orange Public Schools. Nearby schools include Windermere Elem, Chain of Lakes Middle and Olympia High. 9725 CHESTNUT RIDGE DRIVE is a 7-bed, 7-bath, 8,000 sqft single family home built in 1999.