9725 Chestnut Ridge Drive, Windermere, FL 34786
Local realty services provided by:Better Homes and Gardens Real Estate Lifestyles Realty
Listed by: dianna desboyaux, adriana morris
Office: douglas elliman
MLS#:O6370294
Source:MFRMLS
Price summary
- Price:$5,975,000
- Price per sq. ft.:$499.92
- Monthly HOA dues:$1,043
About this home
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....
Contact an agent
Home facts
- Year built:1999
- Subdivision & Development:ISLEWORTH
- Listing ID #:O6370294
- Added:235 day(s) ago
- Updated:August 25, 2026 at 02:34 PM
Rooms and interior
- Bedrooms:7
- Total bathrooms:7
- Full bathrooms:5
- Half bathrooms:2
- Flooring:Tile, Travertine, Wood
- Dining Description:Living Room/Dining Room Combo
- Kitchen Description:Bar Fridge, Built-In Oven, Dishwasher, Disposal, Exhaust Fan, Freezer, Ice Maker, Kitchen/Family Room Combo, Microwave, Range, Range Hood, Refrigerator, Stone Counters, Wet Bar
- Bedroom Description:High Ceilings, Primary Bedroom Main Floor, Split Bedroom, Walk-In Closet(s)
- Living area:8,000 sq. ft.
Heating and cooling
- Cooling:Central Air, Zoned
- Heating:Central
- Central air:Yes
Structure and exterior
- Roof:Tile
- Year built:1999
- Building area:8,000 sq. ft.
- Lot area:0.56 Acres
- Lot Features:Landscaped, Near Golf Course, Paved
- Construction Materials:Block, Stucco
- Exterior Features:Covered Porch/Patio, Enclosed, Outdoor Kitchen, Rear Porch, Screened
- Foundation Description:Slab
- Levels:Three Or More Story
Schools
- High school:Olympia High
- Middle school:Chain of Lakes Middle
- Elementary school:Windermere Elem
Utilities
- Water:Public, Water Connected
- Sewer:Septic Tank
Finances and disclosures
- Price:$5,975,000
- Price per sq. ft.:$499.92
- Tax amount:$29,046 (2024)
Features and amenities
- Appliances:Bar Fridge, Built-in Oven, Dishwasher, Disposal, Dryer, Exhaust Fan, Freezer, Ice Maker, Microwave, Range, Range Hood, Refrigerator, Washer
- Laundry features:Dryer, Laundry Room, Washer
- Amenities:Built-In Features, Ceiling Fans(s), Clubhouse, Elevator, Fitness Center, Gated, Golf Course, High Ceilings, Kitchen/Family Room Combo, Living Room/Dining Room Combo, Maintenance, Open Floorplan, Park, Pickleball Court(s), Playground, Pool, Primary Bedroom Main Floor, Racquetball, Recreation Facilities, Sauna, Security, Spa/Hot Tub, Split Bedroom, Stone Counters, Storage, Tennis Court(s), Thermostat, Walk-In Closet(s), Wet Bar
- Pool features:Heated, In Ground, Indoor, Lap, Outside Bath Access, Pool, Private Pool, Screen Enclosure, Tile
Parking
- Parking description:Attached Garage, Driveway, Garage Faces Side
- Garage:Yes
- Garage spaces:3
New listings near 9725 Chestnut Ridge Drive
- Coming Soon
$1,495,000Coming Soon5 beds 5 baths4,238 sq. ft.6239 Rydal Court, WINDERMERE, FL 34786
MLS# O6435610Listed by: INFINITY REALTY GROUP LLC - New
$445,000Active3 beds 3 baths1,727 sq. ft.11734 Water Run Alley, WINDERMERE, FL 34786
MLS# S5156211Listed by: REMAX PREMIER PROPERTIES - New
$354,900Active2 beds 3 baths1,412 sq. ft.7430 Bentonshire Avenue, WINDERMERE, FL 34786
MLS# O6436022Listed by: EXP REALTY LLC - New
$775,000Active4 beds 3 baths2,224 sq. ft.8291 Procida Isle Lane, WINDERMERE, FL 34786
MLS# O6436040Listed by: KELLER WILLIAMS REALTY AT THE LAKES - New
$990,000Active4 beds 3 baths2,728 sq. ft.1243 Dingens Avenue, WINDERMERE, FL 34786
MLS# O6435494Listed by: REALMULTIPROPERTY LLC - Open Sun, 11am to 1pmNew
$560,000Active3 beds 2 baths1,723 sq. ft.5125 Sun Palm Drive, WINDERMERE, FL 34786
MLS# O6435175Listed by: THE SIMON SIMAAN GROUP - New
$200,000Active0.25 AcresPark Ridge Gotha Road, WINDERMERE, FL 34786
MLS# S5156135Listed by: OLYMPUS EXECUTIVE REALTY INC - New
$964,500Active5 beds 3 baths2,717 sq. ft.11348 Willow Gardens Drive, WINDERMERE, FL 34786
MLS# O6435449Listed by: VINTAGE REALTY GROUP LLC - New
$1,760,000Active5 beds 5 baths4,219 sq. ft.1480 Hempel Avenue, WINDERMERE, FL 34786
MLS# S5156040Listed by: AROD PARTNERS REALTY - New
$575,000Active4 beds 3 baths2,064 sq. ft.6828 Helmsley Circle, WINDERMERE, FL 34786
MLS# O6435655Listed by: LPT REALTY, LLC