9725 Chestnut Ridge Drive, Windermere, FL 34786
For Sale $6,950,000
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Contact the Listing Agent directly:
Listing Agent: Dianna Desboyaux
Agent Phone:
407-920-4601
Agent Email:
diannadesboyaux@gmail.com
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Private showings are easily accommodated, including same-day requests. Newly renovated and fully turnkey, 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.
Built-in Features
Ceiling Fans(s)
Elevator
High Ceilings
Kitchen/Family Room Combo
Living Room/Dining Room Combo
Open Floorplan
Primary Bedroom Main Floor
Split Bedroom
Stone Counters
Thermostat
Walk-In Closet(s)
Wet Bar
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)
Taxes: $29.00
Tax Year: 2024
Association Fee: $3,129.00
Association Fee Frequency: Quarterly
Condo Fee Frequency: Quarterly
Fire Pit
French Doors
Outdoor Kitchen
Bar Fridge
Built-In Oven
Dishwasher
Disposal
Dryer
Exhaust Fan
Freezer
Ice Maker
Microwave
Range
Range Hood
Refrigerator
Washer
Garden
Pool
Water
Pond
Elementary School: Windermere Elem
Middle School: Chain Of Lakes Middle
Junior High: Chain Of Lakes Middle
High School: Olympia High
MLS Area: 34786 - Windermere
Price per Square Feet: $868.75
Total Floors: 2
Water: Public
Lot Desc.: Landscaped, Near Golf Course, Paved
Construction: Block, Stucco
Date Listed: 2026-01-02 05:14:07
Pool: Yes
Pool Type: Heated, In Ground, Indoor, Lap, Outside Bath Access, Screen Enclosure, Tile
Private Spa: Yes
Furnished: Furnished
Windows: Skylight(S), Energy Star Qualified Windows
Parking: Driveway, Garage Faces Side
Garage Spaces: 3
Flooring: Tile, Travertine, Wood
Roof: Tile
Heating: Central
Cooling: Central Air, Zoned
Pets: Yes
Sewer: Septic Tank
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)
Listing Courtesy Of: Douglas Elliman
diannadesboyaux@gmail.com
Private showings are easily accommodated, including same-day requests. Newly renovated and fully turnkey, 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.
Property Details
Price: $6,950,000
Sq Ft: 8,000
($869 per sqft)
Bedrooms: 7
Bathrooms: 5
Partial Baths: 2
City: Windermere
County: Orange
Type: Single Family Reside
Development: Isleworth
Acres: 0.56
Virtual Tour/Floorplan: View
Year Built: 1999
Listing Number: O6370294
Status Code: A-Active
Taxes: $29.00
Tax Year: 2024
Garage:
3
Furnishings: Furnished
Pets Allowed: Yes
Interior Features:
Built-in Features
Ceiling Fans(s)
Elevator
High Ceilings
Kitchen/Family Room Combo
Living Room/Dining Room Combo
Open Floorplan
Primary Bedroom Main Floor
Split Bedroom
Stone Counters
Thermostat
Walk-In Closet(s)
Wet Bar
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)
Financial Information:
Taxes: $29.00
Tax Year: 2024
Association Fee: $3,129.00
Association Fee Frequency: Quarterly
Condo Fee Frequency: Quarterly
Exterior Features:
Fire Pit
French Doors
Outdoor Kitchen
Equipment:
Bar Fridge
Built-In Oven
Dishwasher
Disposal
Dryer
Exhaust Fan
Freezer
Ice Maker
Microwave
Range
Range Hood
Refrigerator
Washer
View:
Garden
Pool
Water
Waterfront Description:
Pond
School Information:
Elementary School: Windermere Elem
Middle School: Chain Of Lakes Middle
Junior High: Chain Of Lakes Middle
High School: Olympia High
Additional Information:
MLS Area: 34786 - Windermere
Price per Square Feet: $868.75
Total Floors: 2
Water: Public
Lot Desc.: Landscaped, Near Golf Course, Paved
Construction: Block, Stucco
Date Listed: 2026-01-02 05:14:07
Pool: Yes
Pool Type: Heated, In Ground, Indoor, Lap, Outside Bath Access, Screen Enclosure, Tile
Private Spa: Yes
Furnished: Furnished
Windows: Skylight(S), Energy Star Qualified Windows
Parking: Driveway, Garage Faces Side
Garage Spaces: 3
Flooring: Tile, Travertine, Wood
Roof: Tile
Heating: Central
Cooling: Central Air, Zoned
Pets: Yes
Sewer: Septic Tank
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)
Map of 9725 Chestnut Ridge Drive, Windermere, FL 34786
Listing Courtesy Of: Douglas Elliman
diannadesboyaux@gmail.com