- Overview
- Description
- Property Details
- Location
- HOA Management
- Facts & Features
- Getting Around
- Nearby Homes
$5,975,000
Monthly Est:$29,740
7 Beds
- 7 Baths
5 full baths + 2 half baths
8,000sqft
9725 Chestnut Ridge Dr, Windermere, FL 34786
$5,975,000
$29,740/moEst:
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Single Family Residence
Built in 1999
$1,043/mo HOA
24,349 sqft lot
$747/sq.ft
Description
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.
- Houzeo last checked: 2 hours ago
- Listing updated: September 22, 2026 at 7:52 pm
- Listing Provided by: Dianna Desboyaux (407) 920-4601 , Adriana Morris | DOUGLAS ELLIMAN (561) 655-8600
- Source: Stellar MLS-FL | MLS#: O6370294

Property Details
Status
Active
Type
Single Family Residence
No. of Stories
2
County
City
Neighborhood
--
Year Built
1999
HOA Fees
$1043/mo
Finished Area
8,000 sqft
Lot Size
24,349 sqft lot
Basement Area
- sqft
MLS Name
Stellar MLS
MLS Number
O6370294
MLS Status
Active
Days on Market
299
Cumulative Days on Market
263

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Location
HOA Management
Dan O'Connell
HOA Fees
$3,129/ Quarterly
Amenities
Amenities and services may be covered by one or multiple associations and service providers.
Elevator
Security Gate
Club House
Golf
Tennis
Spa
Security Guard
Pool
Maintenance
Gym
Storage
Park Playground
Sports Court
Recreation Facilities
Management
Disclaimer: Amenities are based on third-party information and may vary; buyers must independently verify all amenities, as information is deemed reliable but not guaranteed.
Facts & Features
Rooms
Bedrooms & bathrooms
Bedrooms: 7
Bathrooms: 7
Family Room
Level: First
Area: 441.00 Square Feet
Dimensions: 21x21
Kitchen
Level: First
Area: 320.00 Square Feet
Dimensions: 20x16
Dining Room
Level: First
Area: 300.00 Square Feet
Dimensions: 20x15
Living Room
Level: First
Area: 260.00 Square Feet
Dimensions: 20x13
Primary Bedroom
Level: First
Interior
Sewer
Septic Tank
Flooring
Tile, Travertine, Wood
Appliances
Bar Fridge, Built In Oven, Dishwasher, Disposal, Dryer, Exhaust Fan, Freezer, Ice Maker, Microwave, Range, Range Hood, Refrigerator, Washer
Cooling
Central Air, Zoned
Window Features
Skylight(s), Energy Star Qualified Windows
Exterior Features
Fire Pit, Outdoor Kitchen
Heating
Central
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
Construction
Year Built
Year Built: 1999
Home type
Single Family Residence
Foundation Details
Slab
Construction Materials
Block, Stucco
Roof
Tile
Utilities & Energy
Parking Features
Driveway, Garage Faces Side
Utilities
Electricity Connected, Water Connected
Laundry Features
Laundry Room
Pool Features
Heated, In Ground, Indoor, Lap, Outside Bath Access, Screen Enclosure, Tile
Security Features
Gated Community, Smoke Detector(s)
Association Amenities
Clubhouse, Elevators, Fitness Center, Gated, Golf Course, Maintenance, Park, Pickleball Court(s), Playground, Pool, Racquetball, Recreation Facilities, Sauna, Security, Spa/hot Tub, Storage, Tennis Court(s)
Water Source
Public
Fireplace Features
Gas, Living Room, Primary Bedroom
Other Features
Community Features
Buyer Approval Required, Clubhouse, Fitness Center, Gated Community Guard, Golf Carts Ok, Golf, No Truck/rv/motorcycle Parking, Playground, Pool, Racquetball, Restaurant, Tennis Court(s)
Patio And Porch Features
Covered, Enclosed, Rear Porch, Screened
Lot Features
Landscaped, Near Golf Course, Paved
Subdivision Name
Isleworth
Vegetation
Mature Landscaping, Trees/landscaped
Price History
| Date | Event | Price |
|---|---|---|
08/22/2026 Source: | Price Decreased | $5,975,000 -0.42% $747/sqft |
05/02/2026 Source: | Price Decreased | $6,000,000 -2.44% $750/sqft |
04/15/2026 Source: | Price Increased | $6,150,000 +2.93% $769/sqft |
01/02/2026 Source: | Listed for Sale | $5,975,000 -14.03% $747/sqft |
01/02/2026 Source: | Price Increased | $6,950,000 +75.11% $869/sqft |
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Based on information from Stellar MLS® through Oct 28, 2026, 02:15PM as submitted to and distributed by MLS GRID. All data is obtained from various sources and may not have been verified by the broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. IDX information is provided exclusively for consumers’ personal non-commercial use. It may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The data is deemed reliable but is not guaranteed by MLS GRID. The use of the MLS GRID Data may be subject to an end-user license agreement prescribed by the Member Participant’s applicable MLS, if any, and as amended from time to time. © 2026 Stellar MLS. All Rights Reserved.
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