9725 CHESTNUT RIDGE DRIVE Windermere, FL $ 6,950,000
9725 CHESTNUT RIDGE DRIVE
$ 6,950,000
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9725 CHESTNUT RIDGE DRIVE

Windermere, FL, 34786
$ 6,950,000
Bedrooms7 Baths5.2 Sq 8,000

Monthly Estimate*

$ 42,792

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Single Family Home for sale in Windermere, FL

for $6,950,000 with 7 bedrooms and 5 full baths, 2 half baths. This 8,000 square foot home was built in 1999 on a lot size of 0.56.

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.

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Single Family Active

Price

$ 6,950,000

Bedrooms

7

Full Bath

5

Half Bath

2

Property Type

Single Family

Taxes

$ 29,046

Style

Single Family Residence

Lot Size

0.56

Year Built

1999

Town/City

Windermere

County/Region

Orange

MLS | Web ID

O6370294

Features
General
Sewer Septic Tank
Heating Central
Cooling Central Air Zoned
Utilities Electricity Connected Water Connected
Roof Tile
Appliances Bar Fridge Built-In Oven Dishwasher Disposal Dryer Exhaust Fan Freezer Ice Maker Microwave Range Range Hood Refrigerator Washer
Zoning P-D
HOA Fee 3129
Garage Spaces 3
Association Fee Includes 24-Hour Guard Community Pool Maintenance Grounds Manager Pool Maintenance Security
Patio/Porch Features Covered Enclosed Rear Porch Screened
Pool Features Heated In Ground Indoor Lap Outside Bath Access Screen Enclosure Tile
Security Features Gated Community Smoke Detector(s)
Construction Materials Block Stucco
Pets Allowed Yes
Year Built 1999
View Garden Pool Water
Levels Three Or More
Property Subtype Single Family Residence
Tax Year 2024
Ownership Fee Simple
Waterfront Features Waterfront Pond
Community Features Private Boat Ramp Water Access Waterfront 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)
Assoc Fee Paid Per Quarterly
County Orange
New Construction false
Property Type Residential
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)
Attached Garage true
Subdivision Name ISLEWORTH
Facing Direction West
Garage Y/N true
Total Rooms 5
Full Baths 5
Status Active
Directions I-4 to Conroy Windermere Road west to Isleworth Golf and Country Club which will be on the left turn right onto Latrobe Drive and next right onto Chestnut Ridge Drive the home will be situated on the right.
High School Olympia High
City WINDERMERE
Association Name Dan O'Connell
Senior Community Y/N false
MLS Area 34786 - Windermere
Lot Size Units Square Feet
Lot Size Square Feet 24349
Carport Y/N false
Listing Terms Cash Conventional
Spa Features Heated In Ground
Elementary School Windermere Elem
Land Lease Y/N false
Tax Annual Amount 29046.23
Middle/Junior High School Chain of Lakes Middle
Additional Parcels Y/N false
Lease Considered Y/N true
Virtual Tour https://youtu.be/C3xoT2aYH7o?si=aW5Fx8ZQZmxSgUZA https://youtu.be/C3xoT2aYH7o?si=aW5Fx8ZQZmxSgUZA
Building Area Units Square Feet
Living Area Units Square Feet
Standard Status Active
Occupancy Type Vacant
Tax Lot 6
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
Water View Pond
Water Access Type Lake - Chain of Lakes Pond
Minimum Lease 8-12 Months
Water Access Y/N true
Monthly HOA Amount 1043
Additional Rooms Den/Library/Office Family Room Formal Living Room Separate Interior In-Law Suite w/Private Entry Media Room
Water View Y/N true
Flood Zone Code X
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Interior
Interior Amenities 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
Flooring Porcelain Tile Travertine Hardwood
Furnished Y/N Furnished
Fireplace Features Gas Living Room Master Bedroom
Total Stories 2
Air Conditioning Y/N true
Heating Y/N true
Window Features ENERGY STAR Qualified Windows
Fireplace Y/N true
Half Baths 2
Laundry Features Laundry Room
Total Bedrooms 7
Total Baths 7
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Exterior
Exterior Amenities Fire Pit French Doors Outdoor Kitchen
Vegetation Mature Landscaping Trees/Landscaped
Parking Features Driveway Garage Faces Side
Lot Features Landscaped Near Golf Course
Water Source Public
Lot Size Area 24349
Foundation Details Slab
Spa true
Building Area Total 11952
Lot Size Acres 0.56
Road Surface Type Paved Asphalt
Private Pool true
Waterfront Y/N true
Covered Spaces 3
Road Frontage Type Street Paved
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* Excluded Features
List By
Douglas Elliman

Broker

diannadesboyaux@gmail.com

Email

Affordability Calculator

$45,213
Per Month
95%
5%
0%
Monthly Principal & Interest
$42,792
Monthly Property Taxes
$2,421
Monthly Home Insurance
--
Default based on a 30-year fixed rate of 6.25% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
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Nearby
0 Elementary School
0 Middle School
Olympia High High School High School
Pricing History
DatePricePrice ChangeDescription
1/2/2026$6,950,000 Listed Price

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9725 CHESTNUT RIDGE DRIVE, Windermere, FL, 34786 is a Single Family Home for sale at $6,950,000 with 8,000 sqft and a lot size of 0.56. 9725 CHESTNUT RIDGE DRIVE has 7 bedrooms, 5.2 baths, and was built in 1999. The property's zip code is 34786 which is in Windermere, FL