9731 CHESTNUT RIDGE DRIVE WINDERMERE FL 34786 MLS #O6336655

9731 CHESTNUT RIDGE DRIVE
WINDERMERE, FL, 34786
$3,400,000
4 Beds
4 Baths
4,877 SqFt
0.54 Acres
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MLS #O6336655 image #0
Nestled within the gates of the renowned Isleworth Golf & Country Club, this beautiful four-bedroom estate offers nearly 5,000 square feet and showcases an elegant transitional style. The main level welcomes you with gracious formal living and dining rooms, each crowned with sparkling chandeliers and framed by oversized windows that capture elevated views of the resort-style pool and spa below. Travertine floors flow seamlessly into the gourmet kitchen appointed with stainless steel appliances, a sunlit casual dining space, and direct access to both the intimate family room and an outdoor balcony for effortless indoor-outdoor living. Also on the primary level, the serene master suite offers a separate access to the terrace along with a luxuriously updated bath, and dual closets. Completing the primary level is a richly detailed wood-paneled office and a well-appointed laundry room, adding both warmth and function. The home’s thoughtful layout places the secondary bedrooms on the lower level, ensuring privacy and comfort for family or guests. Here, glass doors open to the multi-level terrace that gracefully surrounds the sparkling pool and spa, featuring generous deck space for year-round lounging and entertaining under the Florida sun. Offering an exceptional combination of timeless design, resort-inspired grounds, and a premier location within the gates, this remarkable residence is truly a sanctuary to call home.

Property Details

Price:
$3,400,000
MLS #:
O6336655
Status:
Active
Beds:
4
Baths:
4
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
ISLEWORTH
Neighborhood:
34786windermere
Listed Date:
Aug 16, 2025
Finished Sq Ft:
4,877
Total Sq Ft:
6,151
Lot Size:
23,624 sqft / 0.54 acres (approx)
Year Built:
1986
PoolPrimary Bedroom Main FloorCommunity Gated34786 – Windermere34786windermereIsleworthWindermere ElemChain Of Lakes MiddleOlympia HighLake Butler Chain Of LakesPoolPer Isleworth Community Association (ica)No MinimumBreed Restrictions

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Schools

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

Interior

Appliances
Bar Fridge, Built-In Oven, Dishwasher, Disposal, Dryer, Exhaust Fan, Gas Water Heater, Ice Maker, Microwave, Range, Range Hood, Refrigerator, Trash Compactor, Washer, Water Filtration System, Water Purifier, Water Softener
Bathrooms
4 Full Bathrooms
Cooling
Central Air, Zoned
Flooring
Marble, Travertine
Heating
Central, Electric, Natural Gas
Interior Features
Cathedral Ceiling(s), Ceiling Fan(s), Kitchen/Family Room Combo, Primary Bedroom Main Floor, Stone Counters, Thermostat, Walk-In Closet(s)
Laundry Features
Laundry Room
Levels
Two

Exterior

Association Amenities
Cable TV, Playground, Security
Attached Garage YN
1
Community Features
Community Boat Ramp, Water Access, Community Mailbox, Gated Community – No Guard, Golf Carts OK, Golf, Playground
Construction Materials
Block, Stucco
Covered Spaces
2
Direction Faces
Northeast
Exterior Features
Balcony, Irrigation System, Outdoor Grill, Rain Gutters
Garage Spaces
2
Lot Features
Landscaped, Near Golf Course
Open Parking YN
1
Parking Features
Circular Driveway, Golf Cart Garage
Roof
Tile
Security Features
Gated Community, Security Lights, Security System, Smoke Detector(s)
Spa Features
Heated, In Ground
View
Pool

Financial

HOA Fee
$3,672
HOA Fee Frequency
Quarterly
HOA Includes
24-Hour Guard, Cable TV, Escrow Reserves Fund, Internet, Maintenance Grounds, Maintenance Repairs, Security
HOA Name
Dan O’Connell
HOA Phone
407-909-2071
Tax Year
2024
Taxes
$19,867

Map

Community

Subdivisions in WINDERMERE

Market Summary

Current real estate data for Single Family in WINDERMERE as of Apr 29, 2026
290
Single Family Listed
97
Avg DOM
461
Avg $ / SqFt
$2,249,900
Avg List Price

Property Summary

    Located in the ISLEWORTH subdivision, 9731 CHESTNUT RIDGE DRIVE WINDERMERE FL is a Single Family for sale in WINDERMERE, FL, 34786. It is listed for $3,400,000 and features 4 beds, 4 baths, and has approximately 4,877 square feet of living space, and was originally constructed in 1986. The current price per square foot is $697. The average price per square foot for Single Family listings in WINDERMERE is $461. The average listing price for Single Family in WINDERMERE is $2,249,900. To schedule a showing of MLS#o6336655 at 9731 CHESTNUT RIDGE DRIVE in WINDERMERE, FL, contact your Charles Rutenberg Realty agent at (407) 619-0129.

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9731 CHESTNUT RIDGE DRIVE
WINDERMERE, FL
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