$3,400,000 for Sale

9731 chestnut ridge drive , windermere, FL 34786

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Beds 4 Baths 4 4,877 Sqft 0.54 Acres 1 of 57
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Property Description
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.
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General Information
Sale Price: $3,400,000
Price/SqFt: $697
Est. Payments: $21,827
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Status: Active
MLS#: O6336655
City: windermere
Post Office: windermere
Schools: olympia high
County: Orange
Subdivision: isleworth
Acres: 0.54
Bedrooms:4
Bathrooms:4   (4 full, 0 half)
House Size: 4,877 sq.ft.
Acreage: 0.54 est.
Year Built: 1986
Property Type: Single Family Residence
Style:
Features & Room Sizes
Paved Road:  Paved
Construction:  Block, Stucco
Exterior Misc:  Balcony, Irrigation System, Outdoor Grill, Rain Gutters
Pool:  Yes
Pool Description:  Heated, In Ground, Lighting, Self Cleaning
Basement:  No
Foundation :  Block, Slab
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
Cooling:  Central Air, Zoned
Heating:  Central, Electric, Natural Gas
Waste:  Septic Tank
Watersource:  Public
Tax, Fees & Legal
Est. Summer Taxes:  $0
Est. Winter Taxes:  $19,867
HOA fees:  3129
HOA fees Period:  Quarterly
Legal Description:  ISLEWORTH 16/118 LOT 7


Information provided by My Florida Regional MLS DBA Stellar MLS, Copyright 2026
All information provided is deemed reliable but is not guaranteed and should be independently verified. Participants are required to indicate on their websites that the information being provided is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Listing By: Monica Lochmandy of ISLEWORTH REALTY LLC, Phone: 407-909-9000
(941) 875-4503 Call Scott Standriff for more information about this property.

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This Home located at
9731 chestnut ridge drive, windermere FL 34786
is currently for sale priced at $3,400,000 and was listed on July, 30, 2025 and has been on the market for 232 days and was last updated on August, 17, 2025.

9731 chestnut ridge drive has 4 bedrooms, 4 bathrooms, and approximately 4,877 square feet. This home is in the olympia high school district with 0.54 acres and was built in 1986. 9731 chestnut ridge drive is in the 34786 ZIP Code area of windermere.

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