9731 Chestnut Ridge Drive, WINDERMERE, FL

$3,400,000

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4

Beds

4

Baths

4,877

Square feet

0.54

Acres

About 9731 Chestnut Ridge Drive

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.

Features of 9731 Chestnut Ridge Drive

MLS® # O6336655
Price $3,400,000
Bedrooms 4
Bathrooms 4.00
Full Baths 4
Square Footage 4,877
Acres 0.54
Year Built 1986
Type Residential
Sub-Type Single Family Residence
Status Active

Community Information

Address 9731 Chestnut Ridge Drive
Area Windermere
Subdivision ISLEWORTH
City WINDERMERE
County Orange
State FL
Zip Code 34786-8945

Amenities

Amenities Cable TV, Playground, Security
Parking Circular Driveway, Golf Cart Garage
# of Garages 2
View Pool
Is Waterfront No
Has Pool Yes

Interior

Interior Features Cathedral Ceiling(s), Ceiling Fan(s), Kitchen/Family Room Combo, Primary Bedroom Main Floor, Stone Counters, Thermostat, Walk-In Closet(s)
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
Heating Central, Electric, Natural Gas
Cooling Central Air, Zoned
Fireplace No
# of Stories 2

Exterior

Exterior Features Balcony, Irrigation System, Outdoor Grill, Rain Gutters
Lot Description Landscaped, Near Golf Course
Roof Tile
Foundation Block, Slab

School Information

Elementary Windermere Elem
Middle Chain of Lakes Middle
High Olympia High

Additional Information

Date Listed August 16th, 2025
Days on Market 49
Zoning P-D
Foreclosure No
Short Sale No
RE / Bank Owned No

Listing Details

OfficeISLEWORTH REALTY LLC

Listing Map

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