9743 Chestnut Ridge Drive, WINDERMERE, FL

$3,250,000

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5

Beds

7

Baths

6,328

Square feet

1.15

Acres

About 9743 Chestnut Ridge Drive

Nestled at the end of a quiet cul-de-sac on 1.15 acres within the renowned Isleworth Golf & Country Club, this exceptional residence offers refined luxury, thoughtful design, and exceptional grounds designed for outdoor enjoyment all year round. Featuring five bedrooms, six full bathrooms, and a powder room, the home spans more than 6,300 square feet, with lovely architectural style and beautifully appointed interiors. The stunning great room is a true centerpiece, featuring soaring cathedral ceilings, exposed wood beams, and abundant natural light. Formal living and dining rooms provide ideal spaces for entertaining, while the chef’s kitchen boasts granite countertops, white cabinetry, and high-end Bosch and Sub-Zero appliances. The primary suite is a serene retreat, featuring a luxurious en-suite bath and direct access to the pergola and pool for seamless indoor-outdoor living. Upstairs, a versatile bonus room offers flexible space for a yoga studio, home gym, game room or creative retreat, complemented by a stylish loft office perfect for work-from-home needs. Step outside to discover the expansive backyard complete with modern pool is surrounded by low-maintenance artificial turf, expansive lanai spaces for alfresco dining, and multiple seating areas ideal for gatherings or quiet relaxation—all framed by a vast, fenced yard. This extraordinary home offers both comfort and sophistication in a community renowned for its golf, amenities, and lifestyle. A rare opportunity to live luxuriously in a premier setting.

Features of 9743 Chestnut Ridge Drive

MLS® # O6314871
Price $3,250,000
Bedrooms 5
Bathrooms 7.00
Full Baths 6
Half Baths 1
Square Footage 6,328
Acres 1.15
Year Built 1987
Type Residential
Sub-Type Single Family Residence
Status Pending

Community Information

Address 9743 Chestnut Ridge Drive
Area Windermere
Subdivision ISLEWORTH
City WINDERMERE
County Orange
State FL
Zip Code 34786

Amenities

Parking Garage Faces Side
# of Garages 4
View Pool
Is Waterfront No
Has Pool Yes

Interior

Interior Features Built-in Features, Ceiling Fans(s), High Ceilings, Primary Bedroom Main Floor, Vaulted Ceiling(s), Walk-In Closet(s), Wet Bar
Appliances Bar Fridge, Built-In Oven, Dishwasher, Disposal, Dryer, Freezer, Microwave, Refrigerator, Washer, Wine Refrigerator
Heating Central, Electric
Cooling Central Air
Fireplace Yes
Fireplaces Family Room, Primary Bedroom

Exterior

Exterior Features Awning(s), Lighting
Lot Description Landscaped, Oversized Lot
Roof Tile
Foundation Slab

School Information

Elementary Windermere Elem
Middle Chain of Lakes Middle
High Olympia High

Additional Information

Date Listed June 4th, 2025
Days on Market 40
Zoning P-D
Foreclosure No
Short Sale No
RE / Bank Owned No

Listing Details

OfficeISLEWORTH REALTY LLC

Listing Map

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