9724 CHESTNUT RIDGE DR
WINDERMERE, FL 34786
$4,800,000 (Pending)
Beds: 5
Baths: 6
Sq. Ft.: 5,557
Type: House
Listing #O6310606
Motivated Seller - Experience refined lakefront living in this exceptional estate, ideally located within the renowned Isleworth Golf & Country Club. Set along the shores of Lake Bessie on a beautifully landscaped 0.56-acre lot, the home spans 5,557 square feet of luxurious living space. A NEW METAL ROOF in 2024 adds both modern appeal and long-term durability, enhancing the home's overall value and aesthetic. Grand mahogany French doors welcome you into an expansive formal living room, where large picture windows perfectly frame the breathtaking lake vistas. Adjacent, the elegant formal dining room connects to a gourmet kitchen featuring smooth granite countertops, a center island with a professional-grade range and contemporary hood, stainless steel appliances, and travertine flooring. A cozy breakfast nook and inviting family room--both with stunning lake views--complete the heart of the home. Wine enthusiasts will appreciate the custom wine cellar, adorned with a reclaimed Old World wooden door and capacity for over 500 bottles. This space seamlessly connects to a richly appointed home office and trophy room, each featuring bespoke wooden built-ins. The primary suite offers a tranquil sitting area overlooking the lake, along with a luxurious en-suite bath that includes dual vanities, a garden tub, and a walk-in shower. Upstairs, three additional bedrooms accompany a home theater with soundproof walls, a built-in wet bar, and intricate wood detailing, creating the ultimate cinematic experience. Outdoors, a spacious lanai with a summer kitchen overlooks an elevated terrace, pool, and spa, perfect for entertaining or relaxing while enjoying spectacular sunsets and nightly fireworks from nearby theme parks. This rare lakefront gem blends timeless elegance with a prime location, offering an unparalleled lifestyle in one of Central Florida's most exclusive communities.
Property Features
County: Orange
MLS Area: Windermere
Community: Cable TV, Gated, Maintenance, Playground, Security
Latitude: 28.491518
Longitude: -81.523011
Subdivision: ISLEWORTH
Location: Landscaped, Near Golf Course, Paved
Directions: I-4 to Conroy Windermere Road west to Isleworth subdivision. Stay straight on Isleworth Country Club Drive.Turn right on Latrobe, turn right on Chestnut Ridge Drive. Estate will be on the Left.
Association Name: Dan O'Connell
Is a Gated Community: Yes
Interior: Ceiling Fans(s), Crown Molding, Eat-in Kitchen, High Ceilings, Primary Bedroom Main Floor, Solid Surface Counters, Solid Wood Cabinets, Thermostat, Walk-In Closet(s), Wet Bar, Window Treatments
Full Baths: 6
Has Fireplace: No
Heat/Cool: Central, Zoned
Cooling: Central Air
Floors: Carpet, Tile, Travertine, Wood
Appliances: Bar Fridge, Built-In Oven, Cooktop, Dishwasher, Disposal, Dryer, Freezer, Gas Water Heater, Microwave, Range Hood, Refrigerator, Washer, Wine Refrigerator
Has Private Pool: Yes
Style: Custom, Mediterranean
Water View: Lake
Stories: Two
Stories: Two story
Direction Faces: Northeast
Is New Construction: No
Construction: Block, Stucco
Exterior: French Doors, Lighting, Outdoor Grill, Outdoor Kitchen, Rain Gutters
Foundation: Block, Slab
Roof: Metal
Water Extras: Lift, Skiing Allowed
Utilities: BB/HS Internet Available, Cable Connected, Electricity Connected, Fire Hydrant, Natural Gas Connected, Public, Underground Utilities
Parking Description: Circular Driveway, Golf Cart Garage, Golf Cart Parking, Ground Level
Has Garage: Yes
Garage Spaces: 6
Fencing: Fenced
Has a Pool: Yes
Pool Description: In Ground, Salt Water
Has Golf Course: Yes
Lot Description: 1/2 to less than 1
Lot Number: 15
Lot Size in Acres: 0.56
Lot Size in Sq. Ft.: 24,255
Zoning: P-D
Flood Zone Code: AE
Improvements: Irrigation Equipment
Water Body: LAKE BESSIE
Water Frontage: 100
Waterfront Description: Lake Front
Has Waterfront: Yes
Water Access: Lake
Elementary School: Windermere Elem
Jr. High School: Chain of Lakes Middle
High School: Olympia High
Property Type: SFR
Property SubType: Single Family Residence
Year Built: 1990
Status: Pending
Housing For Older Persons (55+): No
Maintenance Includes: Guard - 24 Hour, Cable TV, Escrow Reserves Fund, Internet, Maintenance Grounds, Maintenance, Private Road, Security
Association Fee Requirement: Required
Monthly HOA Amount: $1043.00
Association Fee: $3,129
Association Fee Frequency: Quarterly
Pets: Breed Restrictions
Community Features: Cable TV, Gated, Maintenance, Playground, Security
Tax Amount: $38,334.25
$ per month
Year Fixed. % Interest Rate.
Principal + Interest: | $ |
Monthly Tax: | $ |
Monthly Insurance: | $ |
Listing Courtesy of ISLEWORTH REALTY LLC 407-909-9000

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Stellar (MFR) data last updated at July 5, 2025, 8:12 AM ET
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