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$4,800,000 - 9724 Chestnut Ridge Dr, WINDERMERE

5
Bedrooms
6
Baths
5,557
SQ. Feet
0.56
Acres

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.

Essential Information

  • MLS® #:
    O6310606
  • Price:
    $4,800,000
  • Bedrooms:
    5
  • Bathrooms:
    6.00
  • Full Baths:
    6
  • Square Footage:
    5,557
  • Acres:
    0.56
  • Year Built:
    1990
  • Type:
    Residential
  • Sub-Type:
    Single Family Residence
  • Style:
    Custom, Mediterranean
  • Status:
    Pending

Community Information

  • Address:
    9724 Chestnut Ridge Dr
  • Area:
    Windermere
  • Subdivision:
    ISLEWORTH
  • City:
    WINDERMERE
  • County:
    Orange
  • State:
    FL
  • Zip Code:
    34786

Amenities

  • Amenities:
    Cable TV, Gated, Maintenance, Playground, Security
  • Parking:
    Circular Driveway, Golf Cart Garage, Golf Cart Parking, Ground Level
  • # of Garages:
    6
  • View:
    Pool, Water
  • Is Waterfront:
    Yes
  • Waterfront:
    Lake Front
  • Has Pool:
    Yes

Interior

  • Interior Features:
    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
  • Appliances:
    Bar Fridge, Built-In Oven, Cooktop, Dishwasher, Disposal, Dryer, Freezer, Gas Water Heater, Microwave, Range Hood, Refrigerator, Washer, Wine Refrigerator
  • Heating:
    Central, Zoned
  • Cooling:
    Central Air

Exterior

  • Exterior Features:
    French Doors, Lighting, Outdoor Grill, Outdoor Kitchen, Rain Gutters
  • Lot Description:
    Landscaped, Near Golf Course, Paved
  • Roof:
    Metal
  • Foundation:
    Block, Slab

School Information

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

Additional Information

  • Days on Market:
    51
  • Zoning:
    P-D

Listing Details

  • Listing Office:
    Isleworth Realty Llc

Listing information courtesy of Isleworth Realty Llc.

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Listing data comes from My Florida Regional MLS.

Listing information last updated on July 11th, 2025 at 2:49am EDT.