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$3,400,000 - 9731 Chestnut Ridge Drive, WINDERMERE

4
Bedrooms
4
Baths
4,877
SQ. Feet
0.54
Acres

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.

Essential Information

  • 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

Amenities

  • Amenities:
    Cable TV, Playground, Security
  • Parking:
    Circular Driveway, Golf Cart Garage
  • # of Garages:
    2
  • View:
    Pool
  • Has Pool:
    Yes

Interior

  • Interior Features:
    Cathedral Ceiling(s), Ceiling Fans(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
  • # of Stories:
    2

Exterior

  • Exterior Features:
    Balcony, Outdoor Grill, Rain Gutters
  • Lot Description:
    Landscaped, Near Golf Course, Paved
  • Roof:
    Tile
  • Foundation:
    Block, Slab

School Information

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

Additional Information

  • Days on Market:
    128
  • 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 December 22nd, 2025 at 11:20am EST.