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For sale
  • $3,400,000

    9731 Chestnut Ridge Dr, Windermere, FL 34786

    4beds
    4,877sqft
    : 
    Single Family Residence
    Built in 1986
    0.54 Acres Lot
    $3,172,600 Zestimate®
    $697/sqft
    $1,043/mo HOA

    What's special

    Oversized windowsSecondary bedroomsMulti-level terraceLuxuriously updated bathRichly detailed wood-paneled officeResort-inspired groundsResort-style pool and spa
    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.
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    Zillow last checked: 7 hours ago

    Listing updated: 7 hours ago

    Listing Provided by:

    Monica Lochmandy 407-230-6888,

    ISLEWORTH REALTY LLC 407-909-9000,

    Michelle Corbin 407-491-2690,

    ISLEWORTH REALTY LLC

    Source: Stellar MLS,MLS#: O6336655MLS LogoOriginating MLS: Orlando Regional

    Travel times

    Tour with a buyer's agent

    We'll find a local expert to take you on a private tour of 9731 Chestnut Ridge Dr.

    Next available tour time:Today at 11am

    Facts & features

    Interior

    Bedrooms & bathrooms
    • Bedrooms: 4
    • Bathrooms: 4
    • Full bathrooms: 4
    Primary bedroom
    • Features: Dual Closets
    • Level: Second
    Bedroom 2
    • Features: Built-in Closet
    • Level: First
    Bedroom 3
    • Features: Built-in Closet
    • Level: First
    Bedroom 4
    • Features: Built-in Closet
    • Level: First
    Primary bathroom
    • Level: Second
    Dining room
    • Level: Second
    Family room
    • Level: Second
    Kitchen
    • Level: Second
    Living room
    • Level: Second
    Office
    • Level: Second
    Heating
    • Central, Electric, Natural Gas
    Cooling
    • Central Air, Zoned
    Appliances
    • Included: Bar Fridge, 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
    • Laundry: Laundry Room
    Features
    • Cathedral Ceiling(s), Ceiling Fan(s), Kitchen/Family Room Combo, Primary Bedroom Main Floor, Stone Counters, Thermostat, Walk-In Closet(s)
    • Flooring: Marble, Travertine
    • Doors: Outdoor Grill
    • Has fireplace: No
    Interior area
    • Total structure area: 6,151
    • Total interior livable area: 4,877 sqft

    Property

    Parking
    • Total spaces: 2
    • Parking features: Circular Driveway, Golf Cart Garage
    • Attached garage spaces: 2
    • Has uncovered spaces: Yes
    Features
    • Levels: Two
    • Stories: 2
    • Exterior features: Balcony, Irrigation System, Outdoor Grill, Rain Gutters
    • Has private pool: Yes
    • Pool features: Heated, In Ground, Lighting, Self Cleaning
    • Spa features: Heated, In Ground
    • Has view: Yes
    • View description: Pool
    • Waterfront features: Lake Privileges
    • Body of water: LAKE BUTLER CHAIN OF LAKES
    Lot
    • Size: 0.54 Acres
    • Features: Landscaped, Near Golf Course
    Details
    • Parcel number: 162328389900070
    • Zoning: P-D
    • Special conditions: None

    Construction

    Type & style
    • Home type: SingleFamily
    • Property subtype: Single Family Residence
    Materials
    • Block, Stucco
    • Foundation: Block, Slab
    • Roof: Tile
    Condition
    • New construction: No
    • Year built: 1986

    Utilities & green energy

    • Sewer: Septic Tank
    • Water: Public
    • Utilities for property: BB/HS Internet Available, Cable Connected, Electricity Connected, Natural Gas Connected, Street Lights, Water Connected

    Community & HOA

    Community
    • Features: Community Boat Ramp, Water Access, Community Mailbox, Gated Community - No Guard, Golf Carts OK, Golf, Playground
    • Security: Gated Community, Security Lights, Security System, Smoke Detector(s)
    • Subdivision: ISLEWORTH
    HOA
    • Has HOA: Yes
    • Amenities included: Cable TV, Playground, Security
    • Services included: 24-Hour Guard, Cable TV, Reserve Fund, Internet, Maintenance Grounds, Maintenance Repairs, Security
    • HOA fee: $1,043 monthly
    • HOA name: Dan O'Connell
    • HOA phone: 407-909-2071
    • Pet fee: $0 monthly
    Location
    • Region: Windermere

    Financial & listing details

    • Price per square foot: $697/sqft
    • Tax assessed value: $1,879,096
    • Annual tax amount: $19,866
    • Date on market: 8/16/2025
    • Listing terms: Cash,Conventional
    • Ownership: Fee Simple
    • Total actual rent: 0
    • Electric utility on property: Yes
    • Road surface type: Paved
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