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9731 CHESTNUT RIDGE DRIVE
WINDERMERE FL 34786 US

$3,400,000

Active Listing ID O6336655
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4 bed
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4.00 Bath (4 Full)
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Lot: 0.54 Acres
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Single Family Residence

$3,400,000

Active Listing ID O6336655
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9731 CHESTNUT RIDGE DRIVE 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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Property Features

  • Facts
  • Lot Size: 0.54 Acres
  • Property Type: Residential
  • Property Sub-type: Single Family Residence
  • Features
  • Full Bathrooms: 4
  • Cooling System: Central Air, Zoned
  • Exterior Finish: Paved, Balcony, Outdoor Grill, Rain Gutters, Pool, Security Lights
  • Floor Covering: Marble
  • Roof Type: Tile
  • Heating Fuels: Central, Electric (Heating), Natural Gas
  • Additional Features
  • Pool

School Information

  • School
  • Windermere Elem(Elementary)
  • Chain of Lakes Middle(MiddleSchool)
  • Olympia High(HighSchool)

Property

  • propertytype: Residential
  • propertysubtype: Single Family Residence
  • listprice: 3400000
  • unparsedaddress: 9731 CHESTNUT RIDGE DRIVE
  • postalcity: WINDERMERE
  • stateorprovince: FL
  • country: US
  • postalcode: 34786
  • bathroomsfull: 4
  • bathroomshalf: 0
  • bathroomsonequarter: 0
  • bathroomsthreequarter: 0
  • lotsizeacres: 0.54
  • lotsizeunits: Acres
  • lotsizearea: 0.54
  • livingarea: 4877
  • livingareaunits: Square Feet
  • latitude: 28.492813
  • longitude: -81.522664
  • listagentfullname: Monica Lochmandy
  • listagentemail: mlochmandy@isleworth.com
  • listagentkey: 3yd-MFRMLSFL-261067417
  • listagentmlsid: 261067417
  • listagentpreferredphone: 4072306888
  • listagentofficephone: 4079099000
  • listofficekey: 3yd-MFRMLSFL-261013260
  • listagentstatelicense: 3237911
  • listofficemlsid: 261013260
  • disclaimer: Copyright © 2025 Stellar MLS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.
  • sourcesystemid: MFRMLSFL
  • yearbuilt: 1986
  • listingcontractdate: 2025-07-30
  • listagenturl: https://isleworth.com/
  • countyorparish: Orange
  • parcelnumber: 16-23-28-3899-00-070
  • elementaryschool: Windermere Elem
  • highschool: Olympia High
  • appliances: Dishwasher, Dryer, Garbage Disposer, Ice Maker, Microwave, Range, Refrigerator, Trash Compactor, Washer, Water - Purifier, Water - Softener
  • cooling: Central Air, Zoned
  • constructionmaterials: Block, Stucco
  • flooring: Marble
  • heating: Central, Electric (Heating), Natural Gas
  • fireplaceyn: False
  • transactiontype: ForSale
  • storiestotal: 0
  • parkingtotal: 0
  • parkingfeatures: Driveway, Garage, Garage - Attached, Golf Cart
  • roof: Tile
  • waterfrontyn: False
  • interiorfeatures: Cathedral Ceiling(s), Ceiling Fans(s), Kitchen/Family Room Combo, Primary Bedroom Main Floor, Stone Counters, Thermostat, Walk-in Closet(s)
  • exteriorfeatures: Paved, Balcony, Outdoor Grill, Rain Gutters, Pool, Security Lights
  • architecturalstyle: Other
  • rooms: Bathroom 1, Bathroom 2, Bathroom 3, Bathroom 4, Bedroom 1, Bedroom 2, Bedroom 3, Bedroom 4, Dining Room, Family Room, Kitchen, Living Room, Office
  • securityfeatures: Gated Community, Security Lighting, Security System, Smoke Detector(s)
  • dock: False
  • poolprivateyn: True
  • spayn: False
  • fencing: Gate
  • internetaddressdisplayyn: True
  • internetautomatedvaluationdisplayyn: True
  • internetconsumercommentyn: False
  • location: -81.52267, 28.492813
  • customfields: {"AdditionalInformation":{}, "AlternatePrices":[], "BrokerName":"Isleworth Realty, LLC", "BuilderEmail":null, "BuilderFax":null, "BuilderPhone":null, "City":null, "Country":null, "Expenses":[{"ExpenseCategory":"Home Owner Assessments Fee", "ExpenseFrequency":"Monthly", "ExpenseValue":1043}], "GeocodeOptions":null, "LeadRoutingEmail":"mlochmandy@isleworth.com", "ListBrokerageCity":"Windermere", "ListBrokerageCountry":"US", "ListBrokerageEmail":"sales@isleworth.com", "ListBrokerageLogoUrl":null, "ListBrokerageName":"Isleworth Realty, LLC", "ListBrokeragePhone":"(407) 876-0111", "ListBrokeragePostalCode":"34786", "ListBrokerageStateOrProvince":"FL", "ListBrokerageUnitNumber":null, "ListBrokerageUnparsedAddress":"9350 Conroy Windermere Road", "ListBrokerageWebsiteUrl":"https://isleworth.com/", "ListOfficeAddress1":"9350 Conroy Windermere Rd", "ListOfficeAddress2":null, "ListOfficeBrokerMlsId":null, "ListOfficeCity":"Windermere", "ListOfficeCountry":"US", "ListOfficeEmail":"sales@isleworth.com", "ListOfficePostalCode":"34786", "ListOfficeStateOrProvince":"FL", "ListPriceCurrencyType":"USD", "ListingTitle":"Single Family Residence - WINDERMERE, FL", "ListingURL":"https://www.realtor.com/realestateandhomes-detail/9731-Chestnut-Ridge-Dr_Windermere_FL_34786_M62409-45375?f=listhub&s=MFRMLSFL&m=O6336655&c=rexren", "MLSModificationTimestamp":"2025-08-16T19:26:10Z", "Neighborhoods":[], "PostalCode":null, "RawPropertySubType":"Single Family Residence", "RawPropertyType":"Residential", "RoomCount":10, "StateOrProvince":null, "Taxes":[{"TaxAnnualAmount":19866.86, "TaxDescription":null, "TaxYear":"2024"}], "UnitNumber":null, "UnparsedAddress":null}
Listing Changed: 10/23/2025 11:12:34 PM GMT
Source Updated Date: 12/6/2025 6:41:39 AM GMT

Courtesy of: Monica Lochmandy, ISLEWORTH REALTY LLC, mlochmandy@isleworth.com

Copyright © 2025 Stellar MLS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.