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5138 FAIRWAY OAKS DR
WINDERMERE FL 34786 US

$5,500,000

Active Listing ID O6401757
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4 bed
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5.00 Bath (5 Full)
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Lot: 0.50 Acres
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Single Family Residence

$5,500,000

Active Listing ID O6401757
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5138 FAIRWAY OAKS DR Set along Isleworth’s signature 12th fairway, this fully reimagined estate captures the essence of refined golf course living within the renowned Isleworth Golf & Country Club—recognized among the finest private club communities in the world. Encompassing more than 4, 300 square feet, the single-story residence has been completely transformed inside and out. Thoughtfully redesigned interiors showcase all-new flooring throughout, beautifully renovated bedrooms and baths, and a striking glass-enclosed wine tower serving as a true centerpiece that is both functional and an unforgettable conversation element anchoring the main living spaces. Every detail throughout the home has been elevated, from designer lighting installations that bring character and sophistication to each room, to the seamless flow of living and entertaining spaces. The kitchen is a true showpiece, featuring all-new appliances—including a striking black range with matching hood, refrigerator, and microwave—all accented with elegant gold detailing for a bold, designer-forward statement. Custom cabinetry is paired with exquisite countertops, highlighted by a dramatic waterfall-edge island that anchors the space and seamlessly blends everyday functionality with elevated, modern style.The outdoor living area features a reimagined pool and all-new pool deck creating a resort-style setting, perfectly positioned to take in breathtaking sunsets over the golf course and water. The half-acre homesite has been thoughtfully cleared and fenced to maximize both privacy and panoramic views, offering an exceptional backdrop for everyday living and entertaining alike. Framed by the fairways, the residence captures views of Lake Brenda - also known as Hourglass Pond - a small, privately maintained 10-acre water body that serves as a peaceful and picturesque part of the community setting. Additional features include a home office, in-home laundry room, and a three-car garage. Residents of Isleworth enjoy an unparalleled lifestyle surrounded by the Butler Chain of Lakes, with access to world-class golf, dining, and amenities, all just moments from Central Florida’s premier shopping, dining, and entertainment destinations.

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Property Features

  • Facts
  • Lot Size: 0.50 Acres
  • Property Type: Residential
  • Property Sub-type: Single Family Residence
  • Features
  • Full Bathrooms: 5
  • Cooling System: Central Air, Zoned
  • Exterior Finish: French Doors, Lighting, Rain Gutters, Pool
  • Floor Covering: Tile
  • Roof Type: Tile
  • Heating Fuels: Electric (Heating), Fireplace(s), Natural Gas
  • Additional Features
  • Fireplace
  • Pool

School Information

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

Property

  • propertytype: Residential
  • propertysubtype: Single Family Residence
  • listprice: 5500000
  • unparsedaddress: 5138 FAIRWAY OAKS DR
  • postalcity: WINDERMERE
  • stateorprovince: FL
  • country: US
  • postalcode: 34786
  • bathroomsfull: 5
  • bathroomshalf: 0
  • bathroomsonequarter: 0
  • bathroomsthreequarter: 0
  • lotsizeacres: 0.5
  • lotsizeunits: Acres
  • lotsizearea: 0.5
  • livingarea: 4330
  • livingareaunits: Square Feet
  • latitude: 28.484272
  • longitude: -81.530447
  • 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 © 2026 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: 1994
  • listingcontractdate: 2026-04-23
  • listagenturl: https://isleworth.com/
  • countyorparish: Orange
  • parcelnumber: 16-23-28-3899-01-080
  • elementaryschool: Windermere Elem
  • highschool: Olympia High
  • appliances: Dishwasher, Dryer, Freezer, Garbage Disposer, Ice Maker, Microwave, Range, Refrigerator, Refrigerator - Wine Storage, Washer
  • cooling: Central Air, Zoned
  • constructionmaterials: Block, Stucco
  • flooring: Tile
  • heating: Electric (Heating), Fireplace(s), Natural Gas
  • fireplaceyn: True
  • transactiontype: ForSale
  • storiestotal: 0
  • parkingtotal: 0
  • parkingfeatures: Driveway, Garage, Garage - Attached
  • roof: Tile
  • waterfrontyn: False
  • interiorfeatures: Built-in Features, Ceiling Fans(s), Crown Molding, Eat-in Kitchen, Kitchen/Family Room Combo, Living Room/Dining Room Combo, Solid Surface Counters, Stone Counters, Thermostat, Walk-in Closet(s)
  • exteriorfeatures: French Doors, Lighting, Rain Gutters, Pool
  • architecturalstyle: New Traditional
  • rooms: Bathroom 1, Bathroom 2, Bathroom 3, Bathroom 4, Bathroom 5, Bedroom 1, Bedroom 2, Bedroom 3, Bedroom 4, Dining Room, Family Room, Kitchen, Living Room, Office
  • securityfeatures: Gated Community, Security Gate
  • dock: False
  • poolprivateyn: True
  • spayn: False
  • fencing: Gate
  • internetaddressdisplayyn: True
  • internetautomatedvaluationdisplayyn: True
  • internetconsumercommentyn: False
  • location: -81.53045, 28.484272
  • 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":1224}], "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, Traditional - WINDERMERE, FL", "ListingURL":"https://www.realtor.com/realestateandhomes-detail/5138-Fairway-Oaks-Dr_Windermere_FL_34786_M62650-56440?f=listhub&s=MFRMLSFL&m=O6401757&c=rexren", "MLSModificationTimestamp":"2026-04-25T08:25:09Z", "Neighborhoods":[], "PostalCode":null, "RawPropertySubType":"Single Family Residence", "RawPropertyType":"Residential", "RoomCount":13, "StateOrProvince":null, "Taxes":[{"TaxAnnualAmount":19599.37, "TaxDescription":null, "TaxYear":"2025"}], "UnitNumber":null, "UnparsedAddress":null}
Listing Changed: 4/27/2026 8:33:53 PM GMT
Source Updated Date: 5/4/2026 6:54:04 PM GMT

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

Copyright © 2026 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.