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5050 ISLEWORTH COUNTRY CLUB Drive
WINDERMERE FL 34786 US

$3,189,000

Active Listing ID O6438618
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4 bed
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3,365 square feet
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5.00 Bath (4 Full , 1 Half)
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Lot: 0.52 Acres
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Single Family Residence

$3,189,000

Active Listing ID O6438618
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5050 ISLEWORTH COUNTRY CLUB Drive Positioned along the 6th fairway of Isleworth Golf & Country Club, this thoughtfully updated single-story residence offers a rare combination of privacy, golf-course views and effortless everyday living. A welcoming circular drive and mature oaks set the stage, while inside, nearly 3, 400 square feet unfolds in a light-filled collection of spaces designed to feel equally comfortable for quiet evenings at home or a house full of guests. Natural light pours through the glass entry into a dramatic foyer with a groin-vaulted ceiling, introducing the architectural character found throughout the home. Arched openings lead into the formal living room, where a striking stone fireplace creates a natural gathering place and walls of glass frame views of the garden and fairway beyond. The formal dining space provides an elegant backdrop for entertaining while remaining connected to the heart of the home. The renovated kitchen is both inviting and exceptionally functional, featuring a professional-style gas range, integrated appliances and a 40-bottle wine refrigerator. Custom cabinetry, marble countertops and a distinctive tile range hood complete the space, while additional cabinetry flows seamlessly into the family room to create a built-in entertainment center. Natural light reflects beautifully across the large-format tile floors, creating a bright, cohesive feel from room to room. The primary suite is privately positioned on the northeast wing, welcoming golden morning light into the space. The retreat features a distinctive dual-bath arrangement-one with a walk-in shower and the other with a freestanding soaking tub-along with a cedar-lined walk-in closet with custom built-ins. Three additional bedrooms provide comfortable accommodations for family and guests, including one with an ensuite bath, while the updated hall bath offers dual sinks and convenient pool access. A separate flex room easily adapts as an office, library, fitness room or additional retreat. Outside, a covered patio with fireplace extends the living space year-round, overlooking the open-air pool and spa with the manicured fairway beyond. A rear motor court, two-car garage and dedicated golf-cart parking complete the property. Recent improvements, including a 2020 slate roof, refreshed exterior paint, renovated kitchen and baths, complement the home's established character. With its single-story footprint, private setting and half-acre golf-course homesite, the opportunity is as compelling as the lifestyle within the gates.

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Property Features

  • Facts
  • Lot Size: 0.52 Acres
  • Property Type: Residential
  • Property Sub-type: Single Family Residence
  • Features
  • Full Bathrooms: 4
  • 1/2 Bathrooms: 1
  • Cooling System: Central Air, Zoned
  • Exterior Finish: Lighting, Rain Gutters, Sprinkler Metered
  • Floor Covering: Tile
  • Roof Type: Tile, Concrete
  • Heating Fuels: Central, Zoned, Electric (Heating)
  • Additional Features
  • Fireplace
  • Patio
  • Pool

School Information

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

Property

  • propertytype: Residential
  • propertysubtype: Single Family Residence
  • listprice: 3189000
  • unparsedaddress: 5050 ISLEWORTH COUNTRY CLUB Drive
  • postalcity: WINDERMERE
  • stateorprovince: FL
  • country: US
  • postalcode: 34786
  • bathroomsfull: 4
  • bathroomshalf: 1
  • bathroomsonequarter: 0
  • bathroomsthreequarter: 0
  • lotsizeacres: 0.52
  • lotsizeunits: Acres
  • lotsizearea: 0.52
  • livingarea: 3365
  • livingareaunits: Square Feet
  • latitude: 28.490873
  • longitude: -81.519346
  • listagentfullname: Toni Cafferty
  • listagentemail: toni.cafferty@compass.com
  • listagentkey: 3yd-MFRMLSFL-261215231
  • listagentmlsid: 261215231
  • listagentpreferredphone: 9044492184
  • listagentofficephone: 9044492184
  • listofficekey: 3yd-MFRMLSFL-261020334
  • listofficemlsid: 261020334
  • 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: 1987
  • listingcontractdate: 2026-08-28
  • listagentfax: 7867333644
  • listagenturl: http://www.ToniMarieProperties.com
  • countyorparish: Orange
  • parcelnumber: 16-23-28-3899-00-410
  • elementaryschool: Windermere Elem
  • highschool: Olympia High
  • appliances: Dishwasher, Disposal, Dryer, Gas Water Heater, Microwave, Range, Range Hood, Refrigerator, Tankless Water Heater, Washer, Water Softener, Wine Refrigerator
  • cooling: Central Air, Zoned
  • constructionmaterials: Block, Stucco
  • flooring: Tile
  • heating: Central, Zoned, Electric (Heating)
  • fireplaceyn: True
  • transactiontype: ForSale
  • storiestotal: 1
  • parkingtotal: 0
  • parkingfeatures: Driveway, Garage, Open, Golf Cart, Oversize
  • roof: Tile, Concrete
  • view: Golf Course
  • waterfrontyn: False
  • franchiseaffiliation: None
  • interiorfeatures: Built-in Features, Central Vaccum, Eat-in Kitchen, High Ceilings, Kitchen/Family Room Combo, Primary Bedroom Main Floor, Solid Wood Cabinets, Stone Counters, Walk-In Closet(s), Window Treatments
  • exteriorfeatures: Lighting, Rain Gutters, Sprinkler Metered
  • windowfeatures: Drapes, Tinted Windows, Blinds
  • rooms: Bedroom 2, Laundry Room, Bedroom 1, Dining Room, Family Room, Bedroom 3, Bathroom 4, Den, Bedroom 4, Bathroom 5, Bathroom 3, Bathroom 1, Laundry Room, Bathroom 2
  • utilities: Cable Available
  • patioandporchfeatures: Porch
  • dock: False
  • poolprivateyn: True
  • spayn: True
  • fencing: Fenced
  • internetaddressdisplayyn: True
  • internetautomatedvaluationdisplayyn: False
  • internetconsumercommentyn: False
  • location: -81.51935, 28.490873
  • customfields: {"AdditionalInformation":{}, "AlternatePrices":[], "BrokerName":"Compass", "BuilderEmail":null, "BuilderFax":null, "BuilderPhone":null, "City":null, "Country":null, "CustomSourceId":null, "Expenses":[], "GeocodeOptions":null, "LeadRoutingEmail":"toni.cafferty@compass.com", "ListBrokerageCity":"FL", "ListBrokerageCountry":"US", "ListBrokerageEmail":"brokerfl@compass.com", "ListBrokerageLogoUrl":null, "ListBrokerageName":"Compass", "ListBrokeragePhone":"(305) 851-2820", "ListBrokeragePostalCode":"33139", "ListBrokerageStateOrProvince":"FL", "ListBrokerageUnitNumber":"7th Floor", "ListBrokerageUnparsedAddress":"605 Lincoln Road", "ListBrokerageWebsiteUrl":"https://www.compass.com/", "ListOfficeAddress1":"851 W Morse Blvd ", "ListOfficeAddress2":"7th Floor", "ListOfficeBrokerMlsId":"261020334", "ListOfficeCity":"Winter Park", "ListOfficeCountry":"US", "ListOfficeEmail":"brokerfl@compass.com", "ListOfficePostalCode":"32789", "ListOfficeStateOrProvince":"FL", "ListPriceCurrencyType":"USD", "ListingTitle":"Residential, WINDERMERE, FL", "ListingURL":"https://www.realtor.com/realestateandhomes-detail/5050-Isleworth-Country-Club-Dr_Windermere_FL_34786_M63939-62299?f=listhub&s=MFRMLSFL&m=O6438618&c=rexren", "MLSModificationTimestamp":"2026-09-04 12:46:09", "Neighborhoods":[{"Description":null, "Name":"ISLEWORTH"}], "PostalCode":null, "RoomCount":13, "StateOrProvince":null, "Taxes":[{"TaxAnnualAmount":28793, "TaxDescription":"ISLEWORTH 16/118 LOT 41", "TaxYear":"2025"}], "UnitNumber":null, "UnparsedAddress":null}
Listing Changed: 9/4/2026 12:53:15 PM GMT
Source Updated Date: 9/5/2026 6:54:38 PM GMT

Courtesy of: Toni Cafferty, COMPASS FLORIDA LLC, toni.cafferty@compass.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.