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5244 WINDING WAY
SARASOTA FL 34242 US

$1,250,000

Active Listing ID A4669581
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4 bed
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4.00 Bath (4 Full)
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Lot: 0.22 Acres
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Single Family Residence

$1,250,000

Active Listing ID A4669581
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5244 WINDING WAY Expansive Coastal Modern Property in a Serene and Peaceful Setting, Seconds to Siesta Key Beach ** 4 Bedrooms, 4 Full Baths with Detached Studio/ADU above the 3 Car Garage (5 Total Bedrooms, 5 Bathrooms) ** Gorgeous Pool among Lush Native Landscape ** NEW ROOF! There is no better value on Siesta Key for your primary occupancy or 2nd home with opportunities to cash flow this investment. The entire property has been updated with wood-looking vinyl, interior/exterior paint, custom baseboard and trim, contemporary lighting fixtures, modern fans and fresh marcite in the refinished pool. The studio provides new vinyl windows and a mini-split AC unit for energy efficient climate controlling of this private space. You will love the floor plan of both the main house and studio! The main house provides a great room concept with an abundance of joyful natural light and multiple sets of French doors leading to the pool. Each bedroom receives a private bath with 2 primary suites enjoying idyllic views of the pool and tropical landscape. Simply stated, this estate property is meant for hosting large groups, comfortably. Located inside the charming Canopy Roads of Twin Oak, this beach property is private, serene and inspiring. Live by the beach, but away from the noise. The good life is found here

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Property Features

  • Facts
  • Lot Size: 0.22 Acres
  • Property Type: Residential
  • Property Sub-type: Single Family Residence
  • Features
  • Full Bathrooms: 4
  • Cooling System: Central Air, Ductless, Multi Units
  • Exterior Finish: French Doors, Pool
  • Floor Covering: Tile, Tile - Ceramic, Vinyl
  • Roof Type: Shingle
  • Heating Fuels: Central
  • Additional Features
  • Pool

Property

  • propertytype: Residential
  • propertysubtype: Single Family Residence
  • listprice: 1250000
  • unparsedaddress: 5244 WINDING WAY
  • postalcity: SARASOTA
  • stateorprovince: FL
  • country: US
  • postalcode: 34242
  • bathroomsfull: 4
  • bathroomshalf: 0
  • bathroomsonequarter: 0
  • bathroomsthreequarter: 0
  • lotsizeacres: 0.22
  • lotsizeunits: Acres
  • lotsizearea: 0.22
  • livingarea: 2100
  • livingareaunits: Square Feet
  • latitude: 27.275066
  • longitude: -82.548322
  • listagentfullname: Justin Shirley
  • listagentemail: jshir12@aol.com
  • listagentkey: 3yd-MFRMLSFL-281505527
  • listagentmlsid: 281505527
  • listagentpreferredphone: 9414484872
  • listagentofficephone: 9414484872
  • listofficekey: 3yd-MFRMLSFL-281515962
  • listagentstatelicense: 3116512
  • listofficemlsid: 281515962
  • 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: 1967
  • listingcontractdate: 2025-10-23
  • listagenturl: http://www.JustinShirley.com
  • countyorparish: Sarasota
  • parcelnumber: 0082010022
  • appliances: Dishwasher, Dryer, Microwave, Range, Refrigerator, Washer
  • cooling: Central Air, Ductless, Multi Units
  • constructionmaterials: Wood Siding
  • flooring: Tile, Tile - Ceramic, Vinyl
  • heating: Central
  • fireplaceyn: False
  • transactiontype: ForSale
  • storiestotal: 0
  • parkingtotal: 0
  • parkingfeatures: Garage
  • roof: Shingle
  • waterfrontyn: False
  • interiorfeatures: Kitchen/Family Room Combo, Open Floorplan, Solid Surface Counters, Walk-in Closet(s)
  • exteriorfeatures: French Doors, Pool
  • architecturalstyle: Other
  • rooms: Bathroom 1, Bathroom 2, Bathroom 3, Bathroom 4, Bedroom 1, Bedroom 2, Bedroom 3, Bedroom 4, Kitchen, Living Room
  • dock: False
  • poolprivateyn: True
  • spayn: False
  • internetaddressdisplayyn: True
  • internetautomatedvaluationdisplayyn: True
  • internetconsumercommentyn: False
  • location: -82.548325, 27.275066
  • customfields: {"AdditionalInformation":{}, "AlternatePrices":[], "BrokerName":"Shirley International Realty", "BuilderEmail":null, "BuilderFax":null, "BuilderPhone":null, "City":null, "Country":null, "Expenses":[], "GeocodeOptions":null, "LeadRoutingEmail":"jshir12@aol.com", "ListBrokerageCity":"Sarasota", "ListBrokerageCountry":"US", "ListBrokerageEmail":"Justin@JustinShirley.com", "ListBrokerageLogoUrl":"http://brokerlogos.listhub.net/95/270115/20140717152433194.png", "ListBrokerageName":"Shirley International Realty", "ListBrokeragePhone":"(941) 448-4872", "ListBrokeragePostalCode":"34231", "ListBrokerageStateOrProvince":"FL", "ListBrokerageUnitNumber":"#181", "ListBrokerageUnparsedAddress":"2100 Constitution Blvd", "ListBrokerageWebsiteUrl":"http://www.JustinShirley.com", "ListOfficeAddress1":"2100 Constitution Blvd Ste 180", "ListOfficeAddress2":null, "ListOfficeBrokerMlsId":null, "ListOfficeCity":"Sarasota", "ListOfficeCountry":"US", "ListOfficeEmail":"jshir12@aol.com", "ListOfficePostalCode":"34231", "ListOfficeStateOrProvince":"FL", "ListPriceCurrencyType":"USD", "ListingTitle":"Single Family Residence - SARASOTA, FL", "ListingURL":"https://www.realtor.com/realestateandhomes-detail/5244-Winding-Way_Sarasota_FL_34242_M60145-92560?f=listhub&s=MFRMLSFL&m=A4669581&c=rexren", "MLSModificationTimestamp":"2025-10-23T22:19:09Z", "Neighborhoods":[], "PostalCode":null, "RawPropertySubType":"Single Family Residence", "RawPropertyType":"Residential", "RoomCount":3, "StateOrProvince":null, "Taxes":[{"TaxAnnualAmount":9776, "TaxDescription":null, "TaxYear":"2025"}], "UnitNumber":null, "UnparsedAddress":null}
Listing Changed: 10/24/2025 4:08:53 AM GMT
Source Updated Date: 12/14/2025 6:48:19 AM GMT

Courtesy of: Justin Shirley, SHIRLEY INTERNATIONAL REALTY, jshir12@aol.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.