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For sale by owner
  • $650,000

    5232 Winding Way, Sarasota, FL 34242

    3beds
    1,430sqft
    : 
    $4,122/mo
    Get pre-qualified
    SingleFamily
    Built in 1963
    9,000 Square Feet Lot
    $-- Zestimate®
    $455/sqft
    $35/mo HOA

    What's special

    Caged poolBlock structureKey west roof
    Reduced to $650,000. Now accepting pre-listing offers on an amazing Siesta Key property at 5232 Winding Way, Siesta Key, FL 34242. Your opportunity to live on one of the most popular Barrier Islands on the west coast of Florida walking distance from the Gulf and Siesta Beach. Trip Advisor just named Siesta Beach the #1 Beach in the United States and the #4 Beach in the world. Sadly, the interior of this block house was affected by hurricane Helene and it is being offered AS/IS for $649,000, the appraised value of the property. I’m told homes in this subdivision rent during the season for between $4000-$6000 per month making this property a premium investment. In addition, the protected canopy road around this small subdivision was just graded and paved this year. NOTE: We are not able to provide special purchase terms on this property. The existing structure on the property is a 3-bedroom 2-bath 1400+ square-foot home on a 75x100 foot lot with a caged pool. Both the block structure and Key West roof are considered to be structurally sound. The inside is completely framed. Drywall from the floor to about 4 feet high has been removed. Floors are tile and Terrazzo. The property is dotted with lots of tropical foliage including 37 palm trees and the backyard is adjacent to Glebe Park. The park includes a concession stand with restrooms, soccer fields, a baseball field, playground, basketball court, and a shell walking trail, which my wife and I used often. To make an offer, ask questions or tour the inside please contact owner, Trebor Britt at 941-320-4309.
    What the owner loves about this home
    My late wife always felt living in this home was living in paradise this side of heaven.
    31 days
    |
    1,702
    |
    90
    |
    Listed by:

    Property Owner (941) 320-4309

    This property is for sale by owner and Zillow, Inc. is displaying it at the owner's request. It is not subject to a listing agreement with Zillow, Inc. or its affiliates.

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 3
      • Bathrooms: 2
      • Full bathrooms: 2
      Interior area
      • Total interior livable area: 1,430 sqft

      Property

      Lot
      • Size: 9,000 Square Feet

      Construction

      Type & style
      • Home type: SingleFamily
      Condition
      • New construction: No
      • Year built: 1963

      Community & HOA

      HOA
      • Has HOA: Yes
      • HOA fee: $35 monthly
      Location
      • Region: Sarasota

      Financial & listing details

      • Price per square foot: $455/sqft
      • Date on market: 7/27/2026

        Estimated market value

        Not available

        Estimated sales range

        Not available

        $4,601/mo

        Price history

        DateEventPrice
        7/27/2026Listed for sale$650,000$455/sqft
        Source: Owner Report a problem
        2/8/2026Listing removed--
        Source: Owner Report a problem
        11/10/2025Listed for sale$650,000$455/sqft
        Source: Owner Report a problem

        Public tax history

        Tax history is unavailable.

        Monthly payment

        Est. payment

        Payment breakdown

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        All calculations are estimates and provided by Zillow, Inc. for informational purposes only. Actual amounts may vary.
        HOA fees may include property taxes on listings classified as Co-Ops. Contact the listing agent and/or owner for fee details.
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        Climate risks

        Neighborhood: 34242

        Getting around

        1 / 100
        Car-Dependent
        0 / 100
        No Nearby Transit
        47 / 100
        Somewhat Bikeable

        Nearby schools

        GreatSchools rating

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