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Off market
  • $629,700

    5255 Winding Way, Sarasota, FL 34242

    2beds
    1,300sqft
    Single Family Residence
    Built in ----
    -- sqft lot
    $629,700 Zestimate®
    $484/sqft
    $3,136 Estimated rent

    Home value

    $629,700

    $567,000 - $699,000

    $3,136/mo

    Zestimate® history
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    What's special

    Fully furnishedBig lanaiWood burning fireplaceTile floorsNew bathroomsNew kitchenLarge screened porch

    Available 7/1/2026 Vacation rental or Long terms flexible lease options. Fully furnished. 5 min bike ride from the #1 beach in the country New Kitchen, New Bathrooms. One of a kind cottage. Pond with fountain in the backyard, New Kitchen, new bathrooms. Can be unfurnished for long term tenancy. Brand New Ice cold A/C. 2 solar Tubes. Big Lanai Walk to the beach. Sweetheart house on Twin Oak Pond. Sit in front of your fireplace, watch and listen to the fountain in the pond outside your window. Ground level 2 bedrooms and 2 full baths, large screened porch, tile floors, open kitchen and wood burning fireplace. Pet friendly. Deal with the owner directly. Not a management company. $4200 30 day min $3500. 12 month lease Shorter than 30 day is available at a higher rate. Tenant is responsible for Power bill Water / sewer / trash Internet when renting long term. Pet Fee if applicable

    This property is off market, which means it's not currently listed for sale or rent on Zillow. This may be different from what's available on other websites or public sources.

    Zillow last checked:

    Listing updated:

    Source: Zillow Rentals

    Facts & features

    Interior

    Bedrooms & bathrooms
    • Bedrooms: 2
    • Bathrooms: 2
    • Full bathrooms: 2
    Heating
    • Heat Pump
    Cooling
    • Central Air
    Appliances
    • Included: Dishwasher, Freezer, Microwave, Oven, Refrigerator
    • Laundry: Shared
    Features
    • Flooring: Tile
    • Furnished: Yes
    Interior area
    • Total interior livable area: 1,300 sqft

    Property

    Parking
    • Parking features: Attached, Off Street
    • Has attached garage: Yes
    • Details: Contact manager
    Accessibility
    • Accessibility features: Disabled access
    Features
    • Exterior features: Bicycle storage, Just minutes away from siesta beach
    Details
    • Parcel number: 0082010044

    Construction

    Type & style
    • Home type: SingleFamily
    • Property subtype: Single Family Residence

    Community & neighborhood

    Location
    • Region: Sarasota

    HOA & financial

    Other fees
    • Deposit fee: $3,499

    Other

    Other facts
    • Available date: 07/01/2026

    Price history

    DateEventPrice
    5/1/2026Listing removed$3,499$3/sqft
    Source: Zillow Rentals Report a problem
    2/2/2026Price change$3,499-16.7%$3/sqft
    Source: Zillow Rentals Report a problem
    1/8/2026Price change$4,199+27.3%$3/sqft
    Source: Zillow Rentals Report a problem
    12/24/2025Price change$3,299-5.7%$3/sqft
    Source: Zillow Rentals Report a problem
    11/21/2025Price change$3,499-7.9%$3/sqft
    Source: Zillow Rentals Report a problem
    11/13/2025Price change$3,799-5%$3/sqft
    Source: Zillow Rentals Report a problem
    10/28/2025Price change$3,999-4.8%$3/sqft
    Source: Zillow Rentals Report a problem
    10/22/2025Listed for rent$4,200+5%$3/sqft
    Source: Zillow Rentals Report a problem
    10/13/2025Listing removed$3,999$3/sqft
    Source: Zillow Rentals Report a problem
    9/29/2025Price change$3,999-4.8%$3/sqft
    Source: Zillow Rentals Report a problem
    9/3/2025Listed for rent$4,200+44.9%$3/sqft
    Source: Zillow Rentals Report a problem
    6/20/2024Listing removed--
    Source: Zillow Rentals Report a problem
    5/31/2024Price change$2,899-2.6%$2/sqft
    Source: Zillow Rentals Report a problem
    5/21/2024Price change$2,975-4%$2/sqft
    Source: Zillow Rentals Report a problem
    5/20/2024Price change$3,100-1.6%$2/sqft
    Source: Zillow Rentals Report a problem
    5/10/2024Listed for rent$3,150$2/sqft
    Source: Zillow Rentals Report a problem
    4/30/2024Listing removed--
    Source: Zillow Rentals Report a problem
    4/29/2024Price change$3,150-1.6%$2/sqft
    Source: Zillow Rentals Report a problem
    4/25/2024Listed for rent$3,200+166.9%$2/sqft
    Source: Zillow Rentals Report a problem
    2/25/2021Listing removed--
    Source: Owner Report a problem
    3/7/2019Listing removed$1,199$1/sqft
    Source: Owner Report a problem
    3/6/2019Listed for rent$1,199$1/sqft
    Source: Owner Report a problem
    12/12/2018Sold$311,100-25%$239/sqft
    Source: Public Record Report a problem
    4/5/2018Sold$415,000-3.3%$319/sqft
    Source: Public Record Report a problem
    2/7/2018Pending sale$429,000$330/sqft
    Source: Michael Saunders & Company - Licensed Real Estate Broker Report a problem
    1/2/2018Listed for sale$429,000+0.9%$330/sqft
    Source: Michael Saunders & Company - Licensed Real Estate Broker Report a problem
    6/22/2015Sold$425,000+39.3%$327/sqft
    Source: Public Record Report a problem
    9/2/2008Sold$305,000$235/sqft
    Source: Public Record Report a problem

    Public tax history

    YearProperty taxesTax assessment
    2025$6,520 -3.6%$503,929 +10%
    2024$6,762 +2.2%$458,117 +10%
    2023$6,620 +8.1%$416,470 +10%
    2022$6,123 +25.3%$378,609 +10%
    2021$4,888 +13.1%$344,190 +10%
    2020$4,322 +9.7%$312,900 +9.4%
    2019$3,939 $285,900 -10.2%
    2018$3,939 -8.9%$318,200 +4.9%
    2017$4,322 +54.7%$303,400 -0.1%
    2016$2,794 $303,700 -2.7%
    2015$2,794 +0.4%$312,200 +46.4%
    2014$2,782 +0.4%$213,265
    2013$2,772 +2.8%$213,265 +1.7%
    2012$2,697 -1.5%$209,700 -2.9%
    2011$2,738 -4.8%$216,000 -2.2%
    2010$2,877 -36.1%$220,900 -13.7%
    2009$4,504 $256,000 -22.3%
    2008$4,504 -27%$329,500 -28.2%
    2007$6,169 $459,200 +171.5%
    2006-- $169,148 +3%
    2005-- $164,221 +3%
    2004$2,315 -0.9%$159,438 +1.9%
    2003$2,335 +1.8%$156,465 +2.4%
    2002$2,295 +7%$152,798 +1.6%
    2001$2,145 +2.2%$150,392 +3%
    2000$2,100 $146,012

    Find assessor info on the county website

    Neighborhood: 34242

    Nearby schools

    GreatSchools rating
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    Estimated market value
    $629,700
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    Estimated market value
    $629,700