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Sold for $630,000
    • $630,000

    5239 WINDING WAY, SARASOTA, FL 34242

    3beds
    1,512sqft
    Single Family Residence
    Built in 1958
    9,100 Square Feet Lot
    $1,000,300 Zestimate®
    $417/sqft
    $5,669 Estimated rent

    Home value

    $1,000,300

    $890,000 - $1.12M

    $5,669/mo

    Zestimate® history
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    What's special

    Rear waterPeninsula islandHeated poolLarge pantryLush treesPerimeter privacy fenceLarge backyard
    ***PRICE IMPROVMENT*** ***PRICE IMPROVEMET*** Discover your own private oasis at 5239 Winding Way, just minutes from Siesta Beach. Come and see for yourself this lovely and charming home that is an absolute MUST SEE! Nestled in a canopy-protected neighborhood, this property features a spacious open floor plan that connects the kitchen and living areas, creating a perfect space for entertaining friends and family. The kitchen is fully equipped with a large pantry, ceiling-to-counter tiled backsplash, and a peninsula island. The living room is filled with natural lighting from the numerous windows, and features custom built-in shelves, a tongue and groove ceiling, ship lap paneling that makes the space feel inviting and cozy. The primary bedroom is filled with natural light and boasts two large windows. The primary bathroom is equally impressive with marble tile shower surround, penny tile shower floor and frameless glass shower frame. The secondary bedrooms are spacious and quaint. The large backyard and heated pool make outdoor events a breeze, and the perimeter privacy fence, lush trees, and rear water provide ultimate privacy. Siesta Key, is an 8-mile-long island located just a short bridge crossing west of Sarasota, offers stunning quartz-sand beaches and a plethora of outdoor recreational activities – from fishing to parasailing.

    Zillow last checked:

    Listing updated:

    Listed by:

    Brian Cirillo 321-231-1068,

    BALDWIN PARK REALTY LLC 407-986-9800

    Bought with:

    Brian Cirillo, 577152

    BALDWIN PARK REALTY LLC

    Source: Stellar MLS,MLS#: O6278642MLS LogoOriginating MLS: Orlando Regional

    Facts & features

    Interior

    Bedrooms & bathrooms
    • Bedrooms: 3
    • Bathrooms: 2
    • Full bathrooms: 2
    Rooms
    • Room types: Den/Library/Office
    Primary bedroom
    • Features: Built-in Closet
    • Level: First
    • Area: 156 Square Feet
    • Dimensions: 12x13
    Bedroom 2
    • Features: Built-in Closet
    • Level: First
    • Area: 132 Square Feet
    • Dimensions: 11x12
    Bedroom 3
    • Features: Built-in Closet
    • Level: First
    • Area: 154 Square Feet
    • Dimensions: 14x11
    Primary bathroom
    • Level: First
    • Area: 35 Square Feet
    • Dimensions: 5x7
    Bathroom 2
    • Level: First
    • Area: 81 Square Feet
    • Dimensions: 9x9
    Dining room
    • Level: First
    • Area: 154 Square Feet
    • Dimensions: 11x14
    Foyer
    • Level: First
    • Area: 105 Square Feet
    • Dimensions: 5x21
    Kitchen
    • Level: First
    • Area: 132 Square Feet
    • Dimensions: 11x12
    Laundry
    • Level: First
    • Area: 42 Square Feet
    • Dimensions: 7x6
    Living room
    • Level: First
    • Area: 272 Square Feet
    • Dimensions: 17x16
    Heating
    • Electric
    Cooling
    • Central Air
    Appliances
    • Included: Oven, Dishwasher, Disposal, Dryer, Microwave, Range, Range Hood, Refrigerator, Washer
    • Laundry: Inside, Laundry Room
    Features
    • Built-in Features, Cathedral Ceiling(s), Ceiling Fan(s), Crown Molding, High Ceilings, Living Room/Dining Room Combo, Open Floorplan
    • Flooring: Luxury Vinyl
    • Doors: French Doors
    • Has fireplace: Yes
    • Fireplace features: Electric, Family Room
    Interior area
    • Total structure area: 1,912
    • Total interior livable area: 1,512 sqft

    Property

    Parking
    • Total spaces: 2
    • Parking features: Covered
    • Carport spaces: 2
    Features
    • Levels: One
    • Stories: 1
    • Exterior features: Awning(s), Other
    • Has private pool: Yes
    • Pool features: Gunite, Heated, In Ground
    • Fencing: Fenced
    • Has view: Yes
    • View description: Garden, Trees/Woods, Water, Pond
    • Has water view: Yes
    • Water view: Water,Pond
    • Waterfront features: Lake Front, Pond
    Lot
    • Size: 9,100 Square Feet
    • Residential vegetation: Mature Landscaping, Trees/Landscaped
    Details
    • Parcel number: 0082010056
    • Zoning: RSF3
    • Special conditions: None

    Construction

    Type & style
    • Home type: SingleFamily
    • Property subtype: Single Family Residence
    Materials
    • Wood Frame, Wood Frame (FSC Certified), Wood Siding
    • Foundation: Other, Slab
    • Roof: Shingle
    Condition
    • New construction: No
    • Year built: 1958

    Utilities & green energy

    • Sewer: Public Sewer
    • Water: Public
    • Utilities for property: BB/HS Internet Available, Cable Available, Cable Connected, Electricity Available, Electricity Connected, Sewer Connected, Water Available, Water Connected

    Community & HOA

    Community
    • Features: Deed Restrictions
    • Pet fee: $0 monthly
    • Subdivision: TWIN OAK POND
    HOA
    • Has HOA: Yes
    • HOA fee: $35 monthly
    Location
    • Region: Sarasota

    Financial & listing details

    • Price per square foot: $417/sqft
    • Tax assessed value: $662,100
    • Annual tax amount: $10,388
    • Date on market: 2/7/2025
    • Cumulative days on market: 69 days
    • Listing terms: Cash,Conventional,VA Loan
    • Ownership: Fee Simple
    • Total actual rent: 0
    • Electric utility on property: Yes
    • Road surface type: Paved

    Price history

    DateEventPrice
    4/30/2025Sold$630,000-21.2%$417/sqft
    Source: Stellar MLS #O6278642 Report a problem
    4/17/2025Pending sale$799,000$528/sqft
    Source: Stellar MLS #O6278642 Report a problem
    4/8/2025Price change$799,000-8.2%$528/sqft
    Source: Stellar MLS #O6278642 Report a problem
    3/19/2025Price change$870,000-7.3%$575/sqft
    Source: Stellar MLS #O6278642 Report a problem
    2/7/2025Listed for sale$939,000-21.1%$621/sqft
    Source: Stellar MLS #O6278642 Report a problem
    8/14/2024Listing removed--
    Source: Stellar MLS #O6170281 Report a problem
    2/14/2024Pending sale$1,189,900$787/sqft
    Source: Stellar MLS #O6170281 Report a problem
    1/19/2024Listed for sale$1,189,900-6.7%$787/sqft
    Source: Stellar MLS #O6170281 Report a problem
    1/12/2024Listing removed--
    Source: Stellar MLS #A4590359 Report a problem
    12/19/2023Price change$1,274,900-3.8%$843/sqft
    Source: Stellar MLS #A4590359 Report a problem
    11/22/2023Listed for sale$1,324,900+94%$876/sqft
    Source: Stellar MLS #A4590359 Report a problem
    12/3/2020Listing removed$6,000$4/sqft
    Source: ASCENDIA REAL ESTATE #A4465647 Report a problem
    4/22/2020Listed for rent$6,000$4/sqft
    Source: ASCENDIA REAL ESTATE #A4465647 Report a problem
    2/7/2020Listing removed$6,000$4/sqft
    Source: ASCENDIA REAL ESTATE #A4426534 Report a problem
    1/24/2020Sold$683,000-2.3%$452/sqft
    Source: Stellar MLS #A4455170 Report a problem
    1/24/2020Listed for sale$699,000$462/sqft
    Source: KELLER WILLIAMS CLASSIC GROUP #A4455170 Report a problem
    1/8/2020Pending sale$699,000$462/sqft
    Source: KELLER WILLIAMS CLASSIC GROUP #A4455170 Report a problem
    1/6/2020Listed for sale$699,000+6.6%$462/sqft
    Source: KELLER WILLIAMS CLASSIC GROUP #A4455170 Report a problem
    2/5/2019Listed for rent$6,000$4/sqft
    Source: ASCENDIA REAL ESTATE #A4426534 Report a problem
    11/30/2018Sold$655,900-0.6%$434/sqft
    Source: Public Record Report a problem
    10/21/2018Pending sale$659,900$436/sqft
    Source: Coldwell Banker Residential Real Estate - Sarasota Downtown #A4415304 Report a problem
    10/10/2018Price change$659,900-10.7%$436/sqft
    Source: Coldwell Banker Residential Real Estate - Sarasota Downtown #A4415304 Report a problem
    10/5/2018Listed for sale$739,000+55.6%$489/sqft
    Source: COLDWELL BANKER RES R E #A4415304 Report a problem
    12/1/2017Sold$475,000-4.6%$314/sqft
    Source: Public Record Report a problem
    10/28/2017Listed for sale$498,000+4.8%$329/sqft
    Source: ROSEBAY INTERNATIONAL, INC #A4200024 Report a problem
    5/10/2013Sold$475,000$314/sqft
    Source: Public Record Report a problem

    Public tax history

    YearProperty taxesTax assessment
    2025$8,252 -20.6%$662,100 -25.4%
    2024$10,388 +2.9%$887,549 +3%
    2023$10,096 +2.4%$861,698 +3%
    2022$9,858 +28.4%$836,600 +41.1%
    2021$7,680 +19.7%$592,900 +31.5%
    2020$6,415 +16.7%$451,000 +10%
    2019$5,498 $410,000 +11.4%
    2018$5,498 +21.9%$368,100 +4.8%
    2017$4,509 -8.9%$351,200 -2.4%
    2016$4,951 $359,700 +4.2%
    2015$4,951 $345,300 +86.2%
    2014$4,951 +106.5%$185,434 -29.7%
    2013$2,397 +2.5%$263,700 +44.6%
    2012$2,339 +4.7%$182,334 +3%
    2011$2,234 -1%$177,023 +1.5%
    2010$2,256 +10%$174,407 +2.7%
    2009$2,051 $169,822 +0.1%
    2008$2,051 -4.1%$169,652 +3%
    2007$2,138 $164,711 +2.5%
    2006-- $160,694 +3%
    2005-- $156,014 +3%
    2004$2,206 -0.8%$151,470 +1.9%
    2003$2,224 +1.6%$148,646 +2.4%
    2002$2,189 +6.9%$145,162 +1.6%
    2001$2,047 +2.1%$142,876 +3%
    2000$2,004 $138,715
    Find assessor info on the county website

    Neighborhood: 34242

    Nearby homes

    Nearby schools

    GreatSchools rating
    Schools provided by the listing agent
    • Elementary: Phillippi Shores Elementary
    • Middle: Brookside Middle
    • High: Sarasota High

    Source: Stellar MLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.

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    Estimated market value
    $1,000,300
    Get a cash offer in 3 minutes
    Find out how much your home could sell for in as little as 3 minutes with a no-obligation cash offer.
    Estimated market value
    $1,000,300

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