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For sale
    • Price cut: $101K (5/20)
    $949,000

    3435 WINDING OAKS DRIVE #18, LONGBOAT KEY, FL 34228

    3beds
    2,555sqft
    : 
    $8,264/mo
    Get pre-qualified
    Condominium
    Built in 1988
    -- sqft lot
    $-- Zestimate®
    $371/sqft
    $2,167/mo HOA

    What's special

    Quartz countertopsStainless steel appliancesBright white cabinetsAmple pantry storage
    Own your own slice of tropical paradise on Longboat Key with this beautiful two bedroom two and on half bath Villa in the exclusive Winding Oaks Community located behind the gates of Bay Isles Association. Sweeping views of the Longboat Key Club Harbourside Golf Course and a sparkling inland waterway from your primary bedroom and expansive living/dining room combo that both exit through sliders to a fully enclosed wrap around deck to further enhance your tropical lifestyle. Open floor plan with soaring ceilings and enclosed atrium help to maximize the natural light and make the 2,555 sq feet feel even larger. Beautifully updated eat in kitchen with striking tray ceiling, ample pantry storage, bright white cabinets, quartz countertops and stainless steel appliances. Primary owners suite includes an designer walk in closet, updated bath with ceramic tile, walk in shower, double sinks and quartz counter tops. Split layout offers a private guest suite, with walk in closet, updated ensuite bathroom with ceramic tile, walk in shower and quartz counter tops. Large office with desk nook could easily be converted to another bedroom. Laundry room with storage and sink adjacent to large 2 car garage with epoxy floors and storage cabinets. Meticulously maintained, Impact Windows and sliders throughout, low maintenance mature plantings in private enclosed front courtyard. Dog friendly community. Beautiful updated community pool with bathrooms. Beach access via Bay Isles Beach Club which offers a private pavilion with bathrooms, volleyball, picnic tables, grills and ample parking. Low maintenance community where all exteriors and court yards are maintained by the association. Conveniently located mid key, one mile from Publix and CVS and a short drive to the restaurants and shops of St Armand’s and Downtown Sarasota.
    154 days
    |
    282
    |
    9
    |

    Zillow last checked:

    Listing updated:

    Listed by:

    Sean Clark 941-312-1146,

    MICHAEL SAUNDERS & COMPANY 941-383-7591

    Source: Stellar MLS,MLS#: A4680403MLS LogoOriginating MLS: Sarasota - Manatee

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 3
      • Bathrooms: 3
      • Full bathrooms: 2
      • 1/2 bathrooms: 1
      Rooms
      • Room types: Den/Library/Office, Utility Room
      Primary bedroom
      • Features: En Suite Bathroom, Walk-In Closet(s)
      • Level: First
      • Area: 252 Square Feet
      • Dimensions: 18x14
      Bedroom 2
      • Features: En Suite Bathroom, Walk-In Closet(s)
      • Level: First
      • Area: 169 Square Feet
      • Dimensions: 13x13
      Bathroom 1
      • Features: No Closet
      • Level: First
      • Area: 120 Square Feet
      • Dimensions: 12x10
      Bathroom 2
      • Features: Shower No Tub, No Closet
      • Level: First
      • Area: 25 Square Feet
      • Dimensions: 5x5
      Den
      • Features: No Closet
      • Level: First
      • Area: 168 Square Feet
      • Dimensions: 12x14
      Dining room
      • Features: No Closet
      • Level: First
      • Area: 209 Square Feet
      • Dimensions: 11x19
      Kitchen
      • Features: Breakfast Bar, No Closet
      • Level: First
      • Area: 165 Square Feet
      • Dimensions: 11x15
      Laundry
      • Features: No Closet
      • Level: First
      • Area: 50 Square Feet
      • Dimensions: 5x10
      Living room
      • Features: Ceiling Fan(s), No Closet
      • Level: First
      • Area: 304 Square Feet
      • Dimensions: 16x19
      Office
      • Features: No Closet
      • Level: First
      • Area: 126 Square Feet
      • Dimensions: 18x7
      Heating
      • Central, Electric
      Cooling
      • Central Air, Humidity Control
      Appliances
      • Included: Oven, Dishwasher, Disposal, Dryer, Electric Water Heater, Microwave, Range, Refrigerator, Washer
      • Laundry: Inside, Laundry Room
      Features
      • Ceiling Fan(s), Eating Space In Kitchen, Living Room/Dining Room Combo, Open Floorplan, Primary Bedroom Main Floor, Split Bedroom, Tray Ceiling(s)
      • Flooring: Carpet, Tile, Vinyl, Hardwood
      • Doors: Sliding Doors
      • Windows: Blinds, Window Treatments
      • Has fireplace: Yes
      • Fireplace features: Living Room
      • Furnished: Yes
      • Common walls with other units/homes: Corner Unit
      Interior area
      • Total structure area: 3,270
      • Total interior livable area: 2,555 sqft

      Property

      Parking
      • Total spaces: 2
      • Parking features: Garage Door Opener
      • Attached garage spaces: 2
      Features
      • Levels: One
      • Stories: 1
      • Patio & porch: Patio, Rear Porch, Screened
      • Exterior features: Awning(s), Courtyard, Garden, Lighting, Private Entrance, Private Yard
      • Fencing: Masonry
      • Has view: Yes
      • View description: Golf Course, Water, Pond
      • Has water view: Yes
      • Water view: Water,Pond
      • Waterfront features: Gulf/Ocean Front, Bay/Harbor Access, Beach Access, Gulf/Ocean Access, Pond Access
      Lot
      • Size: 13.84 Acres
      Details
      • Parcel number: 0004121018
      • Zoning: MUC1
      • Special conditions: None

      Construction

      Type & style
      • Home type: Condo
      • Property subtype: Condominium
      Materials
      • HardiPlank Type
      • Foundation: Block, Slab
      • Roof: Tile
      Condition
      • New construction: No
      • Year built: 1988

      Utilities & green energy

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

      Community & HOA

      Community
      • Features: Gulf/Ocean Front, Association Recreation - Owned, Buyer Approval Required, Deed Restrictions, Gated Community - Guard, Pool
      • Security: Gated Community, Security Gate, Security System, Security System Leased, Smoke Detector(s)
      • Pet fee: $0 monthly
      • Subdivision: WINDING OAKS
      HOA
      • Has HOA: Yes
      • Amenities included: Pool, Vehicle Restrictions
      • Services included: 24-Hour Guard, Cable TV, Common Area Taxes, Community Pool, Reserve Fund, Fidelity Bond, Maintenance Structure, Maintenance Grounds, Pool Maintenance, Recreational Facilities, Trash
      • HOA fee: $2,167 monthly
      • HOA name: Neil Fleet
      • HOA phone: 941-383-3200
      • Second HOA name: Bay Isle Association
      Location
      • Region: Longboat Key

      Financial & listing details

      • Price per square foot: $371/sqft
      • Tax assessed value: $880,400
      • Annual tax amount: $8,564
      • Date on market: 2/26/2026
      • Cumulative days on market: 155 days
      • Listing terms: Cash,Conventional
      • Ownership: Condominium
      • Total actual rent: 0
      • Electric utility on property: Yes
      • Road surface type: Asphalt

        Estimated market value

        Not available

        Estimated sales range

        Not available

        Not available

        Price history

        DateEventPrice
        5/20/2026Price change$949,000-9.6%$371/sqft
        Source: Stellar MLS #A4680403 Report a problem
        3/24/2026Price change$1,050,000-8.7%$411/sqft
        Source: Stellar MLS #A4680403 Report a problem
        2/26/2026Listed for sale$1,150,000+49%$450/sqft
        Source: Stellar MLS #A4680403 Report a problem
        9/18/2015Sold$772,000-3.4%$302/sqft
        Source: Stellar MLS #A4121123 Report a problem
        4/29/2015Listed for sale$799,000+83.7%$313/sqft
        Source: Coldwell Banker Residential Real Estate - Longboat Key #A4121123 Report a problem
        8/28/1998Sold$435,000$170/sqft
        Source: Public Record Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2025$8,565 +2.5%$702,794 +2.9%
        2024$8,353 +2.1%$682,987 +3%
        2023$8,178 +1.1%$663,094 +3%
        2022$8,087 -1.6%$643,781 +3%
        2021$8,218 -0.8%$625,030 +1.4%
        2020$8,281 -1.5%$616,400 -2.2%
        2019$8,404 $630,423 +8.5%
        2018$8,404 +8.7%$581,200 -0.9%
        2017$7,735 +22.7%$586,500 -0.9%
        2016$6,306 $591,900 +14.5%
        2015$6,306 +0.1%$517,100 +15.5%
        2014$6,300 +2.3%$447,860
        2013$6,160 +4.1%$447,860 +1.7%
        2012$5,915 +4.9%$440,374 +3%
        2011$5,638 -1.3%$427,548 +1.5%
        2010$5,710 +12.7%$421,230 +2.7%
        2009$5,067 $410,156 +0.1%
        2008$5,067 -0.2%$409,746 +3%
        2007$5,075 $397,812 +2.5%
        2006-- $388,109 +3%
        2005-- $376,805 +3%
        2004$5,374 -3%$365,830 +1.9%
        2003$5,540 -1.4%$359,009 +2.4%
        2002$5,620 +5.7%$350,595 +1.6%
        2001$5,318 +1.4%$345,074 +3%
        2000$5,244 $335,023
        Find assessor info on the county website

        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.
        Mortgage interest rates are dependent on a number of factors, including credit score, down payment, and repayment length. Interest rate data provided by Zillow Group Marketplace, Inc. as of 1/1/1970 from various mortgage lenders with which we have lead or other similar arrangements; the Estimated Payment is an average of those rates.
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        Climate risks

        Neighborhood: 34228

        Getting around

        5 / 100
        Car-Dependent
        27 / 100
        Somewhat Bikeable

        Nearby schools

        GreatSchools rating
        Schools provided by the listing agent
        • Elementary: Southside Elementary
        • Middle: Booker Middle
        • High: Booker 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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