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Sold for $1,100,000
    • $1,100,000

    3427 WINDING OAKS DRIVE #14, LONGBOAT KEY, FL 34228

    3beds
    2,555sqft
    Condominium
    Built in 1988
    -- sqft lot
    $1,098,500 Zestimate®
    $431/sqft
    $7,800 Estimated rent

    Home value

    $1,098,500

    $1.04M - $1.15M

    $7,800/mo

    Zestimate® history
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    What's special

    Secure gated settingCustom gas fireplaceBeautifully updated three-bedroom villaTwo additional en-suite bedroomsSoft coastal breezesSpa-like bathRecently refreshed community pool
    Privately tucked away within the private Winding Oaks community on Longboat Key, this beautifully updated three-bedroom villa offers an easy, elevated way to enjoy Sarasota’s coastal lifestyle. Overlooking the Harbourside Golf Course, the home captures peaceful water views and the scenic 5th hole, creating a backdrop that feels both open and serene. Designed for effortless living, this turnkey furnished residence blends the comfort of a single-family home with the simplicity of maintenance-free ownership—ideal for seasonal stays or extended escapes. Inside, an airy open layout, soaring ceilings, and wide-plank tile floors create a light, welcoming feel, while floor-to-ceiling sliders connect seamlessly to the outdoor living spaces. The kitchen is both stylish and functional, featuring Italian white-lacquer cabinetry, stone countertops, and premium appliances—perfect for casual evenings at home or hosting friends. The living room centers around a custom gas fireplace and flows naturally to a spacious screened lanai, where you can unwind with long water views and soft coastal breezes. The home features many new furnishings and many recent updates. A private courtyard with a heated pool adds another layer of relaxation, offering a quiet place to start the day or wind down after time on the water, golf course or tennis courts. The primary suite is a calm retreat of its own, with tranquil water views, a spa-like bath, and a generous walk-in closet. Two additional en-suite bedrooms provide flexibility for visiting guests or a comfortable home office. Ownership includes access to the Bay Isles Beach Club, where days can be spent on pristine Gulf-front sands with thoughtfully appointed amenities. Within Winding Oaks, residents enjoy a recently refreshed community pool, walking paths, and a secure, gated setting. Optional golf, tennis and social memberships are available at the Longboat Key Club. Just minutes from dining and shopping on world-renowned St. Armands Circle and the cultural amenities of downtown Sarasota, this retreat makes it easy to step into the best of the area—while always having a peaceful place to return to. Simple, sophisticated, and distinctly Longboat Key.

    Zillow last checked:

    Listing updated:

    Listed by:

    Carolyn Donnelly, PA 941-350-9900,

    COLDWELL BANKER REALTY 941-383-6411

    Bought with:

    Sean Clark, 3440725

    MICHAEL SAUNDERS & COMPANY

    Source: Stellar MLS,MLS#: A4686623MLS LogoOriginating MLS: Sarasota - Manatee

    Facts & features

    Interior

    Bedrooms & bathrooms
    • Bedrooms: 3
    • Bathrooms: 3
    • Full bathrooms: 3
    Rooms
    • Room types: Utility Room
    Primary bedroom
    • Features: Walk-In Closet(s)
    • Level: First
    • Area: 300 Square Feet
    • Dimensions: 20x15
    Bedroom 2
    • Features: Walk-In Closet(s)
    • Level: First
    • Area: 196 Square Feet
    • Dimensions: 14x14
    Bedroom 3
    • Features: Built-in Closet
    • Level: First
    • Area: 180 Square Feet
    • Dimensions: 12x15
    Balcony porch lanai
    • Level: First
    • Area: 165 Square Feet
    • Dimensions: 11x15
    Balcony porch lanai
    • Level: First
    • Area: 100 Square Feet
    • Dimensions: 10x10
    Balcony porch lanai
    • Level: First
    • Area: 1334 Square Feet
    • Dimensions: 29x46
    Dining room
    • Level: First
    • Area: 273 Square Feet
    • Dimensions: 13x21
    Kitchen
    • Features: Built-in Closet
    • Level: First
    • Area: 589 Square Feet
    • Dimensions: 19x31
    Laundry
    • Level: First
    • Area: 55 Square Feet
    • Dimensions: 5x11
    Living room
    • Level: First
    • Area: 285 Square Feet
    • Dimensions: 15x19
    Heating
    • Central, Electric, Natural Gas
    Cooling
    • Central Air
    Appliances
    • Included: Oven, Cooktop, Dishwasher, Dryer, Electric Water Heater, Microwave, Refrigerator, Washer, Wine Refrigerator
    • Laundry: Inside, Laundry Room
    Features
    • Built-in Features, Ceiling Fan(s), Eating Space In Kitchen, High Ceilings, Living Room/Dining Room Combo, Open Floorplan, Primary Bedroom Main Floor, Solid Surface Counters, Split Bedroom, Stone Counters, Thermostat, Walk-In Closet(s)
    • Flooring: Luxury Vinyl, Tile
    • Doors: Sliding Doors
    • Windows: Blinds, Window Treatments
    • Has fireplace: Yes
    • Fireplace features: Gas, Living Room, Wood Burning
    Interior area
    • Total structure area: 3,270
    • Total interior livable area: 2,555 sqft

    Property

    Parking
    • Total spaces: 2
    • Parking features: Deeded, Driveway, Garage Door Opener
    • Attached garage spaces: 2
    • Has uncovered spaces: Yes
    Features
    • Levels: One
    • Stories: 1
    • Patio & porch: Covered, Deck, Front Porch, Patio, Rear Porch, Screened
    • Exterior features: Awning(s), Irrigation System, Lighting
    • Has private pool: Yes
    • Pool features: Gunite, Heated, In Ground
    • Has view: Yes
    • View description: Golf Course, Water, Lake, Pond
    • Has water view: Yes
    • Water view: Water,Lake,Pond
    • Waterfront features: Lake, Lake Front, Pond, Lake Privileges, Pond Access
    Lot
    • Residential vegetation: Mature Landscaping
    Details
    • Parcel number: 0004121014
    • Zoning: MUC1
    • Special conditions: None

    Construction

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

    Utilities & green energy

    • Sewer: Public Sewer
    • Water: Public
    • Utilities for property: Electricity Connected, Natural Gas Available, Sewer Connected, Underground Utilities, Water Connected

    Community & HOA

    Community
    • Features: Lake, Buyer Approval Required, Deed Restrictions, Gated Community - Guard, Golf, Pool, Sidewalks
    • Security: Gated Community
    • Pet fee: $0 monthly
    • Subdivision: WINDING OAKS
    HOA
    • Has HOA: Yes
    • Amenities included: Maintenance, Pool, Spa/Hot Tub, Tennis Court(s)
    • Services included: 24-Hour Guard, Community Pool, Reserve Fund, Insurance, Maintenance Structure, Maintenance Grounds, Manager, Pest Control, Private Road, Security
    • HOA fee: $2,398 monthly
    • HOA name: Winding Oaks/Neil Fleet
    • HOA phone: 941-383-3200
    • Second HOA name: Bay Isles Homeowners Association
    • Second HOA phone: 941-383-3200
    Location
    • Region: Longboat Key

    Financial & listing details

    • Price per square foot: $431/sqft
    • Tax assessed value: $1,064,600
    • Annual tax amount: $13,849
    • Date on market: 3/23/2026
    • Cumulative days on market: 36 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
    6/18/2026Sold$1,100,000-4.3%$431/sqft
    Source: Stellar MLS #A4686623 Report a problem
    6/1/2026Pending sale$1,150,000$450/sqft
    Source: Stellar MLS #A4686623 Report a problem
    5/18/2026Listed for sale$1,150,000$450/sqft
    Source: Stellar MLS #A4686623 Report a problem
    4/16/2026Pending sale$1,150,000$450/sqft
    Source: Stellar MLS #A4686623 Report a problem
    3/23/2026Listed for sale$1,150,000-3.8%$450/sqft
    Source: Stellar MLS #A4686623 Report a problem
    3/10/2025Sold$1,195,000$468/sqft
    Source: Stellar MLS #A4633113 Report a problem
    1/29/2025Pending sale$1,195,000$468/sqft
    Source: Stellar MLS #A4633113 Report a problem
    1/6/2025Listed for sale$1,195,000$468/sqft
    Source: Stellar MLS #A4633113 Report a problem
    1/1/2025Pending sale$1,195,000$468/sqft
    Source: Stellar MLS #A4633113 Report a problem
    12/30/2024Listed for sale$1,195,000+42.3%$468/sqft
    Source: Stellar MLS #A4633113 Report a problem
    12/1/2020Sold$840,000-0.6%$329/sqft
    Source: Public Record Report a problem
    11/4/2020Pending sale$845,000$331/sqft
    Source: Michael Saunders & Company - Licensed Real Estate Broker #A4480415 Report a problem
    10/9/2020Price change$845,000-0.6%$331/sqft
    Source: Michael Saunders & Company - Licensed Real Estate Broker #A4480415 Report a problem
    5/30/2020Price change$850,000-2.9%$333/sqft
    Source: COLDWELL BANKER REALTY #A4447011 Report a problem
    5/19/2020Price change$875,000-2.7%$342/sqft
    Source: COLDWELL BANKER REALTY #A4447011 Report a problem
    2/18/2020Price change$899,000-1.7%$352/sqft
    Source: Coldwell Banker Realty - Longboat Key #A4447011 Report a problem
    1/14/2020Price change$915,000-2.1%$358/sqft
    Source: Coldwell Banker Realty - Longboat Key #A4447011 Report a problem
    10/3/2019Listed for sale$935,000-79.7%$366/sqft
    Source: COLDWELL BANKER RES R E #A4447011 Report a problem
    9/1/2017Sold$4,614,545+516.1%$1,806/sqft
    Source: Public Record Report a problem
    7/27/2017Pending sale$749,000$293/sqft
    Source: Coldwell Banker Residential Real Estate - Longboat Key #A4190241 Report a problem
    6/29/2017Listed for sale$749,000-3.7%$293/sqft
    Source: Coldwell Banker Residential Real Estate - Longboat Key #A4190241 Report a problem
    5/12/2017Listing removed$777,777$304/sqft
    Source: RELAX REALTY GROUP INC #A4173807 Report a problem
    4/10/2017Price change$777,777-2.8%$304/sqft
    Source: RELAX REALTY GROUP INC #A4173807 Report a problem
    3/27/2017Price change$799,777-4.2%$313/sqft
    Source: RELAX REALTY GROUP INC #A4173807 Report a problem
    3/8/2017Price change$834,777-4%$327/sqft
    Source: RELAX REALTY GROUP INC #A4173807 Report a problem
    2/20/2017Price change$869,777-0.6%$340/sqft
    Source: RELAX REALTY GROUP INC #A4173807 Report a problem
    1/6/2017Listed for sale$874,777+121.5%$342/sqft
    Source: RELAX REALTY GROUP INC #A4173807 Report a problem
    5/27/1998Sold$395,000$155/sqft
    Source: Public Record Report a problem

    Public tax history

    YearProperty taxesTax assessment
    2025$13,850 +3.2%$1,045,367 +10%
    2024$13,423 +3.9%$950,334 +10%
    2023$12,917 +5.7%$863,940 +10%
    2022$12,220 +20%$785,400 +10%
    2021$10,181 +8%$714,000 +4.5%
    2020$9,429 +0.5%$683,100 -0.3%
    2019$9,378 $685,343 +17.7%
    2018$9,378 +17.9%$582,500 +18.9%
    2017$7,953 +20.8%$489,834 -14.5%
    2016$6,586 $572,600 +5.2%
    2015$6,586 +0.1%$544,400 +16.9%
    2014$6,580 +2.3%$465,658
    2013$6,434 +4.1%$465,658 +1.7%
    2012$6,179 +9.4%$457,874 +7.1%
    2011$5,645 -1.1%$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

    Neighborhood: 34228

    Nearby homes

    Nearby schools

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

    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
    $1,098,500
    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
    $1,098,500

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