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Off market
  • $761,800

    123 Windward Dr, Osprey, FL 34229

    3beds
    1,894sqft
    Single Family Residence
    Built in 1979
    0.25 Acres Lot
    $761,800 Zestimate®
    $402/sqft
    $2,846 Estimated rent

    Home value

    $761,800

    $724,000 - $800,000

    $2,846/mo

    Zestimate® history
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    $5,502/mo

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    What's special

    This immaculate and meticulously maintained 3-bedroom, 2-bath home in the sought-after Southbay Yacht & Racquet community is move-in ready and packed with beautiful updates. The open-concept kitchen has been tastefully remodeled with stainless steel appliances, center isle and lighting, and both bathrooms have also been updated. Natural light fills the home through replaced windows and elegant French doors, all of which are provided with hurricane protection for peace of mind. Crown molding and plantation shutters on all windows add a refined touch throughout, and engineered wood flooring enhances the living room and bedrooms, while ceramic tile flooring is featured in the kitchen and cozy family room complete with a charming wood-burning fireplace. Additional highlights include: a spacious utility room with ample cabinet storage, a new roof and fresh exterior paint in 2024 and new A/C system, dishwasher and garbage disposal in 2025. Florida-friendly landscaping with an abundance of fruit trees and native vegetation surrounding the home are perfect for the gardening enthusiast. Southbay Yacht & Racquet is a golf cart community that offers an array of community features and exceptional lifestyle with a recently remodeled 10,000 sq. ft. clubhouse featuring a well equipped fitness center, adjacent swimming pool, and expansive patio. The community-owned marina with residents only boat slips offers direct access to the Intracoastal Waterway with no fixed bridges to hinder your journey to the Gulf. Enjoy a wide range of amenities, including: pickleball and tennis courts, bocce and shuffleboard court, scenic walking and biking paths throughout the community and playground. Ideal location conveniently nestled between downtown Sarasota and downtown Venice, this home is close to top-rated dining, shopping, and entertainment. Youre just a short drive from world-renowned Siesta Key and Nokomis Beach, the Legacy Trail, and the nationally ranked Pine View School. Dont miss this opportunity to own a beautiful home in one of the Gulf Coasts most desirable boating communities

    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:

    Source: William Raveis Real Estate, Mortgage & Insurance,MLS#: A4656319MLS Logo

    Facts & features

    Interior

    Bedrooms & bathrooms
    • Bedrooms: 3
    • Bathrooms: 2
    • Full bathrooms: 2
    Heating
    • Other
    Cooling
    • Central Air
    Appliances
    • Included: Dishwasher, Dryer, Disposal, Microwave, Refrigerator, Washer
    Features
    • Furnished
    • Basement: Yes
    • Furnished: Yes
    Interior area
    • Total structure area: 1,894
    • Total interior livable area: 1,894 sqft

    Property

    Parking
    • Total spaces: 2
    Features
    • Has view: Yes
    • View description: Park/Greenbelt
    Lot
    • Size: 0.25 Acres
    Details
    • Parcel number: 0157080013

    Construction

    Type & style
    • Home type: SingleFamily
    • Property subtype: Single Family Residence
    Condition
    • Year built: 1979

    Community & HOA

    HOA
    • Has HOA: Yes
    • Services included: HOA
    • HOA fee: $600 quarterly
    Location
    • Region: Osprey

    Financial & listing details

    • Price per square foot: $402/sqft
    • Tax assessed value: $565,100
    • Annual tax amount: $3,485
    • Date on market: 9/24/2025
    • Lease term: Contact For Details

    Price history

    DateEventPrice
    3/24/2026Listing removed$820,000$433/sqft
    Source: Stellar MLS #A4656319 Report a problem
    1/9/2026Price change$820,000-3.5%$433/sqft
    Source: Stellar MLS #A4656319 Report a problem
    9/24/2025Listed for sale$850,000+226.9%$449/sqft
    Source: Stellar MLS #A4656319 Report a problem
    8/16/2011Sold$260,000-11.9%$137/sqft
    Source: Public Record Report a problem
    5/4/2011Listed for sale$295,000+47.5%$156/sqft
    Source: CTC Alliance LLC #A3942964 Report a problem
    4/26/2011Sold$200,000-19.7%$106/sqft
    Source: Public Record Report a problem
    2/25/2011Price change$249,000-9.1%$131/sqft
    Source: BILLIB & BILLIB P A #A3936619 Report a problem
    12/19/2010Listed for sale$274,000$145/sqft
    Source: BILLIB & BILLIB P A #A3936619 Report a problem

    Public tax history

    YearProperty taxesTax assessment
    2025$3,485 +12.1%$278,568 +2.9%
    2024$3,109 +3.8%$270,717 +3%
    2023$2,996 +2%$262,832 +3%
    2022$2,936 +1.4%$255,177 +3%
    2021$2,897 -0.2%$247,745 +1.4%
    2020$2,901 +3.9%$244,324 +2.3%
    2019$2,792 $238,831 +1.9%
    2018$2,792 +2.7%$234,378 +2.1%
    2017$2,717 -0.9%$229,557 -14.9%
    2016$2,741 $269,600 +3.5%
    2015$2,741 +0.4%$260,600 +24.1%
    2014$2,729 +4.4%$209,909
    2013$2,613 +2.9%$209,909 +1.7%
    2012$2,539 -20.6%$206,400 -7.9%
    2011$3,196 +8.8%$224,000 -4.2%
    2010$2,938 +10.7%$233,772 +2.7%
    2009$2,654 $227,626 +0.1%
    2008$2,654 -2.6%$227,399 +3%
    2007$2,724 $220,776 +2.5%
    2006-- $215,391 +3%
    2005-- $209,117 +3%
    2004$2,839 -1%$203,026 +1.9%
    2003$2,869 +1.7%$199,240 +2.4%
    2002$2,820 +6.9%$194,570 +1.6%
    2001$2,638 +2.1%$191,506 +3%
    2000$2,584 $185,928
    Find assessor info on the county website

    Neighborhood: 34229

    Nearby schools

    GreatSchools rating
    Schools provided by the listing agent
    • Elementary: Laurel Nokomis Elementary
    • Middle: Laurel Nokomis Middle
    • High: Venice Senior High

    Source: William Raveis Real Estate, Mortgage & Insurance. 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
    $761,800
    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
    $761,800