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For sale
  • $399,900

    919 Winding Oak Trl, Lexington, KY 40511

    5beds
    3,300sqft
    : 
    $2,618/mo
    Get pre-qualified
    Single Family Residence
    Built in 2005
    5,140 Square Feet Lot
    $390,300 Zestimate®
    $121/sqft
    $10/mo HOA

    What's special

    Finished walk-out basementUpdated laminate flooringNewer upgraded appliancesLarge walk-in closetGarden tubOpen kitchenOversized deck
    This Ball Homes Montego floor plan is the perfect blend of space, comfort, and versatility! Offering approximately 3,300 square feet of finished living space, 5 bedrooms, 3.5 baths, a finished walk-out basement, and a 2-car garage, this home provides plenty of room for family, guests, and entertaining. A welcoming two-story foyer with a custom front door opens to the spacious great room, featuring beautiful hardwood floors and a stunning tumbled-marble gas log fireplace—perfect for cozy evenings. The open kitchen offers plenty of room for a table or island, newer upgraded appliances, a nice pantry, crown molding, and a sink overlooking the backyard. A formal dining room provides ample space for family meals and a hutch, while the first-floor bonus/formal living room offers the flexibility to serve as an office, playroom, or additional gathering space. The main level features desirable 9-foot ceilings and updated laminate flooring. Upstairs, you'll find three generously sized bedrooms, including a huge primary suite with a private bath, garden tub, and large walk-in closet. The additional bedrooms also offer excellent space and storage. The finished walk-out basement takes this home to another level, featuring two additional bedrooms, One is non complying, a full bathroom, kitchenette, and spacious family room—an ideal setup for guests, extended family, a mother-in-law suite, or a private recreation area. Outside, enjoy the oversized deck and fenced backyard, creating a wonderful space for relaxing, grilling, and entertaining. With its flexible floor plan, abundant living space, finished walk-out basement, and convenient features, this is so much home for the money! HOA is mandatory but pool membership is optional. The A/C is not working. We are getting a quote to fix. This cost may be added to the offer price. Sold As-Is. Inspections are welcome.
    14 days
    1,065
    70

    Likely to sell faster than

    Zillow last checked:

    Listing updated:

    Listed by:

    Roger Browning 859-396-7295,

    Four Seasons Realty,

    Christal Browning 859-227-2183,

    Four Seasons Realty

    Source: Imagine MLS,MLS#: 26022611MLS Logo

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 5
      • Bathrooms: 4
      • Full bathrooms: 3
      • 1/2 bathrooms: 1
      Primary bedroom
      • Level: Second
      Bedroom 1
      • Level: Second
      Bedroom 2
      • Level: Second
      Bedroom 3
      • Level: Lower
      Bedroom 4
      • Level: Lower
      Bathroom 1
      • Description: Full Bath
      • Level: Second
      Bathroom 2
      • Description: Full Bath
      • Level: Second
      Bathroom 3
      • Description: Full Bath
      • Level: Lower
      Bathroom 4
      • Description: Half Bath
      • Level: First
      Dining room
      • Level: First
      Family room
      • Level: Lower
      Great room
      • Level: First
      Kitchen
      • Level: First
      Kitchen
      • Level: Lower
      Heating
      • Heat Pump
      Cooling
      • Electric, Heat Pump
      Appliances
      • Included: Dishwasher, Microwave, Refrigerator, Range
      • Laundry: Electric Dryer Hookup, Washer Hookup
      Features
      • Entrance Foyer, Eat-in Kitchen, Walk-In Closet(s), Ceiling Fan(s)
      • Flooring: Laminate, Tile
      • Windows: Blinds
      • Basement: Finished,Full,Walk-Out Access
      • Number of fireplaces: 1
      • Fireplace features: Gas Log, Great Room
      Interior area
      • Total structure area: 3,300
      • Total interior livable area: 3,300 sqft
      • Finished area above ground: 2,165
      • Finished area below ground: 1,135

      Property

      Parking
      • Total spaces: 2
      • Parking features: Attached Garage, Driveway
      • Garage spaces: 2
      • Has uncovered spaces: Yes
      Features
      • Levels: Two
      • Fencing: Privacy,Wood
      • Has view: Yes
      • View description: Neighborhood
      Lot
      • Size: 5,140 Square Feet
      Details
      • Parcel number: 38127170

      Construction

      Type & style
      • Home type: SingleFamily
      • Property subtype: Single Family Residence
      Materials
      • Brick Veneer, Vinyl Siding
      • Foundation: Concrete Perimeter
      • Roof: Dimensional Style
      Condition
      • Year built: 2005

      Utilities & green energy

      • Sewer: Public Sewer
      • Water: Public

      Community & HOA

      Community
      • Features: Park, Pool
      • Subdivision: Masterson Station
      HOA
      • Has HOA: Yes
      • Amenities included: Other, Playground
      • Services included: Maintenance Grounds
      • HOA fee: $120 annually
      Location
      • Region: Lexington

      Financial & listing details

      • Price per square foot: $121/sqft
      • Tax assessed value: $376,000
      • Annual tax amount: $4,650
      • Date on market: 8/20/2026

        Estimated market value

        $390,300

        $371,000 - $410,000

        $3,303/mo

        Price history

        DateEventPrice
        8/20/2026Listed for sale$399,900-4.8%$121/sqft
        Source: Imagine MLS #26022611 Report a problem
        8/9/2026Listing removed$420,000$127/sqft
        Source: Imagine MLS #26007554 Report a problem
        5/9/2026Listed for sale$420,000$127/sqft
        Source: Imagine MLS #26007554 Report a problem
        4/16/2026Pending sale$420,000$127/sqft
        Source: Imagine MLS #26007554 Report a problem
        4/10/2026Listed for sale$420,000+11.7%$127/sqft
        Source: Imagine MLS #26007554 Report a problem
        5/26/2023Sold$376,000+1.6%$114/sqft
        Source: Imagine MLS #23006659 Report a problem
        4/19/2023Pending sale$370,000$112/sqft
        Source: Imagine MLS #23006659 Report a problem
        4/19/2023Contingent$370,000$112/sqft
        Source: Imagine MLS #23006659 Report a problem
        4/16/2023Listed for sale$370,000$112/sqft
        Source: Imagine MLS #23006659 Report a problem
        6/9/2022Listing removed--
        Source: Imagine MLS #22008967 Report a problem
        5/5/2022Listed for sale$370,000+37%$112/sqft
        Source: Imagine MLS #22008967 Report a problem
        9/29/2020Sold$270,000-2.1%$82/sqft
        Source: Imagine MLS #20006150 Report a problem
        4/6/2020Price change$275,900+2.2%$84/sqft
        Source: Rector Hayden, Realtors #20006150 Report a problem
        4/6/2020Pending sale$269,900$82/sqft
        Source: Rector Hayden, Realtors #20006150 Report a problem
        3/31/2020Listed for sale$269,900$82/sqft
        Source: Rector Hayden, Realtors #20006150 Report a problem
        2/17/2020Listing removed$269,900$82/sqft
        Source: Metro Max Realty #1919252 Report a problem
        9/18/2019Price change$269,900-1.8%$82/sqft
        Source: Metro Max Realty #1919252 Report a problem
        8/16/2019Listed for sale$274,900+45.2%$83/sqft
        Source: Metro Max Realty #1919252 Report a problem
        10/19/2005Sold$189,297$57/sqft
        Source: Imagine MLS #504560 Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2025$4,650 $376,000
        2024$4,650 +39.3%$376,000 +39.3%
        2023$3,339 -3.2%$270,000
        2022$3,449 $270,000
        2021$3,449 +19%$270,000 +19%
        2020$2,898 $226,900
        2019$2,898 $226,900
        2018$2,898 +4.9%$226,900
        2017$2,762 +30.4%$226,900 +19.9%
        2015$2,118 $189,300
        2014$2,118 $189,300
        2012$2,118 $189,300
        2011-- --
        2010-- --
        2009-- --
        2008-- $189,300
        2006-- --
        2005-- --
        2004-- --
        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.
        See how much you could borrow to make a competitive offer.

        Climate risks

        Neighborhood: Masterson

        Getting around

        2 / 100
        Car-Dependent
        26 / 100
        Somewhat Bikeable

        Nearby schools

        GreatSchools rating
        Schools provided by the listing agent
        • Elementary: Sandersville
        • Middle: Leestown
        • High: Bryan Station

        Source: Imagine 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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