Imagine Your Home
  • Buy
  • Rent
  • Commercial
  • Find a REALTOR®
  • Our Association
    Price range
    $
    $
    Bedrooms
    Bathrooms
    Property type
    Square feet
    Lot size
    Heating
    Cooling
    Parking spots
    Garage
    Basement
    Year built
    Max HOA
    Tours
    View
    More amenities
    288 homes

    KY/Clark/Winchester

    KY/Clark/Winchester

    Winchester Real Estate and Homes for Sale

    288 homes available
    865 Pretty Run Road, Winchester, KY 40391
    $472,000
    3beds
    2bath
    2,727sqft
    1.56acres
    House for Sale

    865 Pretty Run Road, Winchester, KY 40391

    Listing by: Keller Williams Commonwealth
    Price Reduced $24,900 Aug 24
    160 Agawam Road, Winchester, KY 40391
    $550,000
    3beds
    2.5bath
    4,933sqft
    5.1acres
    House for Sale

    160 Agawam Road, Winchester, KY 40391

    Listing by: Keller Williams Legacy Group
    1200 Craig Crossing, Winchester, KY 40391
    $125,000
    2.5acres
    Land for Sale

    1200 Craig Crossing, Winchester, KY 40391

    Listing by: Lifstyl Real Estate
    Contingent
    314 Carolina Ave, Winchester, KY 40391
    $248,000
    4beds
    2bath
    1,800sqft
    0.3acres
    House for Sale

    314 Carolina Ave, Winchester, KY 40391

    Listing by: Paragon Realty Partners
    ContingentVirtual Tour
    7934 Ironworks Road, Winchester, KY 40391
    $295,000
    3beds
    1bath
    1,633sqft
    4.86acres
    House for Sale

    7934 Ironworks Road, Winchester, KY 40391

    Listing by: Freedom Realty & Property Management
    Pending
    10 Howard Drive, Winchester, KY 40391
    $284,900
    3beds
    2bath
    1,588sqft
    0.34acres
    House for Sale

    10 Howard Drive, Winchester, KY 40391

    Listing by: The Agency
    Price Reduced $15,000 Aug 22
    219 Hampton Avenue, Winchester, KY 40391
    $350,000
    4beds
    2.5bath
    2,929sqft
    0.31acres
    House for Sale

    219 Hampton Avenue, Winchester, KY 40391

    Listing by: Keller Williams Bluegrass Realty
    Contingent
    140 Cherokee Drive, Winchester, KY 40391
    $219,900
    3beds
    1bath
    1,134sqft
    0.2acres
    House for Sale

    140 Cherokee Drive, Winchester, KY 40391

    Listing by: Coldwell Banker McMahan
    Pending
    329 Hanover Drive, Winchester, KY 40391
    $308,000
    3beds
    2.5bath
    1,903sqft
    0.17acres
    House for Sale

    329 Hanover Drive, Winchester, KY 40391

    Listing by: Century 21 Pinnacle
    Contingent
    122 LeAnn Lane, Winchester, KY 40391
    $379,000
    4beds
    2.5bath
    2,587sqft
    0.6acres
    House for Sale

    122 LeAnn Lane, Winchester, KY 40391

    Listing by: Tom Goebel & Company
    Contingent
    307 Blair Avenue, Winchester, KY 40391
    $179,900
    3beds
    1bath
    1,000sqft
    0.18acres
    House for Sale

    307 Blair Avenue, Winchester, KY 40391

    Listing by: RO&CO Real Estate
    309 Gallahadion Court, Winchester, KY 40391
    $369,900
    3beds
    2.5bath
    1,920sqft
    0.11acres
    House for Sale

    309 Gallahadion Court, Winchester, KY 40391

    Listing by: Freedom Realty & Property Management
    Contingent
    616 Colby Ridge Boulevard, Winchester, KY 40391
    $364,900
    3beds
    2bath
    1,612sqft
    0.19acres
    House for Sale

    616 Colby Ridge Boulevard, Winchester, KY 40391

    Listing by: Freedom Realty & Property Management
    16 Linden Avenue, Winchester, KY 40391
    $1,350,000
    beds
    sqft
    0.34acres
    Sale

    16 Linden Avenue, Winchester, KY 40391

    Listing by: National Real Estate
    Pending
    4560 Pine Ridge Road, Winchester, KY 40391
    $610,000
    3beds
    2bath
    1,848sqft
    86.33acres
    House for Sale

    4560 Pine Ridge Road, Winchester, KY 40391

    Listing by: Berkshire Hathaway HomeServices Foster Realtors
    433 Fairholme Way, Winchester, KY 40391
    $624,000
    3beds
    3.5bath
    2,900sqft
    0.42acres
    House for Sale

    433 Fairholme Way, Winchester, KY 40391

    Listing by: Coldwell Banker McMahan
    118 Windridge Drive, Winchester, KY 40391
    $335,000
    3beds
    2bath
    1,617sqft
    0.23acres
    House for Sale

    118 Windridge Drive, Winchester, KY 40391

    Listing by: RE/MAX Creative, Winchester
    Pending
    407 Walnut Street, Winchester, KY 40391
    $254,900
    3beds
    2bath
    2,146sqft
    1.19acres
    House for Sale

    407 Walnut Street, Winchester, KY 40391

    Listing by: THRIVE Realty
    ContingentVirtual Tour
    635 Lisletown Lane, Winchester, KY 40391
    $219,000
    2beds
    2bath
    1,628sqft
    1.12acres
    House for Sale

    635 Lisletown Lane, Winchester, KY 40391

    Listing by: Keller Williams Legacy Group
    39 South Highland Street, Winchester, KY 40391
    $102,000
    2beds
    1bath
    552sqft
    0.04acres
    House for Sale

    39 South Highland Street, Winchester, KY 40391

    Listing by: Bluegrass Realty Pros, Inc
    228 Jackson Street, Winchester, KY 40391
    $146,000
    3beds
    1bath
    1,020sqft
    0.17acres
    House for Sale

    228 Jackson Street, Winchester, KY 40391

    Listing by: Bluegrass Realty Pros, Inc
    150 Cook Avenue, Winchester, KY 40391
    $144,000
    3beds
    1bath
    805sqft
    0.12acres
    House for Sale

    150 Cook Avenue, Winchester, KY 40391

    Listing by: Bluegrass Realty Pros, Inc
    101 East Lexington Avenue, Winchester, KY 40391
    $388,000
    5beds
    3bath
    2,762sqft
    0.2acres
    Sale

    101 East Lexington Avenue, Winchester, KY 40391

    Listing by: Bluegrass Realty Pros, Inc
    202 South Maple Street, Winchester, KY 40391
    $650,000
    8beds
    5bath
    3,834sqft
    0.1acres
    Sale

    202 South Maple Street, Winchester, KY 40391

    Listing by: Bluegrass Realty Pros, Inc
    206 South Maple Street, Winchester, KY 40391
    $255,000
    4beds
    2bath
    2,732sqft
    0.1acres
    Sale

    206 South Maple Street, Winchester, KY 40391

    Listing by: Bluegrass Realty Pros, Inc
    117 Linden Avenue, Winchester, KY 40391
    $295,000
    6beds
    4bath
    3,035sqft
    0.17acres
    Sale

    117 Linden Avenue, Winchester, KY 40391

    Listing by: Bluegrass Realty Pros, Inc
    124-128 South Burns Avenue, Winchester, KY 40391
    $292,000
    6beds
    2bath
    3,196sqft
    0.3acres
    Sale

    124-128 South Burns Avenue, Winchester, KY 40391

    Listing by: Bluegrass Realty Pros, Inc
    223 West Hickman Street, Winchester, KY 40391
    $221,000
    4beds
    2bath
    2,600sqft
    0.13acres
    Sale

    223 West Hickman Street, Winchester, KY 40391

    Listing by: Bluegrass Realty Pros, Inc
    135 Winn Avenue, Winchester, KY 40391
    $274,000
    5beds
    3bath
    2,384sqft
    0.25acres
    Sale

    135 Winn Avenue, Winchester, KY 40391

    Listing by: Bluegrass Realty Pros, Inc
    210 Moss Court, Winchester, KY 40391
    $245,000
    3beds
    2bath
    1,201sqft
    0.18acres
    House for Sale

    210 Moss Court, Winchester, KY 40391

    Listing by: Kentucky Residential Real Estate, LLC
    $713,500
    6beds
    4.5bath
    6,243sqft
    0.64acres
    House for Sale

    418 David Lane, Winchester, KY 40391

    Listing by: Bridgewater Real Estate
    13015 lot 5/6 Irvine Road, Winchester, KY 40391
    $219,000
    16.68acres
    Farm for Sale

    13015 lot 5/6 Irvine Road, Winchester, KY 40391

    Listing by: Natural Bridge Realty
    Contingent
    3560 Wades Mill Road, Winchester, KY 40391
    $359,900
    3beds
    2bath
    1,305sqft
    5acres
    House for Sale

    3560 Wades Mill Road, Winchester, KY 40391

    Listing by: Kentucky Land and Home
    5 Fairwood Lane, Winchester, KY 40391
    $559,000
    4beds
    3bath
    2,482sqft
    0.37acres
    House for Sale

    5 Fairwood Lane, Winchester, KY 40391

    Listing by: Coldwell Banker McMahan
    110 Hampton Avenue, Winchester, KY 40391
    $389,900
    3beds
    3bath
    2,516sqft
    0.56acres
    House for Sale

    110 Hampton Avenue, Winchester, KY 40391

    Listing by: Dixon Properties
    $639,000
    6beds
    4.5bath
    4,021sqft
    3.56acres
    House for Sale

    4455 Colby Road, Winchester, KY 40391

    Listing by: Keller Williams Legacy Group
    7875 Bybee Road, Winchester, KY 40391
    $389,900
    20.4acres
    Farm for Sale

    7875 Bybee Road, Winchester, KY 40391

    Listing by: Tom Goebel & Company
    81 - 120 of 288 results

    winchester

    Median Sale Price

    $ 239,900

    NaN % year-over-year

    # of Homes Sold

    340

    NaN % year-over-year

    Median Days On Market

    25

    NaN % year-over-year

    © 2025 Imagine MLS
    Display of MLS Data is usually deemed reliable but is NOT guaranteed accurate by the MLS. Buyers are responsible for verifying the accuracy of all information and should investigate the data themselves or retain appropriate professionals.
    Equal opportunity
    Membio