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
    284 homes

    KY/Clark/Winchester

    KY/Clark/Winchester

    Winchester Real Estate and Homes for Sale

    284 homes available
    265 Evergreen Drive, Winchester, KY 40391
    $430,000
    3beds
    2bath
    1,855sqft
    1acres
    House for Sale

    265 Evergreen Drive, Winchester, KY 40391

    Listing by: United Real Estate Bluegrass
    250 Evergreen Drive, Winchester, KY 40391
    $430,000
    3beds
    2bath
    1,855sqft
    1acres
    House for Sale

    250 Evergreen Drive, Winchester, KY 40391

    Listing by: United Real Estate Bluegrass
    230 Evergreen Drive, Winchester, KY 40391
    $380,000
    3beds
    2bath
    1,677sqft
    1acres
    House for Sale

    230 Evergreen Drive, Winchester, KY 40391

    Listing by: United Real Estate Bluegrass
    225 Evergreen Drive, Winchester, KY 40391
    $345,000
    3beds
    2bath
    1,677sqft
    1acres
    House for Sale

    225 Evergreen Drive, Winchester, KY 40391

    Listing by: United Real Estate Bluegrass
    220 Evergreen Drive, Winchester, KY 40391
    $430,000
    3beds
    2bath
    1,855sqft
    1.03acres
    House for Sale

    220 Evergreen Drive, Winchester, KY 40391

    Listing by: United Real Estate Bluegrass
    215 Evergreen Drive, Winchester, KY 40391
    $345,000
    3beds
    2bath
    1,800sqft
    1acres
    House for Sale

    215 Evergreen Drive, Winchester, KY 40391

    Listing by: United Real Estate Bluegrass
    Contingent
    205 Evergreen Drive, Winchester, KY 40391
    $395,000
    3beds
    2bath
    1,855sqft
    1acres
    House for Sale

    205 Evergreen Drive, Winchester, KY 40391

    Listing by: United Real Estate Bluegrass
    200 Evergreen Drive, Winchester, KY 40391
    $380,000
    3beds
    2bath
    1,677sqft
    1.11acres
    House for Sale

    200 Evergreen Drive, Winchester, KY 40391

    Listing by: United Real Estate Bluegrass
    Contingent
    148 Gibson Way, Winchester, KY 40391
    $372,500
    4beds
    2.5bath
    2,456sqft
    0.13acres
    House for Sale

    148 Gibson Way, Winchester, KY 40391

    Listing by: Keller Williams Commonwealth
    155 Spring Ridge Way, Winchester, KY 40391
    $240,000
    12.1acres
    Farm for Sale

    155 Spring Ridge Way, Winchester, KY 40391

    Listing by: Keller Williams Bluegrass Realty
    113 Mayfair Court, Winchester, KY 40391
    $40,000
    0.19acres
    Land for Sale

    113 Mayfair Court, Winchester, KY 40391

    Listing by: Keller Williams Bluegrass Realty
    105 Bella Court, Winchester, KY 40391
    $40,000
    0.26acres
    Land for Sale

    105 Bella Court, Winchester, KY 40391

    Listing by: Keller Williams Bluegrass Realty
    108 Dorset Lane, Winchester, KY 40391
    $42,500
    0.2acres
    Land for Sale

    108 Dorset Lane, Winchester, KY 40391

    Listing by: Keller Williams Bluegrass Realty
    407 Fairholme Way, Winchester, KY 40391
    $334,900
    3beds
    2bath
    1,805sqft
    0.17acres
    House for Sale

    407 Fairholme Way, Winchester, KY 40391

    Listing by: Freedom Realty & Property Management
    Contingent
    9 Linden Avenue, Winchester, KY 40391
    $149,000
    2beds
    1bath
    886sqft
    0.17acres
    House for Sale

    9 Linden Avenue, Winchester, KY 40391

    Listing by: CENTURY 21 Advantage Realty
    Pending
    24 Fairview Avenue, Winchester, KY 40391
    $189,000
    3beds
    2bath
    1,238sqft
    0.08acres
    House for Sale

    24 Fairview Avenue, Winchester, KY 40391

    Listing by: Tom Goebel & Company
    Contingent
    1778 Elkin Station Road, Winchester, KY 40391
    $530,000
    3beds
    2.5bath
    2,020sqft
    8.83acres
    House for Sale

    1778 Elkin Station Road, Winchester, KY 40391

    Listing by: Pacesetters Real Estate
    1775 Irvine Road, Winchester, KY 40391
    $699,000
    3beds
    4bath
    4,123sqft
    5.13acres
    House for Sale

    1775 Irvine Road, Winchester, KY 40391

    Listing by: Lifstyl Real Estate
    Virtual Tour
    3505 Basin Springs Road, Winchester, KY 40391
    $1,300,000
    73.81acres
    Farm for Sale

    3505 Basin Springs Road, Winchester, KY 40391

    Listing by: Coldwell Banker McMahan
    Pending
    360 North Middletown Road, Winchester, KY 40391
    $329,500
    3beds
    2bath
    1,792sqft
    –acres
    House for Sale

    360 North Middletown Road, Winchester, KY 40391

    Listing by: Keller Williams Commonwealth
    Pending
    374 North Middletown Road, Winchester, KY 40391
    $329,500
    3beds
    2bath
    1,719sqft
    10acres
    House for Sale

    374 North Middletown Road, Winchester, KY 40391

    Listing by: Keller Williams Commonwealth
    133 South Burns Avenue, Winchester, KY 40391
    $239,900
    4beds
    2bath
    3,295sqft
    0.12acres
    Sale

    133 South Burns Avenue, Winchester, KY 40391

    Listing by: Freedom Realty & Property Management
    Pending
    3235 Colby Road, Winchester, KY 40391
    $175,000
    2.4acres
    Land for Sale

    3235 Colby Road, Winchester, KY 40391

    Listing by: Steven D Adams Real Estate Services, LLC
    133 South Burns Avenue, Winchester, KY 40391
    $239,900
    4beds
    2bath
    3,295sqft
    0.12acres
    House for Sale

    133 South Burns Avenue, Winchester, KY 40391

    Listing by: Freedom Realty & Property Management
    204 Wigeon Court, Winchester, KY 40391
    $49,500
    0.98acres
    Land for Sale

    204 Wigeon Court, Winchester, KY 40391

    Listing by: RE/MAX Creative, Winchester
    12569-B Ironworks Road, Winchester, KY 40391
    $70,000
    1.92acres
    Land for Sale

    12569-B Ironworks Road, Winchester, KY 40391

    Listing by: Coldwell Banker McMahan
    150 Spencer Lane, Winchester, KY 40391
    $70,000
    2.04acres
    Land for Sale

    150 Spencer Lane, Winchester, KY 40391

    Listing by: Coldwell Banker McMahan
    175 Magnolia Street, Winchester, KY 40391
    $135,000
    3beds
    1bath
    1,046sqft
    0.17acres
    House for Sale

    175 Magnolia Street, Winchester, KY 40391

    Listing by: Woods Realty Group
    7575 Irvine Road, Winchester, KY 40391
    $187,500
    7.44acres
    Land for Sale

    7575 Irvine Road, Winchester, KY 40391

    Listing by: Kentucky Residential Real Estate, LLC
    10 Upper Street, Winchester, KY 40391
    $265,000
    3beds
    2.5bath
    2,380sqft
    0.56acres
    House for Sale

    10 Upper Street, Winchester, KY 40391

    Listing by: Real Estate Appraisal Services
    Price Reduced $20,100 Aug 12
    110 Knox Court, Winchester, KY 40391
    $134,800
    2.3acres
    Land for Sale

    110 Knox Court, Winchester, KY 40391

    Listing by: The Agency
    1860 ford Road, Winchester, KY 40391
    $83,000
    2beds
    1bath
    825sqft
    0.88acres
    House for Sale

    1860 ford Road, Winchester, KY 40391

    Listing by: Tru Life Real Estate
    186 Chardonnay Court, Winchester, KY 40391
    $825,000
    4beds
    2.5bath
    5,290sqft
    0.78acres
    House for Sale

    186 Chardonnay Court, Winchester, KY 40391

    Listing by: WEICHERT REALTORS - ABG Properties
    104 Colby Hills Drive, Winchester, KY 40391
    $445,000
    4beds
    2bath
    1,950sqft
    0.6acres
    House for Sale

    104 Colby Hills Drive, Winchester, KY 40391

    Listing by: Milton and Associates Real Estate
    Contingent
    128 Alabama Street, Winchester, KY 40391
    $210,000
    3beds
    2bath
    1,526sqft
    0.15acres
    House for Sale

    128 Alabama Street, Winchester, KY 40391

    Listing by: Woods Realty Group
    14568
    161 - 200 of 284 results

    Nearby City

    Clay City Homes For SaleLexington Homes For SaleMt Sterling Homes For SaleN Middletown Homes For SaleParis Homes For SaleRichmond Homes For SaleWaco Homes For SaleWinchester Homes For Sale

    Nearby Zip Code

    40312 Homes For Sale40353 Homes For Sale40357 Homes For Sale40361 Homes For Sale40385 Homes For Sale40391 Homes For Sale40475 Homes For Sale40509 Homes For Sale40515 Homes For Sale40516 Homes For Sale

    Nearby County

    Bourbon Homes For SaleClark Homes For SaleFayette Homes For SaleMadison Homes For SaleMontgomery Homes For SalePowell Homes For Sale
    Imagine Your Home
    About UsLeadership TeamNewsMarket Stats
    Privacy PolicyTerms of UseADADMCAReal Estate Sitemap
    2250 Regency Road Lexington, KY 40503
     help@imaginemls.com   (859) 276-3503
    © 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