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
    255 homes

    KY/Clark/Winchester

    KY/Clark/Winchester

    Winchester, Undefined Real Estate and Homes for Sale

      255 homes available
      Sort:
      2996 Irvine Road, Winchester, KY 40391
      2996 Irvine Road, Winchester, KY 40391
      $195,000
      –beds
      –sqft
      11.36acres
      Farm for Sale

      2996 Irvine Road, Winchester, KY 40391

      Listing by: Rector Hayden Realtors
      2996/3056 Irvine Road, Winchester, KY 40391
      Virtual Tour
      2996/3056 Irvine Road, Winchester, KY 40391
      $475,000
      –beds
      –sqft
      25.87acres
      Farm for Sale

      2996/3056 Irvine Road, Winchester, KY 40391

      Listing by: Rector Hayden Realtors
      2110 Athens Boonesboro Road, Winchester, KY 40391
      2110 Athens Boonesboro Road, Winchester, KY 40391
      $225,000
      8.09acres
      Land for Sale

      2110 Athens Boonesboro Road, Winchester, KY 40391

      Listing by: Keller Williams Legacy Group
      206 Jett Drive, Winchester, KY 40391
      206 Jett Drive, Winchester, KY 40391
      $369,900
      3beds
      2bath
      1,635sqft
      0.23acres
      House for Sale

      206 Jett Drive, Winchester, KY 40391

      Listing by: Ensor Real Estate, LLC
      4040 Muddy Creek Road, Winchester, KY 40391
      4040 Muddy Creek Road, Winchester, KY 40391
      $795,000
      4beds
      3.5bath
      4,584sqft
      13.65acres
      House for Sale

      4040 Muddy Creek Road, Winchester, KY 40391

      Listing by: RE/MAX Creative, Winchester
      550 E Broadway Street, Winchester, KY 40391
      550 E Broadway Street, Winchester, KY 40391
      $299,000
      –beds
      –sqft
      8.26acres
      Farm for Sale

      550 E Broadway Street, Winchester, KY 40391

      Listing by: Coldwell Banker McMahan
      2100 Irvine Road, 40391, Winchester, KY 40391
      2100 Irvine Road, 40391, Winchester, KY 40391
      $1,149,000
      3beds
      3.5bath
      3,672sqft
      28acres
      House for Sale

      2100 Irvine Road, 40391, Winchester, KY 40391

      Listing by: Ensor Real Estate, LLC
      308 Duclair Drive, Winchester, KY 40391
      308 Duclair Drive, Winchester, KY 40391
      $50,000
      0.41acres
      Land for Sale

      308 Duclair Drive, Winchester, KY 40391

      Listing by: Keller Williams Commonwealth
      1395 Two Mile Road, Winchester, KY 40391
      1395 Two Mile Road, Winchester, KY 40391
      $2,500,000
      148acres
      Land for Sale

      1395 Two Mile Road, Winchester, KY 40391

      Listing by: Tom Goebel & Company
      1395 Two Mile Road, Winchester, KY 40391
      1395 Two Mile Road, Winchester, KY 40391
      $1,200,000
      24.15acres
      Land for Sale

      1395 Two Mile Road, Winchester, KY 40391

      Listing by: Tom Goebel & Company
      1395 Two Mile Road, Winchester, KY 40391
      1395 Two Mile Road, Winchester, KY 40391
      $2,500,000
      148acres
      Land for Sale

      1395 Two Mile Road, Winchester, KY 40391

      Listing by: Tom Goebel & Company
      1395 Two Mile Road, Winchester, KY 40391
      1395 Two Mile Road, Winchester, KY 40391
      $550,500
      20.78acres
      Land for Sale

      1395 Two Mile Road, Winchester, KY 40391

      Listing by: Tom Goebel & Company
      102 W Hickman Street, Winchester, KY 40391
      102 W Hickman Street, Winchester, KY 40391
      $171,000
      2beds
      1bath
      870sqft
      0.1acres
      House for Sale

      102 W Hickman Street, Winchester, KY 40391

      Listing by: Bluegrass Realty Pros, Inc
      5045 Van Meter Road, Winchester, KY 40391
      5045 Van Meter Road, Winchester, KY 40391
      $3,500,000
      6beds
      5.5bath
      7,274sqft
      78acres
      House for Sale

      5045 Van Meter Road, Winchester, KY 40391

      Listing by: Keller Williams Bluegrass Realty
      3056 Irvine Road, Winchester, KY 40391
      Virtual Tour
      3056 Irvine Road, Winchester, KY 40391
      $285,000
      14.51acres
      Land for Sale

      3056 Irvine Road, Winchester, KY 40391

      Listing by: Rector Hayden Realtors
      2996 Irvine Road, Winchester, KY 40391
      2996 Irvine Road, Winchester, KY 40391
      $195,000
      11.36acres
      Land for Sale

      2996 Irvine Road, Winchester, KY 40391

      Listing by: Rector Hayden Realtors
      2996/3056 Irvine Road, Winchester, KY 40391
      Virtual Tour
      2996/3056 Irvine Road, Winchester, KY 40391
      $475,000
      25.87acres
      Land for Sale

      2996/3056 Irvine Road, Winchester, KY 40391

      Listing by: Rector Hayden Realtors
      271 April Way, Winchester, KY 40391
      Pending
      271 April Way, Winchester, KY 40391
      $215,000
      2beds
      1.5bath
      1,120sqft
      0.15acres
      Townhouse for Sale

      271 April Way, Winchester, KY 40391

      Listing by: Keller Williams Commonwealth
      2395 Paris Road, Winchester, KY 40391
      2395 Paris Road, Winchester, KY 40391
      $14,100,000
      274.52acres
      Land for Sale

      2395 Paris Road, Winchester, KY 40391

      Listing by: Keller Williams Legacy Group
      101 E Lexington Avenue, Winchester, KY 40391
      101 E Lexington Avenue, Winchester, KY 40391
      $388,000
      5beds
      3bath
      2,762sqft
      0.2acres
      House for Sale

      101 E Lexington Avenue, Winchester, KY 40391

      Listing by: Bluegrass Realty Pros, Inc
      150 Cook Avenue, Winchester, KY 40391
      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
      39 S Highland Street, Winchester, KY 40391
      39 S Highland Street, Winchester, KY 40391
      $102,000
      2beds
      1bath
      552sqft
      0.04acres
      House for Sale

      39 S Highland Street, Winchester, KY 40391

      Listing by: Bluegrass Realty Pros, Inc
      800 Interstate Drive, Winchester, KY 40391
      800 Interstate Drive, Winchester, KY 40391
      $270,000
      0.84acres
      Land for Sale

      800 Interstate Drive, Winchester, KY 40391

      Listing by: Ensor Real Estate, LLC
      1005 Early Drive, Winchester, KY 40391
      1005 Early Drive, Winchester, KY 40391
      $500,000
      1.52acres
      Land for Sale

      1005 Early Drive, Winchester, KY 40391

      Listing by: Ensor Real Estate, LLC
      250 Evergreen Drive, Winchester, KY 40391
      Pending
      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
      270 Evergreen Drive, Winchester, KY 40391
      Pending
      270 Evergreen Drive, Winchester, KY 40391
      $380,000
      3beds
      2bath
      1,677sqft
      1acres
      House for Sale

      270 Evergreen Drive, Winchester, KY 40391

      Listing by: United Real Estate Bluegrass
      5045 Van Meter Road, Winchester, KY 40391
      5045 Van Meter Road, Winchester, KY 40391
      $2,650,000
      6beds
      5.5bath
      7,274sqft
      10acres
      House for Sale

      5045 Van Meter Road, Winchester, KY 40391

      Listing by: Keller Williams Bluegrass Realty
      1940 Athens Boonesboro Road, Winchester, KY 40391
      1940 Athens Boonesboro Road, Winchester, KY 40391
      $125,000
      4.01acres
      Land for Sale

      1940 Athens Boonesboro Road, Winchester, KY 40391

      Listing by: Kentucky Land and Home
      1108 W Lexington Avenue, Winchester, KY 40391
      Pending
      1108 W Lexington Avenue, Winchester, KY 40391
      $800,000
      4.87acres
      Land for Sale

      1108 W Lexington Avenue, Winchester, KY 40391

      Listing by: Kentucky Residential Real Estate, LLC
      205 Evergreen Drive, Winchester, KY 40391
      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
      205 Codella Drive, Winchester, KY 40391
      205 Codella Drive, Winchester, KY 40391
      $650,000
      3acres
      Land for Sale

      205 Codella Drive, Winchester, KY 40391

      Listing by: Block + Lot Real Estate
      145 Codella Drive, Winchester, KY 40391
      145 Codella Drive, Winchester, KY 40391
      $400,000
      2.19acres
      Land for Sale

      145 Codella Drive, Winchester, KY 40391

      Listing by: Block + Lot Real Estate
      3385 Colby Road, Winchester, KY 40391
      3385 Colby Road, Winchester, KY 40391
      $150,000
      2.77acres
      Land for Sale

      3385 Colby Road, Winchester, KY 40391

      Listing by: Steven D Adams Real Estate Services, LLC
      990 Craig Crossing Road, Winchester, KY 40391
      990 Craig Crossing Road, Winchester, KY 40391
      $175,000
      6.59acres
      Land for Sale

      990 Craig Crossing Road, Winchester, KY 40391

      Listing by: Coldwell Banker McMahan
      1185 Craig Crossing Road, Winchester, KY 40391
      1185 Craig Crossing Road, Winchester, KY 40391
      $110,000
      2.06acres
      Land for Sale

      1185 Craig Crossing Road, Winchester, KY 40391

      Listing by: Coldwell Banker McMahan
      1030 Craig Crossing Road, Winchester, KY 40391
      1030 Craig Crossing Road, Winchester, KY 40391
      $150,000
      4.21acres
      Land for Sale

      1030 Craig Crossing Road, Winchester, KY 40391

      Listing by: Coldwell Banker McMahan
      374 N Middletown Road, Winchester, KY 40391
      Pending
      374 N Middletown Road, Winchester, KY 40391
      $329,500
      3beds
      2bath
      1,719sqft
      10acres
      House for Sale

      374 N Middletown Road, Winchester, KY 40391

      Listing by: Keller Williams Commonwealth
      360 N Middletown Road, Winchester, KY 40391
      Pending
      360 N Middletown Road, Winchester, KY 40391
      $329,500
      3beds
      2bath
      1,792sqft
      –acres
      House for Sale

      360 N Middletown Road, Winchester, KY 40391

      Listing by: Keller Williams Commonwealth
      1045 Gay Evans Road, Winchester, KY 40391
      Pending
      1045 Gay Evans Road, Winchester, KY 40391
      $189,900
      10.73acres
      Land for Sale

      1045 Gay Evans Road, Winchester, KY 40391

      Listing by: The Agency
      395 Croxton Way, Winchester, KY 40391
      Contingent
      395 Croxton Way, Winchester, KY 40391
      $374,900
      1.29acres
      Land for Sale

      395 Croxton Way, Winchester, KY 40391

      Listing by: Rector Hayden Realtors
      123567
      201 - 240 of 255 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
      © 2026 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