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, Undefined Real Estate and Homes for Sale

      288 homes available
      Sort:
      208 4th Street, Winchester, KY 40391
      208 4th Street, Winchester, KY 40391
      $130,000
      2beds
      1bath
      1,254sqft
      0.27acres
      House for Sale

      208 4th Street, Winchester, KY 40391

      Listing by: Keller Williams Bluegrass Realty
      4590 Four Mile Road, Winchester, KY 40391
      4590 Four Mile Road, Winchester, KY 40391
      $108,500
      11.34acres
      Land for Sale

      4590 Four Mile Road, Winchester, KY 40391

      Listing by: Tom Goebel & Company
      160 Rector Lane, Winchester, KY 40391
      160 Rector Lane, Winchester, KY 40391
      $84,900
      3.39acres
      Land for Sale

      160 Rector Lane, Winchester, KY 40391

      Listing by: United Real Estate Bluegrass
      404 Mount Vernon Drive, Winchester, KY 40391
      404 Mount Vernon Drive, Winchester, KY 40391
      $139,000
      2beds
      2bath
      1,360sqft
      0.14acres
      House for Sale

      404 Mount Vernon Drive, Winchester, KY 40391

      Listing by: Dream Maker Realty, LLC
      3934 Trapp-Goffs Corner Road, Winchester, KY 40391
      3934 Trapp-Goffs Corner Road, Winchester, KY 40391
      $225,000
      24acres
      Land for Sale

      3934 Trapp-Goffs Corner Road, Winchester, KY 40391

      Listing by: Top Ten Realty
      564 Trapp-Goffs Cor Road, Winchester, KY 40391
      Pending
      564 Trapp-Goffs Cor Road, Winchester, KY 40391
      $259,000
      3beds
      2bath
      1,960sqft
      12.04acres
      House for Sale

      564 Trapp-Goffs Cor Road, Winchester, KY 40391

      Listing by: The Real Estate Co.
      1025 Colby Road, Winchester, KY 40391
      1025 Colby Road, Winchester, KY 40391
      $575,000
      1.71acres
      Land for Sale

      1025 Colby Road, Winchester, KY 40391

      Listing by: Keller Williams Bluegrass Realty
      190 Privacy Lane, Winchester, KY 40391
      190 Privacy Lane, Winchester, KY 40391
      $245,000
      6.08acres
      Land for Sale

      190 Privacy Lane, Winchester, KY 40391

      Listing by: Keller Williams Commonwealth
      155 Spring Ridge Way, Winchester, KY 40391
      155 Spring Ridge Way, Winchester, KY 40391
      $188,500
      12.1acres
      Land for Sale

      155 Spring Ridge Way, Winchester, KY 40391

      Listing by: Keller Williams Bluegrass Realty
      133 Shala-Mar Rue, Winchester, KY 40391
      Pending
      133 Shala-Mar Rue, Winchester, KY 40391
      $359,000
      3beds
      2bath
      2,000sqft
      0.36acres
      House for Sale

      133 Shala-Mar Rue, Winchester, KY 40391

      Listing by: Tom Goebel & Company
      113 Mayfair Court, Winchester, KY 40391
      Pending
      113 Mayfair Court, Winchester, KY 40391
      $42,500
      0.19acres
      Land for Sale

      113 Mayfair Court, Winchester, KY 40391

      Listing by: Keller Williams Bluegrass Realty
      105 Bella Court, Winchester, KY 40391
      Pending
      105 Bella Court, Winchester, KY 40391
      $42,500
      0.26acres
      Land for Sale

      105 Bella Court, Winchester, KY 40391

      Listing by: Keller Williams Bluegrass Realty
      1128-1130 Dale Drive, Winchester, KY 40391
      1128-1130 Dale Drive, Winchester, KY 40391
      $269,500
      4beds
      2 full, 2 halfbath
      2,072sqft
      0.15acres
      House for Sale

      1128-1130 Dale Drive, Winchester, KY 40391

      Listing by: Coldwell Banker McMahan
      108 Dorset Lane, Winchester, KY 40391
      Pending
      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
      41 7th Street, Winchester, KY 40391
      41 7th Street, Winchester, KY 40391
      $184,900
      3beds
      2bath
      1,116sqft
      0.29acres
      House for Sale

      41 7th Street, Winchester, KY 40391

      Listing by: Re/Max Elite Realty - Hamburg
      7210 Ecton Road, Winchester, KY 40391
      Pending
      7210 Ecton Road, Winchester, KY 40391
      $924,900
      5beds
      4.5bath
      6,314sqft
      7acres
      House for Sale

      7210 Ecton Road, Winchester, KY 40391

      Listing by: Keller Williams Legacy Group
      1291-1299 Muddy Creek Road, Winchester, KY 40391
      1291-1299 Muddy Creek Road, Winchester, KY 40391
      $329,900
      3beds
      2bath
      1,222sqft
      0.78acres
      House for Sale

      1291-1299 Muddy Creek Road, Winchester, KY 40391

      Listing by: FC Tucker Bluegrass
      265 S Highland Street, Winchester, KY 40391
      265 S Highland Street, Winchester, KY 40391
      $479,000
      8beds
      4bath
      5,058sqft
      0.14acres
      House for Sale

      265 S Highland Street, Winchester, KY 40391

      Listing by: RE/MAX Elite Lexington
      327 Newcastle Lane, Winchester, KY 40391
      327 Newcastle Lane, Winchester, KY 40391
      $284,900
      4beds
      2.5bath
      1,693sqft
      0.09acres
      House for Sale

      327 Newcastle Lane, Winchester, KY 40391

      Listing by: Bluegrass Property Exchange
      221 Moundale Avenue, Winchester, KY 40391
      221 Moundale Avenue, Winchester, KY 40391
      $345,000
      3beds
      2.5bath
      2,628sqft
      0.3acres
      House for Sale

      221 Moundale Avenue, Winchester, KY 40391

      Listing by: KY Property Hunters
      1407 Ironworks Road, Winchester, KY 40391
      Contingent
      1407 Ironworks Road, Winchester, KY 40391
      $249,900
      3beds
      2bath
      1,530sqft
      0.17acres
      House for Sale

      1407 Ironworks Road, Winchester, KY 40391

      Listing by: The Agency
      240 Athens Boonesboro Road, Winchester, KY 40391
      240 Athens Boonesboro Road, Winchester, KY 40391
      $429,900
      4beds
      2.5bath
      1,500sqft
      2.89acres
      House for Sale

      240 Athens Boonesboro Road, Winchester, KY 40391

      Listing by: Dream Maker Realty, LLC
      1860 Ford Road, Winchester, KY 40391
      1860 Ford Road, Winchester, KY 40391
      $74,950
      2beds
      1bath
      825sqft
      0.88acres
      House for Sale

      1860 Ford Road, Winchester, KY 40391

      Listing by: Dream Maker Realty, LLC
      104 Colby Hills Drive, Winchester, KY 40391
      Price Reduced $66,000 May 26
      104 Colby Hills Drive, Winchester, KY 40391
      $398,000
      4beds
      2bath
      1,950sqft
      0.6acres
      House for Sale

      104 Colby Hills Drive, Winchester, KY 40391

      Listing by: Milton and Associates Real Estate
      130 E Broadway Street, Winchester, KY 40391
      130 E Broadway Street, Winchester, KY 40391
      $265,000
      4beds
      3bath
      2,445sqft
      0.17acres
      House for Sale

      130 E Broadway Street, Winchester, KY 40391

      Listing by: Mayca Property Solutions
      7919 Mt Sterling Road, Winchester, KY 40391
      7919 Mt Sterling Road, Winchester, KY 40391
      $635,000
      4beds
      3.5bath
      3,431sqft
      3acres
      House for Sale

      7919 Mt Sterling Road, Winchester, KY 40391

      Listing by: Coldwell Banker McMahan
      23 Windridge Drive, Winchester, KY 40391
      23 Windridge Drive, Winchester, KY 40391
      $344,900
      3beds
      2bath
      1,858sqft
      0.47acres
      House for Sale

      23 Windridge Drive, Winchester, KY 40391

      Listing by: The Agency
      55 Hillcrest Drive, Winchester, KY 40391
      55 Hillcrest Drive, Winchester, KY 40391
      $279,000
      5beds
      2bath
      2,214sqft
      0.96acres
      House for Sale

      55 Hillcrest Drive, Winchester, KY 40391

      Listing by: RE/MAX Elite Lexington
      500 Hidden Hills Way, Winchester, KY 40391
      Pending
      500 Hidden Hills Way, Winchester, KY 40391
      $204,900
      3beds
      2bath
      1,120sqft
      0.09acres
      House for Sale

      500 Hidden Hills Way, Winchester, KY 40391

      Listing by: Taylor Real Estate, LLC
      322 S Burns Avenue, Winchester, KY 40391
      322 S Burns Avenue, Winchester, KY 40391
      $315,000
      3beds
      2.5bath
      1,794sqft
      0.29acres
      House for Sale

      322 S Burns Avenue, Winchester, KY 40391

      Listing by: CENTURY 21 Advantage Realty
      141 Duclair Drive, Winchester, KY 40391
      Virtual Tour
      141 Duclair Drive, Winchester, KY 40391
      $100,000
      0.32acres
      Land for Sale

      141 Duclair Drive, Winchester, KY 40391

      Listing by: Bluegrass Properties Group
      270 Duclair Drive, Winchester, KY 40391
      Virtual Tour
      270 Duclair Drive, Winchester, KY 40391
      $100,000
      1.1acres
      Land for Sale

      270 Duclair Drive, Winchester, KY 40391

      Listing by: Bluegrass Properties Group
      200 Duclair Drive, Winchester, KY 40391
      Virtual Tour
      200 Duclair Drive, Winchester, KY 40391
      $110,000
      0.38acres
      Land for Sale

      200 Duclair Drive, Winchester, KY 40391

      Listing by: Bluegrass Properties Group
      111 Jacob Court, Winchester, KY 40391
      Virtual Tour
      111 Jacob Court, Winchester, KY 40391
      $100,000
      0.32acres
      Land for Sale

      111 Jacob Court, Winchester, KY 40391

      Listing by: Bluegrass Properties Group
      160 Duclair Drive, Winchester, KY 40391
      Virtual Tour
      160 Duclair Drive, Winchester, KY 40391
      $110,000
      0.29acres
      Land for Sale

      160 Duclair Drive, Winchester, KY 40391

      Listing by: Bluegrass Properties Group
      150 Duclair Drive, Winchester, KY 40391
      Virtual Tour
      150 Duclair Drive, Winchester, KY 40391
      $110,000
      0.35acres
      Land for Sale

      150 Duclair Drive, Winchester, KY 40391

      Listing by: Bluegrass Properties Group
      120 Duclair Drive, Winchester, KY 40391
      Virtual Tour
      120 Duclair Drive, Winchester, KY 40391
      $110,000
      0.38acres
      Land for Sale

      120 Duclair Drive, Winchester, KY 40391

      Listing by: Bluegrass Properties Group
      115 Duclair Drive, Winchester, KY 40391
      Virtual Tour
      115 Duclair Drive, Winchester, KY 40391
      $100,000
      0.32acres
      Land for Sale

      115 Duclair Drive, Winchester, KY 40391

      Listing by: Bluegrass Properties Group
      155 Duclair Drive, Winchester, KY 40391
      Virtual Tour
      155 Duclair Drive, Winchester, KY 40391
      $100,000
      0.32acres
      Land for Sale

      155 Duclair Drive, Winchester, KY 40391

      Listing by: Bluegrass Properties Group
      165 Duclair Drive, Winchester, KY 40391
      Virtual Tour
      165 Duclair Drive, Winchester, KY 40391
      $100,000
      0.32acres
      Land for Sale

      165 Duclair Drive, Winchester, KY 40391

      Listing by: Bluegrass Properties Group
      14568
      161 - 200 of 288 results

      Nearby City

      Lexington Homes For SaleMt Sterling Homes For SaleN Middletown Homes For SaleParis Homes For SaleRichmond Homes For SaleWinchester Homes For Sale

      Nearby Zip Code

      40353 Homes For Sale40357 Homes For Sale40361 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 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