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
    273 homes

    Winchester, Undefined Real Estate and Homes for Sale

      273 homes available
      Sort:
      Lot 3 Plantations Drive, Winchester, KY 40391
      Lot 3 Plantations Drive, Winchester, KY 40391
      $78,500
      0.22acres
      Land for Sale

      Lot 3 Plantations Drive, Winchester, KY 40391

      Listing by: Keller Williams Legacy Group
      Lot 1 - 12 Plantations Drive, Winchester, KY 40391
      Lot 1 - 12 Plantations Drive, Winchester, KY 40391
      $882,000
      3.93acres
      Land for Sale

      Lot 1 - 12 Plantations Drive, Winchester, KY 40391

      Listing by: Keller Williams Legacy Group
      605 College Street, Winchester, KY 40391
      605 College Street, Winchester, KY 40391
      $199,900
      2beds
      1bath
      1,484sqft
      0.13acres
      House for Sale

      605 College Street, Winchester, KY 40391

      Listing by: Steven D Adams Real Estate Services, LLC
      3166 Colby Road, Winchester, KY 40391
      3166 Colby Road, Winchester, KY 40391
      $1,789,000
      3beds
      2.5bath
      4,518sqft
      32.87acres
      House for Sale

      3166 Colby Road, Winchester, KY 40391

      Listing by: Coldwell Banker McMahan
      222 Bracken Court, Winchester, KY 40391
      Contingent
      222 Bracken Court, Winchester, KY 40391
      $269,000
      3beds
      2.5bath
      1,456sqft
      0.22acres
      House for Sale

      222 Bracken Court, Winchester, KY 40391

      Listing by: RE/MAX Creative, Winchester
      1503 Schollsville Road, Winchester, KY 40391
      Price Reduced $99,100 Mar 28
      1503 Schollsville Road, Winchester, KY 40391
      $399,900
      5beds
      3bath
      3,718sqft
      5acres
      House for Sale

      1503 Schollsville Road, Winchester, KY 40391

      Listing by: Coldwell Banker McMahan
      101 S Burns Avenue 1,2,3,4, Winchester, KY 40391
      101 S Burns Avenue 1,2,3,4, Winchester, KY 40391
      $600,000
      8beds
      4bath
      5,046sqft
      0.14acres
      House for Sale

      101 S Burns Avenue 1,2,3,4, Winchester, KY 40391

      Listing by: Big Blue Realty
      6239 Old Boonesboro Road, Winchester, KY 40391
      Pending
      6239 Old Boonesboro Road, Winchester, KY 40391
      $389,900
      4beds
      2bath
      2,659sqft
      1.9acres
      House for Sale

      6239 Old Boonesboro Road, Winchester, KY 40391

      Listing by: United Real Estate Bluegrass
      218 E Washington Street, Winchester, KY 40391
      218 E Washington Street, Winchester, KY 40391
      $210,000
      4beds
      1bath
      1,743sqft
      0.11acres
      House for Sale

      218 E Washington Street, Winchester, KY 40391

      Listing by: Rector Hayden Realtors
      404 Wellington Way, Winchester, KY 40391
      404 Wellington Way, Winchester, KY 40391
      $275,700
      3beds
      2bath
      1,682sqft
      0.13acres
      House for Sale

      404 Wellington Way, Winchester, KY 40391

      Listing by: Bridgewater Real Estate
      228 Jackson Street, Winchester, KY 40391
      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
      5039 Combs Ferry Road, Winchester, KY 40391
      5039 Combs Ferry Road, Winchester, KY 40391
      $2,450,000
      5beds
      3 full, 2 halfbath
      6,284sqft
      12.81acres
      House for Sale

      5039 Combs Ferry Road, Winchester, KY 40391

      Listing by: The Agency
      204 Wigeon Court, Winchester, KY 40391
      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
      174 Hidden Grove Lane, Winchester, KY 40391
      Contingent
      174 Hidden Grove Lane, Winchester, KY 40391
      $265,000
      2beds
      2bath
      1,521sqft
      0.5acres
      House for Sale

      174 Hidden Grove Lane, Winchester, KY 40391

      Listing by: Coldwell Banker McMahan
      7950 Four Mile Road, Winchester, KY 40391
      Virtual Tour
      7950 Four Mile Road, Winchester, KY 40391
      $123,000
      11.47acres
      Land for Sale

      7950 Four Mile Road, Winchester, KY 40391

      Listing by: RE/MAX Creative Realty
      110 Knox Court, Winchester, KY 40391
      110 Knox Court, Winchester, KY 40391
      $129,300
      2.3acres
      Land for Sale

      110 Knox Court, Winchester, KY 40391

      Listing by: The Agency
      175 Magnolia Street, Winchester, KY 40391
      175 Magnolia Street, Winchester, KY 40391
      $194,000
      3beds
      1bath
      1,046sqft
      0.17acres
      House for Sale

      175 Magnolia Street, Winchester, KY 40391

      Listing by: Woods Realty Group
      1508 Ford Hampton Road, Winchester, KY 40391
      ContingentVirtual Tour
      1508 Ford Hampton Road, Winchester, KY 40391
      $300,000
      2beds
      1bath
      1,531sqft
      5.02acres
      House for Sale

      1508 Ford Hampton Road, Winchester, KY 40391

      Listing by: RE/MAX Creative, Winchester
      114 Mallard Lane, Winchester, KY 40391
      Pending
      114 Mallard Lane, Winchester, KY 40391
      $365,000
      4beds
      3bath
      2,105sqft
      0.55acres
      House for Sale

      114 Mallard Lane, Winchester, KY 40391

      Listing by: Keller Williams Legacy Group
      1015 Old Stone Church Road, Winchester, KY 40391
      1015 Old Stone Church Road, Winchester, KY 40391
      $1,500,000
      –beds
      –sqft
      60.65acres
      Farm for Sale

      1015 Old Stone Church Road, Winchester, KY 40391

      Listing by: Bluegrass Property Exchange
      75 4th Street, Winchester, KY 40391
      75 4th Street, Winchester, KY 40391
      $10,000
      0.06acres
      Land for Sale

      75 4th Street, Winchester, KY 40391

      Listing by: eXp Realty, LLC
      101 Royal Oak Drive, Winchester, KY 40391
      Contingent
      101 Royal Oak Drive, Winchester, KY 40391
      $64,900
      0.52acres
      Land for Sale

      101 Royal Oak Drive, Winchester, KY 40391

      Listing by: Keller Williams Legacy Group
      102 Royal Oak Drive, Winchester, KY 40391
      Contingent
      102 Royal Oak Drive, Winchester, KY 40391
      $64,900
      0.64acres
      Land for Sale

      102 Royal Oak Drive, Winchester, KY 40391

      Listing by: Keller Williams Legacy Group
      12 Apache Trail, Winchester, KY 40391
      Contingent
      12 Apache Trail, Winchester, KY 40391
      $168,500
      3beds
      2bath
      1,026sqft
      0.14acres
      House for Sale

      12 Apache Trail, Winchester, KY 40391

      Listing by: Keller Williams Commonwealth
      103 Yorktowne Court, Winchester, KY 40391
      103 Yorktowne Court, Winchester, KY 40391
      $130,000
      3beds
      1bath
      1,150sqft
      0.15acres
      House for Sale

      103 Yorktowne Court, Winchester, KY 40391

      Listing by: Allied Realty
      8538 Winchester Road, Clay City, KY 40312
      Pending
      8538 Winchester Road, Clay City, KY 40312
      $24,900
      1.7acres
      Land for Sale

      8538 Winchester Road, Clay City, KY 40312

      Listing by: WTC Realty LLC
      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
      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
      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
      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
      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
      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
      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
      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
      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
      123567
      201 - 240 of 273 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