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
    303 homes

    Winchester, Undefined Real Estate and Homes for Sale

      303 homes available
      Sort:
      265 Cunningham Lane, Winchester, KY 40391
      NEW 29 hrs ago
      265 Cunningham Lane, Winchester, KY 40391
      $200,000
      3beds
      2bath
      1,140sqft
      1.43acres
      House for Sale

      265 Cunningham Lane, Winchester, KY 40391

      Listing by: Berkshire Hathaway HomeServices Foster Realtors
      4784 Van Meter Road, Winchester, KY 40391
      Pending
      4784 Van Meter Road, Winchester, KY 40391
      $165,000
      5.01acres
      Land for Sale

      4784 Van Meter Road, Winchester, KY 40391

      Listing by: Steven D Adams Real Estate Services, LLC
      414 Fairholme Way, Winchester, KY 40391
      NEW 4 days ago
      414 Fairholme Way, Winchester, KY 40391
      $484,900
      4beds
      3bath
      2,418sqft
      0.37acres
      House for Sale

      414 Fairholme Way, Winchester, KY 40391

      Listing by: The Brokerage
      1478 Donaldson Road, Winchester, KY 40391
      Pending
      1478 Donaldson Road, Winchester, KY 40391
      $444,000
      3beds
      2bath
      2,442sqft
      5.24acres
      House for Sale

      1478 Donaldson Road, Winchester, KY 40391

      Listing by: RE/MAX Creative, Winchester
      339 S Main Street, Winchester, KY 40391
      Listed 5 days ago
      339 S Main Street, Winchester, KY 40391
      $219,900
      4beds
      1.5bath
      1,848sqft
      0.16acres
      House for Sale

      339 S Main Street, Winchester, KY 40391

      Listing by: RE/MAX Creative, Winchester
      287 Logan Lick Road, Winchester, KY 40391
      Listed 5 days ago
      287 Logan Lick Road, Winchester, KY 40391
      $465,000
      3beds
      2bath
      1,680sqft
      10.02acres
      House for Sale

      287 Logan Lick Road, Winchester, KY 40391

      Listing by: Dream Maker Realty, LLC
      209 Boone Avenue, Winchester, KY 40391
      Listed 5 days agoVirtual Tour
      209 Boone Avenue, Winchester, KY 40391
      $299,900
      3beds
      2.5bath
      2,260sqft
      0.23acres
      House for Sale

      209 Boone Avenue, Winchester, KY 40391

      Listing by: Lois Ann Disponett Real Est
      5127 Combs Ferry Road, Winchester, KY 40391
      Listed 5 days ago
      5127 Combs Ferry Road, Winchester, KY 40391
      $249,000
      8.03acres
      Land for Sale

      5127 Combs Ferry Road, Winchester, KY 40391

      Listing by: Exit Realty Crutcher Frankfort
      18 Casa Landa Way, Winchester, KY 40391
      Pending
      18 Casa Landa Way, Winchester, KY 40391
      $395,000
      3beds
      2bath
      1,883sqft
      0.68acres
      House for Sale

      18 Casa Landa Way, Winchester, KY 40391

      Listing by: Freedom Realty & Property Management
      2900 Winchester Road, Paris, KY 40361
      Listed 5 days agoVirtual Tour
      2900 Winchester Road, Paris, KY 40361
      $2,600,000
      3beds
      2bath
      1,680sqft
      78.61acres
      Farm for Sale

      2900 Winchester Road, Paris, KY 40361

      Listing by: Turf Town Properties
      217 Short Street, Winchester, KY 40391
      217 Short Street, Winchester, KY 40391
      $250,000
      3beds
      1bath
      1,042sqft
      0.17acres
      House for Sale

      217 Short Street, Winchester, KY 40391

      Listing by: Freedom Realty & Property Management
      13 Arlington Road, Winchester, KY 40391
      13 Arlington Road, Winchester, KY 40391
      $235,000
      4beds
      2bath
      1,431sqft
      0.17acres
      House for Sale

      13 Arlington Road, Winchester, KY 40391

      Listing by: Ensor Real Estate, LLC
      280 Pine Ridge Road, Winchester, KY 40391
      280 Pine Ridge Road, Winchester, KY 40391
      $260,000
      3beds
      1bath
      1,296sqft
      12.04acres
      House for Sale

      280 Pine Ridge Road, Winchester, KY 40391

      Listing by: Keller Williams Commonwealth
      1108 W Lexington Avenue, Winchester, KY 40391
      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
      147 Sunset Heights, Winchester, KY 40391
      147 Sunset Heights, Winchester, KY 40391
      $299,900
      3beds
      2bath
      2,128sqft
      0.36acres
      House for Sale

      147 Sunset Heights, Winchester, KY 40391

      Listing by: Kentucky Land and Home
      314 Snowden Drive, Winchester, KY 40391
      Pending
      314 Snowden Drive, Winchester, KY 40391
      $224,900
      3beds
      1bath
      1,196sqft
      0.17acres
      House for Sale

      314 Snowden Drive, Winchester, KY 40391

      Listing by: Freedom Realty & Property Management
      450 Jameson Way, Winchester, KY 40391
      450 Jameson Way, Winchester, KY 40391
      $225,000
      4beds
      2bath
      1,458sqft
      0.23acres
      House for Sale

      450 Jameson Way, Winchester, KY 40391

      Listing by: The Brokerage
      368 Flanagan Station Road, Winchester, KY 40391
      368 Flanagan Station Road, Winchester, KY 40391
      $199,500
      7.77acres
      Land for Sale

      368 Flanagan Station Road, Winchester, KY 40391

      Listing by: Keller Williams Commonwealth
      146 Hawthorne Drive, Winchester, KY 40391
      146 Hawthorne Drive, Winchester, KY 40391
      $539,900
      5beds
      3.5bath
      2,711sqft
      0.27acres
      House for Sale

      146 Hawthorne Drive, Winchester, KY 40391

      Listing by: COLOR Real Estate
      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 4 Plantations Drive, Winchester, KY 40391
      Lot 4 Plantations Drive, Winchester, KY 40391
      $78,500
      0.22acres
      Land for Sale

      Lot 4 Plantations Drive, Winchester, KY 40391

      Listing by: Keller Williams Legacy Group
      Lot 5 Plantations Drive, Winchester, KY 40391
      Lot 5 Plantations Drive, Winchester, KY 40391
      $78,500
      0.22acres
      Land for Sale

      Lot 5 Plantations Drive, Winchester, KY 40391

      Listing by: Keller Williams Legacy Group
      Lot 1 - 7 Plantations Drive, Winchester, KY 40391
      Lot 1 - 7 Plantations Drive, Winchester, KY 40391
      $882,000
      3.93acres
      Land for Sale

      Lot 1 - 7 Plantations Drive, Winchester, KY 40391

      Listing by: Keller Williams Legacy Group
      205 Providence Lane, Winchester, KY 40391
      205 Providence Lane, Winchester, KY 40391
      $269,900
      3beds
      1bath
      1,644sqft
      5.05acres
      House for Sale

      205 Providence Lane, 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
      155 April Way, Winchester, KY 40391
      155 April Way, Winchester, KY 40391
      $1,350,000
      3.02acres
      Land for Sale

      155 April Way, Winchester, KY 40391

      Listing by: Block + Lot Real Estate
      207 Hibiscus Lane, Winchester, KY 40391
      Contingent
      207 Hibiscus Lane, Winchester, KY 40391
      $449,900
      4beds
      3bath
      3,126sqft
      0.55acres
      House for Sale

      207 Hibiscus Lane, Winchester, KY 40391

      Listing by: HomeLand Real Estate Inc - Mt Sterling
      609 Bullion Boulevard 3A, Winchester, KY 40391
      609 Bullion Boulevard 3A, Winchester, KY 40391
      $550,000
      3acres
      Land for Sale

      609 Bullion Boulevard 3A, Winchester, KY 40391

      Listing by: Block + Lot Real Estate
      301 Snowden Drive, Winchester, KY 40391
      Contingent
      301 Snowden Drive, Winchester, KY 40391
      $210,000
      3beds
      1bath
      1,386sqft
      0.16acres
      House for Sale

      301 Snowden Drive, Winchester, KY 40391

      Listing by: The Brokerage
      529 Bullion Boulevard 3B, Winchester, KY 40391
      529 Bullion Boulevard 3B, Winchester, KY 40391
      $575,000
      2.6acres
      Land for Sale

      529 Bullion Boulevard 3B, Winchester, KY 40391

      Listing by: Block + Lot Real Estate
      274 Greenway Drive, Winchester, KY 40391
      Contingent
      274 Greenway Drive, Winchester, KY 40391
      $350,000
      4beds
      2bath
      2,208sqft
      0.55acres
      House for Sale

      274 Greenway Drive, Winchester, KY 40391

      Listing by: RE/MAX Creative, Winchester
      86 Brink Avenue, Winchester, KY 40391
      Pending
      86 Brink Avenue, Winchester, KY 40391
      $230,000
      3beds
      2bath
      1,136sqft
      0.15acres
      House for Sale

      86 Brink Avenue, Winchester, KY 40391

      Listing by: RE/MAX Elite Lexington
      5865 Van Meter Road, Winchester, KY 40391
      5865 Van Meter Road, Winchester, KY 40391
      $675,000
      3beds
      3bath
      2,765sqft
      5.05acres
      House for Sale

      5865 Van Meter Road, Winchester, KY 40391

      Listing by: Keller Williams Commonwealth
      405 Tremont Lane, Winchester, KY 40391
      Pending
      405 Tremont Lane, Winchester, KY 40391
      $349,000
      4beds
      2.5bath
      2,274sqft
      0.16acres
      House for Sale

      405 Tremont Lane, Winchester, KY 40391

      Listing by: Guide Realty, Inc.
      108 Bella Shae Way, Winchester, KY 40391
      108 Bella Shae Way, Winchester, KY 40391
      $569,900
      3beds
      2bath
      2,280sqft
      0.31acres
      House for Sale

      108 Bella Shae Way, Winchester, KY 40391

      Listing by: RE/MAX Elite Lexington
      27 Hampton Avenue, Winchester, KY 40391
      27 Hampton Avenue, Winchester, KY 40391
      $359,900
      3beds
      2bath
      2,835sqft
      0.34acres
      House for Sale

      27 Hampton Avenue, Winchester, KY 40391

      Listing by: Keller Williams Commonwealth
      5434 Pine Ridge Road, Winchester, KY 40391
      5434 Pine Ridge Road, Winchester, KY 40391
      $189,000
      2beds
      2bath
      1,000sqft
      0.58acres
      House for Sale

      5434 Pine Ridge Road, Winchester, KY 40391

      Listing by: RE/MAX Creative, Winchester
      502 W Lexington Avenue, Winchester, KY 40391
      502 W Lexington Avenue, Winchester, KY 40391
      $360,000
      4beds
      4.5bath
      4,798sqft
      0.18acres
      House for Sale

      502 W Lexington Avenue, Winchester, KY 40391

      Listing by: Kentucky Residential Real Estate, LLC
      16 Manor Drive, Winchester, KY 40391
      16 Manor Drive, Winchester, KY 40391
      $499,900
      4beds
      3bath
      5,646sqft
      0.66acres
      House for Sale

      16 Manor Drive, Winchester, KY 40391

      Listing by: Tom Goebel & Company
      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
      123678
      1 - 40 of 303 results

      Nearby City

      Lexington 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

      40353 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 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