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
    269 homes

    KY/Clark/Winchester

    KY/Clark/Winchester

    Winchester Real Estate and Homes for Sale

      269 results available
      204 Jett Drive, Winchester, KY 40391
      NEW 47 hrs ago
      204 Jett Drive, Winchester, KY 40391
      $369,900
      9,016.92sqft
      0.21acres
      House for Sale

      204 Jett Drive, Winchester, KY 40391

      Listing by: Ensor Real Estate, LLC
      6595 Mt Sterling Road, Winchester, KY 40391
      NEW 47 hrs ago
      6595 Mt Sterling Road, Winchester, KY 40391
      $609,900
      100,188sqft
      2.59acres
      House for Sale

      6595 Mt Sterling Road, Winchester, KY 40391

      Listing by: RO&CO Real Estate
      134 Hud Road, Winchester, KY 40391
      NEW 47 hrs ago
      134 Hud Road, Winchester, KY 40391
      $155,000
      18,730.8sqft
      0.43acres
      Land for Sale

      134 Hud Road, Winchester, KY 40391

      Listing by: Kentucky Residential Real Estate, LLC
      394 S Main Street, Winchester, KY 40391
      NEW 3 days ago
      394 S Main Street, Winchester, KY 40391
      $229,000
      7,840.8sqft
      0.18acres
      House for Sale

      394 S Main Street, Winchester, KY 40391

      Listing by: Tom Goebel & Company
      217 S Highland Street, Winchester, KY 40391
      NEW 4 days ago
      217 S Highland Street, Winchester, KY 40391
      $259,900
      8,276.4sqft
      0.19acres
      House for Sale

      217 S Highland Street, Winchester, KY 40391

      Listing by: The Agency
      233 Cunningham Lane, Winchester, KY 40391
      Listed 5 days ago
      233 Cunningham Lane, Winchester, KY 40391
      $450,000
      291,852sqft
      6.7acres
      House for Sale

      233 Cunningham Lane, Winchester, KY 40391

      Listing by: Berkshire Hathaway HomeServices Foster Realtors
      3600 Crowe Ridge Road, Winchester, KY 40391
      3600 Crowe Ridge Road, Winchester, KY 40391
      $384,900
      175,111.2sqft
      4.02acres
      House for Sale

      3600 Crowe Ridge Road, Winchester, KY 40391

      Listing by: Napier Realtors
      24 N Burns Avenue, Winchester, KY 40391
      24 N Burns Avenue, Winchester, KY 40391
      $309,900
      7,405.2sqft
      0.17acres
      House for Sale

      24 N Burns Avenue, Winchester, KY 40391

      Listing by: Keller Williams Commonwealth
      133 Shala-Mar Rue, Winchester, KY 40391
      133 Shala-Mar Rue, Winchester, KY 40391
      $379,000
      15,681.6sqft
      0.36acres
      House for Sale

      133 Shala-Mar Rue, Winchester, KY 40391

      Listing by: Tom Goebel & Company
      21 Virginia Avenue, Winchester, KY 40391
      21 Virginia Avenue, Winchester, KY 40391
      $260,000
      7,840.8sqft
      0.18acres
      House for Sale

      21 Virginia Avenue, Winchester, KY 40391

      Listing by: EXP Realty, LLC
      117 Buffalo Trace, Winchester, KY 40391
      117 Buffalo Trace, Winchester, KY 40391
      $199,900
      7,840.8sqft
      0.18acres
      House for Sale

      117 Buffalo Trace, Winchester, KY 40391

      Listing by: Tom Goebel & Company
      3622 Stamper Drive, Winchester, KY 40391
      3622 Stamper Drive, Winchester, KY 40391
      $349,900
      11,325.6sqft
      0.26acres
      House for Sale

      3622 Stamper Drive, Winchester, KY 40391

      Listing by: Freedom Realty & Property Management
      22 N Bloomfield Road, Winchester, KY 40391
      Virtual Tour
      22 N Bloomfield Road, Winchester, KY 40391
      $318,000
      29,286sqft
      0.67acres
      House for Sale

      22 N Bloomfield Road, Winchester, KY 40391

      Listing by: Marshall Lane Real Estate - Lexington
      314 E Broadway Street, Winchester, KY 40391
      Virtual Tour
      314 E Broadway Street, Winchester, KY 40391
      $229,000
      11,325.6sqft
      0.26acres
      House for Sale

      314 E Broadway Street, Winchester, KY 40391

      Listing by: Keller Williams Commonwealth
      443 Jameson Way, Winchester, KY 40391
      443 Jameson Way, Winchester, KY 40391
      $225,000
      11,761.2sqft
      0.27acres
      House for Sale

      443 Jameson Way, Winchester, KY 40391

      Listing by: The Brokerage
      120 Jackson Street, Winchester, KY 40391
      120 Jackson Street, Winchester, KY 40391
      $248,000
      6,055sqft
      0.14acres
      House for Sale

      120 Jackson Street, Winchester, KY 40391

      Listing by: Coldwell Banker McMahan
      1783 Gay Evans Road, Winchester, KY 40391
      1783 Gay Evans Road, Winchester, KY 40391
      $775,000
      316,681.2sqft
      7.27acres
      House for Sale

      1783 Gay Evans Road, Winchester, KY 40391

      Listing by: United Real Estate Bluegrass
      3049 Ironworks Road, Winchester, KY 40391
      3049 Ironworks Road, Winchester, KY 40391
      $3,100,000
      6,534,000sqft
      150acres
      House for Sale

      3049 Ironworks Road, Winchester, KY 40391

      Listing by: Keller Williams Legacy Group
      4074 Ironworks Road, Winchester, KY 40391
      Virtual Tour
      4074 Ironworks Road, Winchester, KY 40391
      $309,000
      176,853.6sqft
      4.06acres
      House for Sale

      4074 Ironworks Road, Winchester, KY 40391

      Listing by: Keller Williams Commonwealth
      19 Cherokee Court, Winchester, KY 40391
      Contingent
      19 Cherokee Court, Winchester, KY 40391
      $230,000
      10,018.8sqft
      0.23acres
      House for Sale

      19 Cherokee Court, Winchester, KY 40391

      Listing by: Freedom Realty & Property Management
      184 Casa Landa Way, Winchester, KY 40391
      Pending
      184 Casa Landa Way, Winchester, KY 40391
      $590,000
      24,393.6sqft
      0.56acres
      House for Sale

      184 Casa Landa Way, Winchester, KY 40391

      Listing by: RE/MAX Creative, Winchester
      110 Albany Lane, Winchester, KY 40391
      Pending
      110 Albany Lane, Winchester, KY 40391
      $269,000
      10,019sqft
      0.23acres
      House for Sale

      110 Albany Lane, Winchester, KY 40391

      Listing by: Kentucky Residential Real Estate, LLC
      2721 Pretty Run Road, Winchester, KY 40391
      ContingentPrice Reduced $80,000 Dec 11
      2721 Pretty Run Road, Winchester, KY 40391
      $220,000
      217,800sqft
      5acres
      House for Sale

      2721 Pretty Run Road, Winchester, KY 40391

      Listing by: RE/MAX Creative, Winchester
      3049 Ironworks Road, Winchester, KY 40391
      3049 Ironworks Road, Winchester, KY 40391
      $3,100,000
      6,534,000sqft
      150acres
      Farm for Sale

      3049 Ironworks Road, Winchester, KY 40391

      Listing by: Keller Williams Legacy Group
      208 Watercrest Way, Winchester, KY 40391
      Contingent
      208 Watercrest Way, Winchester, KY 40391
      $255,000
      6,233sqft
      0.14acres
      House for Sale

      208 Watercrest Way, Winchester, KY 40391

      Listing by: The Brokerage
      245 Ecton Road, Winchester, KY 40391
      Pending
      245 Ecton Road, Winchester, KY 40391
      $209,900
      11,325.6sqft
      0.26acres
      House for Sale

      245 Ecton Road, Winchester, KY 40391

      Listing by: ListWithFreedom.com
      595 Earlymeade Drive, Winchester, KY 40391
      595 Earlymeade Drive, Winchester, KY 40391
      $499,000
      13,503.6sqft
      0.31acres
      House for Sale

      595 Earlymeade Drive, Winchester, KY 40391

      Listing by: Bridgewater Real Estate
      214 S Burns Avenue, Winchester, KY 40391
      214 S Burns Avenue, Winchester, KY 40391
      $318,500
      8,276.4sqft
      0.19acres
      House for Sale

      214 S Burns Avenue, Winchester, KY 40391

      Listing by: Keller Williams Commonwealth
      246 Geronimo Court, Winchester, KY 40391
      Pending
      246 Geronimo Court, Winchester, KY 40391
      $210,000
      10,890sqft
      0.25acres
      House for Sale

      246 Geronimo Court, Winchester, KY 40391

      Listing by: The Brokerage
      180 Casa Landa Way, Winchester, KY 40391
      180 Casa Landa Way, Winchester, KY 40391
      $609,900
      16,988sqft
      0.39acres
      House for Sale

      180 Casa Landa Way, Winchester, KY 40391

      Listing by: United Real Estate Bluegrass
      720 Estes Drive, Winchester, KY 40391
      720 Estes Drive, Winchester, KY 40391
      $249,900
      7,840.8sqft
      0.18acres
      House for Sale

      720 Estes Drive, Winchester, KY 40391

      Listing by: HomeLand Real Estate Inc - Mt Sterling
      808 Bypass Road, Winchester, KY 40391
      808 Bypass Road, Winchester, KY 40391
      $525,000
      18,295sqft
      0.42acres
      House for Sale

      808 Bypass Road, Winchester, KY 40391

      Listing by: Lifstyl Real Estate
      146 Cook Avenue, Winchester, KY 40391
      146 Cook Avenue, Winchester, KY 40391
      $167,500
      7,187sqft
      0.17acres
      House for Sale

      146 Cook Avenue, Winchester, KY 40391

      Listing by: National Real Estate
      41 7th Street, Winchester, KY 40391
      41 7th Street, Winchester, KY 40391
      $190,000
      12,632.4sqft
      0.29acres
      House for Sale

      41 7th Street, Winchester, KY 40391

      Listing by: Re/Max Elite Realty - Hamburg
      145 Shanahan Lane, Winchester, KY 40391
      Contingent
      145 Shanahan Lane, Winchester, KY 40391
      $349,900
      9,583.2sqft
      0.22acres
      House for Sale

      145 Shanahan Lane, Winchester, KY 40391

      Listing by: Freedom Realty & Property Management
      130 E Broadway Street, Winchester, KY 40391
      130 E Broadway Street, Winchester, KY 40391
      $245,000
      7,405.2sqft
      0.17acres
      House for Sale

      130 E Broadway Street, Winchester, KY 40391

      Listing by: Lifstyl Real Estate
      590 Craig Crossing, Winchester, KY 40391
      590 Craig Crossing, Winchester, KY 40391
      $159,900
      115,782sqft
      2.66acres
      Land for Sale

      590 Craig Crossing, Winchester, KY 40391

      Listing by: Coldwell Banker McMahan
      202 Dubuy Drive, Winchester, KY 40391
      Contingent
      202 Dubuy Drive, Winchester, KY 40391
      $305,000
      7,616sqft
      0.17acres
      House for Sale

      202 Dubuy Drive, Winchester, KY 40391

      Listing by: Keller Williams Bluegrass Realty
      357 Crescent Avenue, Winchester, KY 40391
      357 Crescent Avenue, Winchester, KY 40391
      $255,000
      6,534sqft
      0.15acres
      House for Sale

      357 Crescent Avenue, Winchester, KY 40391

      Listing by: National Real Estate
      8 Village Drive, Winchester, KY 40391
      8 Village Drive, Winchester, KY 40391
      $295,000
      11,325.6sqft
      0.26acres
      House for Sale

      8 Village Drive, Winchester, KY 40391

      Listing by: Coldwell Banker McMahan
      123567
      1 - 40 of 269 results

      Nearby City

      Clay City Commercial RentLexington Commercial RentMt Sterling Commercial RentN Middletown Commercial RentParis Commercial RentRichmond Commercial RentWaco Commercial RentWinchester Commercial Rent

      Nearby Zip Code

      40312 Commercial Rent40353 Commercial Rent40357 Commercial Rent40361 Commercial Rent40385 Commercial Rent40391 Commercial Rent40475 Commercial Rent40509 Commercial Rent40515 Commercial Rent40516 Commercial Rent

      Nearby County

      Bourbon Commercial RentClark Commercial RentFayette Commercial RentMadison Commercial RentMontgomery Commercial RentPowell Commercial Rent
      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