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
    279 homes

    Winchester Real Estate and Homes for Sale

      279 homes available
      6595 Mt Sterling Road, Winchester, KY 40391
      NEW 31 hrs ago
      6595 Mt Sterling Road, Winchester, KY 40391
      $609,900
      5beds
      4bath
      4,515sqft
      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 31 hrs ago
      134 Hud Road, Winchester, KY 40391
      $155,000
      0.43acres
      Land for Sale

      134 Hud Road, Winchester, KY 40391

      Listing by: Kentucky Residential Real Estate, LLC
      204 Jett Drive, Winchester, KY 40391
      NEW 31 hrs ago
      204 Jett Drive, Winchester, KY 40391
      $369,900
      3beds
      2bath
      1,558sqft
      0.21acres
      House for Sale

      204 Jett Drive, Winchester, KY 40391

      Listing by: Ensor Real Estate, LLC
      394 S Main Street, Winchester, KY 40391
      NEW 3 days ago
      394 S Main Street, Winchester, KY 40391
      $229,000
      4beds
      2bath
      1,858sqft
      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
      4beds
      2bath
      2,683sqft
      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
      3beds
      2.5bath
      2,258sqft
      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
      4beds
      4.5bath
      –sqft
      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
      3beds
      3.5bath
      2,526sqft
      0.17acres
      House for Sale

      24 N Burns Avenue, Winchester, KY 40391

      Listing by: Keller Williams Commonwealth
      21 Virginia Avenue, Winchester, KY 40391
      21 Virginia Avenue, Winchester, KY 40391
      $260,000
      3beds
      2bath
      1,749sqft
      0.18acres
      House for Sale

      21 Virginia Avenue, Winchester, KY 40391

      Listing by: EXP Realty, LLC
      133 Shala-Mar Rue, Winchester, KY 40391
      133 Shala-Mar Rue, Winchester, KY 40391
      $379,000
      3beds
      2bath
      2,000sqft
      0.36acres
      House for Sale

      133 Shala-Mar Rue, Winchester, KY 40391

      Listing by: Tom Goebel & Company
      314 E Broadway Street, Winchester, KY 40391
      Virtual Tour
      314 E Broadway Street, Winchester, KY 40391
      $229,000
      3beds
      1bath
      1,188sqft
      0.26acres
      House for Sale

      314 E Broadway Street, Winchester, KY 40391

      Listing by: Keller Williams Commonwealth
      3622 Stamper Drive, Winchester, KY 40391
      3622 Stamper Drive, Winchester, KY 40391
      $349,900
      3beds
      3bath
      2,821sqft
      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
      3beds
      2bath
      1,913sqft
      0.67acres
      House for Sale

      22 N Bloomfield Road, Winchester, KY 40391

      Listing by: Marshall Lane Real Estate - Lexington
      117 Buffalo Trace, Winchester, KY 40391
      117 Buffalo Trace, Winchester, KY 40391
      $199,900
      3beds
      2bath
      1,072sqft
      0.18acres
      House for Sale

      117 Buffalo Trace, Winchester, KY 40391

      Listing by: Tom Goebel & Company
      443 Jameson Way, Winchester, KY 40391
      443 Jameson Way, Winchester, KY 40391
      $225,000
      4beds
      2bath
      1,400sqft
      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
      3beds
      2.5bath
      1,342sqft
      0.14acres
      House for Sale

      120 Jackson Street, Winchester, KY 40391

      Listing by: Coldwell Banker McMahan
      3049 Ironworks Road, Winchester, KY 40391
      3049 Ironworks Road, Winchester, KY 40391
      $3,100,000
      3beds
      3bath
      3,693sqft
      150acres
      House for Sale

      3049 Ironworks Road, Winchester, KY 40391

      Listing by: Keller Williams Legacy Group
      2821 Winchester Road, Lexington, KY 40509
      2821 Winchester Road, Lexington, KY 40509
      $1,950,000
      10acres
      Land for Sale

      2821 Winchester Road, Lexington, KY 40509

      Listing by: The Gibson Company
      19 Cherokee Court, Winchester, KY 40391
      Contingent
      19 Cherokee Court, Winchester, KY 40391
      $230,000
      3beds
      1bath
      1,134sqft
      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
      4beds
      3.5bath
      3,585sqft
      0.56acres
      House for Sale

      184 Casa Landa Way, Winchester, KY 40391

      Listing by: RE/MAX Creative, Winchester
      4074 Ironworks Road, Winchester, KY 40391
      Virtual Tour
      4074 Ironworks Road, Winchester, KY 40391
      $309,000
      3beds
      1.5bath
      1,356sqft
      4.06acres
      House for Sale

      4074 Ironworks Road, Winchester, KY 40391

      Listing by: Keller Williams Commonwealth
      1783 Gay Evans Road, Winchester, KY 40391
      1783 Gay Evans Road, Winchester, KY 40391
      $775,000
      5beds
      3.5bath
      2,904sqft
      7.27acres
      House for Sale

      1783 Gay Evans Road, Winchester, KY 40391

      Listing by: United Real Estate Bluegrass
      110 Albany Lane, Winchester, KY 40391
      Pending
      110 Albany Lane, Winchester, KY 40391
      $269,000
      3beds
      2bath
      1,306sqft
      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
      3beds
      2bath
      1,456sqft
      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
      3beds
      3bath
      3,693sqft
      150acres
      Farm for Sale

      3049 Ironworks Road, Winchester, KY 40391

      Listing by: Keller Williams Legacy Group
      245 Ecton Road, Winchester, KY 40391
      Pending
      245 Ecton Road, Winchester, KY 40391
      $209,900
      3beds
      1bath
      1,074sqft
      0.26acres
      House for Sale

      245 Ecton Road, Winchester, KY 40391

      Listing by: ListWithFreedom.com
      208 Watercrest Way, Winchester, KY 40391
      Contingent
      208 Watercrest Way, Winchester, KY 40391
      $255,000
      3beds
      2.5bath
      1,416sqft
      0.14acres
      House for Sale

      208 Watercrest Way, Winchester, KY 40391

      Listing by: The Brokerage
      595 Earlymeade Drive, Winchester, KY 40391
      595 Earlymeade Drive, Winchester, KY 40391
      $499,000
      5beds
      3.5bath
      3,823sqft
      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
      4beds
      1.5bath
      2,170sqft
      0.19acres
      House for Sale

      214 S Burns Avenue, Winchester, KY 40391

      Listing by: Keller Williams Commonwealth
      180 Casa Landa Way, Winchester, KY 40391
      180 Casa Landa Way, Winchester, KY 40391
      $609,900
      4beds
      3.5bath
      4,779sqft
      0.39acres
      House for Sale

      180 Casa Landa Way, Winchester, KY 40391

      Listing by: United Real Estate Bluegrass
      246 Geronimo Court, Winchester, KY 40391
      Pending
      246 Geronimo Court, Winchester, KY 40391
      $210,000
      3beds
      2bath
      1,092sqft
      0.25acres
      House for Sale

      246 Geronimo Court, Winchester, KY 40391

      Listing by: The Brokerage
      720 Estes Drive, Winchester, KY 40391
      720 Estes Drive, Winchester, KY 40391
      $249,900
      3beds
      1bath
      1,494sqft
      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
      2beds
      1.5bath
      5,054sqft
      0.42acres
      House for Sale

      808 Bypass Road, Winchester, KY 40391

      Listing by: Lifstyl Real Estate
      41 7th Street, Winchester, KY 40391
      41 7th Street, Winchester, KY 40391
      $190,000
      3beds
      2bath
      1,116sqft
      0.29acres
      House for Sale

      41 7th Street, Winchester, KY 40391

      Listing by: Re/Max Elite Realty - Hamburg
      146 Cook Avenue, Winchester, KY 40391
      146 Cook Avenue, Winchester, KY 40391
      $167,500
      3beds
      1bath
      1,274sqft
      0.17acres
      House for Sale

      146 Cook Avenue, Winchester, KY 40391

      Listing by: National Real Estate
      357 Crescent Avenue, Winchester, KY 40391
      357 Crescent Avenue, Winchester, KY 40391
      $255,000
      3beds
      1.5bath
      2,188sqft
      0.15acres
      House for Sale

      357 Crescent Avenue, Winchester, KY 40391

      Listing by: National Real Estate
      145 Shanahan Lane, Winchester, KY 40391
      Contingent
      145 Shanahan Lane, Winchester, KY 40391
      $349,900
      4beds
      3bath
      2,520sqft
      0.22acres
      House for Sale

      145 Shanahan Lane, Winchester, KY 40391

      Listing by: Freedom Realty & Property Management
      590 Craig Crossing, Winchester, KY 40391
      590 Craig Crossing, Winchester, KY 40391
      $159,900
      2.66acres
      Land for Sale

      590 Craig Crossing, Winchester, KY 40391

      Listing by: Coldwell Banker McMahan
      130 E Broadway Street, Winchester, KY 40391
      130 E Broadway Street, Winchester, KY 40391
      $245,000
      5beds
      3bath
      2,445sqft
      0.17acres
      House for Sale

      130 E Broadway Street, Winchester, KY 40391

      Listing by: Lifstyl Real Estate
      202 Dubuy Drive, Winchester, KY 40391
      Contingent
      202 Dubuy Drive, Winchester, KY 40391
      $305,000
      3beds
      2.5bath
      1,800sqft
      0.17acres
      House for Sale

      202 Dubuy Drive, Winchester, KY 40391

      Listing by: Keller Williams Bluegrass Realty
      123567
      1 - 40 of 279 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
      © 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