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:
      28 Churchill Drive, Winchester, KY 40391
      Virtual Tour
      28 Churchill Drive, Winchester, KY 40391
      $310,000
      5beds
      3bath
      2,624sqft
      0.23acres
      House for Sale

      28 Churchill Drive, Winchester, KY 40391

      Listing by: Marshall Lane Real Estate - Lexington
      412 Pueblo Court, Winchester, KY 40391
      Virtual Tour
      412 Pueblo Court, Winchester, KY 40391
      $312,000
      3beds
      2.5bath
      2,648sqft
      0.25acres
      House for Sale

      412 Pueblo Court, Winchester, KY 40391

      Listing by: Rector Hayden Realtors
      9 Linden Avenue, Winchester, KY 40391
      9 Linden Avenue, Winchester, KY 40391
      $139,000
      2beds
      1bath
      886sqft
      0.17acres
      House for Sale

      9 Linden Avenue, Winchester, KY 40391

      Listing by: CENTURY 21 Advantage Realty
      200 Dubuy Drive, Winchester, KY 40391
      200 Dubuy Drive, Winchester, KY 40391
      $312,000
      3beds
      2.5bath
      1,858sqft
      0.24acres
      House for Sale

      200 Dubuy Drive, Winchester, KY 40391

      Listing by: RE/MAX Creative Realty
      110 Buckingham Lane, Winchester, KY 40391
      Contingent
      110 Buckingham Lane, Winchester, KY 40391
      $275,000
      3beds
      2bath
      1,240sqft
      0.21acres
      House for Sale

      110 Buckingham Lane, Winchester, KY 40391

      Listing by: ERA Select Real Estate
      229 S Highland Street, Winchester, KY 40391
      229 S Highland Street, Winchester, KY 40391
      $180,000
      4beds
      3bath
      3,462sqft
      0.11acres
      House for Sale

      229 S Highland Street, Winchester, KY 40391

      Listing by: RE/MAX Creative, Winchester
      175 Magnolia Street, Winchester, KY 40391
      175 Magnolia Street, Winchester, KY 40391
      $179,000
      3beds
      1bath
      1,046sqft
      0.17acres
      House for Sale

      175 Magnolia Street, Winchester, KY 40391

      Listing by: Woods Realty Group
      213 Short Street, Winchester, KY 40391
      Pending
      213 Short Street, Winchester, KY 40391
      $229,000
      3beds
      2bath
      1,068sqft
      0.17acres
      House for Sale

      213 Short Street, Winchester, KY 40391

      Listing by: Kentucky Residential Real Estate, LLC
      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
      230 Duclair Drive, Winchester, KY 40391
      Virtual Tour
      230 Duclair Drive, Winchester, KY 40391
      $110,000
      0.34acres
      Land for Sale

      230 Duclair Drive, Winchester, KY 40391

      Listing by: Bluegrass Properties Group
      306 Trapp-Goffs Cor Road, Winchester, KY 40391
      Pending
      306 Trapp-Goffs Cor Road, Winchester, KY 40391
      $299,900
      4beds
      2bath
      1,840sqft
      2.33acres
      House for Sale

      306 Trapp-Goffs Cor Road, Winchester, KY 40391

      Listing by: Keller Williams Commonwealth
      697 Goose Creek Road, Winchester, KY 40391
      697 Goose Creek Road, Winchester, KY 40391
      $180,000
      3beds
      2bath
      1,848sqft
      2.61acres
      House for Sale

      697 Goose Creek Road, Winchester, KY 40391

      Listing by: Dream Maker Realty, LLC
      7 Hiawatha Trail, Winchester, KY 40391
      Contingent
      7 Hiawatha Trail, Winchester, KY 40391
      $217,500
      3beds
      1bath
      1,190sqft
      0.12acres
      House for Sale

      7 Hiawatha Trail, Winchester, KY 40391

      Listing by: Coldwell Banker McMahan
      142 Clubhouse Drive, Winchester, KY 40391
      Pending
      142 Clubhouse Drive, Winchester, KY 40391
      $650,000
      6beds
      4bath
      4,351sqft
      –acres
      House for Sale

      142 Clubhouse Drive, Winchester, KY 40391

      Listing by: Threshold Real Estate Services
      443 S Maple Street, Winchester, KY 40391
      443 S Maple Street, Winchester, KY 40391
      $350,000
      4beds
      2bath
      3,261sqft
      0.39acres
      House for Sale

      443 S Maple Street, Winchester, KY 40391

      Listing by: Keller Williams Commonwealth
      13 Maryland Avenue, Winchester, KY 40391
      13 Maryland Avenue, Winchester, KY 40391
      $169,000
      2beds
      1bath
      1,472sqft
      0.14acres
      House for Sale

      13 Maryland Avenue, Winchester, KY 40391

      Listing by: ERA Select Real Estate
      722 Colby Road #2, Winchester, KY 40391
      722 Colby Road #2, Winchester, KY 40391
      $600,000
      6.13acres
      Land for Sale

      722 Colby Road #2, Winchester, KY 40391

      Listing by: CMI Properties
      110 Powe Drive, Winchester, KY 40391
      110 Powe Drive, Winchester, KY 40391
      $329,900
      4beds
      2.5bath
      2,010sqft
      0.25acres
      House for Sale

      110 Powe Drive, Winchester, KY 40391

      Listing by: The Agency
      722 Colby Road #1, Winchester, KY 40391
      722 Colby Road #1, Winchester, KY 40391
      $1,800,000
      4.36acres
      Land for Sale

      722 Colby Road #1, Winchester, KY 40391

      Listing by: CMI Properties
      905 Pretty Run Road, Winchester, KY 40391
      Pending
      905 Pretty Run Road, Winchester, KY 40391
      $600,000
      3beds
      3.5bath
      3,391sqft
      2.19acres
      House for Sale

      905 Pretty Run Road, Winchester, KY 40391

      Listing by: Bluegrass Sotheby's International Realty
      3385 Colby Road, Winchester, KY 40391
      3385 Colby Road, Winchester, KY 40391
      $150,000
      2.77acres
      Land for Sale

      3385 Colby Road, Winchester, KY 40391

      Listing by: Steven D Adams Real Estate Services, LLC
      2509 Mount Sterling Road, Winchester, KY 40391
      Price Reduced $24,900 May 15
      2509 Mount Sterling Road, Winchester, KY 40391
      $775,000
      4beds
      3.5bath
      4,922sqft
      10.17acres
      House for Sale

      2509 Mount Sterling Road, Winchester, KY 40391

      Listing by: Freedom Realty & Property Management
      432 Country Club Drive, Winchester, KY 40391
      Pending
      432 Country Club Drive, Winchester, KY 40391
      $175,000
      2beds
      2bath
      1,260sqft
      0.11acres
      Townhouse for Sale

      432 Country Club Drive, Winchester, KY 40391

      Listing by: Rector Hayden Realtors
      4152 Winchester Road, Irvine, KY 40336
      Pending
      4152 Winchester Road, Irvine, KY 40336
      $165,000
      3beds
      1bath
      648sqft
      8acres
      House for Sale

      4152 Winchester Road, Irvine, KY 40336

      Listing by: KY Real Estate Professionals, LLC
      426 E Broadway Street, Winchester, KY 40391
      Contingent
      426 E Broadway Street, Winchester, KY 40391
      $289,000
      5beds
      2bath
      1,838sqft
      0.43acres
      House for Sale

      426 E Broadway Street, Winchester, KY 40391

      Listing by: Coldwell Banker McMahan
      614 Colby Ridge Boulevard, Winchester, KY 40391
      614 Colby Ridge Boulevard, Winchester, KY 40391
      $349,900
      4beds
      2.5bath
      2,100sqft
      0.19acres
      House for Sale

      614 Colby Ridge Boulevard, Winchester, KY 40391

      Listing by: HomeLand Real Estate Inc - Mt Sterling
      222 Ashton Oak Way, Winchester, KY 40391
      Pending
      222 Ashton Oak Way, Winchester, KY 40391
      $450,000
      3beds
      2.5bath
      3,444sqft
      0.5acres
      House for Sale

      222 Ashton Oak Way, Winchester, KY 40391

      Listing by: Ensor Real Estate, LLC
      16 Linden Avenue, Winchester, KY 40391
      16 Linden Avenue, Winchester, KY 40391
      $1,200,000
      16beds
      16bath
      7,480sqft
      0.34acres
      Apartment for Sale

      16 Linden Avenue, Winchester, KY 40391

      Listing by: KB Realty Group
      19 3rd Street, Winchester, KY 40391
      19 3rd Street, Winchester, KY 40391
      $148,000
      3beds
      1bath
      864sqft
      0.1acres
      House for Sale

      19 3rd Street, Winchester, KY 40391

      Listing by: ListWithFreedom.com
      3614 Stamper Drive, Winchester, KY 40391
      3614 Stamper Drive, Winchester, KY 40391
      $259,500
      3beds
      2bath
      1,247sqft
      0.13acres
      House for Sale

      3614 Stamper Drive, Winchester, KY 40391

      Listing by: Dream Maker Realty, LLC
      201 Boone Avenue, Winchester, KY 40391
      Contingent
      201 Boone Avenue, Winchester, KY 40391
      $335,000
      4beds
      2.5bath
      2,513sqft
      0.22acres
      House for Sale

      201 Boone Avenue, Winchester, KY 40391

      Listing by: Rector Hayden Realtors
      720 Estes Drive, Winchester, KY 40391
      Contingent
      720 Estes Drive, Winchester, KY 40391
      $244,900
      3beds
      1.5bath
      1,494sqft
      0.18acres
      House for Sale

      720 Estes Drive, Winchester, KY 40391

      Listing by: HomeLand Real Estate Inc - Mt Sterling
      220 Hibiscus Lane, Winchester, KY 40391
      Pending
      220 Hibiscus Lane, Winchester, KY 40391
      $350,000
      3beds
      2bath
      1,640sqft
      0.23acres
      House for Sale

      220 Hibiscus Lane, Winchester, KY 40391

      Listing by: Threshold Real Estate Services
      17 W Lexington Avenue, Winchester, KY 40391
      Contingent
      17 W Lexington Avenue, Winchester, KY 40391
      $388,000
      8beds
      8bath
      4,000sqft
      0.06acres
      Apartment for Sale

      17 W Lexington Avenue, Winchester, KY 40391

      Listing by: Marshall Lane Real Estate - Lexington
      34 Hays Street, Winchester, KY 40391
      Contingent
      34 Hays Street, Winchester, KY 40391
      $210,000
      4beds
      1.5bath
      2,450sqft
      0.19acres
      House for Sale

      34 Hays Street, Winchester, KY 40391

      Listing by: RE/MAX Elite Lexington
      465 Morris Road, Winchester, KY 40391
      465 Morris Road, Winchester, KY 40391
      $775,000
      5beds
      3bath
      4,437sqft
      16.06acres
      House for Sale

      465 Morris Road, Winchester, KY 40391

      Listing by: United Real Estate Bluegrass
      740 Pilot Ridge Lane, Winchester, KY 40391
      Contingent
      740 Pilot Ridge Lane, Winchester, KY 40391
      $339,900
      3beds
      2.5bath
      1,608sqft
      1.26acres
      House for Sale

      740 Pilot Ridge Lane, Winchester, KY 40391

      Listing by: The Agency
      101 Alabama Street, Winchester, KY 40391
      101 Alabama Street, Winchester, KY 40391
      $169,900
      1beds
      2bath
      1,056sqft
      0.1acres
      House for Sale

      101 Alabama Street, Winchester, KY 40391

      Listing by: Woods Realty Group
      118 Windridge Drive, Winchester, KY 40391
      Pending
      118 Windridge Drive, Winchester, KY 40391
      $307,900
      3beds
      2bath
      1,617sqft
      0.23acres
      House for Sale

      118 Windridge Drive, Winchester, KY 40391

      Listing by: Whalen & Company
      3760 Old Boonesboro Road, Winchester, KY 40391
      Pending
      3760 Old Boonesboro Road, Winchester, KY 40391
      $1,290,000
      5beds
      5bath
      5,666sqft
      12.98acres
      House for Sale

      3760 Old Boonesboro Road, Winchester, KY 40391

      Listing by: Freedom Realty & Property Management
      123678
      81 - 120 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