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:
      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
      8538 Winchester Road, Clay City, KY 40312
      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
      1121 Winchester Road, Irvine, KY 40336
      1121 Winchester Road, Irvine, KY 40336
      $159,900
      3beds
      1bath
      1,550sqft
      1acres
      House for Sale

      1121 Winchester Road, Irvine, KY 40336

      Listing by: Century 21 Pinnacle
      403 Pueblo Court, Winchester, KY 40391
      Pending
      403 Pueblo Court, Winchester, KY 40391
      $274,900
      3beds
      2bath
      1,311sqft
      0.2acres
      House for Sale

      403 Pueblo Court, Winchester, KY 40391

      Listing by: Freedom Realty & Property Management
      2002 Winchester Avenue, Middlesboro, KY 40965
      2002 Winchester Avenue, Middlesboro, KY 40965
      $135,000
      2beds
      1bath
      1,120sqft
      0.17acres
      House for Sale

      2002 Winchester Avenue, Middlesboro, KY 40965

      Listing by: Coldwell Banker Bisceglia Realty & Auction Co
      407 Pueblo Court, Winchester, KY 40391
      Pending
      407 Pueblo Court, Winchester, KY 40391
      $240,000
      3beds
      2bath
      1,244sqft
      0.18acres
      House for Sale

      407 Pueblo Court, Winchester, KY 40391

      Listing by: Keller Williams Legacy Group
      221 W Hickman Street, Winchester, KY 40391
      221 W Hickman Street, Winchester, KY 40391
      $349,500
      4beds
      3bath
      2,800sqft
      0.15acres
      House for Sale

      221 W Hickman Street, Winchester, KY 40391

      Listing by: Keller Williams Bluegrass Realty
      103 Yorktowne Court, Winchester, KY 40391
      Contingent
      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
      42 Mockingbird Valley Road, Winchester, KY 40391
      42 Mockingbird Valley Road, Winchester, KY 40391
      $445,500
      3beds
      2.5bath
      2,961sqft
      0.33acres
      House for Sale

      42 Mockingbird Valley Road, Winchester, KY 40391

      Listing by: McCallie Real Estate
      3622 Stamper Drive, Winchester, KY 40391
      3622 Stamper Drive, Winchester, KY 40391
      $319,900
      3beds
      3bath
      2,821sqft
      0.26acres
      House for Sale

      3622 Stamper Drive, Winchester, KY 40391

      Listing by: Freedom Realty & Property Management
      108 Spruce Court, Winchester, KY 40391
      108 Spruce Court, Winchester, KY 40391
      $230,000
      4beds
      2bath
      2,106sqft
      0.24acres
      House for Sale

      108 Spruce Court, Winchester, KY 40391

      Listing by: Keller Williams Commonwealth
      38 N Burns Avenue, Winchester, KY 40391
      38 N Burns Avenue, Winchester, KY 40391
      $350,000
      4beds
      2.5bath
      2,310sqft
      0.09acres
      House for Sale

      38 N Burns Avenue, Winchester, KY 40391

      Listing by: RE/MAX Creative Realty
      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
      2247 Muddy Creek Road, Winchester, KY 40391
      Pending
      2247 Muddy Creek Road, Winchester, KY 40391
      $89,000
      3beds
      1bath
      1,145sqft
      1.37acres
      House for Sale

      2247 Muddy Creek Road, Winchester, KY 40391

      Listing by: Hunter Real Estate
      22 Magnolia Street, Winchester, KY 40391
      22 Magnolia Street, Winchester, KY 40391
      $162,900
      2beds
      1bath
      842sqft
      0.17acres
      House for Sale

      22 Magnolia Street, Winchester, KY 40391

      Listing by: RE/MAX Creative Realty
      162 French Avenue, Winchester, KY 40391
      162 French Avenue, Winchester, KY 40391
      $319,900
      4beds
      1bath
      2,327sqft
      0.18acres
      House for Sale

      162 French Avenue, Winchester, KY 40391

      Listing by: HomeLand Real Estate Inc - Mt Sterling
      4664 Lexington Road, Winchester, KY 40391
      4664 Lexington Road, Winchester, KY 40391
      $2,750,000
      8beds
      7.5bath
      13,433sqft
      35acres
      House for Sale

      4664 Lexington Road, Winchester, KY 40391

      Listing by: Block + Lot Real Estate
      17 Holiday Road, Winchester, KY 40391
      Pending
      17 Holiday Road, Winchester, KY 40391
      $259,900
      3beds
      1.5bath
      1,161sqft
      0.16acres
      House for Sale

      17 Holiday Road, Winchester, KY 40391

      Listing by: Freedom Realty & Property Management
      6356 Van Meter Road, Winchester, KY 40391
      Virtual Tour
      6356 Van Meter Road, Winchester, KY 40391
      $849,900
      3beds
      3bath
      3,336sqft
      13.74acres
      House for Sale

      6356 Van Meter Road, Winchester, KY 40391

      Listing by: Freedom Realty & Property Management
      86 Bon-Haven Avenue, Winchester, KY 40391
      Contingent
      86 Bon-Haven Avenue, Winchester, KY 40391
      $269,000
      4beds
      2bath
      2,295sqft
      0.04acres
      House for Sale

      86 Bon-Haven Avenue, Winchester, KY 40391

      Listing by: Tom Goebel & Company
      123 Sunset Heights, Winchester, KY 40391
      123 Sunset Heights, Winchester, KY 40391
      $255,900
      3beds
      2bath
      1,446sqft
      0.27acres
      House for Sale

      123 Sunset Heights, Winchester, KY 40391

      Listing by: Coldwell Banker McMahan
      363 S Main Street, Winchester, KY 40391
      Contingent
      363 S Main Street, Winchester, KY 40391
      $250,000
      3beds
      2bath
      2,142sqft
      0.49acres
      House for Sale

      363 S Main Street, Winchester, KY 40391

      Listing by: HomeLand Real Estate Inc
      935 Stoner-Ephesus Road, Winchester, KY 40391
      935 Stoner-Ephesus Road, Winchester, KY 40391
      $525,000
      3beds
      2bath
      2,563sqft
      5.28acres
      House for Sale

      935 Stoner-Ephesus Road, Winchester, KY 40391

      Listing by: Threshold Real Estate Services
      618 Westmeade Drive, Winchester, KY 40391
      618 Westmeade Drive, Winchester, KY 40391
      $296,900
      4beds
      2bath
      2,116sqft
      0.17acres
      House for Sale

      618 Westmeade Drive, Winchester, KY 40391

      Listing by: United Real Estate Bluegrass
      164 Buckingham Lane, Winchester, KY 40391
      Contingent
      164 Buckingham Lane, Winchester, KY 40391
      $270,000
      3beds
      2bath
      1,190sqft
      0.21acres
      House for Sale

      164 Buckingham Lane, Winchester, KY 40391

      Listing by: Rector Hayden Realtors
      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
      219 Bartram Court, Winchester, KY 40391
      Pending
      219 Bartram Court, Winchester, KY 40391
      $310,000
      3beds
      2.5bath
      1,696sqft
      0.1acres
      House for Sale

      219 Bartram Court, Winchester, KY 40391

      Listing by: Turf Town Properties
      228 Holiday Road, Winchester, KY 40391
      228 Holiday Road, Winchester, KY 40391
      $334,900
      4beds
      2bath
      1,843sqft
      0.17acres
      House for Sale

      228 Holiday Road, Winchester, KY 40391

      Listing by: CENTURY 21 Commonwealth R E
      54 Locust Drive, Winchester, KY 40391
      54 Locust Drive, Winchester, KY 40391
      $299,000
      3beds
      2bath
      1,692sqft
      0.28acres
      House for Sale

      54 Locust Drive, Winchester, KY 40391

      Listing by: Berkshire Hathaway HomeServices Foster Realtors
      2697 Pine Ridge Road, Winchester, KY 40391
      2697 Pine Ridge Road, Winchester, KY 40391
      $209,000
      41.69acres
      Land for Sale

      2697 Pine Ridge Road, Winchester, KY 40391

      Listing by: Keller Williams Commonwealth
      5039 Combs Ferry Road, Winchester, KY 40391
      Price Reduced $145,100 May 17
      5039 Combs Ferry Road, Winchester, KY 40391
      $2,349,900
      5beds
      3 full, 2 halfbath
      6,284sqft
      12.81acres
      House for Sale

      5039 Combs Ferry Road, Winchester, KY 40391

      Listing by: The Agency
      2107 Winchester Avenue, Middlesboro, KY 40965
      2107 Winchester Avenue, Middlesboro, KY 40965
      $35,000
      0.34acres
      Land for Sale

      2107 Winchester Avenue, Middlesboro, KY 40965

      Listing by: Coldwell Banker Bisceglia Realty & Auction Co
      720 Terry Drive, Winchester, KY 40391
      Contingent
      720 Terry Drive, Winchester, KY 40391
      $275,000
      3beds
      2bath
      1,779sqft
      0.18acres
      House for Sale

      720 Terry Drive, Winchester, KY 40391

      Listing by: Keller Williams Commonwealth
      11 Taylor Avenue, Winchester, KY 40391
      Contingent
      11 Taylor Avenue, Winchester, KY 40391
      $149,900
      3beds
      1bath
      1,362sqft
      0.23acres
      House for Sale

      11 Taylor Avenue, Winchester, KY 40391

      Listing by: Coldwell Banker McMahan
      148 W Lexington Avenue, Winchester, KY 40391
      148 W Lexington Avenue, Winchester, KY 40391
      $199,900
      5beds
      2bath
      2,444sqft
      0.01acres
      House for Sale

      148 W Lexington Avenue, Winchester, KY 40391

      Listing by: Coldwell Banker McMahan
      345 Providence Lane, Winchester, KY 40391
      345 Providence Lane, Winchester, KY 40391
      $1,115,000
      120acres
      Land for Sale

      345 Providence Lane, Winchester, KY 40391

      Listing by: Keller Williams Legacy Group
      382 S Main Street, Winchester, KY 40391
      382 S Main Street, Winchester, KY 40391
      $395,000
      4beds
      3bath
      3,310sqft
      0.27acres
      House for Sale

      382 S Main Street, Winchester, KY 40391

      Listing by: RE/MAX Creative, Winchester
      505 LaSalle Court, Winchester, KY 40391
      Contingent
      505 LaSalle Court, Winchester, KY 40391
      $405,000
      5beds
      3bath
      2,944sqft
      0.96acres
      House for Sale

      505 LaSalle Court, Winchester, KY 40391

      Listing by: The Agency
      414 Pueblo Court, Winchester, KY 40391
      414 Pueblo Court, Winchester, KY 40391
      $309,999
      3beds
      2.5bath
      2,648sqft
      0.27acres
      House for Sale

      414 Pueblo Court, Winchester, KY 40391

      Listing by: The Local Agents
      1450 Ford Road, Winchester, KY 40391
      1450 Ford Road, Winchester, KY 40391
      $69,900
      4.48acres
      Land for Sale

      1450 Ford Road, Winchester, KY 40391

      Listing by: Dream Maker Realty, LLC
      123678
      41 - 80 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