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
    270 homes

    KY/Clark/Winchester

    KY/Clark/Winchester

    Winchester Real Estate and Homes for Sale

      270 results available
      225 Evergreen Drive, Winchester, KY 40391
      225 Evergreen Drive, Winchester, KY 40391
      $345,000
      43,604sqft
      1acres
      House for Sale

      225 Evergreen Drive, Winchester, KY 40391

      Listing by: United Real Estate Bluegrass
      220 Evergreen Drive, Winchester, KY 40391
      220 Evergreen Drive, Winchester, KY 40391
      $430,000
      44,867sqft
      1.03acres
      House for Sale

      220 Evergreen Drive, Winchester, KY 40391

      Listing by: United Real Estate Bluegrass
      215 Evergreen Drive, Winchester, KY 40391
      215 Evergreen Drive, Winchester, KY 40391
      $345,000
      43,560sqft
      1acres
      House for Sale

      215 Evergreen Drive, Winchester, KY 40391

      Listing by: United Real Estate Bluegrass
      270 Evergreen Drive, Winchester, KY 40391
      270 Evergreen Drive, Winchester, KY 40391
      $380,000
      43,821sqft
      1acres
      House for Sale

      270 Evergreen Drive, Winchester, KY 40391

      Listing by: United Real Estate Bluegrass
      265 Evergreen Drive, Winchester, KY 40391
      265 Evergreen Drive, Winchester, KY 40391
      $430,000
      43,604sqft
      1acres
      House for Sale

      265 Evergreen Drive, Winchester, KY 40391

      Listing by: United Real Estate Bluegrass
      250 Evergreen Drive, Winchester, KY 40391
      250 Evergreen Drive, Winchester, KY 40391
      $430,000
      43,821sqft
      1acres
      House for Sale

      250 Evergreen Drive, Winchester, KY 40391

      Listing by: United Real Estate Bluegrass
      200 Evergreen Drive, Winchester, KY 40391
      200 Evergreen Drive, Winchester, KY 40391
      $380,000
      48,221sqft
      1.11acres
      House for Sale

      200 Evergreen Drive, Winchester, KY 40391

      Listing by: United Real Estate Bluegrass
      5045 Van Meter Road, Winchester, KY 40391
      5045 Van Meter Road, Winchester, KY 40391
      $2,650,000
      435,600sqft
      10acres
      House for Sale

      5045 Van Meter Road, Winchester, KY 40391

      Listing by: Keller Williams Bluegrass Realty
      5515 Van Meter Road, Winchester, KY 40391
      Pending
      5515 Van Meter Road, Winchester, KY 40391
      $524,900
      217,800sqft
      5acres
      House for Sale

      5515 Van Meter Road, Winchester, KY 40391

      Listing by: Woods Realty Group
      1940 Athens Boonesboro Road, Winchester, KY 40391
      1940 Athens Boonesboro Road, Winchester, KY 40391
      $125,000
      174,676sqft
      4.01acres
      Land for Sale

      1940 Athens Boonesboro Road, Winchester, KY 40391

      Listing by: Kentucky Land and Home
      6237 Bybee Road, Winchester, KY 40391
      6237 Bybee Road, Winchester, KY 40391
      $1,200,000
      191,228sqft
      4.39acres
      House for Sale

      6237 Bybee Road, Winchester, KY 40391

      Listing by: Berkshire Hathaway HomeServices Foster Realtors
      40 Garner Street, Winchester, KY 40391
      40 Garner Street, Winchester, KY 40391
      $210,500
      7,405sqft
      0.17acres
      House for Sale

      40 Garner Street, Winchester, KY 40391

      Listing by: Guide Realty, Inc.
      1108 W Lexington Avenue, Winchester, KY 40391
      Pending
      1108 W Lexington Avenue, Winchester, KY 40391
      $800,000
      212,137sqft
      4.87acres
      Land for Sale

      1108 W Lexington Avenue, Winchester, KY 40391

      Listing by: Kentucky Residential Real Estate, LLC
      1150 Craig Crossing, Winchester, KY 40391
      1150 Craig Crossing, Winchester, KY 40391
      $925,000
      110,817sqft
      2.54acres
      House for Sale

      1150 Craig Crossing, Winchester, KY 40391

      Listing by: Kentucky Residential Real Estate, LLC
      205 Evergreen Drive, Winchester, KY 40391
      Contingent
      205 Evergreen Drive, Winchester, KY 40391
      $395,000
      43,604sqft
      1acres
      House for Sale

      205 Evergreen Drive, Winchester, KY 40391

      Listing by: United Real Estate Bluegrass
      145 Codella Drive, Winchester, KY 40391
      145 Codella Drive, Winchester, KY 40391
      $400,000
      95,396.49sqft
      2.19acres
      Land for Sale

      145 Codella Drive, Winchester, KY 40391

      Listing by: Block + Lot Real Estate
      205 Codella Drive, Winchester, KY 40391
      205 Codella Drive, Winchester, KY 40391
      $650,000
      130,680sqft
      3acres
      Land for Sale

      205 Codella Drive, Winchester, KY 40391

      Listing by: Block + Lot Real Estate
      3385 Colby Road, Winchester, KY 40391
      3385 Colby Road, Winchester, KY 40391
      $150,000
      120,835sqft
      2.77acres
      Land for Sale

      3385 Colby Road, Winchester, KY 40391

      Listing by: Steven D Adams Real Estate Services, LLC
      1030 Craig Crossing Road, Winchester, KY 40391
      1030 Craig Crossing Road, Winchester, KY 40391
      $180,000
      193,842sqft
      4.45acres
      Land for Sale

      1030 Craig Crossing Road, Winchester, KY 40391

      Listing by: Coldwell Banker McMahan
      990 Craig Crossing Road, Winchester, KY 40391
      990 Craig Crossing Road, Winchester, KY 40391
      $195,000
      268,025sqft
      6.15acres
      Land for Sale

      990 Craig Crossing Road, Winchester, KY 40391

      Listing by: Coldwell Banker McMahan
      1185 Craig Crossing Road, Winchester, KY 40391
      1185 Craig Crossing Road, Winchester, KY 40391
      $110,000
      89,646sqft
      2.06acres
      Land for Sale

      1185 Craig Crossing Road, Winchester, KY 40391

      Listing by: Coldwell Banker McMahan
      360 N Middletown Road, Winchester, KY 40391
      Pending
      360 N Middletown Road, Winchester, KY 40391
      $329,500
      –sqft
      –acres
      House for Sale

      360 N Middletown Road, Winchester, KY 40391

      Listing by: Keller Williams Commonwealth
      374 N Middletown Road, Winchester, KY 40391
      Pending
      374 N Middletown Road, Winchester, KY 40391
      $329,500
      435,600sqft
      10acres
      House for Sale

      374 N Middletown Road, Winchester, KY 40391

      Listing by: Keller Williams Commonwealth
      186 Chardonnay Court, Winchester, KY 40391
      186 Chardonnay Court, Winchester, KY 40391
      $799,999
      33,977sqft
      0.78acres
      House for Sale

      186 Chardonnay Court, Winchester, KY 40391

      Listing by: WEICHERT REALTORS - ABG Properties
      2447 Clintonville Road, Winchester, KY 40391
      Virtual Tour
      2447 Clintonville Road, Winchester, KY 40391
      $899,000
      130,680sqft
      3acres
      House for Sale

      2447 Clintonville Road, Winchester, KY 40391

      Listing by: Berkshire Hathaway de Movellan Properties
      1045 Gay Evans Road, Winchester, KY 40391
      Pending
      1045 Gay Evans Road, Winchester, KY 40391
      $189,900
      467,399sqft
      10.73acres
      Land for Sale

      1045 Gay Evans Road, Winchester, KY 40391

      Listing by: The Agency
      425 Alexis Way, Winchester, KY 40391
      425 Alexis Way, Winchester, KY 40391
      $785,000
      13,504sqft
      0.31acres
      House for Sale

      425 Alexis Way, Winchester, KY 40391

      Listing by: Keller Williams Commonwealth
      395 Croxton Way, Winchester, KY 40391
      Contingent
      395 Croxton Way, Winchester, KY 40391
      $374,900
      56,192sqft
      1.29acres
      Land for Sale

      395 Croxton Way, Winchester, KY 40391

      Listing by: Rector Hayden Realtors
      107 Bella Shae Way, Winchester, KY 40391
      107 Bella Shae Way, Winchester, KY 40391
      $550,000
      13,504sqft
      0.31acres
      House for Sale

      107 Bella Shae Way, Winchester, KY 40391

      Listing by: Keller Williams Commonwealth
      106 Bella Shae Way, Winchester, KY 40391
      106 Bella Shae Way, Winchester, KY 40391
      $645,000
      13,504sqft
      0.31acres
      House for Sale

      106 Bella Shae Way, Winchester, KY 40391

      Listing by: Keller Williams Commonwealth
      422 Alexis Way, Winchester, KY 40391
      422 Alexis Way, Winchester, KY 40391
      $635,000
      13,504sqft
      0.31acres
      House for Sale

      422 Alexis Way, Winchester, KY 40391

      Listing by: Keller Williams Commonwealth
      424 Alexis Way, Winchester, KY 40391
      424 Alexis Way, Winchester, KY 40391
      $625,000
      13,504sqft
      0.31acres
      House for Sale

      424 Alexis Way, Winchester, KY 40391

      Listing by: Keller Williams Commonwealth
      113 Bella Shae Way, Winchester, KY 40391
      113 Bella Shae Way, Winchester, KY 40391
      $670,000
      13,504sqft
      0.31acres
      House for Sale

      113 Bella Shae Way, Winchester, KY 40391

      Listing by: Keller Williams Commonwealth
      415 Alexis Way, Winchester, KY 40391
      415 Alexis Way, Winchester, KY 40391
      $700,000
      13,504sqft
      0.31acres
      House for Sale

      415 Alexis Way, Winchester, KY 40391

      Listing by: Keller Williams Commonwealth
      414 Alexis Way, Winchester, KY 40391
      414 Alexis Way, Winchester, KY 40391
      $665,000
      13,504sqft
      0.31acres
      House for Sale

      414 Alexis Way, Winchester, KY 40391

      Listing by: Keller Williams Commonwealth
      111 Bella Shae Way, Winchester, KY 40391
      111 Bella Shae Way, Winchester, KY 40391
      $825,000
      13,504sqft
      0.31acres
      House for Sale

      111 Bella Shae Way, Winchester, KY 40391

      Listing by: Keller Williams Commonwealth
      300 Rolling Hills Lane, Winchester, KY 40391
      300 Rolling Hills Lane, Winchester, KY 40391
      $925,000
      164,221.35sqft
      3.77acres
      Land for Sale

      300 Rolling Hills Lane, Winchester, KY 40391

      Listing by: Freedom Realty & Property Management
      1509 Boonesboro Road, Winchester, KY 40391
      1509 Boonesboro Road, Winchester, KY 40391
      $2,000,000
      778,417sqft
      17.87acres
      Land for Sale

      1509 Boonesboro Road, Winchester, KY 40391

      Listing by: CMI Properties
      155 Duclair Drive, Winchester, KY 40391
      Virtual Tour
      155 Duclair Drive, Winchester, KY 40391
      $100,000
      13,939sqft
      0.32acres
      Land for Sale

      155 Duclair Drive, Winchester, KY 40391

      Listing by: Bluegrass Properties Group
      115 Duclair Drive, Winchester, KY 40391
      Virtual Tour
      115 Duclair Drive, Winchester, KY 40391
      $100,000
      13,939sqft
      0.32acres
      Land for Sale

      115 Duclair Drive, Winchester, KY 40391

      Listing by: Bluegrass Properties Group
      123567
      201 - 240 of 270 results

      Nearby City

      Lexington Commercial RentMt Sterling Commercial RentParis Commercial RentRichmond Commercial RentWaco Commercial RentWinchester Commercial Rent

      Nearby Zip Code

      40353 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 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