View 23 Windridge Drive Winchester, KY MLS# 26004120
    1 of 29
    OPEN HOUSE: Sunday 5/17 2:00 PM - 4:00 PM
    $344,900
    3

    Beds

    2.0

    Baths

    1,858

    Sq.Ft.

    23 Windridge Drive

    Winchester, KY

    Bluegrass
    View 740 Pilot Ridge Lane Winchester, KY MLS# 26006680
    $339,900
    3

    Beds

    2.1

    Baths

    1,608

    Sq.Ft.

    740 Pilot Ridge Lane

    Winchester, KY

    Bluegrass
    View 201 Boone Avenue Winchester, KY MLS# 26007703
    $335,000
    4

    Beds

    2.1

    Baths

    2,513

    Sq.Ft.

    201 Boone Avenue

    Winchester, KY

    Bluegrass
    The time to sell is now! THE TIME TO SELL IS NOW!
    View 228 Holiday Road Winchester, KY MLS# 26006679
    $334,900
    4

    Beds

    2.0

    Baths

    1,843

    Sq.Ft.

    228 Holiday Road

    Winchester, KY

    Bluegrass
    View 1291-1299 Muddy Creek Road Winchester, KY MLS# 26005152
    $329,900
    3

    Beds

    2.0

    Baths

    1,222

    Sq.Ft.

    1291-1299 Muddy Creek Road

    Winchester, KY

    Bluegrass
    View 110 Powe Drive Winchester, KY MLS# 26008249
    $329,900
    4

    Beds

    2.1

    Baths

    2,010

    Sq.Ft.

    110 Powe Drive

    Winchester, KY

    Bluegrass
    View 374 N Middletown Road Winchester, KY MLS# 25005575
    $329,500
    3

    Beds

    2.0

    Baths

    1,719

    Sq.Ft.

    374 N Middletown Road

    Winchester, KY

    Bluegrass
    View 360 N Middletown Road Winchester, KY MLS# 25005577
    $329,500
    3

    Beds

    2.0

    Baths

    1,792

    Sq.Ft.

    360 N Middletown Road

    Winchester, KY

    Bluegrass
    View 215 Old Log Lick Road Winchester, KY MLS# 26003717
    $325,000
    3

    Beds

    2.0

    Baths

    1,450

    Sq.Ft.

    215 Old Log Lick Road

    Winchester, KY

    Bluegrass
    View 322 S Burns Avenue Winchester, KY MLS# 26004053
      1 of 97
      OPEN HOUSE: Sunday 5/17 1:00 PM - 3:00 PM
      $325,000
      3

      Beds

      2.1

      Baths

      1,794

      Sq.Ft.

      322 S Burns Avenue

      Winchester, KY

      Bluegrass
      View 225 Plantations Drive Winchester, KY MLS# 25506523
      $324,900
      3

      Beds

      2.1

      Baths

      3,868

      Sq.Ft.

      225 Plantations Drive

      Winchester, KY

      Bluegrass
      View 128 Cherokee Drive Winchester, KY MLS# 26003806
      $319,900
      5

      Beds

      2.0

      Baths

      2,082

      Sq.Ft.

      128 Cherokee Drive

      Winchester, KY

      Bluegrass
      View 162 French Avenue Winchester, KY MLS# 26009734
      • Recently Listed
      1 of 38
      OPEN HOUSE: Sunday 5/17 2:00 PM - 4:00 PM
      $319,900
      4

      Beds

      1.0

      Baths

      2,327

      Sq.Ft.

      162 French Avenue

      Winchester, KY

      Bluegrass
      View 3622 Stamper Drive Winchester, KY MLS# 26009877
      • Recently Listed
      1 of 43
      $319,900
      3

      Beds

      3.0

      Baths

      2,821

      Sq.Ft.

      3622 Stamper Drive

      Winchester, KY

      Bluegrass
      View 200 Dubuy Drive Winchester, KY MLS# 26008021
      $312,000
      3

      Beds

      2.1

      Baths

      1,858

      Sq.Ft.

      200 Dubuy Drive

      Winchester, KY

      Bluegrass
      View 412 Pueblo Court Winchester, KY MLS# 26008794
      • Virtual Tour
      1 of 30
      OPEN HOUSE: Sunday 5/17 1:00 PM - 3:00 PM
      $312,000
      3

      Beds

      2.1

      Baths

      2,648

      Sq.Ft.

      412 Pueblo Court

      Winchester, KY

      Bluegrass
      View 28 Churchill Drive Winchester, KY MLS# 26008797
      • Virtual Tour
      1 of 31
      OPEN HOUSE: Saturday 5/16 3:00 PM - 5:00 PM
      $310,000
      5

      Beds

      3.0

      Baths

      2,624

      Sq.Ft.

      28 Churchill Drive

      Winchester, KY

      Bluegrass
      View 219 Bartram Court Winchester, KY MLS# 26009207
      $310,000
      3

      Beds

      2.1

      Baths

      1,696

      Sq.Ft.

      219 Bartram Court

      Winchester, KY

      Bluegrass
      View 414 Pueblo Court Winchester, KY MLS# 26008330
      $309,999
      3

      Beds

      2.1

      Baths

      2,648

      Sq.Ft.

      414 Pueblo Court

      Winchester, KY

      Bluegrass
      View 144 Holly Avenue Winchester, KY MLS# 26002633
      $308,500
      8

      Beds

      5.0

      Baths

      3,637

      Sq.Ft.

      144 Holly Avenue

      Winchester, KY

      Bluegrass

      About Winchester

      Listings in Winchester, KY

      307

      Estimated median home price

      $270,000
      Winchester KY Homes for Sale & Properties

      Weichert Realtors is one of the nation's leading providers of Winchester, Kentucky real estate for sale and home ownership services. Contact Weichert today to buy or sell real estate in Winchester, KY.

      Homes for Sale by Price in Winchester, KY

      PriceCount
      $0 - 100K35
      $100K - 200K67
      $200K - 300K71
      $300K - 400K43
      $400K - 500K22
      $500K - 600K17
      $600K - 700K11
      $700K - 800K13
      $800K - 900K4
      $900K - 1M2
      $1M - Max22

      Homes for Sale by Type in Winchester, KY

      Property TypeCount
      Single Family176
      Townhouse2
      Condo0
      Commercial16
      Rental17
      Lots and Land96
      Condo/Town/CoOp0
      CoOp0
      Multi Family11
      Mobile Home0
      Farms6

      (Data as of 5/16/2026)

      Information deemed reliable but not guaranteed.

      Listing data provided courtesy of the Internet Data Exchange Program of Bluegrass REALTORS.

      The data relating to real estate for sale on this web site comes in part from the Internet Data Exchange Program of Bluegrass REALTORS. Real Estate listings held by brokerage firms (licensees) other than Weichert Realtors include the name of the listing brokers.

      The information being provided is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

      Data is updated as of 5/16/2026.