View 297 S Main Street Winchester, KY MLS# 25501793
    1 of 70
    OPEN HOUSE: Saturday 1/17 12:00 PM - 2:00 PM
    $335,000
    6

    Beds

    4.0

    Baths

    3,544

    Sq.Ft.

    297 S Main Street

    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
    The time to sell is now! THE TIME TO SELL IS NOW!
    View 213 Orchid Court Winchester, KY MLS# 25502706
    $325,000
    4

    Beds

    3.0

    Baths

    1,776

    Sq.Ft.

    213 Orchid Court

    Winchester, KY

    Bluegrass
    View 128 Cherokee Drive Winchester, KY MLS# 25502349
    $319,900
    5

    Beds

    2.0

    Baths

    2,082

    Sq.Ft.

    128 Cherokee Drive

    Winchester, KY

    Bluegrass
    View 22 N Bloomfield Road Winchester, KY MLS# 25507403
    $318,000
    3

    Beds

    2.0

    Baths

    1,913

    Sq.Ft.

    22 N Bloomfield Road

    Winchester, KY

    Bluegrass
    View 1508 Ford Hampton Road Winchester, KY MLS# 25503339
    $315,000
    2

    Beds

    1.0

    Baths

    1,531

    Sq.Ft.

    1508 Ford Hampton Road

    Winchester, KY

    Bluegrass
    View 214 S Burns Avenue Winchester, KY MLS# 25506625
      1 of 55
      OPEN HOUSE: Sunday 1/18 2:00 PM - 5:00 PM
      $312,000
      4

      Beds

      1.1

      Baths

      2,116

      Sq.Ft.

      214 S Burns Avenue

      Winchester, KY

      Bluegrass
      View 398 Pine Ridge Road Winchester, KY MLS# 26000601
      • Recently Listed
      1 of 25
      $310,000
      2

      Beds

      1.0

      Baths

      1,170

      Sq.Ft.

      398 Pine Ridge Road

      Winchester, KY

      Bluegrass
      View 398 Pine Ridge Road Winchester, KY MLS# 26000610
      • Recently Listed
      1 of 25
      $310,000
      Studio

      Beds

      0.0

      Baths

      398 Pine Ridge Road

      Winchester, KY

      Bluegrass
      View 1045 Early Drive Winchester, KY MLS# 20111875
      $300,000
      1,675

      Sq.Ft.

      1045 Early Drive

      Winchester, KY

      Bluegrass
      View 18 N Main Street Winchester, KY MLS# 25004978
      $299,900

      18 N Main Street

      Winchester, KY

      Bluegrass
      View 402 McDowell Drive Winchester, KY MLS# 26000341
      • Recently Listed with Virtual Tour
      1 of 36
      $299,500
      4

      Beds

      2.1

      Baths

      2,136

      Sq.Ft.

      402 McDowell Drive

      Winchester, KY

      Bluegrass
      View 3056 Irvine Road Winchester, KY MLS# 25017326
      $299,000
      Studio

      Beds

      0.0

      Baths

      3056 Irvine Road

      Winchester, KY

      Bluegrass
      View 3056 Irvine Road Winchester, KY MLS# 25500166
      $299,000
      Studio

      Beds

      0.0

      Baths

      3056 Irvine Road

      Winchester, KY

      Bluegrass
      View 4074 Ironworks Road Winchester, KY MLS# 25505744
      $299,000
      3

      Beds

      1.1

      Baths

      1,356

      Sq.Ft.

      4074 Ironworks Road

      Winchester, KY

      Bluegrass
      View 24 N Burns Avenue Winchester, KY MLS# 25507536
        1 of 28
        OPEN HOUSE: Sunday 1/18 1:00 PM - 4:00 PM
        $298,900
        3

        Beds

        3.1

        Baths

        2,526

        Sq.Ft.

        24 N Burns Avenue

        Winchester, KY

        Bluegrass
        View 8 Village Drive Winchester, KY MLS# 25506553
        $295,000
        3

        Beds

        2.0

        Baths

        1,979

        Sq.Ft.

        8 Village Drive

        Winchester, KY

        Bluegrass
        View 420 Willowbrook Road Winchester, KY MLS# 25508189
        $295,000
        3

        Beds

        3.0

        Baths

        1,738

        Sq.Ft.

        420 Willowbrook Road

        Winchester, KY

        Bluegrass
        View 149 Winn Ave Winchester, KY MLS# 26000197
        • Recently Listed
        1 of 24
        $290,000
        12

        Beds

        4.0

        Baths

        4,010

        Sq.Ft.

        149 Winn Ave

        Winchester, KY

        Bluegrass

        About Winchester

        Listings in Winchester, KY

        256

        Estimated median home price

        $299,000
        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 - 100K22
        $100K - 200K48
        $200K - 300K63
        $300K - 400K39
        $400K - 500K23
        $500K - 600K10
        $600K - 700K11
        $700K - 800K10
        $800K - 900K8
        $900K - 1M2
        $1M - Max20

        Homes for Sale by Type in Winchester, KY

        Property TypeCount
        Single Family152
        Townhouse3
        Condo0
        Commercial11
        Rental17
        Lots and Land67
        Condo/Town/CoOp0
        CoOp0
        Multi Family9
        Mobile Home0
        Farms14

        (Data as of 1/16/2026)

        Information deemed reliable but not guaranteed.

        The data relating to real estate for sale on this web site comes in part from the Internet Data Exchange Program of Metro Search Multiple Listing Service. Real Estate listings held by IDX brokers (licensees) other than Weichert Realtors are marked with the IDX logo and detailed information about them includes the name of the IDX 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.

        © 2026 Metro Search Multiple Listing Service, Inc. All rights reserved.

        Data is updated as of 1/17/2026.

        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 1/17/2026.