View 424 Waycross Drive Winchester, KY MLS# 25508213
$289,900
4

Beds

3.0

Baths

1,944

Sq.Ft.

424 Waycross Drive

Winchester, KY

Bluegrass
View 35 Cherokee Court Winchester, KY MLS# 25508113
$265,000
4

Beds

2.0

Baths

2,332

Sq.Ft.

35 Cherokee Court

Winchester, KY

Bluegrass
View 394 S Main Street Winchester, KY MLS# 25507786
$229,000
4

Beds

2.0

Baths

1,858

Sq.Ft.

394 S Main Street

Winchester, KY

Bluegrass
The time to sell is now! THE TIME TO SELL IS NOW!
View 217 S Highland Street Winchester, KY MLS# 25507680
$259,900
4

Beds

2.0

Baths

2,683

Sq.Ft.

217 S Highland Street

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
    $309,900
    3

    Beds

    3.1

    Baths

    2,526

    Sq.Ft.

    24 N Burns Avenue

    Winchester, KY

    Bluegrass
    View 117 Buffalo Trace Winchester, KY MLS# 25507380
    $199,900
    3

    Beds

    2.0

    Baths

    1,072

    Sq.Ft.

    117 Buffalo Trace

    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 3622 Stamper Drive Winchester, KY MLS# 25507430
    $349,900
    3

    Beds

    3.0

    Baths

    2,821

    Sq.Ft.

    3622 Stamper Drive

    Winchester, KY

    Bluegrass
    View 314 E Broadway Street Winchester, KY MLS# 25507471
    $224,000
    3

    Beds

    1.0

    Baths

    1,188

    Sq.Ft.

    314 E Broadway Street

    Winchester, KY

    Bluegrass
    View 120 Jackson Street Winchester, KY MLS# 25507377
    $248,000
    3

    Beds

    2.1

    Baths

    1,342

    Sq.Ft.

    120 Jackson Street

    Winchester, KY

    Bluegrass
    View 19 Cherokee Court Winchester, KY MLS# 25507379
    $230,000
    3

    Beds

    1.0

    Baths

    1,134

    Sq.Ft.

    19 Cherokee Court

    Winchester, KY

    Bluegrass
    View 2721 Pretty Run Road Winchester, KY MLS# 24025198
    $215,000
    3

    Beds

    2.0

    Baths

    1,456

    Sq.Ft.

    2721 Pretty Run Road

    Winchester, KY

    Bluegrass
    View 208 Watercrest Way Winchester, KY MLS# 25507056
    $255,000
    3

    Beds

    2.1

    Baths

    1,416

    Sq.Ft.

    208 Watercrest Way

    Winchester, KY

    Bluegrass
    View 214 S Burns Avenue Winchester, KY MLS# 25506625
      1 of 54
      OPEN HOUSE: Sunday 1/18 2:00 PM - 5:00 PM
      $312,000
      4

      Beds

      1.1

      Baths

      2,170

      Sq.Ft.

      214 S Burns Avenue

      Winchester, KY

      Bluegrass
      View 720 Estes Drive Winchester, KY MLS# 25506836
      $249,900
      3

      Beds

      1.0

      Baths

      1,494

      Sq.Ft.

      720 Estes Drive

      Winchester, KY

      Bluegrass
      View 21 Virginia Avenue Winchester, KY MLS# 25506127
      $255,000
      3

      Beds

      2.0

      Baths

      1,749

      Sq.Ft.

      21 Virginia Avenue

      Winchester, KY

      Bluegrass
      View 590 Craig Crossing Winchester, KY MLS# 25506729
      $159,900
      Studio

      Beds

      0.0

      Baths

      590 Craig Crossing

      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 102 Augusta Drive Winchester, KY MLS# 24022901
      $29,000
      Studio

      Beds

      0.0

      Baths

      102 Augusta Drive

      Winchester, KY

      Bluegrass
      View 3208 Ford Hampton Road Winchester, KY MLS# 25506476
      $147,000
      2

      Beds

      1.0

      Baths

      807

      Sq.Ft.

      3208 Ford Hampton Road

      Winchester, KY

      Bluegrass
      Courtesy of Lexington - WEICHERT, REALTORS® - ABG

      About Winchester

      Listings in Winchester, KY

      262

      Estimated median home price

      $292,500
      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 - 100K29
      $100K - 200K48
      $200K - 300K62
      $300K - 400K37
      $400K - 500K24
      $500K - 600K10
      $600K - 700K11
      $700K - 800K10
      $800K - 900K9
      $900K - 1M2
      $1M - Max20

      Homes for Sale by Type in Winchester, KY

      Property TypeCount
      Single Family151
      Townhouse3
      Condo0
      Commercial12
      Rental18
      Lots and Land74
      Condo/Town/CoOp0
      CoOp0
      Multi Family8
      Mobile Home0
      Farms14

      (Data as of 1/14/2026)

      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 1/14/2026.

      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 1/14/2026.