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 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
The time to sell is now! THE TIME TO SELL IS NOW!
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
      View 4180 Bybee Road Winchester, KY MLS# 26001069
      • Recently Listed
      1 of 45
      $290,000
      3

      Beds

      1.0

      Baths

      1,523

      Sq.Ft.

      4180 Bybee Road

      Winchester, KY

      Bluegrass
      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

      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 1/19/2026.

      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 1/19/2026.