View 137 East Broadway Street Winchester, KY MLS# 25508602
$399,000
1,536

Sq.Ft.

137 East Broadway Street

Winchester, KY

Bluegrass
View 20 Bon-Haven Avenue Winchester, KY MLS# 25500083
$275,000
4

Beds

3.0

Baths

1,850

Sq.Ft.

20 Bon-Haven Avenue

Winchester, KY

Bluegrass
View 417 Mt Vernon Drive Winchester, KY MLS# 25508464
  • Recently Listed
1 of 22
$145,000
3

Beds

2.0

Baths

1,300

Sq.Ft.

417 Mt Vernon Drive

Winchester, KY

Bluegrass
The time to sell is now! THE TIME TO SELL IS NOW!
View 9 Linden Avenue Winchester, KY MLS# 25007762
$139,000
2

Beds

1.0

Baths

886

Sq.Ft.

9 Linden Avenue

Winchester, KY

Bluegrass
View 146 W Lexington Avenue Winchester, KY MLS# 25508389
$269,900
7

Beds

3.0

Baths

3,393

Sq.Ft.

146 W Lexington Avenue

Winchester, KY

Bluegrass
View 146 W Lexington Avenue Winchester, KY MLS# 25508390
$269,900
7

Beds

3.0

Baths

3,393

Sq.Ft.

146 W Lexington Avenue

Winchester, KY

Bluegrass
View 125 Casa Landa Way Winchester, KY MLS# 25508316
$550,000
4

Beds

3.1

Baths

3,848

Sq.Ft.

125 Casa Landa Way

Winchester, KY

Bluegrass
View 33-41 Winn Avenue Winchester, KY MLS# 25508043
$550,000
Studio

Beds

0.0

Baths

33-41 Winn Avenue

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 313 S Burns Avenue Winchester, KY MLS# 25508192
$250,000
3

Beds

2.0

Baths

1,518

Sq.Ft.

313 S Burns Avenue

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
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 6595 Mt Sterling Road Winchester, KY MLS# 25507834
$609,900
5

Beds

4.0

Baths

4,515

Sq.Ft.

6595 Mt Sterling Road

Winchester, KY

Bluegrass
View 204 Jett Drive Winchester, KY MLS# 25507850
  • New Construction
1 of 2
$369,900
3

Beds

2.0

Baths

1,558

Sq.Ft.

204 Jett Drive

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
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 233 Cunningham Lane Winchester, KY MLS# 25507450
$450,000
3

Beds

2.1

Baths

2,258

Sq.Ft.

233 Cunningham Lane

Winchester, KY

Bluegrass
View 3600 Crowe Ridge Road Winchester, KY MLS# 25507522
  • New Construction
1 of 38
$384,900
4

Beds

4.1

Baths

3600 Crowe Ridge 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
    $309,900
    3

    Beds

    3.1

    Baths

    2,526

    Sq.Ft.

    24 N Burns Avenue

    Winchester, KY

    Bluegrass
    View 133 Shala-Mar Rue Winchester, KY MLS# 25507513
    $379,000
    3

    Beds

    2.0

    Baths

    2,000

    Sq.Ft.

    133 Shala-Mar Rue

    Winchester, KY

    Bluegrass

    About Winchester

    Listings in Winchester, KY

    257

    Estimated median home price

    $295,000
    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 - 100K29
    $100K - 200K48
    $200K - 300K58
    $300K - 400K38
    $400K - 500K25
    $500K - 600K10
    $600K - 700K11
    $700K - 800K8
    $800K - 900K8
    $900K - 1M2
    $1M - Max20

    Homes for Sale by Type in Winchester, KY

    Property TypeCount
    Single Family147
    Townhouse3
    Condo0
    Commercial12
    Rental17
    Lots and Land74
    Condo/Town/CoOp0
    CoOp0
    Multi Family8
    Mobile Home0
    Farms13

    (Data as of 1/11/2026)

    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.