View 505 LaSalle Court Winchester, KY MLS# 26008961
$405,000
5

Beds

3.0

Baths

2,944

Sq.Ft.

505 LaSalle Court

Winchester, KY

Bluegrass
View 1503 Schollsville Road Winchester, KY MLS# 25505942
$399,900
5

Beds

3.0

Baths

3,718

Sq.Ft.

1503 Schollsville Road

Winchester, KY

Bluegrass
View 205 Evergreen Drive Winchester, KY MLS# 25009077
  • New Construction
1 of 3
$395,000
3

Beds

2.0

Baths

1,855

Sq.Ft.

205 Evergreen Drive

Winchester, KY

Bluegrass
The time to sell is now! THE TIME TO SELL IS NOW!
View 382 S Main Street Winchester, KY MLS# 26008931
$395,000
4

Beds

3.0

Baths

3,310

Sq.Ft.

382 S Main Street

Winchester, KY

Bluegrass
View 18 Casa Landa Way Winchester, KY MLS# 26011118
$395,000
3

Beds

2.0

Baths

1,883

Sq.Ft.

18 Casa Landa Way

Winchester, KY

Bluegrass
View 17 W Lexington Avenue Winchester, KY MLS# 26007617
$388,000
8

Beds

8.0

Baths

4,000

Sq.Ft.

17 W Lexington Avenue

Winchester, KY

Bluegrass
View 270 Evergreen Drive Winchester, KY MLS# 25009085
  • New Construction
1 of 3
$380,000
3

Beds

2.0

Baths

1,677

Sq.Ft.

270 Evergreen Drive

Winchester, KY

Bluegrass
View 4305 Old Boonesboro Road Winchester, KY MLS# 26000275
$375,000
3

Beds

2.0

Baths

1,512

Sq.Ft.

4305 Old Boonesboro Road

Winchester, KY

Bluegrass
Courtesy of Lexington - WEICHERT, REALTORS® - ABG
View 137 East Broadway Street Winchester, KY MLS# 25508602
$374,000
1,536

Sq.Ft.

137 East Broadway Street

Winchester, KY

Bluegrass
View 206 Jett Drive Winchester, KY MLS# 24018286
  • New Construction
1 of 24
$365,900
3

Beds

2.0

Baths

1,635

Sq.Ft.

206 Jett Drive

Winchester, KY

Bluegrass
View 204 Jett Drive Winchester, KY MLS# 25507850
  • New Construction
1 of 5
$365,900
3

Beds

2.0

Baths

1,558

Sq.Ft.

204 Jett Drive

Winchester, KY

Bluegrass
View 502 W Lexington Avenue Winchester, KY MLS# 26010324
$360,000
4

Beds

4.1

Baths

4,798

Sq.Ft.

502 W Lexington Avenue

Winchester, KY

Bluegrass
View 750 Providence Lane Winchester, KY MLS# 26006323
$359,900
Studio

Beds

0.0

Baths

750 Providence Lane

Winchester, KY

Bluegrass
View 27 Hampton Avenue Winchester, KY MLS# 26010286
  • Recently Listed
1 of 55
$359,900
3

Beds

2.0

Baths

2,835

Sq.Ft.

27 Hampton Avenue

Winchester, KY

Bluegrass
View 133 Shala-Mar Rue Winchester, KY MLS# 26005511
$359,000
3

Beds

2.0

Baths

2,000

Sq.Ft.

133 Shala-Mar Rue

Winchester, KY

Bluegrass
View 1270 Sewell Shop Road Winchester, KY MLS# 26000914
$354,900
5

Beds

2.0

Baths

1,952

Sq.Ft.

1270 Sewell Shop Road

Winchester, KY

Bluegrass
View 220 Hibiscus Lane Winchester, KY MLS# 26007618
$350,000
3

Beds

2.0

Baths

1,640

Sq.Ft.

220 Hibiscus Lane

Winchester, KY

Bluegrass
View 443 S Maple Street Winchester, KY MLS# 26008225
    1 of 57
    OPEN HOUSE: Sunday 5/17 2:00 PM - 4:00 PM
    $350,000
    4

    Beds

    2.0

    Baths

    3,261

    Sq.Ft.

    443 S Maple Street

    Winchester, KY

    Bluegrass
    View 38 N Burns Avenue Winchester, KY MLS# 26009835
    • Recently Listed
    1 of 33
    $350,000
    4

    Beds

    2.1

    Baths

    2,310

    Sq.Ft.

    38 N Burns Avenue

    Winchester, KY

    Bluegrass
    View 274 Greenway Drive Winchester, KY MLS# 26010546
    $350,000
    4

    Beds

    2.0

    Baths

    2,208

    Sq.Ft.

    274 Greenway Drive

    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 5/17/2026.