249 total properties
Did you mean the neighborhood Winchester?
View Lot 1 - 12 Plantations Drive Winchester, KY MLS# 25506246
$882,000
Studio

Beds

0.0

Baths

Lot 1 - 12 Plantations Drive

Winchester, KY

Bluegrass
View Lot 3 Plantations Drive Winchester, KY MLS# 25506247
$78,500
Studio

Beds

0.0

Baths

Lot 3 Plantations Drive

Winchester, KY

Bluegrass
View Lot 4 Plantations Drive Winchester, KY MLS# 25506248
$78,500
Studio

Beds

0.0

Baths

Lot 4 Plantations Drive

Winchester, KY

Bluegrass
The time to sell is now! THE TIME TO SELL IS NOW!
View Lot 5 Plantations Drive Winchester, KY MLS# 25506250
$78,500
Studio

Beds

0.0

Baths

Lot 5 Plantations Drive

Winchester, KY

Bluegrass
View 605 College Street Winchester, KY MLS# 25506124
$199,900
2

Beds

1.0

Baths

1,484

Sq.Ft.

605 College Street

Winchester, KY

Bluegrass
View 222 Bracken Court Winchester, KY MLS# 25505927
$269,000
3

Beds

2.1

Baths

1,456

Sq.Ft.

222 Bracken Court

Winchester, KY

Bluegrass
View 300 W Broadway Street Winchester, KY MLS# 25505929
$249,000

300 W Broadway Street

Winchester, KY

Bluegrass
View 1503 Schollsville Road Winchester, KY MLS# 25505942
$425,000
5

Beds

3.0

Baths

3,718

Sq.Ft.

1503 Schollsville Road

Winchester, KY

Bluegrass
View 101 S Burns Avenue 1 # 1,2,3,4 Winchester, KY MLS# 25505825
$600,000
8

Beds

4.0

Baths

5,046

Sq.Ft.

101 S Burns Avenue 1 # 1,2,3,4

Winchester, KY

Bluegrass
View 6239 Old Boonesboro Road Winchester, KY MLS# 25505595
$389,900
4

Beds

2.0

Baths

2,659

Sq.Ft.

6239 Old Boonesboro Road

Winchester, KY

Bluegrass
View 218 E Washington Street Winchester, KY MLS# 25505534
$215,000
4

Beds

1.0

Baths

1,743

Sq.Ft.

218 E Washington Street

Winchester, KY

Bluegrass
View 404 Wellington Way Winchester, KY MLS# 25505330
$275,700
3

Beds

2.0

Baths

1,682

Sq.Ft.

404 Wellington Way

Winchester, KY

Bluegrass
View 228 Jackson Street Winchester, KY MLS# 25015194
$146,000
3

Beds

1.0

Baths

1,020

Sq.Ft.

228 Jackson Street

Winchester, KY

Bluegrass
View 300 Calmes Boulevard Winchester, KY MLS# 25504889
$379,717
3

Beds

2.1

Baths

2,636

Sq.Ft.

300 Calmes Boulevard

Winchester, KY

Bluegrass
View 1783 Gay Evans Road Winchester, KY MLS# 25504530
    1 of 51
    OPEN HOUSE: Sunday 3/29 1:00 PM - 3:00 PM
    $775,000
    5

    Beds

    3.1

    Baths

    2,904

    Sq.Ft.

    1783 Gay Evans Road

    Winchester, KY

    Bluegrass
    View 204 Wigeon Court Winchester, KY MLS# 25005098
    $49,500
    Studio

    Beds

    0.0

    Baths

    204 Wigeon Court

    Winchester, KY

    Bluegrass
    View 174 Hidden Grove Lane Winchester, KY MLS# 25504354
    $265,000
    2

    Beds

    2.0

    Baths

    1,521

    Sq.Ft.

    174 Hidden Grove Lane

    Winchester, KY

    Bluegrass
    View 7950 Four Mile Road Winchester, KY MLS# 25503896
    $123,000
    Studio

    Beds

    0.0

    Baths

    7950 Four Mile Road

    Winchester, KY

    Bluegrass
    View 110 Knox Court Winchester, KY MLS# 25503832
    $129,300
    Studio

    Beds

    0.0

    Baths

    110 Knox Court

    Winchester, KY

    Bluegrass
    View 175 Magnolia Street Winchester, KY MLS# 25503492
    $194,000
    3

    Beds

    1.0

    Baths

    1,046

    Sq.Ft.

    175 Magnolia Street

    Winchester, KY

    Bluegrass

    About Winchester

    Listings in Winchester, KY

    266

    Estimated median home price

    $285,000
    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 - 100K30
    $100K - 200K54
    $200K - 300K61
    $300K - 400K37
    $400K - 500K18
    $500K - 600K13
    $600K - 700K11
    $700K - 800K11
    $800K - 900K7
    $900K - 1M4
    $1M - Max20

    Homes for Sale by Type in Winchester, KY

    Property TypeCount
    Single Family145
    Townhouse5
    Condo0
    Commercial13
    Rental15
    Lots and Land78
    Condo/Town/CoOp0
    CoOp0
    Multi Family13
    Mobile Home0
    Farms12

    (Data as of 3/18/2026)

    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 3/23/2026.