View 35 Cherokee Court Winchester, KY MLS# 25508113
$255,000
4

Beds

2.0

Baths

2,332

Sq.Ft.

35 Cherokee Court

Winchester, KY

Bluegrass
View 18 N Main Street Winchester, KY MLS# 25004978
$250,000
4,300

Sq.Ft.

18 N Main Street

Winchester, KY

Bluegrass
View 3056 Irvine Road Winchester, KY MLS# 26007074
$250,000
Studio

Beds

0.0

Baths

3056 Irvine Road

Winchester, KY

Bluegrass
The time to sell is now! THE TIME TO SELL IS NOW!
View 363 S Main Street Winchester, KY MLS# 26009123
$250,000
3

Beds

2.0

Baths

2,142

Sq.Ft.

363 S Main Street

Winchester, KY

Bluegrass
View 217 Short Street Winchester, KY MLS# 26010963
  • Recently Listed
1 of 50
$250,000
3

Beds

1.0

Baths

1,042

Sq.Ft.

217 Short Street

Winchester, KY

Bluegrass
View 528 Estes Drive Winchester, KY MLS# 25503055
$249,900
3

Beds

2.0

Baths

1,904

Sq.Ft.

528 Estes Drive

Winchester, KY

Bluegrass
View 120 Windsor Drive Winchester, KY MLS# 26002472
$249,900
4

Beds

1.0

Baths

1,610

Sq.Ft.

120 Windsor Drive

Winchester, KY

Bluegrass
View 1407 Ironworks Road Winchester, KY MLS# 26004591
$249,900
3

Beds

2.0

Baths

1,530

Sq.Ft.

1407 Ironworks Road

Winchester, KY

Bluegrass
View 5127 Combs Ferry Road Winchester, KY MLS# 26011064
$249,000
Studio

Beds

0.0

Baths

5127 Combs Ferry Road

Winchester, KY

Bluegrass
View 190 Privacy Lane Winchester, KY MLS# 25501332
$245,000
Studio

Beds

0.0

Baths

190 Privacy Lane

Winchester, KY

Bluegrass
View 720 Estes Drive Winchester, KY MLS# 26007668
$244,900
3

Beds

1.1

Baths

1,494

Sq.Ft.

720 Estes Drive

Winchester, KY

Bluegrass
View 407 Pueblo Court Winchester, KY MLS# 26010046
$240,000
3

Beds

2.0

Baths

1,244

Sq.Ft.

407 Pueblo Court

Winchester, KY

Bluegrass
View 3610 Stamper Drive Winchester, KY MLS# 26006288
$239,900
3

Beds

2.0

Baths

1,148

Sq.Ft.

3610 Stamper Drive

Winchester, KY

Bluegrass
View 221 S Highland Street Winchester, KY MLS# 26006685
$239,900
5

Beds

3.0

Baths

3,007

Sq.Ft.

221 S Highland Street

Winchester, KY

Bluegrass
View 357 Silverton Way Winchester, KY MLS# 26003487
$235,000
3

Beds

2.0

Baths

1,502

Sq.Ft.

357 Silverton Way

Winchester, KY

Bluegrass
View 13 Arlington Road Winchester, KY MLS# 26005875
$235,000
4

Beds

2.0

Baths

1,431

Sq.Ft.

13 Arlington Road

Winchester, KY

Bluegrass
View 108 Spruce Court Winchester, KY MLS# 26009399
  • Recently Listed
1 of 22
$230,000
4

Beds

2.0

Baths

2,106

Sq.Ft.

108 Spruce Court

Winchester, KY

Bluegrass
View 86 Brink Avenue Winchester, KY MLS# 26010543
$230,000
3

Beds

2.0

Baths

1,136

Sq.Ft.

86 Brink Avenue

Winchester, KY

Bluegrass
View 213 Short Street Winchester, KY MLS# 26008598
$229,000
3

Beds

2.0

Baths

1,068

Sq.Ft.

213 Short Street

Winchester, KY

Bluegrass
View 2110 Athens Boonesboro Road Winchester, KY MLS# 25500014
$225,000
Studio

Beds

0.0

Baths

2110 Athens Boonesboro Road

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 5/16/2026.