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

300 W Broadway Street

Winchester, KY

Bluegrass
View 120 Jackson Street Winchester, KY MLS# 25507377
$248,000
3

Beds

2.1

Baths

1,342

Sq.Ft.

120 Jackson Street

Winchester, KY

Bluegrass
View 130 E Broadway Street Winchester, KY MLS# 25501480
$245,000
5

Beds

3.0

Baths

2,445

Sq.Ft.

130 E Broadway Street

Winchester, KY

Bluegrass
The time to sell is now! THE TIME TO SELL IS NOW!
View 12 Linden Avenue Winchester, KY MLS# 25506319
$240,000
3

Beds

2.0

Baths

1,050

Sq.Ft.

12 Linden Avenue

Winchester, KY

Bluegrass
View 2110 Athens Boonesboro Road Winchester, KY MLS# 25500014
$235,000
Studio

Beds

0.0

Baths

2110 Athens Boonesboro Road

Winchester, KY

Bluegrass
View 23 Kittison Drive Winchester, KY MLS# 25503252
$235,000
3

Beds

2.0

Baths

1,346

Sq.Ft.

23 Kittison Drive

Winchester, KY

Bluegrass
View 209 Allan Place Winchester, KY MLS# 25503412
$234,000
3

Beds

2.0

Baths

1,260

Sq.Ft.

209 Allan Place

Winchester, KY

Bluegrass
View 605 College Street Winchester, KY MLS# 25506124
$230,000
2

Beds

1.0

Baths

1,484

Sq.Ft.

605 College Street

Winchester, KY

Bluegrass
View 19 Cherokee Court Winchester, KY MLS# 25507379
$230,000
3

Beds

1.0

Baths

1,134

Sq.Ft.

19 Cherokee Court

Winchester, KY

Bluegrass
View 314 E Broadway Street Winchester, KY MLS# 25507471
$229,000
3

Beds

1.0

Baths

1,188

Sq.Ft.

314 E Broadway Street

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 3934 Trapp-Goffs Cor Road Winchester, KY MLS# 25503059
$225,000
Studio

Beds

0.0

Baths

3934 Trapp-Goffs Cor Road

Winchester, KY

Bluegrass
View 218 E Washington Street Winchester, KY MLS# 25505534
$225,000
4

Beds

1.0

Baths

1,743

Sq.Ft.

218 E Washington Street

Winchester, KY

Bluegrass
View 443 Jameson Way Winchester, KY MLS# 25507351
$225,000
4

Beds

2.0

Baths

1,400

Sq.Ft.

443 Jameson Way

Winchester, KY

Bluegrass
View 521 Acadia Way Winchester, KY MLS# 25017152
$221,500
4

Beds

2.0

Baths

1,370

Sq.Ft.

521 Acadia Way

Winchester, KY

Bluegrass
View 2721 Pretty Run Road Winchester, KY MLS# 24025198
$220,000
3

Beds

2.0

Baths

1,456

Sq.Ft.

2721 Pretty Run Road

Winchester, KY

Bluegrass
View 13015 Irvine Road Winchester, KY MLS# 25014720
$219,000
Studio

Beds

0.0

Baths

13015 Irvine Road

Winchester, KY

Bluegrass
View 271 April Way Winchester, KY MLS# 25016184
$215,000
2

Beds

1.1

Baths

1,120

Sq.Ft.

271 April Way

Winchester, KY

Bluegrass
View 211 Ashton Oak Way Winchester, KY MLS# 25501640
  • New Construction
1 of 10
$215,000
Studio

Beds

0.0

Baths

211 Ashton Oak Way

Winchester, KY

Bluegrass
View 40 Garner Street Winchester, KY MLS# 25011691
$210,500
3

Beds

1.0

Baths

1,354

Sq.Ft.

40 Garner Street

Winchester, KY

Bluegrass

About Winchester

Listings in Winchester, KY

276

Estimated median home price

$274,900
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 - 100K38
$100K - 200K55
$200K - 300K57
$300K - 400K41
$400K - 500K24
$500K - 600K11
$600K - 700K11
$700K - 800K8
$800K - 900K8
$900K - 1M2
$1M - Max21

Homes for Sale by Type in Winchester, KY

Property TypeCount
Single Family142
Townhouse4
Condo0
Commercial12
Rental19
Lots and Land94
Condo/Town/CoOp0
CoOp0
Multi Family10
Mobile Home0
Farms14

(Data as of 12/24/2025)

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 12/27/2025.