50 total properties
Did you mean the neighborhood Winchester?
View 133 S Highland Street Winchester, KY MLS# 25017462
$251,000
6

Beds

3.0

Baths

2,302

Sq.Ft.

133 S Highland Street

Winchester, KY

Bluegrass
View 6 Hart Avenue Winchester, KY MLS# 26003316
$259,900
4

Beds

1.1

Baths

1,405

Sq.Ft.

6 Hart Avenue

Winchester, KY

Bluegrass
View 334 S Burns Avenue Winchester, KY MLS# 26003334
$209,000
3

Beds

1.1

Baths

1,636

Sq.Ft.

334 S Burns Avenue

Winchester, KY

Bluegrass
The time to sell is now! THE TIME TO SELL IS NOW!
View 211 Lindsey Court Winchester, KY MLS# 26003170
$285,000
3

Beds

2.0

Baths

1,790

Sq.Ft.

211 Lindsey Court

Winchester, KY

Bluegrass
View 120 Windsor Drive Winchester, KY MLS# 26002472
$259,900
4

Beds

1.0

Baths

1,610

Sq.Ft.

120 Windsor Drive

Winchester, KY

Bluegrass
View 11 Shelley Dr Winchester, KY MLS# 26002369
$234,900
3

Beds

2.0

Baths

1,188

Sq.Ft.

11 Shelley Dr

Winchester, KY

Bluegrass
View 115 Watercrest Circle Winchester, KY MLS# 26002338
$279,950
4

Beds

3.0

Baths

2,112

Sq.Ft.

115 Watercrest Circle

Winchester, KY

Bluegrass
View 414 Wellington Way Winchester, KY MLS# 26002092
$254,900
3

Beds

2.0

Baths

1,251

Sq.Ft.

414 Wellington Way

Winchester, KY

Bluegrass
View 564 Trapp-Goffs Cor Road Winchester, KY MLS# 26000897
$269,000
3

Beds

2.0

Baths

1,960

Sq.Ft.

564 Trapp-Goffs Cor Road

Winchester, KY

Bluegrass
View 17 Euclid Avenue Winchester, KY MLS# 26000917
$249,900
3

Beds

2.0

Baths

1,656

Sq.Ft.

17 Euclid Avenue

Winchester, KY

Bluegrass
View 221 S Highland Street Winchester, KY MLS# 26000780
$246,400
5

Beds

3.0

Baths

3,007

Sq.Ft.

221 S Highland Street

Winchester, KY

Bluegrass
View 443 Jameson Way Winchester, KY MLS# 26000614
$221,500
4

Beds

2.0

Baths

1,400

Sq.Ft.

443 Jameson Way

Winchester, KY

Bluegrass
View 646 Laura Dr E Laura Drive Winchester, KY MLS# 26000619
$249,000
3

Beds

2.0

Baths

1,534

Sq.Ft.

646 Laura Dr E Laura Drive

Winchester, KY

Bluegrass
View 313 S Burns Avenue Winchester, KY MLS# 25508192
$215,000
3

Beds

2.0

Baths

1,518

Sq.Ft.

313 S Burns Avenue

Winchester, KY

Bluegrass
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 217 S Highland Street Winchester, KY MLS# 25507680
$229,900
4

Beds

2.0

Baths

2,683

Sq.Ft.

217 S Highland Street

Winchester, KY

Bluegrass
View 720 Estes Drive Winchester, KY MLS# 25506836
$244,900
3

Beds

1.1

Baths

1,494

Sq.Ft.

720 Estes Drive

Winchester, KY

Bluegrass
View 12 Linden Avenue Winchester, KY MLS# 25506319
$235,000
3

Beds

2.0

Baths

1,050

Sq.Ft.

12 Linden Avenue

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

About Winchester

Listings in Winchester, KY

276

Estimated median home price

$272,500
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 - 100K36
$100K - 200K58
$200K - 300K64
$300K - 400K35
$400K - 500K19
$500K - 600K14
$600K - 700K11
$700K - 800K12
$800K - 900K4
$900K - 1M4
$1M - Max19

Homes for Sale by Type in Winchester, KY

Property TypeCount
Single Family144
Townhouse5
Condo0
Commercial14
Rental15
Lots and Land91
Condo/Town/CoOp0
CoOp0
Multi Family11
Mobile Home0
Farms11

(Data as of 3/27/2026)

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 3/30/2026.