4 total properties
Did you mean the neighborhood Winchester?
View 3760 Old Boonesboro Road Winchester, KY MLS# 26006697
$1,290,000
5

Beds

5.0

Baths

5,666

Sq.Ft.

3760 Old Boonesboro Road

Winchester, KY

Bluegrass
View 2 N Main Street Winchester, KY MLS# 25017572
$1,575,000
37

Beds

19.1

Baths

26,124

Sq.Ft.

2 N Main Street

Winchester, KY

Bluegrass
View 250 Shoppers Drive Winchester, KY MLS# 25505209
$1,500,000

250 Shoppers Drive

Winchester, KY

Bluegrass
The time to sell is now! THE TIME TO SELL IS NOW!
View 155 April Way Winchester, KY MLS# 23015568
$1,350,000
Studio

Beds

0.0

Baths

155 April Way

Winchester, KY

Bluegrass

About Winchester

Listings in Winchester, KY

301

Estimated median home price

$269,500
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 - 200K69
$200K - 300K70
$300K - 400K38
$400K - 500K23
$500K - 600K13
$600K - 700K10
$700K - 800K16
$800K - 900K3
$900K - 1M2
$1M - Max21

Homes for Sale by Type in Winchester, KY

Property TypeCount
Single Family171
Townhouse4
Condo0
Commercial15
Rental18
Lots and Land95
Condo/Town/CoOp0
CoOp0
Multi Family10
Mobile Home0
Farms6

(Data as of 5/1/2026)

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 5/2/2026.