72 total properties
Did you mean the neighborhood Winchester?
View 122 Callaway Street SE Callaway Street Winchester, KY MLS# 26000228
$124,500
2

Beds

1.0

Baths

876

Sq.Ft.

122 Callaway Street SE Callaway Street

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 1185 Craig Crossing Road Winchester, KY MLS# 22005014
$110,000
Studio

Beds

0.0

Baths

1185 Craig Crossing Road

Winchester, KY

Bluegrass
The time to sell is now! THE TIME TO SELL IS NOW!
View 120 Duclair Drive Winchester, KY MLS# 22024065
$110,000
Studio

Beds

0.0

Baths

120 Duclair Drive

Winchester, KY

Bluegrass
View 150 Duclair Drive Winchester, KY MLS# 22024072
$110,000
Studio

Beds

0.0

Baths

150 Duclair Drive

Winchester, KY

Bluegrass
View 160 Duclair Drive Winchester, KY MLS# 22024074
$110,000
Studio

Beds

0.0

Baths

160 Duclair Drive

Winchester, KY

Bluegrass
View 200 Duclair Drive Winchester, KY MLS# 22024092
$110,000
Studio

Beds

0.0

Baths

200 Duclair Drive

Winchester, KY

Bluegrass
View 230 Duclair Drive Winchester, KY MLS# 22024095
$110,000
Studio

Beds

0.0

Baths

230 Duclair Drive

Winchester, KY

Bluegrass
View 250 Duclair Drive Winchester, KY MLS# 22024097
$110,000
Studio

Beds

0.0

Baths

250 Duclair Drive

Winchester, KY

Bluegrass
View 260 Duclair Drive Winchester, KY MLS# 22024098
$110,000
Studio

Beds

0.0

Baths

260 Duclair Drive

Winchester, KY

Bluegrass
View 255 Duclair Drive Winchester, KY MLS# 22024102
$110,000
Studio

Beds

0.0

Baths

255 Duclair Drive

Winchester, KY

Bluegrass
View 139 Jacob Court Winchester, KY MLS# 22024111
$110,000
Studio

Beds

0.0

Baths

139 Jacob Court

Winchester, KY

Bluegrass
View 135 Jacob Court Winchester, KY MLS# 22024112
$110,000
Studio

Beds

0.0

Baths

135 Jacob Court

Winchester, KY

Bluegrass
View 125 Jacob Court Winchester, KY MLS# 22024114
$110,000
Studio

Beds

0.0

Baths

125 Jacob Court

Winchester, KY

Bluegrass
View 115 Jacob Court Winchester, KY MLS# 22024116
$110,000
Studio

Beds

0.0

Baths

115 Jacob Court

Winchester, KY

Bluegrass
View 3759 Jackson Ferry Road Winchester, KY MLS# 26007289
$105,000
Studio

Beds

0.0

Baths

3759 Jackson Ferry Road

Winchester, KY

Bluegrass
View 100 Duclair Drive Winchester, KY MLS# 22024061
$100,000
Studio

Beds

0.0

Baths

100 Duclair Drive

Winchester, KY

Bluegrass
View 270 Duclair Drive Winchester, KY MLS# 22024100
$100,000
Studio

Beds

0.0

Baths

270 Duclair Drive

Winchester, KY

Bluegrass
View 111 Jacob Court Winchester, KY MLS# 22024120
$100,000
Studio

Beds

0.0

Baths

111 Jacob Court

Winchester, KY

Bluegrass
View 225 Jacob Court Winchester, KY MLS# 22024121
$100,000
Studio

Beds

0.0

Baths

225 Jacob Court

Winchester, KY

Bluegrass

About Winchester

Listings in Winchester, KY

304

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 - 200K70
$200K - 300K71
$300K - 400K39
$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 Family174
Townhouse4
Condo0
Commercial15
Rental18
Lots and Land95
Condo/Town/CoOp0
CoOp0
Multi Family10
Mobile Home0
Farms6

(Data as of 4/30/2026)

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 5/1/2026.