225 total properties
Did you mean the neighborhood Winchester?
View 122 Callaway Street SE Callaway Street Winchester, KY MLS# 26000228
$129,900
2

Beds

1.0

Baths

876

Sq.Ft.

122 Callaway Street SE Callaway Street

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 120 Knox Court Winchester, KY MLS# 22024088
$150,000
Studio

Beds

0.0

Baths

120 Knox Court

Winchester, KY

Bluegrass
The time to sell is now! THE TIME TO SELL IS NOW!
View 125 Knox Court Winchester, KY MLS# 22024090
$150,000
Studio

Beds

0.0

Baths

125 Knox Court

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

Beds

0.0

Baths

139 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 42 Mockingbird Valley Road Winchester, KY MLS# 26000113
$452,500
3

Beds

2.1

Baths

2,961

Sq.Ft.

42 Mockingbird Valley Road

Winchester, KY

Bluegrass
View 41 7th Street Winchester, KY MLS# 25506758
$185,900
3

Beds

2.0

Baths

1,116

Sq.Ft.

41 7th Street

Winchester, KY

Bluegrass
View 137 East Broadway Street Winchester, KY MLS# 25508602
$374,000
1,536

Sq.Ft.

137 East Broadway Street

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 204 Jett Drive Winchester, KY MLS# 25507850
  • New Construction
1 of 5
$369,900
3

Beds

2.0

Baths

1,558

Sq.Ft.

204 Jett Drive

Winchester, KY

Bluegrass
View 217 S Highland Street Winchester, KY MLS# 25507680
$209,000
4

Beds

2.0

Baths

2,683

Sq.Ft.

217 S Highland Street

Winchester, KY

Bluegrass
View 233 Cunningham Lane Winchester, KY MLS# 25507450
$429,900
3

Beds

2.1

Baths

2,258

Sq.Ft.

233 Cunningham Lane

Winchester, KY

Bluegrass
View 3600 Crowe Ridge Road Winchester, KY MLS# 25507522
  • New Construction
1 of 38
$359,900
4

Beds

4.1

Baths

3600 Crowe Ridge Road

Winchester, KY

Bluegrass
View 590 Craig Crossing Winchester, KY MLS# 25506729
$159,900
Studio

Beds

0.0

Baths

590 Craig Crossing

Winchester, KY

Bluegrass
View 6504 Combs Ferry Road Winchester, KY MLS# 25506634
$419,900
5

Beds

3.1

Baths

2,564

Sq.Ft.

6504 Combs Ferry Road

Winchester, KY

Bluegrass

About Winchester

Listings in Winchester, KY

296

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 - 300K66
$300K - 400K39
$400K - 500K20
$500K - 600K13
$600K - 700K12
$700K - 800K15
$800K - 900K4
$900K - 1M2
$1M - Max20

Homes for Sale by Type in Winchester, KY

Property TypeCount
Single Family163
Townhouse5
Condo0
Commercial14
Rental14
Lots and Land95
Condo/Town/CoOp0
CoOp0
Multi Family12
Mobile Home0
Farms7

(Data as of 4/21/2026)

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 4/22/2026.