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 110 Knox Court Winchester, KY MLS# 25503832
$129,800
Studio

Beds

0.0

Baths

110 Knox Court

Winchester, KY

Bluegrass
View 1940 Athens Boonesboro Road Winchester, KY MLS# 25012636
$125,000
Studio

Beds

0.0

Baths

1940 Athens Boonesboro Road

Winchester, KY

Bluegrass
The time to sell is now! THE TIME TO SELL IS NOW!
View 7950 Four Mile Road Winchester, KY MLS# 25503896
$124,000
Studio

Beds

0.0

Baths

7950 Four Mile Road

Winchester, KY

Bluegrass
View 205 E Washington Street Winchester, KY MLS# 25506086
$115,000
4

Beds

2.1

Baths

2,131

Sq.Ft.

205 E Washington Street

Winchester, KY

Bluegrass
View 114 Magnolia Street Winchester, KY MLS# 25506511
$115,000
2

Beds

1.0

Baths

910

Sq.Ft.

114 Magnolia Street

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
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 400 Wexford Drive Winchester, KY MLS# 26000557
  • Recently Listed
1 of 12
$110,000
3

Beds

2.0

Baths

1,260

Sq.Ft.

400 Wexford Drive

Winchester, KY

Bluegrass
View 39 S Highland Street Winchester, KY MLS# 25015196
$102,000
2

Beds

1.0

Baths

552

Sq.Ft.

39 S Highland 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 13015 Irvine Road Parcel 5 # Parcel 5 Winchester, KY MLS# 25500036
$99,900
Studio

Beds

0.0

Baths

13015 Irvine Road Parcel 5 # Parcel 5

Winchester, KY

Bluegrass
View 113 Mimosa Drive Winchester, KY MLS# 26000273
  • Recently Listed
1 of 5
$95,000
3

Beds

2.0

Baths

750

Sq.Ft.

113 Mimosa Drive

Winchester, KY

Bluegrass
Courtesy of Lexington - WEICHERT, REALTORS® - ABG
View 1385 Sewell Shop Road Winchester, KY MLS# 25505870
$90,000
Studio

Beds

0.0

Baths

1385 Sewell Shop Road

Winchester, KY

Bluegrass
View 13067 Irvine Road Winchester, KY MLS# 25500043
$89,100
Studio

Beds

0.0

Baths

13067 Irvine Road

Winchester, KY

Bluegrass
View 1341 Sewell Shop Road Winchester, KY MLS# 25505866
$80,000
Studio

Beds

0.0

Baths

1341 Sewell Shop Road

Winchester, KY

Bluegrass

About Winchester

Listings in Winchester, KY

252

Estimated median home price

$299,000
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 - 100K27
$100K - 200K47
$200K - 300K56
$300K - 400K38
$400K - 500K25
$500K - 600K10
$600K - 700K11
$700K - 800K8
$800K - 900K8
$900K - 1M2
$1M - Max20

Homes for Sale by Type in Winchester, KY

Property TypeCount
Single Family144
Townhouse3
Condo0
Commercial12
Rental18
Lots and Land72
Condo/Town/CoOp0
CoOp0
Multi Family8
Mobile Home0
Farms13

(Data as of 1/8/2026)

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 1/9/2026.