View 1030 Craig Crossing Road Winchester, KY MLS# 22004993
$180,000
Studio

Beds

0.0

Baths

1030 Craig Crossing Road

Winchester, KY

Bluegrass
View 200 Madison Avenue Winchester, KY MLS# 25505150
$179,000
3

Beds

2.0

Baths

1,124

Sq.Ft.

200 Madison Avenue

Winchester, KY

Bluegrass
View 102 W Hickman Street Winchester, KY MLS# 25017468
$171,000
2

Beds

1.0

Baths

870

Sq.Ft.

102 W Hickman Street

Winchester, KY

Bluegrass
The time to sell is now! THE TIME TO SELL IS NOW!
View 12 Apache Trail Winchester, KY MLS# 25500706
$168,500
3

Beds

2.0

Baths

1,026

Sq.Ft.

12 Apache Trail

Winchester, KY

Bluegrass
View 4590 Four Mile Road Winchester, KY MLS# 25501424
$168,000
Studio

Beds

0.0

Baths

4590 Four Mile Road

Winchester, KY

Bluegrass
View 146 Cook Avenue Winchester, KY MLS# 25503408
$167,500
3

Beds

1.0

Baths

1,274

Sq.Ft.

146 Cook Avenue

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 134 Hud Road Winchester, KY MLS# 25507851
  • Recently Listed
1 of 7
$155,000
Studio

Beds

0.0

Baths

134 Hud Road

Winchester, KY

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

Beds

0.0

Baths

120 Knox Court

Winchester, KY

Bluegrass
View 125 Knox Court Winchester, KY MLS# 22024090
$150,000
Studio

Beds

0.0

Baths

125 Knox Court

Winchester, KY

Bluegrass
View 3385 Colby Road Winchester, KY MLS# 24004160
$150,000
Studio

Beds

0.0

Baths

3385 Colby Road

Winchester, KY

Bluegrass
View 3208 Ford Hampton Road Winchester, KY MLS# 25506476
$147,000
2

Beds

1.0

Baths

807

Sq.Ft.

3208 Ford Hampton Road

Winchester, KY

Bluegrass
Courtesy of Lexington - WEICHERT, REALTORS® - ABG
View 228 Jackson Street Winchester, KY MLS# 25015194
$146,000
3

Beds

1.0

Baths

1,020

Sq.Ft.

228 Jackson Street

Winchester, KY

Bluegrass
View 150 Cook Avenue Winchester, KY MLS# 25015192
$144,000
3

Beds

1.0

Baths

805

Sq.Ft.

150 Cook Avenue

Winchester, KY

Bluegrass
View 208 4th Street Winchester, KY MLS# 25501100
$140,000
2

Beds

1.0

Baths

1

Sq.Ft.

208 4th Street

Winchester, KY

Bluegrass
View 103 Yorktowne Court Winchester, KY MLS# 25500573
$139,900
3

Beds

1.0

Baths

1,150

Sq.Ft.

103 Yorktowne Court

Winchester, KY

Bluegrass
View 12569 Ironworks Road Road Winchester, KY MLS# 25002394
$137,500
Studio

Beds

0.0

Baths

12569 Ironworks Road Road

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
View 205 E Washington Street Winchester, KY MLS# 25506086
$124,900
4

Beds

2.1

Baths

2,131

Sq.Ft.

205 E Washington Street

Winchester, KY

Bluegrass

About Winchester

Listings in Winchester, KY

280

Estimated median home price

$274,900
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 - 100K38
$100K - 200K57
$200K - 300K55
$300K - 400K45
$400K - 500K24
$500K - 600K10
$600K - 700K11
$700K - 800K8
$800K - 900K7
$900K - 1M3
$1M - Max22

Homes for Sale by Type in Winchester, KY

Property TypeCount
Single Family144
Townhouse5
Condo0
Commercial13
Rental19
Lots and Land94
Condo/Town/CoOp0
CoOp0
Multi Family9
Mobile Home0
Farms15

(Data as of 12/14/2025)

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 12/15/2025.