View 13 Maryland Avenue Winchester, KY MLS# 26008307
$155,000
2

Beds

1.0

Baths

1,472

Sq.Ft.

13 Maryland Avenue

Winchester, KY

Bluegrass
View 750 Craig Crossing # Lot #7 Winchester, KY MLS# 26013322
$154,900
0.0

Baths

750 Craig Crossing # Lot #7

Winchester, KY

Bluegrass
View 590 Craig Crossing Winchester, KY MLS# 25506729
$152,500
0.0

Baths

590 Craig Crossing

Winchester, KY

Bluegrass
The time to sell is now! THE TIME TO SELL IS NOW!
View 1030 Craig Crossing Road Winchester, KY MLS# 22004993
$150,000
0.0

Baths

1030 Craig Crossing Road

Winchester, KY

Bluegrass
View 120 Knox Court Winchester, KY MLS# 22024088
$150,000
0.0

Baths

120 Knox Court

Winchester, KY

Bluegrass
View 125 Knox Court Winchester, KY MLS# 22024090
$150,000
0.0

Baths

125 Knox Court

Winchester, KY

Bluegrass
View 3385 Colby Road Winchester, KY MLS# 26008075
$150,000
0.0

Baths

3385 Colby Road

Winchester, KY

Bluegrass
View 65 Fitch Avenue Winchester, KY MLS# 26013935
$146,900
3

Beds

1.1

Baths

1,680

Sq.Ft.

65 Fitch Avenue

Winchester, KY

Bluegrass
View 2170 Cole Road Winchester, KY MLS# 26023370
$145,000
2.0

Baths

2170 Cole Road

Winchester, KY

Bluegrass
View 108 Franklin Avenue Winchester, KY MLS# 26022182
$140,000
2

Beds

1.0

Baths

630

Sq.Ft.

108 Franklin Avenue

Winchester, KY

Bluegrass
View 5 S Burns Avenue Winchester, KY MLS# 26024165
$139,000
3

Beds

1.0

Baths

1,842

Sq.Ft.

5 S Burns Avenue

Winchester, KY

Bluegrass
View 48 Judy Ann Court Winchester, KY MLS# 26022172
$137,500
2

Beds

1.1

Baths

960

Sq.Ft.

48 Judy Ann Court

Winchester, KY

Bluegrass
View 3208 Ford Hampton Road Winchester, KY MLS# 26023193
$135,000
2

Beds

1.0

Baths

807

Sq.Ft.

3208 Ford Hampton Road

Winchester, KY

Bluegrass
View 174 Cook Avenue Winchester, KY MLS# 26006389
$134,900
2

Beds

1.0

Baths

986

Sq.Ft.

174 Cook Avenue

Winchester, KY

Bluegrass
View 103 Yorktowne Court Winchester, KY MLS# 25500573
$130,000
3

Beds

1.0

Baths

1,150

Sq.Ft.

103 Yorktowne Court

Winchester, KY

Bluegrass
View 208 4th Street Winchester, KY MLS# 25501100
$130,000
2

Beds

1.0

Baths

1,254

Sq.Ft.

208 4th Street

Winchester, KY

Bluegrass
View 110 Knox Court Winchester, KY MLS# 26008587
$128,800
0.0

Baths

110 Knox Court

Winchester, KY

Bluegrass
View 6590 Ironworks Road Winchester, KY MLS# 26025849
$125,000
1

Beds

1.0

Baths

779

Sq.Ft.

6590 Ironworks Road

Winchester, KY

Bluegrass
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 404 Mount Vernon Drive Winchester, KY MLS# 26005794
$124,000
2

Beds

2.0

Baths

1,360

Sq.Ft.

404 Mount Vernon Drive

Winchester, KY

Bluegrass

About Winchester

Listings in Winchester, KY

269

Estimated median home price

$269,900
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 - 100K36
$100K - 200K51
$200K - 300K61
$300K - 400K40
$400K - 500K21
$500K - 600K15
$600K - 700K12
$700K - 800K7
$800K - 900K2
$900K - 1M3
$1M - Max21

Homes for Sale by Type in Winchester, KY

Property TypeCount
Single Family151
Townhouse4
Condo0
Commercial14
Rental21
Lots and Land85
Condo/Town/CoOp0
CoOp0
Multi Family6
Mobile Home0
Farms9

(Data as of 10/4/2026)

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 10/5/2026.