66 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 310 W Hickman Street Winchester, KY MLS# 26012783
  • Recently Listed
1 of 13
$109,900
4

Beds

2.1

Baths

1,391

Sq.Ft.

310 W Hickman Street

Winchester, KY

Bluegrass
View 563 Constitution Drive Winchester, KY MLS# 26012893
$104,900
2

Beds

2.0

Baths

924

Sq.Ft.

563 Constitution Drive

Winchester, KY

Bluegrass
The time to sell is now! THE TIME TO SELL IS NOW!
View 590 Craig Crossing Winchester, KY MLS# 25506729
$152,500
Studio

Beds

0.0

Baths

590 Craig Crossing

Winchester, KY

Bluegrass
View 2799 Pine Ridge Road Winchester, KY MLS# 26011430
  • Recently Listed
1 of 23
$99,900
3

Beds

2.0

Baths

675

Sq.Ft.

2799 Pine Ridge Road

Winchester, KY

Bluegrass
View Lot 3 Plantations Drive Winchester, KY MLS# 26011487
$78,500
Studio

Beds

0.0

Baths

Lot 3 Plantations Drive

Winchester, KY

Bluegrass
View Lot 4 Plantations Drive Winchester, KY MLS# 26011488
$78,500
Studio

Beds

0.0

Baths

Lot 4 Plantations Drive

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 11 Taylor Avenue Winchester, KY MLS# 26008944
$149,900
3

Beds

1.0

Baths

1,362

Sq.Ft.

11 Taylor Avenue

Winchester, KY

Bluegrass
View 9 Linden Avenue Winchester, KY MLS# 25007762
$139,000
2

Beds

1.0

Baths

886

Sq.Ft.

9 Linden Avenue

Winchester, KY

Bluegrass
View 110 Knox Court Winchester, KY MLS# 26008587
$129,300
Studio

Beds

0.0

Baths

110 Knox Court

Winchester, KY

Bluegrass
View 697 Goose Creek Road Winchester, KY MLS# 26008440
$155,000
3

Beds

2.0

Baths

1,848

Sq.Ft.

697 Goose Creek Road

Winchester, KY

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

Beds

0.0

Baths

3385 Colby Road

Winchester, KY

Bluegrass
View 19 3rd Street Winchester, KY MLS# 26007798
$143,000
3

Beds

1.0

Baths

864

Sq.Ft.

19 3rd Street

Winchester, KY

Bluegrass
View 3991 Jackson Ferry Road Winchester, KY MLS# 26007285
$97,500
Studio

Beds

0.0

Baths

3991 Jackson Ferry Road

Winchester, KY

Bluegrass
View 3961 Jackson Ferry Road Winchester, KY MLS# 26007286
$97,500
Studio

Beds

0.0

Baths

3961 Jackson Ferry Road

Winchester, KY

Bluegrass
View 3821 Jackson Ferry Road Winchester, KY MLS# 26007288
$150,000
Studio

Beds

0.0

Baths

3821 Jackson Ferry Road

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 150 Spencer Lane Winchester, KY MLS# 26006848
$137,500
Studio

Beds

0.0

Baths

150 Spencer Lane

Winchester, KY

Bluegrass
View 308 Duclair Drive Winchester, KY MLS# 25018185
$50,000
Studio

Beds

0.0

Baths

308 Duclair Drive

Winchester, KY

Bluegrass

About Winchester

Listings in Winchester, KY

280

Estimated median home price

$269,950
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 - 100K29
$100K - 200K62
$200K - 300K74
$300K - 400K42
$400K - 500K17
$500K - 600K14
$600K - 700K5
$700K - 800K10
$800K - 900K1
$900K - 1M3
$1M - Max23

Homes for Sale by Type in Winchester, KY

Property TypeCount
Single Family160
Townhouse4
Condo0
Commercial13
Rental18
Lots and Land89
Condo/Town/CoOp0
CoOp0
Multi Family10
Mobile Home0
Farms4

(Data as of 6/7/2026)

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 6/9/2026.