53 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 2799 Pine Ridge Road Winchester, KY MLS# 26011430
$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 110 Knox Court Winchester, KY MLS# 26008587
$129,300
Studio

Beds

0.0

Baths

110 Knox Court

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 3759 Jackson Ferry Road Winchester, KY MLS# 26007289
$105,000
Studio

Beds

0.0

Baths

3759 Jackson Ferry Road

Winchester, KY

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

Beds

0.0

Baths

308 Duclair Drive

Winchester, KY

Bluegrass
View 117 4th Street Winchester, KY MLS# 25501219
$10,000
Studio

Beds

0.0

Baths

117 4th Street

Winchester, KY

Bluegrass
View 4700 Four Mile Road Winchester, KY MLS# 25501428
$52,000
Studio

Beds

0.0

Baths

4700 Four Mile Road

Winchester, KY

Bluegrass
View 471 Goose Creek Road Winchester, KY MLS# 26006002
$129,999
3

Beds

2.0

Baths

1,248

Sq.Ft.

471 Goose Creek Road

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 250 Spencer Lane Winchester, KY MLS# 26005958
$67,500
Studio

Beds

0.0

Baths

250 Spencer Lane

Winchester, KY

Bluegrass
View 4590 Four Mile Road Winchester, KY MLS# 25501424
$108,500
Studio

Beds

0.0

Baths

4590 Four Mile Road

Winchester, KY

Bluegrass
View 160 Rector Lane Winchester, KY MLS# 26005903
$84,900
Studio

Beds

0.0

Baths

160 Rector Lane

Winchester, KY

Bluegrass
View 113 Mayfair Court Winchester, KY MLS# 26005413
$42,500
Studio

Beds

0.0

Baths

113 Mayfair Court

Winchester, KY

Bluegrass

About Winchester

Listings in Winchester, KY

291

Estimated median home price

$275,000
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 - 100K29
$100K - 200K65
$200K - 300K73
$300K - 400K41
$400K - 500K18
$500K - 600K14
$600K - 700K11
$700K - 800K11
$800K - 900K2
$900K - 1M4
$1M - Max23

Homes for Sale by Type in Winchester, KY

Property TypeCount
Single Family171
Townhouse4
Condo0
Commercial13
Rental19
Lots and Land90
Condo/Town/CoOp0
CoOp0
Multi Family9
Mobile Home0
Farms4

(Data as of 6/10/2026)

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 6/10/2026.