View 52 Hillcrest Dr Winchester, KY MLS# 1706974
  • Recently Listed
1 of 29
$219,000
3

Beds

2.0

Baths

2,050

Sq.Ft.

52 Hillcrest Dr

Winchester, KY

GreaterLouisville
View 52 Hillcrest Drive Winchester, KY MLS# 26000887
  • Recently Listed
1 of 29
$219,000
3

Beds

2.0

Baths

2,050

Sq.Ft.

52 Hillcrest Drive

Winchester, KY

Bluegrass
View 37 7th Street Winchester, KY MLS# 24025642
$220,000
3

Beds

2.0

Baths

1,680

Sq.Ft.

37 7th Street

Winchester, KY

Bluegrass
The time to sell is now! THE TIME TO SELL IS NOW!
View 221 S Highland Street Winchester, KY MLS# 26000780
  • Recently Listed
1 of 26
$248,900
5

Beds

3.0

Baths

3,007

Sq.Ft.

221 S Highland Street

Winchester, KY

Bluegrass
View 111 Quail Ridge Road Winchester, KY MLS# 26000646
  • Recently Listed
1 of 19
$189,500
2

Beds

2.1

Baths

1,197

Sq.Ft.

111 Quail Ridge Road

Winchester, KY

Bluegrass
View 109 Quail Ridge Road Winchester, KY MLS# 26000647
  • Recently Listed
1 of 21
$189,500
2

Beds

2.1

Baths

1,197

Sq.Ft.

109 Quail Ridge Road

Winchester, KY

Bluegrass
View 6699 Boonesboro Road Winchester, KY MLS# 25000480
$195,000
Studio

Beds

0.0

Baths

6699 Boonesboro Road

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 1751 Little Stoner Road Winchester, KY MLS# 26000593
$74,900
Studio

Beds

0.0

Baths

1751 Little Stoner Road

Winchester, KY

Bluegrass
View 443 Jameson Way Winchester, KY MLS# 26000614
  • Recently Listed
1 of 22
$221,500
4

Beds

2.0

Baths

1,400

Sq.Ft.

443 Jameson Way

Winchester, KY

Bluegrass
View 521 Acadia Way Winchester, KY MLS# 26000616
  • Recently Listed
1 of 22
$221,500
4

Beds

2.0

Baths

1,370

Sq.Ft.

521 Acadia Way

Winchester, KY

Bluegrass
View 646 Laura Dr E Laura Drive Winchester, KY MLS# 26000619
$249,000
3

Beds

2.0

Baths

1,534

Sq.Ft.

646 Laura Dr E Laura Drive

Winchester, KY

Bluegrass
View 10 Upper Street Winchester, KY MLS# 25004895
$240,000
3

Beds

2.1

Baths

2,380

Sq.Ft.

10 Upper Street

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 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 100 Duclair Drive Winchester, KY MLS# 22024061
$100,000
Studio

Beds

0.0

Baths

100 Duclair Drive

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 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

About Winchester

Listings in Winchester, KY

257

Estimated median home price

$295,000
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 - 200K48
$200K - 300K58
$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 Family147
Townhouse3
Condo0
Commercial12
Rental17
Lots and Land74
Condo/Town/CoOp0
CoOp0
Multi Family8
Mobile Home0
Farms13

(Data as of 1/11/2026)

Information deemed reliable but not guaranteed.

The data relating to real estate for sale on this web site comes in part from the Internet Data Exchange Program of Metro Search Multiple Listing Service. Real Estate listings held by IDX brokers (licensees) other than Weichert Realtors are marked with the IDX logo and detailed information about them includes the name of the IDX 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.

© 2026 Metro Search Multiple Listing Service, Inc. All rights reserved.

Data is updated as of 1/14/2026.

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 1/14/2026.