View 128 Cherokee Drive Winchester, KY MLS# 26003806
$319,900
5

Beds

2.0

Baths

2,082

Sq.Ft.

128 Cherokee Drive

Winchester, KY

Bluegrass
View 162 French Avenue Winchester, KY MLS# 26009734
  • Recently Listed
1 of 38
$319,900
4

Beds

1.0

Baths

2,327

Sq.Ft.

162 French Avenue

Winchester, KY

Bluegrass
View 3622 Stamper Drive Winchester, KY MLS# 26009877
  • Recently Listed
1 of 43
$319,900
3

Beds

3.0

Baths

2,821

Sq.Ft.

3622 Stamper Drive

Winchester, KY

Bluegrass
The time to sell is now! THE TIME TO SELL IS NOW!
View 200 Dubuy Drive Winchester, KY MLS# 26008021
$312,000
3

Beds

2.1

Baths

1,858

Sq.Ft.

200 Dubuy Drive

Winchester, KY

Bluegrass
View 412 Pueblo Court Winchester, KY MLS# 26008794
  • Virtual Tour
1 of 30
$312,000
3

Beds

2.1

Baths

2,648

Sq.Ft.

412 Pueblo Court

Winchester, KY

Bluegrass
View 28 Churchill Drive Winchester, KY MLS# 26008797
$310,000
5

Beds

3.0

Baths

2,624

Sq.Ft.

28 Churchill Drive

Winchester, KY

Bluegrass
View 219 Bartram Court Winchester, KY MLS# 26009207
$310,000
3

Beds

2.1

Baths

1,696

Sq.Ft.

219 Bartram Court

Winchester, KY

Bluegrass
View 414 Pueblo Court Winchester, KY MLS# 26008330
$309,999
3

Beds

2.1

Baths

2,648

Sq.Ft.

414 Pueblo Court

Winchester, KY

Bluegrass
View 144 Holly Avenue Winchester, KY MLS# 26002633
$308,500
8

Beds

5.0

Baths

3,637

Sq.Ft.

144 Holly Avenue

Winchester, KY

Bluegrass
View 118 Windridge Drive Winchester, KY MLS# 26006695
$307,900
3

Beds

2.0

Baths

1,617

Sq.Ft.

118 Windridge Drive

Winchester, KY

Bluegrass
View 1045 Early Drive Winchester, KY MLS# 20111875
$300,000
1,675

Sq.Ft.

1045 Early Drive

Winchester, KY

Bluegrass
View 4025 Jackson Ferry Road Winchester, KY MLS# 26007284
$300,000
Studio

Beds

0.0

Baths

4025 Jackson Ferry Road

Winchester, KY

Bluegrass
View 306 Trapp-Goffs Cor Road Winchester, KY MLS# 26008462
$299,900
4

Beds

2.0

Baths

1,840

Sq.Ft.

306 Trapp-Goffs Cor Road

Winchester, KY

Bluegrass
View 147 Sunset Heights Winchester, KY MLS# 26011009
  • Recently Listed
1 of 38
$299,900
3

Beds

2.0

Baths

2,128

Sq.Ft.

147 Sunset Heights

Winchester, KY

Bluegrass
View 209 Boone Avenue Winchester, KY MLS# 26011097
  • Recently Listed with Virtual Tour
1 of 24
$299,900
3

Beds

2.1

Baths

2,260

Sq.Ft.

209 Boone Avenue

Winchester, KY

Bluegrass
View 550 E Broadway Street Winchester, KY MLS# 25018505
$299,000
Studio

Beds

0.0

Baths

550 E Broadway Street

Winchester, KY

Bluegrass
View 54 Locust Drive Winchester, KY MLS# 26007779
$299,000
3

Beds

2.0

Baths

1,692

Sq.Ft.

54 Locust Drive

Winchester, KY

Bluegrass
View 409-411 N Main Street Winchester, KY MLS# 26010325
  • Recently Listed
1 of 32
$299,000
300

Sq.Ft.

409-411 N Main Street

Winchester, KY

Bluegrass
View 618 Westmeade Drive Winchester, KY MLS# 26009371
  • Recently Listed
1 of 38
$296,900
4

Beds

2.0

Baths

2,116

Sq.Ft.

618 Westmeade Drive

Winchester, KY

Bluegrass
View 398 Pine Ridge Road Winchester, KY MLS# 26000601
$295,000
2

Beds

1.0

Baths

1,170

Sq.Ft.

398 Pine Ridge Road

Winchester, KY

Bluegrass

About Winchester

Listings in Winchester, KY

309

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 - 100K35
$100K - 200K65
$200K - 300K72
$300K - 400K44
$400K - 500K24
$500K - 600K17
$600K - 700K11
$700K - 800K13
$800K - 900K4
$900K - 1M2
$1M - Max22

Homes for Sale by Type in Winchester, KY

Property TypeCount
Single Family179
Townhouse2
Condo0
Commercial16
Rental17
Lots and Land95
Condo/Town/CoOp0
CoOp0
Multi Family11
Mobile Home0
Farms6

(Data as of 5/18/2026)

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 5/18/2026.