View 410 Wellington Way Winchester, KY MLS# 25506265
$268,000
3

Beds

2.0

Baths

1,192

Sq.Ft.

410 Wellington Way

Winchester, KY

Bluegrass
View 222 Bracken Court Winchester, KY MLS# 25505927
$269,000
3

Beds

2.1

Baths

1,456

Sq.Ft.

222 Bracken Court

Winchester, KY

Bluegrass
View 146 W Lexington Avenue Winchester, KY MLS# 25508389
$269,900
7

Beds

3.0

Baths

3,393

Sq.Ft.

146 W Lexington Avenue

Winchester, KY

Bluegrass
The time to sell is now! THE TIME TO SELL IS NOW!
View 146 W Lexington Avenue Winchester, KY MLS# 25508390
$269,900
7

Beds

3.0

Baths

3,393

Sq.Ft.

146 W Lexington Avenue

Winchester, KY

Bluegrass
View 800 Interstate Drive Winchester, KY MLS# 20111867
$270,000
Studio

Beds

0.0

Baths

800 Interstate Drive

Winchester, KY

Bluegrass
View 35 Cherokee Court Winchester, KY MLS# 25508113
  • Recently Listed
1 of 22
$270,000
4

Beds

2.0

Baths

2,332

Sq.Ft.

35 Cherokee Court

Winchester, KY

Bluegrass
View 165 Hilltop Drive Winchester, KY MLS# 25501723
$274,900
3

Beds

2.0

Baths

1,454

Sq.Ft.

165 Hilltop Drive

Winchester, KY

Bluegrass
View 407 Corinne Court Winchester, KY MLS# 25503382
$274,900
3

Beds

2.0

Baths

1,352

Sq.Ft.

407 Corinne Court

Winchester, KY

Bluegrass
View 20 Bon-Haven Avenue Winchester, KY MLS# 25500083
$275,000
4

Beds

3.0

Baths

1,850

Sq.Ft.

20 Bon-Haven Avenue

Winchester, KY

Bluegrass
View 724 Terry Drive Winchester, KY MLS# 25503172
$279,500
3

Beds

2.0

Baths

2,250

Sq.Ft.

724 Terry Drive

Winchester, KY

Bluegrass
View 404 Wellington Way Winchester, KY MLS# 25505330
$279,700
3

Beds

2.0

Baths

1,682

Sq.Ft.

404 Wellington Way

Winchester, KY

Bluegrass
View 729 Wayland Drive Winchester, KY MLS# 25504199
$284,000
3

Beds

2.0

Baths

1,966

Sq.Ft.

729 Wayland Drive

Winchester, KY

Bluegrass
View 424 Waycross Drive Winchester, KY MLS# 25508213
$289,900
4

Beds

3.0

Baths

1,944

Sq.Ft.

424 Waycross Drive

Winchester, KY

Bluegrass
View 8 Village Drive Winchester, KY MLS# 25506553
$295,000
3

Beds

2.0

Baths

1,979

Sq.Ft.

8 Village Drive

Winchester, KY

Bluegrass
View 420 Willowbrook Road Winchester, KY MLS# 25508189
  • Recently Listed with Virtual Tour
1 of 31
$295,000
3

Beds

3.0

Baths

1,738

Sq.Ft.

420 Willowbrook Road

Winchester, KY

Bluegrass
View 3056 Irvine Road Winchester, KY MLS# 25017326
$299,000
Studio

Beds

0.0

Baths

3056 Irvine Road

Winchester, KY

Bluegrass
View 3056 Irvine Road Winchester, KY MLS# 25500166
$299,000
Studio

Beds

0.0

Baths

3056 Irvine Road

Winchester, KY

Bluegrass
View 4074 Ironworks Road Winchester, KY MLS# 25505744
$299,000
3

Beds

1.1

Baths

1,356

Sq.Ft.

4074 Ironworks Road

Winchester, KY

Bluegrass
View 18 N Main Street Winchester, KY MLS# 25004978
$299,900

18 N Main Street

Winchester, KY

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

Sq.Ft.

1045 Early Drive

Winchester, KY

Bluegrass

About Winchester

Listings in Winchester, KY

239

Estimated median home price

$305,000
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 - 100K25
$100K - 200K39
$200K - 300K55
$300K - 400K40
$400K - 500K22
$500K - 600K9
$600K - 700K11
$700K - 800K8
$800K - 900K8
$900K - 1M2
$1M - Max20

Homes for Sale by Type in Winchester, KY

Property TypeCount
Single Family137
Townhouse3
Condo0
Commercial12
Rental18
Lots and Land64
Condo/Town/CoOp0
CoOp0
Multi Family9
Mobile Home0
Farms14

(Data as of 1/1/2026)

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 1/2/2026.