132 total properties
Did you mean the neighborhood Winchester?
View 115 Watercrest Circle Winchester, KY MLS# 26002338
$279,950
4

Beds

3.0

Baths

2,112

Sq.Ft.

115 Watercrest Circle

Winchester, KY

Bluegrass
View 404 Wellington Way Winchester, KY MLS# 25505330
$275,700
3

Beds

2.0

Baths

1,682

Sq.Ft.

404 Wellington Way

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
The time to sell is now! THE TIME TO SELL IS NOW!
View 800 Interstate Drive Winchester, KY MLS# 20111867
$270,000
Studio

Beds

0.0

Baths

800 Interstate Drive

Winchester, KY

Bluegrass
View 108 Ashley Drive Winchester, KY MLS# 26001564
$270,000
4

Beds

2.0

Baths

1,984

Sq.Ft.

108 Ashley Drive

Winchester, KY

Bluegrass
View 146 W Lexington Avenue Winchester, KY MLS# 25508389
$269,900
8

Beds

3.0

Baths

3,393

Sq.Ft.

146 W Lexington Avenue

Winchester, KY

Bluegrass
View 146 W Lexington Avenue Winchester, KY MLS# 25508390
$269,900
8

Beds

3.0

Baths

3,393

Sq.Ft.

146 W Lexington Avenue

Winchester, KY

Bluegrass
View 120 Windsor Drive Winchester, KY MLS# 26002472
  • Recently Listed
1 of 12
$269,900
4

Beds

1.0

Baths

1,610

Sq.Ft.

120 Windsor Drive

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 564 Trapp-Goffs Cor Road Winchester, KY MLS# 26000897
$269,000
3

Beds

2.0

Baths

1,960

Sq.Ft.

564 Trapp-Goffs Cor Road

Winchester, KY

Bluegrass
View 916 Stratton Lane Winchester, KY MLS# 26003907
  • Recently Listed
1 of 26
$269,000
3

Beds

2.0

Baths

1,400

Sq.Ft.

916 Stratton Lane

Winchester, KY

Bluegrass
View 174 Hidden Grove Lane Winchester, KY MLS# 25504354
$265,000
2

Beds

2.0

Baths

1,521

Sq.Ft.

174 Hidden Grove Lane

Winchester, KY

Bluegrass
View 190 Privacy Lane Winchester, KY MLS# 25501332
$260,000
Studio

Beds

0.0

Baths

190 Privacy Lane

Winchester, KY

Bluegrass
View 35 Cherokee Court Winchester, KY MLS# 25508113
$260,000
4

Beds

2.0

Baths

2,332

Sq.Ft.

35 Cherokee Court

Winchester, KY

Bluegrass
View 414 Wellington Way Winchester, KY MLS# 26002092
$259,900
3

Beds

2.0

Baths

1,251

Sq.Ft.

414 Wellington Way

Winchester, KY

Bluegrass
View 6 Hart Avenue Winchester, KY MLS# 26003316
  • Recently Listed
1 of 30
$259,900
4

Beds

1.1

Baths

1,405

Sq.Ft.

6 Hart Avenue

Winchester, KY

Bluegrass
View 3614 Stamper Drive Winchester, KY MLS# 25017189
$259,500
3

Beds

2.0

Baths

1,247

Sq.Ft.

3614 Stamper Drive

Winchester, KY

Bluegrass
View 21 Virginia Avenue Winchester, KY MLS# 25506127
$255,000
3

Beds

2.0

Baths

1,749

Sq.Ft.

21 Virginia Avenue

Winchester, KY

Bluegrass
View 133 S Highland Street Winchester, KY MLS# 25017462
$251,000
6

Beds

3.0

Baths

2,302

Sq.Ft.

133 S Highland Street

Winchester, KY

Bluegrass
View 528 Estes Drive Winchester, KY MLS# 25503055
$249,900
3

Beds

2.0

Baths

1,904

Sq.Ft.

528 Estes Drive

Winchester, KY

Bluegrass

About Winchester

Listings in Winchester, KY

255

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 - 200K55
$200K - 300K58
$300K - 400K34
$400K - 500K17
$500K - 600K12
$600K - 700K9
$700K - 800K10
$800K - 900K8
$900K - 1M3
$1M - Max20

Homes for Sale by Type in Winchester, KY

Property TypeCount
Single Family135
Townhouse6
Condo0
Commercial13
Rental18
Lots and Land80
Condo/Town/CoOp0
CoOp0
Multi Family11
Mobile Home0
Farms10

(Data as of 3/3/2026)

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 3/3/2026.