58 total properties
Did you mean the neighborhood Winchester?
View 123 Sunset Heights Winchester, KY MLS# 26009360
  • Recently Listed
1 of 31
$255,900
3

Beds

2.0

Baths

1,446

Sq.Ft.

123 Sunset Heights

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 164 Buckingham Lane Winchester, KY MLS# 26009383
  • Recently Listed
1 of 25
$270,000
3

Beds

2.0

Baths

1,190

Sq.Ft.

164 Buckingham Lane

Winchester, KY

Bluegrass
The time to sell is now! THE TIME TO SELL IS NOW!
View 86 Bon-Haven Avenue Winchester, KY MLS# 26009398
$269,000
4

Beds

2.0

Baths

2,295

Sq.Ft.

86 Bon-Haven Avenue

Winchester, KY

Bluegrass
View 54 Locust Drive Winchester, KY MLS# 26007779
  • Recently Listed
1 of 40
OPEN HOUSE: Sunday 5/3 1:00 PM - 3:00 PM
$299,000
3

Beds

2.0

Baths

1,692

Sq.Ft.

54 Locust Drive

Winchester, KY

Bluegrass
View 363 S Main Street Winchester, KY MLS# 26009123
  • Recently Listed
1 of 32
$250,000
3

Beds

2.0

Baths

2,142

Sq.Ft.

363 S Main Street

Winchester, KY

Bluegrass
View 720 Terry Drive Winchester, KY MLS# 26009068
  • Recently Listed
1 of 57
$275,000
3

Beds

2.0

Baths

1,779

Sq.Ft.

720 Terry Drive

Winchester, KY

Bluegrass
View 148 W Lexington Avenue Winchester, KY MLS# 26008946
$239,900
5

Beds

2.0

Baths

2,570

Sq.Ft.

148 W Lexington Avenue

Winchester, KY

Bluegrass
View 110 Buckingham Lane Winchester, KY MLS# 26008814
$275,000
3

Beds

2.0

Baths

1,240

Sq.Ft.

110 Buckingham Lane

Winchester, KY

Bluegrass
View 213 Short Street Winchester, KY MLS# 26008598
$229,000
3

Beds

2.0

Baths

1,068

Sq.Ft.

213 Short Street

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 17 Holiday Road Winchester, KY MLS# 26008222
  • Recently Listed
1 of 62
$264,900
3

Beds

1.1

Baths

1,161

Sq.Ft.

17 Holiday Road

Winchester, KY

Bluegrass
View 426 E Broadway Street Winchester, KY MLS# 26007906
$289,000
5

Beds

2.0

Baths

1,838

Sq.Ft.

426 E Broadway Street

Winchester, KY

Bluegrass
View 720 Estes Drive Winchester, KY MLS# 26007668
  • Recently Listed
1 of 21
$244,900
3

Beds

1.1

Baths

1,494

Sq.Ft.

720 Estes Drive

Winchester, KY

Bluegrass
View 11 Shelley Drive Winchester, KY MLS# 26007607
$224,900
3

Beds

2.0

Baths

1,188

Sq.Ft.

11 Shelley Drive

Winchester, KY

Bluegrass
View 402 Harney Drive Winchester, KY MLS# 26007559
$275,000
3

Beds

1.1

Baths

1,634

Sq.Ft.

402 Harney Drive

Winchester, KY

Bluegrass
View 103 Southern Court Winchester, KY MLS# 26007260
$300,000
3

Beds

1.1

Baths

1,500

Sq.Ft.

103 Southern Court

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 318 Buffalo Trace Winchester, KY MLS# 26007299
  • New Construction
1 of 15
$234,900
3

Beds

2.0

Baths

1,200

Sq.Ft.

318 Buffalo Trace

Winchester, KY

Bluegrass
View 3056 Irvine Road Winchester, KY MLS# 26007074
$250,000
Studio

Beds

0.0

Baths

3056 Irvine Road

Winchester, KY

Bluegrass

About Winchester

Listings in Winchester, KY

304

Estimated median home price

$269,500
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 - 100K36
$100K - 200K70
$200K - 300K71
$300K - 400K39
$400K - 500K23
$500K - 600K13
$600K - 700K10
$700K - 800K16
$800K - 900K3
$900K - 1M2
$1M - Max21

Homes for Sale by Type in Winchester, KY

Property TypeCount
Single Family174
Townhouse4
Condo0
Commercial15
Rental18
Lots and Land95
Condo/Town/CoOp0
CoOp0
Multi Family10
Mobile Home0
Farms6

(Data as of 4/30/2026)

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 4/30/2026.