View 108 Ashley Drive Winchester, KY MLS# 26001564
  • Recently Listed
1 of 23
$270,000
4

Beds

2.0

Baths

1,984

Sq.Ft.

108 Ashley Drive

Winchester, KY

Bluegrass
View 426 Paisley Court Winchester, KY MLS# 26001596
  • Virtual Tour
1 of 35
$244,900
3

Beds

2.1

Baths

1,641

Sq.Ft.

426 Paisley Court

Winchester, KY

Bluegrass
View 414 Wellington Way Winchester, KY MLS# 26001608
  • Recently Listed with Virtual Tour
1 of 32
$259,900
3

Beds

2.0

Baths

1,251

Sq.Ft.

414 Wellington Way

Winchester, KY

Bluegrass
The time to sell is now! THE TIME TO SELL IS NOW!
View 6261 Ironworks Rd Winchester, KY MLS# 1707493
$300,000
Studio

Beds

0.0

Baths

6261 Ironworks Rd

Winchester, KY

GreaterLouisville
View 313 Carolina Avenue Winchester, KY MLS# 26001286
$260,000
4

Beds

1.2

Baths

1,855

Sq.Ft.

313 Carolina Avenue

Winchester, KY

Bluegrass
View 4180 Bybee Road Winchester, KY MLS# 26001069
$290,000
3

Beds

1.0

Baths

1,523

Sq.Ft.

4180 Bybee Road

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 17 Euclid Avenue Winchester, KY MLS# 26000917
  • Recently Listed
1 of 31
$249,900
3

Beds

2.0

Baths

1,656

Sq.Ft.

17 Euclid Avenue

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
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 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
$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 402 McDowell Drive Winchester, KY MLS# 26000341
$299,500
4

Beds

2.1

Baths

2,136

Sq.Ft.

402 McDowell Drive

Winchester, KY

Bluegrass
View 149 Winn Ave Winchester, KY MLS# 26000197
$290,000
12

Beds

4.0

Baths

4,010

Sq.Ft.

149 Winn Ave

Winchester, KY

Bluegrass
View 120 Sunset Heights Winchester, KY MLS# 26000061
$275,000
3

Beds

2.0

Baths

1,440

Sq.Ft.

120 Sunset Heights

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 142 Sturbridge Lane Winchester, KY MLS# 25508586
$249,500
3

Beds

2.0

Baths

1,220

Sq.Ft.

142 Sturbridge Lane

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

About Winchester

Listings in Winchester, KY

259

Estimated median home price

$299,000
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 - 100K21
$100K - 200K48
$200K - 300K67
$300K - 400K38
$400K - 500K24
$500K - 600K9
$600K - 700K10
$700K - 800K13
$800K - 900K8
$900K - 1M2
$1M - Max19

Homes for Sale by Type in Winchester, KY

Property TypeCount
Single Family153
Townhouse4
Condo0
Commercial13
Rental16
Lots and Land67
Condo/Town/CoOp0
CoOp0
Multi Family8
Mobile Home0
Farms14

(Data as of 1/29/2026)

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 1/30/2026.

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 1/30/2026.