View 394 S Main Street Winchester, KY MLS# 25507786
$229,000
4

Beds

2.0

Baths

1,858

Sq.Ft.

394 S Main Street

Winchester, KY

Bluegrass
View 314 E Broadway Street Winchester, KY MLS# 25507471
$224,000
3

Beds

1.0

Baths

1,188

Sq.Ft.

314 E Broadway 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
The time to sell is now! THE TIME TO SELL IS NOW!
View 521 Acadia Way Winchester, KY MLS# 26000616
  • Recently Listed
1 of 22
$221,500
4

Beds

2.0

Baths

1,370

Sq.Ft.

521 Acadia Way

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 13015 Irvine Road Winchester, KY MLS# 25014720
$219,000
Studio

Beds

0.0

Baths

13015 Irvine Road

Winchester, KY

Bluegrass
View 52 Hillcrest Dr Winchester, KY MLS# 1706974
  • Recently Listed
1 of 29
$219,000
3

Beds

2.0

Baths

2,050

Sq.Ft.

52 Hillcrest Dr

Winchester, KY

GreaterLouisville
View 52 Hillcrest Drive Winchester, KY MLS# 26000887
  • Recently Listed
1 of 29
$219,000
3

Beds

2.0

Baths

2,050

Sq.Ft.

52 Hillcrest Drive

Winchester, KY

Bluegrass
View 2721 Pretty Run Road Winchester, KY MLS# 24025198
$215,000
3

Beds

2.0

Baths

1,456

Sq.Ft.

2721 Pretty Run Road

Winchester, KY

Bluegrass
View 271 April Way Winchester, KY MLS# 25016184
$215,000
2

Beds

1.1

Baths

1,120

Sq.Ft.

271 April Way

Winchester, KY

Bluegrass
View 211 Ashton Oak Way Winchester, KY MLS# 25501640
  • New Construction
1 of 10
$215,000
Studio

Beds

0.0

Baths

211 Ashton Oak Way

Winchester, KY

Bluegrass
View 218 E Washington Street Winchester, KY MLS# 25505534
$215,000
4

Beds

1.0

Baths

1,743

Sq.Ft.

218 E Washington Street

Winchester, KY

Bluegrass
View 5434 Pine Ridge Road Winchester, KY MLS# 26001199
  • Recently Listed
1 of 31
$215,000
2

Beds

2.0

Baths

1,000

Sq.Ft.

5434 Pine Ridge Road

Winchester, KY

Bluegrass
View 368 Flanagan Station Road Winchester, KY MLS# 25009200
$206,000
Studio

Beds

0.0

Baths

368 Flanagan Station Road

Winchester, KY

Bluegrass
View 550-A Bullion Boulevard Winchester, KY MLS# 24020455
$200,000
Studio

Beds

0.0

Baths

550-A Bullion Boulevard

Winchester, KY

Bluegrass
View 5105 Combs Ferry Road Winchester, KY MLS# 25502066
$200,000
Studio

Beds

0.0

Baths

5105 Combs Ferry Road

Winchester, KY

Bluegrass
View 5105 Combs Ferry Road Winchester, KY MLS# 25502234
$200,000
Studio

Beds

0.0

Baths

5105 Combs Ferry Road

Winchester, KY

Bluegrass
View 612 Boone Avenue Winchester, KY MLS# 25505318
$200,000
2

Beds

2.0

Baths

1,262

Sq.Ft.

612 Boone Avenue

Winchester, KY

Bluegrass
View 40 Garner Street Winchester, KY MLS# 25011691
$199,900
3

Beds

1.0

Baths

1,354

Sq.Ft.

40 Garner Street

Winchester, KY

Bluegrass
View 2996 Irvine Road Winchester, KY MLS# 25017325
$199,900
Studio

Beds

0.0

Baths

2996 Irvine Road

Winchester, KY

Bluegrass

About Winchester

Listings in Winchester, KY

256

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 - 100K22
$100K - 200K48
$200K - 300K63
$300K - 400K39
$400K - 500K23
$500K - 600K10
$600K - 700K11
$700K - 800K10
$800K - 900K8
$900K - 1M2
$1M - Max20

Homes for Sale by Type in Winchester, KY

Property TypeCount
Single Family152
Townhouse3
Condo0
Commercial11
Rental17
Lots and Land67
Condo/Town/CoOp0
CoOp0
Multi Family9
Mobile Home0
Farms14

(Data as of 1/16/2026)

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 1/18/2026.

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 1/18/2026.