View 1478 Donaldson Road Winchester, KY MLS# 26011075
  • Recently Listed
1 of 34
$444,000
3

Beds

2.0

Baths

2,442

Sq.Ft.

1478 Donaldson Road

Winchester, KY

Bluegrass
View 18 Casa Landa Way Winchester, KY MLS# 26011118
  • Recently Listed
1 of 39
$395,000
3

Beds

2.0

Baths

1,883

Sq.Ft.

18 Casa Landa Way

Winchester, KY

Bluegrass
View 207 Hibiscus Lane Winchester, KY MLS# 26010589
$449,900
4

Beds

3.0

Baths

3,126

Sq.Ft.

207 Hibiscus Lane

Winchester, KY

Bluegrass
The time to sell is now! THE TIME TO SELL IS NOW!
View 27 Hampton Avenue Winchester, KY MLS# 26010286
  • Recently Listed
1 of 55
$359,900
3

Beds

2.0

Baths

2,835

Sq.Ft.

27 Hampton Avenue

Winchester, KY

Bluegrass
View 502 W Lexington Avenue Winchester, KY MLS# 26010324
$360,000
4

Beds

4.1

Baths

4,798

Sq.Ft.

502 W Lexington Avenue

Winchester, KY

Bluegrass
View 20 Edgewood Drive Winchester, KY MLS# 26009517
  • Recently Listed with Virtual Tour
1 of 47
$427,000
3

Beds

2.1

Baths

2,288

Sq.Ft.

20 Edgewood Drive

Winchester, KY

Bluegrass
View 42 Mockingbird Valley Road Winchester, KY MLS# 26009944
$445,500
3

Beds

2.1

Baths

2,961

Sq.Ft.

42 Mockingbird Valley Road

Winchester, KY

Bluegrass
View 382 S Main Street Winchester, KY MLS# 26008931
$395,000
4

Beds

3.0

Baths

3,310

Sq.Ft.

382 S Main Street

Winchester, KY

Bluegrass
View 505 LaSalle Court Winchester, KY MLS# 26008961
$405,000
5

Beds

3.0

Baths

2,944

Sq.Ft.

505 LaSalle Court

Winchester, KY

Bluegrass
View 222 Ashton Oak Way Winchester, KY MLS# 26008003
$450,000
3

Beds

2.1

Baths

3,444

Sq.Ft.

222 Ashton Oak Way

Winchester, KY

Bluegrass
View 17 W Lexington Avenue Winchester, KY MLS# 26007617
$388,000
8

Beds

8.0

Baths

4,000

Sq.Ft.

17 W Lexington Avenue

Winchester, KY

Bluegrass
View 2996/3056 Irvine Road Winchester, KY MLS# 26007128
$425,000
Studio

Beds

0.0

Baths

2996/3056 Irvine Road

Winchester, KY

Bluegrass
View 3886 Jackson Ferry Road Winchester, KY MLS# 26006831
$435,000
4

Beds

2.0

Baths

1,692

Sq.Ft.

3886 Jackson Ferry Road

Winchester, KY

Bluegrass
View 750 Providence Lane Winchester, KY MLS# 26006323
$359,900
Studio

Beds

0.0

Baths

750 Providence Lane

Winchester, KY

Bluegrass
View 1911 Trapp-Goffs Cor Road Winchester, KY MLS# 26005750
$460,000
3

Beds

2.0

Baths

1,288

Sq.Ft.

1911 Trapp-Goffs Cor Road

Winchester, KY

Bluegrass
View 133 Shala-Mar Rue Winchester, KY MLS# 26005511
$359,000
3

Beds

2.0

Baths

2,000

Sq.Ft.

133 Shala-Mar Rue

Winchester, KY

Bluegrass
View 265 S Highland Street Winchester, KY MLS# 26004961
$479,000
8

Beds

4.0

Baths

5,058

Sq.Ft.

265 S Highland Street

Winchester, KY

Bluegrass
View 1911 Trapp-Goffs Cor Road Winchester, KY MLS# 26004732
$460,000
3

Beds

2.0

Baths

1,288

Sq.Ft.

1911 Trapp-Goffs Cor Road

Winchester, KY

Bluegrass
View 240 Athens Boonesboro Road Winchester, KY MLS# 26004512
$429,900
4

Beds

2.1

Baths

1,500

Sq.Ft.

240 Athens Boonesboro Road

Winchester, KY

Bluegrass
View 104 Colby Hills Drive Winchester, KY MLS# 25004009
$410,000
4

Beds

2.0

Baths

1,950

Sq.Ft.

104 Colby Hills Drive

Winchester, KY

Bluegrass

About Winchester

Listings in Winchester, KY

307

Estimated median home price

$270,000
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 - 100K35
$100K - 200K67
$200K - 300K71
$300K - 400K43
$400K - 500K22
$500K - 600K17
$600K - 700K11
$700K - 800K13
$800K - 900K4
$900K - 1M2
$1M - Max22

Homes for Sale by Type in Winchester, KY

Property TypeCount
Single Family176
Townhouse2
Condo0
Commercial16
Rental17
Lots and Land96
Condo/Town/CoOp0
CoOp0
Multi Family11
Mobile Home0
Farms6

(Data as of 5/16/2026)

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 5/16/2026.