247 total properties
Did you mean the neighborhood Winchester?
View 35-37 Hays Street Winchester, KY MLS# 26002170
$515,000
1,440

Sq.Ft.

35-37 Hays Street

Winchester, KY

Bluegrass
View 265 S Highland Street Winchester, KY MLS# 26004961
  • Recently Listed
1 of 31
$505,000
8

Beds

4.0

Baths

5,058

Sq.Ft.

265 S Highland Street

Winchester, KY

Bluegrass
View 1005 Early Drive Winchester, KY MLS# 20111871
$500,000
Studio

Beds

0.0

Baths

1005 Early Drive

Winchester, KY

Bluegrass
The time to sell is now! THE TIME TO SELL IS NOW!
View 595 Earlymeade Drive Winchester, KY MLS# 25506943
$499,000
5

Beds

3.1

Baths

3,823

Sq.Ft.

595 Earlymeade Drive

Winchester, KY

Bluegrass
View 414 Fairholme Way Winchester, KY MLS# 25505996
  • New Construction
1 of 45
$489,900
4

Beds

3.0

Baths

2,300

Sq.Ft.

414 Fairholme Way

Winchester, KY

Bluegrass
View 2996/3056 Irvine Road Winchester, KY MLS# 25017324
$475,000
Studio

Beds

0.0

Baths

2996/3056 Irvine Road

Winchester, KY

Bluegrass
View 2996/3056 Irvine Road Winchester, KY MLS# 25500168
$475,000
Studio

Beds

0.0

Baths

2996/3056 Irvine Road

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 42 Mockingbird Valley Road Winchester, KY MLS# 26000113
$452,500
3

Beds

2.1

Baths

2,961

Sq.Ft.

42 Mockingbird Valley Road

Winchester, KY

Bluegrass
View 5127 Combs Ferry Road Winchester, KY MLS# 26002767
$450,000
Studio

Beds

0.0

Baths

5127 Combs Ferry Road

Winchester, KY

Bluegrass
View 5127 Combs Ferry Road Winchester, KY MLS# 26004544
$450,000
Studio

Beds

0.0

Baths

5127 Combs Ferry Road

Winchester, KY

Bluegrass
View 204 Delaplain Road Winchester, KY MLS# 26002697
$434,900
3

Beds

2.0

Baths

3,563

Sq.Ft.

204 Delaplain Road

Winchester, KY

Bluegrass
View 250 Evergreen Drive Winchester, KY MLS# 25009082
  • New Construction
1 of 3
$430,000
3

Beds

2.0

Baths

1,855

Sq.Ft.

250 Evergreen Drive

Winchester, KY

Bluegrass
View 233 Cunningham Lane Winchester, KY MLS# 25507450
$429,900
3

Beds

2.1

Baths

2,258

Sq.Ft.

233 Cunningham Lane

Winchester, KY

Bluegrass
View 107 Woodduck Court Winchester, KY MLS# 26001532
$429,900
3

Beds

2.1

Baths

2,652

Sq.Ft.

107 Woodduck Court

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
$429,000
4

Beds

2.0

Baths

1,950

Sq.Ft.

104 Colby Hills Drive

Winchester, KY

Bluegrass
View 39 S Main Street Winchester, KY MLS# 25014867
$429,000
3,538

Sq.Ft.

39 S Main Street

Winchester, KY

Bluegrass
View 1503 Schollsville Road Winchester, KY MLS# 25505942
$425,000
5

Beds

3.0

Baths

3,718

Sq.Ft.

1503 Schollsville Road

Winchester, KY

Bluegrass
View 6504 Combs Ferry Road Winchester, KY MLS# 25506634
$419,900
5

Beds

3.1

Baths

2,564

Sq.Ft.

6504 Combs Ferry Road

Winchester, KY

Bluegrass

About Winchester

Listings in Winchester, KY

270

Estimated median home price

$277,350
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 - 100K31
$100K - 200K57
$200K - 300K63
$300K - 400K36
$400K - 500K18
$500K - 600K13
$600K - 700K11
$700K - 800K11
$800K - 900K7
$900K - 1M3
$1M - Max20

Homes for Sale by Type in Winchester, KY

Property TypeCount
Single Family147
Townhouse5
Condo0
Commercial13
Rental15
Lots and Land80
Condo/Town/CoOp0
CoOp0
Multi Family13
Mobile Home0
Farms12

(Data as of 3/16/2026)

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 3/16/2026.