291 total properties
Did you mean the neighborhood Winchester?
View 722 Colby Road # #1 Winchester, KY MLS# 26008233
$1,800,000
Studio

Beds

0.0

Baths

722 Colby Road # #1

Winchester, KY

Bluegrass
View 722 Colby Road # #2 Winchester, KY MLS# 26008236
$600,000
Studio

Beds

0.0

Baths

722 Colby Road # #2

Winchester, KY

Bluegrass
View 110 Powe Drive Winchester, KY MLS# 26008249
  • Recently Listed
1 of 31
$347,500
4

Beds

2.1

Baths

2,010

Sq.Ft.

110 Powe Drive

Winchester, KY

Bluegrass
The time to sell is now! THE TIME TO SELL IS NOW!
View 905 Pretty Run Road Winchester, KY MLS# 26008251
  • Recently Listed
1 of 75
$600,000
3

Beds

3.1

Baths

3,391

Sq.Ft.

905 Pretty Run Road

Winchester, KY

Bluegrass
View 3385 Colby Road Winchester, KY MLS# 26008075
  • Recently Listed
1 of 2
$150,000
Studio

Beds

0.0

Baths

3385 Colby Road

Winchester, KY

Bluegrass
View 215 Short Street Winchester, KY MLS# 26007746
  • Virtual Tour
1 of 27
OPEN HOUSE: Saturday 4/18 2:00 PM - 4:00 PM
$199,900
3

Beds

1.0

Baths

1,036

Sq.Ft.

215 Short Street

Winchester, KY

Bluegrass
View 432 Country Club Drive Winchester, KY MLS# 26008091
$175,000
2

Beds

2.0

Baths

1,260

Sq.Ft.

432 Country Club Drive

Winchester, KY

Bluegrass
View 614 Colby Ridge Boulevard Winchester, KY MLS# 26007904
$369,900
4

Beds

2.1

Baths

2,100

Sq.Ft.

614 Colby Ridge Boulevard

Winchester, KY

Bluegrass
View 426 E Broadway Street Winchester, KY MLS# 26007906
  • Recently Listed
1 of 29
$289,000
5

Beds

2.0

Baths

1,838

Sq.Ft.

426 E Broadway Street

Winchester, KY

Bluegrass
View 16 Linden Avenue Winchester, KY MLS# 26007993
  • Recently Listed
1 of 16
$1,200,000
16

Beds

16.0

Baths

7,480

Sq.Ft.

16 Linden Avenue

Winchester, KY

Bluegrass
View 222 Ashton Oak Way Winchester, KY MLS# 26008003
  • Recently Listed
1 of 43
$450,000
3

Beds

2.1

Baths

3,444

Sq.Ft.

222 Ashton Oak Way

Winchester, KY

Bluegrass
View 200 Dubuy Drive Winchester, KY MLS# 26008021
  • Recently Listed
1 of 20
$316,900
3

Beds

2.1

Baths

1,858

Sq.Ft.

200 Dubuy Drive

Winchester, KY

Bluegrass
View 19 3rd Street Winchester, KY MLS# 26007798
  • Recently Listed
1 of 11
$155,000
3

Beds

1.0

Baths

864

Sq.Ft.

19 3rd Street

Winchester, KY

Bluegrass
View 201 Boone Avenue Winchester, KY MLS# 26007703
  • Recently Listed
1 of 59
$335,000
4

Beds

2.1

Baths

2,513

Sq.Ft.

201 Boone Avenue

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 34 Hays Street Winchester, KY MLS# 26007612
  • Recently Listed
1 of 32
$222,500
4

Beds

1.1

Baths

2,450

Sq.Ft.

34 Hays Street

Winchester, KY

Bluegrass
View 17 W Lexington Avenue Winchester, KY MLS# 26007617
  • Recently Listed
1 of 27
$388,000
8

Beds

8.0

Baths

4,000

Sq.Ft.

17 W Lexington Avenue

Winchester, KY

Bluegrass
View 220 Hibiscus Lane Winchester, KY MLS# 26007618
$350,000
3

Beds

2.0

Baths

1,640

Sq.Ft.

220 Hibiscus Lane

Winchester, KY

Bluegrass
View 465 Morris Road Winchester, KY MLS# 26007545
  • Recently Listed
1 of 72
$775,000
5

Beds

3.0

Baths

4,437

Sq.Ft.

465 Morris Road

Winchester, KY

Bluegrass

About Winchester

Listings in Winchester, KY

289

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 - 200K66
$200K - 300K66
$300K - 400K39
$400K - 500K19
$500K - 600K12
$600K - 700K11
$700K - 800K15
$800K - 900K4
$900K - 1M2
$1M - Max20

Homes for Sale by Type in Winchester, KY

Property TypeCount
Single Family159
Townhouse5
Condo0
Commercial12
Rental14
Lots and Land94
Condo/Town/CoOp0
CoOp0
Multi Family12
Mobile Home0
Farms7

(Data as of 4/17/2026)

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 4/18/2026.