295 total properties
Did you mean the neighborhood Winchester?
View 697 Goose Creek Road Winchester, KY MLS# 26008440
  • Recently Listed
1 of 16
$180,000
3

Beds

2.0

Baths

1,848

Sq.Ft.

697 Goose Creek Road

Winchester, KY

Bluegrass
View 306 Trapp-Goffs Cor Road Winchester, KY MLS# 26008462
$299,900
4

Beds

2.0

Baths

1,960

Sq.Ft.

306 Trapp-Goffs Cor Road

Winchester, KY

Bluegrass
View 17 Holiday Road Winchester, KY MLS# 26008222
  • Recently Listed
1 of 62
$264,900
3

Beds

1.1

Baths

1,161

Sq.Ft.

17 Holiday Road

Winchester, KY

Bluegrass
The time to sell is now! THE TIME TO SELL IS NOW!
View 409 N Main Street Winchester, KY MLS# 26008406
  • Recently Listed with Virtual Tour
1 of 32
$199,000
300

Sq.Ft.

409 N Main Street

Winchester, KY

Bluegrass
View 411 N Main Street Winchester, KY MLS# 26008407
  • Recently Listed with Virtual Tour
1 of 34
$99,000
600

Sq.Ft.

411 N Main Street

Winchester, KY

Bluegrass
View 7 Hiawatha Trail Winchester, KY MLS# 26008410
  • Recently Listed
1 of 18
$225,000
3

Beds

1.0

Baths

1,190

Sq.Ft.

7 Hiawatha Trail

Winchester, KY

Bluegrass
View 443 S Maple Street Winchester, KY MLS# 26008225
  • Recently Listed
1 of 57
$350,000
4

Beds

2.0

Baths

3,261

Sq.Ft.

443 S Maple Street

Winchester, KY

Bluegrass
View 2 Stoney Brook Drive Winchester, KY MLS# 26008275
$435,000
3

Beds

3.1

Baths

3,633

Sq.Ft.

2 Stoney Brook Drive

Winchester, KY

Bluegrass
View 13 Maryland Avenue Winchester, KY MLS# 26008307
  • Recently Listed
1 of 4
$179,000
3

Beds

1.0

Baths

1,472

Sq.Ft.

13 Maryland Avenue

Winchester, KY

Bluegrass
View 142 Clubhouse Drive Winchester, KY MLS# 26008332
  • Recently Listed
1 of 90
$650,000
6

Beds

4.0

Baths

4,351

Sq.Ft.

142 Clubhouse Drive

Winchester, KY

Bluegrass
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
View 905 Pretty Run Road Winchester, KY MLS# 26008251
$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
$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
  • Recently Listed
1 of 26
OPEN HOUSE: Sunday 4/26 2:00 PM - 4:00 PM
$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

About Winchester

Listings in Winchester, KY

296

Estimated median home price

$269,500
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 - 100K36
$100K - 200K69
$200K - 300K66
$300K - 400K39
$400K - 500K20
$500K - 600K13
$600K - 700K12
$700K - 800K15
$800K - 900K4
$900K - 1M2
$1M - Max20

Homes for Sale by Type in Winchester, KY

Property TypeCount
Single Family163
Townhouse5
Condo0
Commercial14
Rental14
Lots and Land95
Condo/Town/CoOp0
CoOp0
Multi Family12
Mobile Home0
Farms7

(Data as of 4/21/2026)

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 4/21/2026.