46 total properties
Did you mean the neighborhood Winchester?
View 229 S Highland Street Winchester, KY MLS# 26008701
  • Recently Listed
1 of 14
$180,000
5

Beds

3.0

Baths

3,462

Sq.Ft.

229 S Highland Street

Winchester, KY

Bluegrass
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 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
The time to sell is now! THE TIME TO SELL IS NOW!
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 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 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 101 Alabama Street Winchester, KY MLS# 26007407
  • Recently Listed
1 of 41
$169,900
1

Beds

2.0

Baths

1,056

Sq.Ft.

101 Alabama Street

Winchester, KY

Bluegrass
View 3925 Jackson Ferry Road Winchester, KY MLS# 26007287
$180,000
Studio

Beds

0.0

Baths

3925 Jackson Ferry Road

Winchester, KY

Bluegrass
View 3821 Jackson Ferry Road Winchester, KY MLS# 26007288
$150,000
Studio

Beds

0.0

Baths

3821 Jackson Ferry Road

Winchester, KY

Bluegrass
View 2996 Irvine Road Winchester, KY MLS# 26007067
  • Recently Listed
1 of 21
$175,000
Studio

Beds

0.0

Baths

2996 Irvine Road

Winchester, KY

Bluegrass
View 403 Country Club Drive Winchester, KY MLS# 26007069
$174,900
2

Beds

2.0

Baths

1,122

Sq.Ft.

403 Country Club Drive

Winchester, KY

Bluegrass
View 41 Hiawatha Trail Winchester, KY MLS# 26006789
  • Recently Listed
1 of 14
$189,999
3

Beds

1.0

Baths

950

Sq.Ft.

41 Hiawatha Trail

Winchester, KY

Bluegrass
View 60 Hiawatha Trail Winchester, KY MLS# 26006850
$204,900
3

Beds

1.0

Baths

1,290

Sq.Ft.

60 Hiawatha Trail

Winchester, KY

Bluegrass
View 47 Buckner Street Winchester, KY MLS# 26006752
  • Recently Listed
1 of 16
$174,900
3

Beds

2.0

Baths

1,635

Sq.Ft.

47 Buckner Street

Winchester, KY

Bluegrass
View 415 L E Junction Road Winchester, KY MLS# 26006620
$205,000
3

Beds

2.0

Baths

1,152

Sq.Ft.

415 L E Junction Road

Winchester, KY

Bluegrass
View 4247 Basin Springs Road Winchester, KY MLS# 26006060
$170,000
Studio

Beds

0.0

Baths

4247 Basin Springs Road

Winchester, KY

Bluegrass
View 29 Euclid Avenue Winchester, KY MLS# 26006180
$190,000
3

Beds

2.0

Baths

1,498

Sq.Ft.

29 Euclid Avenue

Winchester, KY

Bluegrass
View 471 Goose Creek Road Winchester, KY MLS# 26006002
$160,000
3

Beds

2.0

Baths

1,248

Sq.Ft.

471 Goose Creek Road

Winchester, KY

Bluegrass

About Winchester

Listings in Winchester, KY

297

Estimated median home price

$265,000
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 - 100K36
$100K - 200K70
$200K - 300K67
$300K - 400K38
$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 Land96
Condo/Town/CoOp0
CoOp0
Multi Family12
Mobile Home0
Farms7

(Data as of 4/22/2026)

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 4/23/2026.