280 total properties
Did you mean the neighborhood Winchester?
View 178 Hawthorne Drive Winchester, KY MLS# 26012931
$390,000
3

Beds

2.1

Baths

2,156

Sq.Ft.

178 Hawthorne Drive

Winchester, KY

Bluegrass
View 14 Cook Avenue Winchester, KY MLS# 26011961
  • Recently Listed
1 of 37
$233,000
3

Beds

2.0

Baths

1,261

Sq.Ft.

14 Cook Avenue

Winchester, KY

Bluegrass
View 13 Long Avenue Winchester, KY MLS# 26013004
  • Recently Listed
1 of 31
$240,000
3

Beds

2.0

Baths

1,297

Sq.Ft.

13 Long Avenue

Winchester, KY

Bluegrass
The time to sell is now! THE TIME TO SELL IS NOW!
View 23 Windridge Drive Winchester, KY MLS# 26013010
  • Recently Listed
1 of 41
$339,900
3

Beds

2.0

Baths

1,858

Sq.Ft.

23 Windridge Drive

Winchester, KY

Bluegrass
View 200 Old Log Lick Road Winchester, KY MLS# 26013036
  • Recently Listed
1 of 89
$939,000
3

Beds

2.0

Baths

4,019

Sq.Ft.

200 Old Log Lick Road

Winchester, KY

Bluegrass
View 310 W Hickman Street Winchester, KY MLS# 26012783
  • Recently Listed
1 of 13
$109,900
4

Beds

2.1

Baths

1,391

Sq.Ft.

310 W Hickman Street

Winchester, KY

Bluegrass
View 4100 Crowe Ridge Road Winchester, KY MLS# 26012816
$320,000
3

Beds

2.1

Baths

2,100

Sq.Ft.

4100 Crowe Ridge Road

Winchester, KY

Bluegrass
View 20 Jackson Street Winchester, KY MLS# 26012820
  • Recently Listed
1 of 36
$290,000
3

Beds

2.0

Baths

1,650

Sq.Ft.

20 Jackson Street

Winchester, KY

Bluegrass
View 563 Constitution Drive Winchester, KY MLS# 26012893
$104,900
2

Beds

2.0

Baths

924

Sq.Ft.

563 Constitution Drive

Winchester, KY

Bluegrass
View 233 Schollsville Road Winchester, KY MLS# 26012231
$400,000
3

Beds

2.0

Baths

1,347

Sq.Ft.

233 Schollsville Road

Winchester, KY

Bluegrass
View 305 Abbeywood Drive Winchester, KY MLS# 26012645
$315,000
3

Beds

2.1

Baths

1,899

Sq.Ft.

305 Abbeywood Drive

Winchester, KY

Bluegrass
View 162 French Avenue Winchester, KY MLS# 26012319
  • Recently Listed
1 of 40
$299,900
4

Beds

1.0

Baths

2,327

Sq.Ft.

162 French Avenue

Winchester, KY

Bluegrass
View 3359 Trapp-Goffs Corner Road Winchester, KY MLS# 26012322
$370,000
1

Beds

2.0

Baths

2,179

Sq.Ft.

3359 Trapp-Goffs Corner Road

Winchester, KY

Bluegrass
View 528 Estes Drive Winchester, KY MLS# 26012351
$234,900
3

Beds

2.0

Baths

1,904

Sq.Ft.

528 Estes Drive

Winchester, KY

Bluegrass
View 410 W Lexington Avenue Winchester, KY MLS# 26012369
$349,900
5

Beds

4.0

Baths

4,456

Sq.Ft.

410 W Lexington Avenue

Winchester, KY

Bluegrass
View 104 Bay Hill Drive Winchester, KY MLS# 26012179
  • Recently Listed
1 of 14
$215,000
2

Beds

2.0

Baths

1,200

Sq.Ft.

104 Bay Hill Drive

Winchester, KY

Bluegrass
View 217 Short Street Winchester, KY MLS# 26012199
  • Recently Listed
1 of 50
$229,900
3

Beds

1.0

Baths

1,042

Sq.Ft.

217 Short Street

Winchester, KY

Bluegrass
View 3622 Stamper Drive Winchester, KY MLS# 26012206
  • Recently Listed
1 of 43
$299,900
3

Beds

3.0

Baths

2,821

Sq.Ft.

3622 Stamper Drive

Winchester, KY

Bluegrass
View 6356 Van Meter Road Winchester, KY MLS# 26012252
  • Recently Listed
1 of 92
$795,000
3

Beds

3.0

Baths

3,336

Sq.Ft.

6356 Van Meter Road

Winchester, KY

Bluegrass
View 12 Pocahontas Trail Winchester, KY MLS# 26012275
  • Recently Listed
1 of 21
$249,900
3

Beds

2.0

Baths

1,064

Sq.Ft.

12 Pocahontas Trail

Winchester, KY

Bluegrass

About Winchester

Listings in Winchester, KY

280

Estimated median home price

$269,950
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 - 100K29
$100K - 200K62
$200K - 300K74
$300K - 400K42
$400K - 500K17
$500K - 600K14
$600K - 700K5
$700K - 800K10
$800K - 900K1
$900K - 1M3
$1M - Max23

Homes for Sale by Type in Winchester, KY

Property TypeCount
Single Family160
Townhouse4
Condo0
Commercial13
Rental18
Lots and Land89
Condo/Town/CoOp0
CoOp0
Multi Family10
Mobile Home0
Farms4

(Data as of 6/7/2026)

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 6/8/2026.