218 total properties
Did you mean the neighborhood Winchester?
View 18 Casa Landa Way Winchester, KY MLS# 26011118
$395,000
3

Beds

2.0

Baths

1,883

Sq.Ft.

18 Casa Landa Way

Winchester, KY

Bluegrass
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 23 Wheeler Avenue Winchester, KY MLS# 26011905
$389,900
8

Beds

5.0

Baths

4,687

Sq.Ft.

23 Wheeler Avenue

Winchester, KY

Bluegrass
The time to sell is now! THE TIME TO SELL IS NOW!
View 17 W Lexington Avenue Winchester, KY MLS# 26007617
$388,000
8

Beds

8.0

Baths

4,000

Sq.Ft.

17 W Lexington Avenue

Winchester, KY

Bluegrass
View 309 Gallahadion Court Winchester, KY MLS# 26013780
  • Recently Listed
1 of 30
$385,000
3

Beds

2.1

Baths

1,945

Sq.Ft.

309 Gallahadion Court

Winchester, KY

Bluegrass
View 270 Evergreen Drive Winchester, KY MLS# 25009085
  • New Construction
1 of 3
$380,000
3

Beds

2.0

Baths

1,677

Sq.Ft.

270 Evergreen Drive

Winchester, KY

Bluegrass
View 382 S Main Street Winchester, KY MLS# 26008931
$375,000
4

Beds

3.0

Baths

3,310

Sq.Ft.

382 S Main Street

Winchester, KY

Bluegrass
View 206 Jett Drive Winchester, KY MLS# 24018286
  • New Construction
1 of 24
$365,900
3

Beds

2.0

Baths

1,635

Sq.Ft.

206 Jett Drive

Winchester, KY

Bluegrass
View 204 Jett Drive Winchester, KY MLS# 25507850
  • New Construction
1 of 7
$365,900
3

Beds

2.0

Baths

1,558

Sq.Ft.

204 Jett Drive

Winchester, KY

Bluegrass
View 3359 Trapp-Goffs Corner Road Winchester, KY MLS# 26012322
$360,000
1

Beds

2.0

Baths

2,179

Sq.Ft.

3359 Trapp-Goffs Corner Road

Winchester, KY

Bluegrass
View 133 Shala-Mar Rue Winchester, KY MLS# 26005511
$359,000
3

Beds

2.0

Baths

2,000

Sq.Ft.

133 Shala-Mar Rue

Winchester, KY

Bluegrass
View 119 Gibson Way Winchester, KY MLS# 26014834
  • Recently Listed
1 of 28
$355,000
4

Beds

2.1

Baths

2,325

Sq.Ft.

119 Gibson Way

Winchester, KY

Bluegrass
View 107 Gibson Way Winchester, KY MLS# 26013361
  • New Construction
1 of 20
$354,900
3

Beds

2.1

Baths

2,266

Sq.Ft.

107 Gibson Way

Winchester, KY

Bluegrass
View 38 N Burns Avenue Winchester, KY MLS# 26009835
  • New Construction
1 of 31
$350,000
4

Beds

2.1

Baths

2,310

Sq.Ft.

38 N Burns Avenue

Winchester, KY

Bluegrass
View 27 Hampton Avenue Winchester, KY MLS# 26010286
$350,000
3

Beds

2.0

Baths

2,835

Sq.Ft.

27 Hampton Avenue

Winchester, KY

Bluegrass
View 502 W Lexington Avenue Winchester, KY MLS# 26010324
$350,000
4

Beds

2.3

Baths

4,798

Sq.Ft.

502 W Lexington Avenue

Winchester, KY

Bluegrass
View 274 Greenway Drive Winchester, KY MLS# 26010546
$350,000
4

Beds

2.0

Baths

2,208

Sq.Ft.

274 Greenway Drive

Winchester, KY

Bluegrass
View 6888 Bybee Road Winchester, KY MLS# 26014823
  • Recently Listed
1 of 62
$350,000
1

Beds

1.0

Baths

800

Sq.Ft.

6888 Bybee Road

Winchester, KY

Bluegrass
View 221 W Hickman Street Winchester, KY MLS# 26013573
$349,500
4

Beds

3.0

Baths

2,800

Sq.Ft.

221 W Hickman Street

Winchester, KY

Bluegrass
View 405 Tremont Lane Winchester, KY MLS# 26010040
$349,000
4

Beds

2.1

Baths

2,274

Sq.Ft.

405 Tremont Lane

Winchester, KY

Bluegrass

About Winchester

Listings in Winchester, KY

287

Estimated median home price

$280,000
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 - 100K29
$100K - 200K62
$200K - 300K66
$300K - 400K49
$400K - 500K19
$500K - 600K15
$600K - 700K10
$700K - 800K9
$800K - 900K4
$900K - 1M2
$1M - Max22

Homes for Sale by Type in Winchester, KY

Property TypeCount
Single Family172
Townhouse4
Condo0
Commercial11
Rental19
Lots and Land85
Condo/Town/CoOp0
CoOp0
Multi Family8
Mobile Home0
Farms7

(Data as of 7/2/2026)

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 7/2/2026.