54 total properties
Did you mean the neighborhood Winchester?
View 221 W Hickman Street Winchester, KY MLS# 26013573
  • Recently Listed
1 of 42
$349,500
4

Beds

3.0

Baths

2,800

Sq.Ft.

221 W Hickman Street

Winchester, KY

Bluegrass
View 107 Gibson Way Winchester, KY MLS# 26013361
  • Recently Listed
1 of 20
$369,000
3

Beds

2.1

Baths

2,266

Sq.Ft.

107 Gibson Way

Winchester, KY

Bluegrass
View 955 Right Angle Road Winchester, KY MLS# 26013194
  • Recently Listed
1 of 35
$274,900
2

Beds

1.0

Baths

849

Sq.Ft.

955 Right Angle Road

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 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 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
$294,900
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
$360,000
1

Beds

2.0

Baths

2,179

Sq.Ft.

3359 Trapp-Goffs Corner Road

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 3622 Stamper Drive Winchester, KY MLS# 26012206
$299,900
3

Beds

3.0

Baths

2,821

Sq.Ft.

3622 Stamper Drive

Winchester, KY

Bluegrass
View 133 Bay Hill Drive Winchester, KY MLS# 26012064
  • Recently Listed
1 of 24
$280,000
4

Beds

3.1

Baths

3,276

Sq.Ft.

133 Bay Hill Drive

Winchester, KY

Bluegrass
View 207 Abbeywood Drive Winchester, KY MLS# 26011852
$285,000
3

Beds

2.1

Baths

1,894

Sq.Ft.

207 Abbeywood Drive

Winchester, KY

Bluegrass
View 116 Sturbridge Lane Winchester, KY MLS# 26011782
  • New Construction
1 of 37
$279,000
3

Beds

2.0

Baths

1,260

Sq.Ft.

116 Sturbridge Lane

Winchester, KY

Bluegrass
View 137 Eastridge Drive Winchester, KY MLS# 26011465
$274,500
3

Beds

2.0

Baths

1,420

Sq.Ft.

137 Eastridge Drive

Winchester, KY

Bluegrass
View 13 Lakeview Drive Winchester, KY MLS# 26011497
$315,000
3

Beds

2.0

Baths

1,932

Sq.Ft.

13 Lakeview Drive

Winchester, KY

Bluegrass
View 209 Boone Avenue Winchester, KY MLS# 26011097
  • Virtual Tour
1 of 24
$294,900
3

Beds

2.1

Baths

2,260

Sq.Ft.

209 Boone Avenue

Winchester, KY

Bluegrass
View 147 Sunset Heights Winchester, KY MLS# 26011009
$294,900
3

Beds

2.0

Baths

2,128

Sq.Ft.

147 Sunset Heights

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 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

293

Estimated median home price

$274,900
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 - 200K64
$200K - 300K74
$300K - 400K42
$400K - 500K17
$500K - 600K16
$600K - 700K11
$700K - 800K11
$800K - 900K2
$900K - 1M4
$1M - Max23

Homes for Sale by Type in Winchester, KY

Property TypeCount
Single Family176
Townhouse4
Condo0
Commercial12
Rental18
Lots and Land88
Condo/Town/CoOp0
CoOp0
Multi Family9
Mobile Home0
Farms4

(Data as of 6/15/2026)

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 6/16/2026.