247 total properties
Did you mean the neighborhood Winchester?
View 204 Delaplain Road Winchester, KY MLS# 26002697
$434,900
3

Beds

2.0

Baths

3,563

Sq.Ft.

204 Delaplain Road

Winchester, KY

Bluegrass
View 144 Holly Avenue Winchester, KY MLS# 26002633
$319,500
8

Beds

5.0

Baths

3,637

Sq.Ft.

144 Holly Avenue

Winchester, KY

Bluegrass
View 220 E Washington Street Winchester, KY MLS# 26002506
$165,000
3

Beds

1.0

Baths

1,097

Sq.Ft.

220 E Washington Street

Winchester, KY

Bluegrass
The time to sell is now! THE TIME TO SELL IS NOW!
View 600 Boone Avenue Winchester, KY MLS# 25018239
$579,900
4

Beds

3.2

Baths

4,374

Sq.Ft.

600 Boone Avenue

Winchester, KY

Bluegrass
View 35-37 Hays Street Winchester, KY MLS# 26002170
$515,000
1,440

Sq.Ft.

35-37 Hays Street

Winchester, KY

Bluegrass
View 120 Windsor Drive Winchester, KY MLS# 26002472
$269,900
4

Beds

1.0

Baths

1,610

Sq.Ft.

120 Windsor Drive

Winchester, KY

Bluegrass
View 616 Boone Avenue Winchester, KY MLS# 26002364
$198,000
2

Beds

1.0

Baths

1,223

Sq.Ft.

616 Boone Avenue

Winchester, KY

Bluegrass
View 11 Shelley Dr Winchester, KY MLS# 26002369
$234,900
3

Beds

2.0

Baths

1,188

Sq.Ft.

11 Shelley Dr

Winchester, KY

Bluegrass
View 233 E Washington Street Winchester, KY MLS# 26002299
$160,000
2

Beds

1.0

Baths

1,088

Sq.Ft.

233 E Washington Street

Winchester, KY

Bluegrass
View 115 Watercrest Circle Winchester, KY MLS# 26002338
$279,950
4

Beds

3.0

Baths

2,112

Sq.Ft.

115 Watercrest Circle

Winchester, KY

Bluegrass
View 58 hughes Avenue Winchester, KY MLS# 26002214
$199,000
3

Beds

2.0

Baths

1,456

Sq.Ft.

58 hughes Avenue

Winchester, KY

Bluegrass
View 220 Athens Boonsboro Road Winchester, KY MLS# 25012986
$531,000
5,012

Sq.Ft.

220 Athens Boonsboro Road

Winchester, KY

Bluegrass
View 10 Pocahontas Winchester, KY MLS# 26002018
$175,000
2

Beds

1.1

Baths

924

Sq.Ft.

10 Pocahontas

Winchester, KY

Bluegrass
View 414 Wellington Way Winchester, KY MLS# 26002092
$254,900
3

Beds

2.0

Baths

1,251

Sq.Ft.

414 Wellington Way

Winchester, KY

Bluegrass
View 356 Colby Ridge Boulevard Winchester, KY MLS# 26002026
$184,000
2

Beds

1.1

Baths

1,102

Sq.Ft.

356 Colby Ridge Boulevard

Winchester, KY

Bluegrass
View 7075 Ecton Road Winchester, KY MLS# 26001880
$850,000
Studio

Beds

0.0

Baths

7075 Ecton Road

Winchester, KY

Bluegrass
View 1494 Amster Grove Rd. Road Winchester, KY MLS# 26001738
$175,000
2

Beds

1.1

Baths

1,202

Sq.Ft.

1494 Amster Grove Rd. Road

Winchester, KY

Bluegrass
View 108 Ashley Drive Winchester, KY MLS# 26001564
$270,000
4

Beds

2.0

Baths

1,984

Sq.Ft.

108 Ashley Drive

Winchester, KY

Bluegrass
View 107 Woodduck Court Winchester, KY MLS# 26001532
$429,900
3

Beds

2.1

Baths

2,652

Sq.Ft.

107 Woodduck Court

Winchester, KY

Bluegrass
View 4755 Combs Ferry Road Winchester, KY MLS# 26001454
$849,000
3

Beds

2.1

Baths

2,768

Sq.Ft.

4755 Combs Ferry Road

Winchester, KY

Bluegrass

About Winchester

Listings in Winchester, KY

266

Estimated median home price

$285,000
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 - 100K30
$100K - 200K54
$200K - 300K61
$300K - 400K37
$400K - 500K18
$500K - 600K13
$600K - 700K11
$700K - 800K11
$800K - 900K7
$900K - 1M4
$1M - Max20

Homes for Sale by Type in Winchester, KY

Property TypeCount
Single Family145
Townhouse5
Condo0
Commercial13
Rental15
Lots and Land78
Condo/Town/CoOp0
CoOp0
Multi Family13
Mobile Home0
Farms12

(Data as of 3/18/2026)

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 3/20/2026.