132 total properties
Did you mean the neighborhood Winchester?
View 230 Duclair Drive Winchester, KY MLS# 22024095
$110,000
Studio

Beds

0.0

Baths

230 Duclair Drive

Winchester, KY

Bluegrass
View 319 Essex Court Winchester, KY MLS# 26003610
  • Virtual Tour
1 of 21
$199,000
3

Beds

2.1

Baths

1,224

Sq.Ft.

319 Essex Court

Winchester, KY

Bluegrass
View 357 Silverton Way Winchester, KY MLS# 26003487
  • Recently Listed
1 of 18
$243,000
3

Beds

2.0

Baths

1,502

Sq.Ft.

357 Silverton Way

Winchester, KY

Bluegrass
The time to sell is now! THE TIME TO SELL IS NOW!
View 133 S Highland Street Winchester, KY MLS# 25017462
$251,000
6

Beds

3.0

Baths

2,302

Sq.Ft.

133 S Highland Street

Winchester, KY

Bluegrass
View 6 Hart Avenue Winchester, KY MLS# 26003316
  • Recently Listed
1 of 30
$259,900
4

Beds

1.1

Baths

1,405

Sq.Ft.

6 Hart Avenue

Winchester, KY

Bluegrass
View 334 S Burns Avenue Winchester, KY MLS# 26003334
  • Recently Listed
1 of 47
$229,000
3

Beds

1.1

Baths

1,636

Sq.Ft.

334 S Burns Avenue

Winchester, KY

Bluegrass
View 508 Acadia Way Winchester, KY MLS# 26003275
$224,500
4

Beds

2.0

Baths

1,400

Sq.Ft.

508 Acadia Way

Winchester, KY

Bluegrass
View 701 Williamsburg Drive Winchester, KY MLS# 26002779
$97,000
2

Beds

1.0

Baths

996

Sq.Ft.

701 Williamsburg Drive

Winchester, KY

Bluegrass
View 190 Privacy Lane Winchester, KY MLS# 25501332
$260,000
Studio

Beds

0.0

Baths

190 Privacy Lane

Winchester, KY

Bluegrass
View 220 E Washington Street Winchester, KY MLS# 26002506
$169,900
3

Beds

1.0

Baths

1,097

Sq.Ft.

220 E Washington Street

Winchester, KY

Bluegrass
View 120 Windsor Drive Winchester, KY MLS# 26002472
  • Recently Listed
1 of 12
$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
  • Recently Listed
1 of 27
$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
  • Recently Listed
1 of 29
$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 46 Judy Ann Court Winchester, KY MLS# 26002119
$135,000
2

Beds

1.1

Baths

960

Sq.Ft.

46 Judy Ann Court

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
$259,900
3

Beds

2.0

Baths

1,251

Sq.Ft.

414 Wellington Way

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

About Winchester

Listings in Winchester, KY

255

Estimated median home price

$275,000
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 - 200K55
$200K - 300K58
$300K - 400K34
$400K - 500K17
$500K - 600K12
$600K - 700K9
$700K - 800K10
$800K - 900K8
$900K - 1M3
$1M - Max20

Homes for Sale by Type in Winchester, KY

Property TypeCount
Single Family135
Townhouse6
Condo0
Commercial13
Rental18
Lots and Land80
Condo/Town/CoOp0
CoOp0
Multi Family11
Mobile Home0
Farms10

(Data as of 3/3/2026)

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 3/3/2026.