49 total properties
Did you mean the neighborhood Winchester?
View 280 Pine Ridge Road Winchester, KY MLS# 26004070
  • Recently Listed
1 of 18
$260,000
3

Beds

1.0

Baths

1,296

Sq.Ft.

280 Pine Ridge Road

Winchester, KY

Bluegrass
View 59 Holiday Road Winchester, KY MLS# 26004165
  • Recently Listed
1 of 33
$209,900
3

Beds

1.0

Baths

1,050

Sq.Ft.

59 Holiday Road

Winchester, KY

Bluegrass
View 916 Stratton Lane Winchester, KY MLS# 26003907
$269,000
3

Beds

2.0

Baths

1,400

Sq.Ft.

916 Stratton Lane

Winchester, KY

Bluegrass
The time to sell is now! THE TIME TO SELL IS NOW!
View 3614 Stamper Drive Winchester, KY MLS# 25017189
$259,500
3

Beds

2.0

Baths

1,247

Sq.Ft.

3614 Stamper Drive

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

Beds

0.0

Baths

190 Privacy Lane

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 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 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 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 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 426 Paisley Court Winchester, KY MLS# 26001596
  • Virtual Tour
1 of 35
$244,900
3

Beds

2.1

Baths

1,641

Sq.Ft.

426 Paisley Court

Winchester, KY

Bluegrass
View 5434 Pine Ridge Road Winchester, KY MLS# 26001199
$215,000
2

Beds

2.0

Baths

1,000

Sq.Ft.

5434 Pine Ridge Road

Winchester, KY

Bluegrass
View 564 Trapp-Goffs Cor Road Winchester, KY MLS# 26000897
$269,000
3

Beds

2.0

Baths

1,960

Sq.Ft.

564 Trapp-Goffs Cor Road

Winchester, KY

Bluegrass
View 17 Euclid Avenue Winchester, KY MLS# 26000917
$249,900
3

Beds

2.0

Baths

1,656

Sq.Ft.

17 Euclid Avenue

Winchester, KY

Bluegrass
View 37 7th Street Winchester, KY MLS# 24025642
$220,000
3

Beds

2.0

Baths

1,680

Sq.Ft.

37 7th Street

Winchester, KY

Bluegrass

About Winchester

Listings in Winchester, KY

260

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 - 100K30
$100K - 200K57
$200K - 300K61
$300K - 400K36
$400K - 500K15
$500K - 600K12
$600K - 700K9
$700K - 800K10
$800K - 900K7
$900K - 1M3
$1M - Max20

Homes for Sale by Type in Winchester, KY

Property TypeCount
Single Family139
Townhouse6
Condo0
Commercial13
Rental18
Lots and Land81
Condo/Town/CoOp0
CoOp0
Multi Family11
Mobile Home0
Farms10

(Data as of 3/5/2026)

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 3/6/2026.