221 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 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 1407 Ironworks Road Winchester, KY MLS# 26004591
  • Recently Listed
1 of 25
$259,900
3

Beds

2.0

Baths

1,530

Sq.Ft.

1407 Ironworks Road

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 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 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 18 N Main Street Winchester, KY MLS# 25004978
$250,000
4,300

Sq.Ft.

18 N Main Street

Winchester, KY

Bluegrass
View 528 Estes Drive Winchester, KY MLS# 25503055
$249,900
3

Beds

2.0

Baths

1,904

Sq.Ft.

528 Estes Drive

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 300 W Broadway Street Winchester, KY MLS# 25505929
$249,000

300 W Broadway Street

Winchester, KY

Bluegrass
View 646 Laura Dr E Laura Drive Winchester, KY MLS# 26000619
$249,000
3

Beds

2.0

Baths

1,534

Sq.Ft.

646 Laura Dr E Laura Drive

Winchester, KY

Bluegrass
View 221 S Highland Street Winchester, KY MLS# 26000780
$246,400
5

Beds

3.0

Baths

3,007

Sq.Ft.

221 S Highland Street

Winchester, KY

Bluegrass
View 720 Estes Drive Winchester, KY MLS# 25506836
$244,900
3

Beds

1.1

Baths

1,494

Sq.Ft.

720 Estes Drive

Winchester, KY

Bluegrass
View 357 Silverton Way Winchester, KY MLS# 26003487
$243,000
3

Beds

2.0

Baths

1,502

Sq.Ft.

357 Silverton Way

Winchester, KY

Bluegrass
View 23 Kittison Drive Winchester, KY MLS# 25503252
$235,000
3

Beds

2.0

Baths

1,346

Sq.Ft.

23 Kittison Drive

Winchester, KY

Bluegrass
View 12 Linden Avenue Winchester, KY MLS# 25506319
$235,000
3

Beds

2.0

Baths

1,050

Sq.Ft.

12 Linden Avenue

Winchester, KY

Bluegrass
View 217 S Highland Street Winchester, KY MLS# 25507680
$234,900
4

Beds

2.0

Baths

2,683

Sq.Ft.

217 S Highland Street

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 2110 Athens Boonesboro Road Winchester, KY MLS# 25500014
$225,000
Studio

Beds

0.0

Baths

2110 Athens Boonesboro Road

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

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 3/19/2026.