57 total properties
Did you mean the neighborhood Winchester?
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
The time to sell is now! THE TIME TO SELL IS NOW!
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
View 27 Hampton Avenue Winchester, KY MLS# 26010286
$350,000
3

Beds

2.0

Baths

2,835

Sq.Ft.

27 Hampton Avenue

Winchester, KY

Bluegrass
View 502 W Lexington Avenue Winchester, KY MLS# 26010324
$350,000
4

Beds

2.3

Baths

4,798

Sq.Ft.

502 W Lexington Avenue

Winchester, KY

Bluegrass
View 403 Pueblo Court Winchester, KY MLS# 26010021
$274,900
3

Beds

2.0

Baths

1,311

Sq.Ft.

403 Pueblo Court

Winchester, KY

Bluegrass
View 38 N Burns Avenue Winchester, KY MLS# 26009835
  • New Construction
1 of 31
$350,000
4

Beds

2.1

Baths

2,310

Sq.Ft.

38 N Burns Avenue

Winchester, KY

Bluegrass
View 618 Westmeade Drive Winchester, KY MLS# 26009371
$284,900
4

Beds

2.0

Baths

2,116

Sq.Ft.

618 Westmeade Drive

Winchester, KY

Bluegrass
View 54 Locust Drive Winchester, KY MLS# 26007779
$289,000
3

Beds

2.0

Baths

1,692

Sq.Ft.

54 Locust Drive

Winchester, KY

Bluegrass
View 720 Terry Drive Winchester, KY MLS# 26009068
$270,000
3

Beds

2.0

Baths

1,779

Sq.Ft.

720 Terry Drive

Winchester, KY

Bluegrass
View 414 Pueblo Court Winchester, KY MLS# 26008330
$289,999
3

Beds

2.1

Baths

2,648

Sq.Ft.

414 Pueblo Court

Winchester, KY

Bluegrass
View 412 Pueblo Court Winchester, KY MLS# 26008794
  • Virtual Tour
1 of 30
$312,000
3

Beds

2.1

Baths

2,648

Sq.Ft.

412 Pueblo Court

Winchester, KY

Bluegrass
View 28 Churchill Drive Winchester, KY MLS# 26008797
$310,000
5

Beds

3.0

Baths

2,624

Sq.Ft.

28 Churchill Drive

Winchester, KY

Bluegrass
View 443 S Maple Street Winchester, KY MLS# 26008225
$340,000
4

Beds

2.0

Baths

3,261

Sq.Ft.

443 S Maple Street

Winchester, KY

Bluegrass
View 110 Powe Drive Winchester, KY MLS# 26008249
$329,900
4

Beds

2.1

Baths

2,010

Sq.Ft.

110 Powe Drive

Winchester, KY

Bluegrass
View 614 Colby Ridge Boulevard Winchester, KY MLS# 26007904
$349,900
4

Beds

2.1

Baths

2,100

Sq.Ft.

614 Colby Ridge Boulevard

Winchester, KY

Bluegrass
View 200 Dubuy Drive Winchester, KY MLS# 26008021
$312,000
3

Beds

2.1

Baths

1,858

Sq.Ft.

200 Dubuy Drive

Winchester, KY

Bluegrass

About Winchester

Listings in Winchester, KY

291

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 - 100K30
$100K - 200K66
$200K - 300K69
$300K - 400K46
$400K - 500K17
$500K - 600K16
$600K - 700K10
$700K - 800K9
$800K - 900K2
$900K - 1M3
$1M - Max23

Homes for Sale by Type in Winchester, KY

Property TypeCount
Single Family170
Townhouse4
Condo0
Commercial12
Rental18
Lots and Land92
Condo/Town/CoOp0
CoOp0
Multi Family9
Mobile Home0
Farms4

(Data as of 6/23/2026)

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 6/24/2026.