View 28 Churchill Drive Winchester, KY MLS# 26008797
  • Virtual Tour
1 of 31
OPEN HOUSE: Saturday 5/16 3:00 PM - 5:00 PM
$310,000
5

Beds

3.0

Baths

2,624

Sq.Ft.

28 Churchill Drive

Winchester, KY

Bluegrass
View 219 Bartram Court Winchester, KY MLS# 26009207
$310,000
3

Beds

2.1

Baths

1,696

Sq.Ft.

219 Bartram Court

Winchester, KY

Bluegrass
View 414 Pueblo Court Winchester, KY MLS# 26008330
$309,999
3

Beds

2.1

Baths

2,648

Sq.Ft.

414 Pueblo Court

Winchester, KY

Bluegrass
The time to sell is now! THE TIME TO SELL IS NOW!
View 144 Holly Avenue Winchester, KY MLS# 26002633
$308,500
8

Beds

5.0

Baths

3,637

Sq.Ft.

144 Holly Avenue

Winchester, KY

Bluegrass
View 118 Windridge Drive Winchester, KY MLS# 26006695
$307,900
3

Beds

2.0

Baths

1,617

Sq.Ft.

118 Windridge Drive

Winchester, KY

Bluegrass
View 1045 Early Drive Winchester, KY MLS# 20111875
$300,000
1,675

Sq.Ft.

1045 Early Drive

Winchester, KY

Bluegrass
View 4025 Jackson Ferry Road Winchester, KY MLS# 26007284
$300,000
Studio

Beds

0.0

Baths

4025 Jackson Ferry Road

Winchester, KY

Bluegrass
View 306 Trapp-Goffs Cor Road Winchester, KY MLS# 26008462
$299,900
4

Beds

2.0

Baths

1,840

Sq.Ft.

306 Trapp-Goffs Cor Road

Winchester, KY

Bluegrass
View 147 Sunset Heights Winchester, KY MLS# 26011009
  • Recently Listed
1 of 38
$299,900
3

Beds

2.0

Baths

2,128

Sq.Ft.

147 Sunset Heights

Winchester, KY

Bluegrass
View 550 E Broadway Street Winchester, KY MLS# 25018505
$299,000
Studio

Beds

0.0

Baths

550 E Broadway Street

Winchester, KY

Bluegrass
View 54 Locust Drive Winchester, KY MLS# 26007779
  • Recently Listed
1 of 40
$299,000
3

Beds

2.0

Baths

1,692

Sq.Ft.

54 Locust Drive

Winchester, KY

Bluegrass
View 409-411 N Main Street Winchester, KY MLS# 26010325
  • Recently Listed
1 of 32
$299,000
300

Sq.Ft.

409-411 N Main Street

Winchester, KY

Bluegrass
View 618 Westmeade Drive Winchester, KY MLS# 26009371
  • Recently Listed
1 of 38
OPEN HOUSE: Sunday 5/17 2:00 PM - 4:00 PM
$296,900
4

Beds

2.0

Baths

2,116

Sq.Ft.

618 Westmeade Drive

Winchester, KY

Bluegrass
View 398 Pine Ridge Road Winchester, KY MLS# 26000601
$295,000
2

Beds

1.0

Baths

1,170

Sq.Ft.

398 Pine Ridge Road

Winchester, KY

Bluegrass
View 398 Pine Ridge Road Winchester, KY MLS# 26000610
$295,000
Studio

Beds

0.0

Baths

398 Pine Ridge Road

Winchester, KY

Bluegrass
View 103 Southern Court Winchester, KY MLS# 26007260
$295,000
3

Beds

1.1

Baths

1,500

Sq.Ft.

103 Southern Court

Winchester, KY

Bluegrass
View 426 E Broadway Street Winchester, KY MLS# 26007906
$289,000
5

Beds

2.0

Baths

1,838

Sq.Ft.

426 E Broadway Street

Winchester, KY

Bluegrass
View 211 Lindsey Court Winchester, KY MLS# 26003170
$285,000
3

Beds

2.0

Baths

1,790

Sq.Ft.

211 Lindsey Court

Winchester, KY

Bluegrass
View 327 Newcastle Lane Winchester, KY MLS# 26004861
    1 of 15
    OPEN HOUSE: Saturday 5/16 1:00 PM - 4:00 PM
    $284,900
    4

    Beds

    2.1

    Baths

    1,693

    Sq.Ft.

    327 Newcastle Lane

    Winchester, KY

    Bluegrass
    View 55 Hillcrest Drive Winchester, KY MLS# 26004166
    $279,000
    5

    Beds

    2.0

    Baths

    2,214

    Sq.Ft.

    55 Hillcrest Drive

    Winchester, KY

    Bluegrass

    About Winchester

    Listings in Winchester, KY

    307

    Estimated median home price

    $270,000
    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 - 100K35
    $100K - 200K67
    $200K - 300K71
    $300K - 400K43
    $400K - 500K22
    $500K - 600K17
    $600K - 700K11
    $700K - 800K13
    $800K - 900K4
    $900K - 1M2
    $1M - Max22

    Homes for Sale by Type in Winchester, KY

    Property TypeCount
    Single Family176
    Townhouse2
    Condo0
    Commercial16
    Rental17
    Lots and Land96
    Condo/Town/CoOp0
    CoOp0
    Multi Family11
    Mobile Home0
    Farms6

    (Data as of 5/16/2026)

    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 5/16/2026.