225 total properties
Did you mean the neighborhood Winchester?
View 3622 Stamper Drive Winchester, KY MLS# 26012206
$299,900
3

Beds

3.0

Baths

2,821

Sq.Ft.

3622 Stamper Drive

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 147 Sunset Heights Winchester, KY MLS# 26011009
$294,900
3

Beds

2.0

Baths

2,128

Sq.Ft.

147 Sunset Heights

Winchester, KY

Bluegrass
The time to sell is now! THE TIME TO SELL IS NOW!
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
View 162 French Avenue Winchester, KY MLS# 26012319
$294,900
4

Beds

1.0

Baths

2,327

Sq.Ft.

162 French Avenue

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 198 Hilltop Drive Winchester, KY MLS# 26014664
$289,900
4

Beds

2.0

Baths

1,752

Sq.Ft.

198 Hilltop 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 214 S Burns Avenue Winchester, KY MLS# 26014099
  • Recently Listed
1 of 33
$289,000
4

Beds

1.1

Baths

2,170

Sq.Ft.

214 S Burns Avenue

Winchester, KY

Bluegrass
View 110 Buckingham Lane Winchester, KY MLS# 26014133
$289,000
3

Beds

2.0

Baths

1,240

Sq.Ft.

110 Buckingham Lane

Winchester, KY

Bluegrass
View 103 Southern Court Winchester, KY MLS# 26007260
$285,000
3

Beds

1.1

Baths

1,500

Sq.Ft.

103 Southern Court

Winchester, KY

Bluegrass
View 327 Newcastle Lane Winchester, KY MLS# 26004861
$284,900
4

Beds

2.1

Baths

1,693

Sq.Ft.

327 Newcastle Lane

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 133 Bay Hill Drive Winchester, KY MLS# 26012064
$280,000
4

Beds

3.1

Baths

3,276

Sq.Ft.

133 Bay Hill Drive

Winchester, KY

Bluegrass
View 20 Jackson Street Winchester, KY MLS# 26012820
    1 of 36
    OPEN HOUSE: Sunday 6/28 2:00 PM - 4:00 PM
    $280,000
    3

    Beds

    2.0

    Baths

    1,650

    Sq.Ft.

    20 Jackson Street

    Winchester, KY

    Bluegrass
    View 116 Sturbridge Lane Winchester, KY MLS# 26011782
    • New Construction
    1 of 37
    $277,500
    3

    Beds

    2.0

    Baths

    1,260

    Sq.Ft.

    116 Sturbridge Lane

    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 955 Right Angle Road Winchester, KY MLS# 26013194
    • Recently Listed
    1 of 35
    $274,900
    2

    Beds

    1.0

    Baths

    849

    Sq.Ft.

    955 Right Angle Road

    Winchester, KY

    Bluegrass
    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 800 Interstate Drive Winchester, KY MLS# 20111867
    $270,000
    Studio

    Beds

    0.0

    Baths

    800 Interstate Drive

    Winchester, KY

    Bluegrass

    About Winchester

    Listings in Winchester, KY

    298

    Estimated median home price

    $276,200
    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 - 100K31
    $100K - 200K66
    $200K - 300K71
    $300K - 400K49
    $400K - 500K17
    $500K - 600K17
    $600K - 700K10
    $700K - 800K9
    $800K - 900K2
    $900K - 1M3
    $1M - Max23

    Homes for Sale by Type in Winchester, KY

    Property TypeCount
    Single Family174
    Townhouse4
    Condo0
    Commercial12
    Rental18
    Lots and Land92
    Condo/Town/CoOp0
    CoOp0
    Multi Family9
    Mobile Home0
    Farms7

    (Data as of 6/26/2026)

    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 6/26/2026.