297 total properties
Did you mean the neighborhood Winchester?
View 104 Jackson Ferry Road Winchester, KY MLS# 26005196
$269,000
4

Beds

2.0

Baths

2,417

Sq.Ft.

104 Jackson Ferry Road

Winchester, KY

Bluegrass
View 20 Bon Haven Avenue Winchester, KY MLS# 26011883
$269,000
4

Beds

3.0

Baths

1,850

Sq.Ft.

20 Bon Haven Avenue

Winchester, KY

Bluegrass
View 205 Providence Lane Winchester, KY MLS# 26010776
$269,900
3

Beds

1.0

Baths

1,644

Sq.Ft.

205 Providence Lane

Winchester, KY

Bluegrass
The time to sell is now! THE TIME TO SELL IS NOW!
View 800 Interstate Drive Winchester, KY MLS# 20111867
$270,000
Studio

Beds

0.0

Baths

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

    Beds

    2.0

    Baths

    2,128

    Sq.Ft.

    147 Sunset Heights

    Winchester, KY

    Bluegrass

    About Winchester

    Listings in Winchester, KY

    297

    Estimated median home price

    $277,500
    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 - 200K65
    $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 Family173
    Townhouse4
    Condo0
    Commercial12
    Rental18
    Lots and Land92
    Condo/Town/CoOp0
    CoOp0
    Multi Family9
    Mobile Home0
    Farms7

    (Data as of 6/25/2026)

    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.