301 total properties
Did you mean the neighborhood Winchester?
View 1270 Sewell Shop Road Winchester, KY MLS# 26000914
$354,900
5

Beds

2.0

Baths

1,952

Sq.Ft.

1270 Sewell Shop Road

Winchester, KY

Bluegrass
View 220 Hibiscus Lane Winchester, KY MLS# 26007618
$350,000
3

Beds

2.0

Baths

1,640

Sq.Ft.

220 Hibiscus Lane

Winchester, KY

Bluegrass
View 443 S Maple Street Winchester, KY MLS# 26008225
  • Recently Listed
1 of 57
$350,000
4

Beds

2.0

Baths

3,261

Sq.Ft.

443 S Maple Street

Winchester, KY

Bluegrass
The time to sell is now! THE TIME TO SELL IS NOW!
View 538 S Maple Street Winchester, KY MLS# 26000925
  • New Construction
1 of 32
$349,900
3

Beds

2.1

Baths

1,628

Sq.Ft.

538 S Maple Street

Winchester, KY

Bluegrass
View 221 W Hickman Street Winchester, KY MLS# 26004557
$349,500
4

Beds

3.0

Baths

3,440

Sq.Ft.

221 W Hickman Street

Winchester, KY

Bluegrass
View 110 Powe Drive Winchester, KY MLS# 26008249
  • Recently Listed
1 of 31
$347,500
4

Beds

2.1

Baths

2,010

Sq.Ft.

110 Powe Drive

Winchester, KY

Bluegrass
View 221 Moundale Avenue Winchester, KY MLS# 26004551
$345,000
3

Beds

2.1

Baths

2,628

Sq.Ft.

221 Moundale Avenue

Winchester, KY

Bluegrass
View 23 Windridge Drive Winchester, KY MLS# 26004120
$344,900
3

Beds

2.0

Baths

1,858

Sq.Ft.

23 Windridge Drive

Winchester, KY

Bluegrass
View 168 Buckingham Lane Winchester, KY MLS# 26006049
$339,900
4

Beds

2.1

Baths

2,358

Sq.Ft.

168 Buckingham Lane

Winchester, KY

Bluegrass
View 228 Holiday Road Winchester, KY MLS# 26006679
$339,900
4

Beds

2.0

Baths

1,843

Sq.Ft.

228 Holiday Road

Winchester, KY

Bluegrass
View 740 Pilot Ridge Lane Winchester, KY MLS# 26006680
$339,900
3

Beds

2.1

Baths

1,608

Sq.Ft.

740 Pilot Ridge Lane

Winchester, KY

Bluegrass
View 201 Boone Avenue Winchester, KY MLS# 26007703
$335,000
4

Beds

2.1

Baths

2,513

Sq.Ft.

201 Boone Avenue

Winchester, KY

Bluegrass
View 1291-1299 Muddy Creek Road Winchester, KY MLS# 26005152
$334,900
3

Beds

2.0

Baths

1,222

Sq.Ft.

1291-1299 Muddy Creek Road

Winchester, KY

Bluegrass
View 28 Churchill Drive Winchester, KY MLS# 26008797
  • Recently Listed with Virtual Tour
1 of 31
OPEN HOUSE: Sunday 4/26 1:00 PM - 3:00 PM
$330,000
5

Beds

3.0

Baths

2,624

Sq.Ft.

28 Churchill Drive

Winchester, KY

Bluegrass
View 374 N Middletown Road Winchester, KY MLS# 25005575
$329,500
3

Beds

2.0

Baths

1,719

Sq.Ft.

374 N Middletown Road

Winchester, KY

Bluegrass
View 360 N Middletown Road Winchester, KY MLS# 25005577
$329,500
3

Beds

2.0

Baths

1,792

Sq.Ft.

360 N Middletown Road

Winchester, KY

Bluegrass
View 322 S Burns Avenue Winchester, KY MLS# 26004053
$327,500
3

Beds

2.1

Baths

1,794

Sq.Ft.

322 S Burns Avenue

Winchester, KY

Bluegrass
View 225 Plantations Drive Winchester, KY MLS# 25506523
$326,900
3

Beds

2.1

Baths

3,868

Sq.Ft.

225 Plantations Drive

Winchester, KY

Bluegrass
View 215 Old Log Lick Road Winchester, KY MLS# 26003717
$325,000
3

Beds

2.0

Baths

1,450

Sq.Ft.

215 Old Log Lick Road

Winchester, KY

Bluegrass
View 3622 Stamper Drive Winchester, KY MLS# 26003842
    1 of 67
    OPEN HOUSE: Sunday 4/26 1:00 PM - 3:00 PM
    $325,000
    3

    Beds

    3.0

    Baths

    2,821

    Sq.Ft.

    3622 Stamper Drive

    Winchester, KY

    Bluegrass

    About Winchester

    Listings in Winchester, KY

    298

    Estimated median home price

    $264,950
    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 - 100K36
    $100K - 200K72
    $200K - 300K66
    $300K - 400K38
    $400K - 500K20
    $500K - 600K13
    $600K - 700K12
    $700K - 800K15
    $800K - 900K4
    $900K - 1M2
    $1M - Max20

    Homes for Sale by Type in Winchester, KY

    Property TypeCount
    Single Family163
    Townhouse5
    Condo0
    Commercial14
    Rental14
    Lots and Land97
    Condo/Town/CoOp0
    CoOp0
    Multi Family12
    Mobile Home0
    Farms7

    (Data as of 4/23/2026)

    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 4/23/2026.