246 total properties
Did you mean the neighborhood Winchester?
View 175 Overlooking Drive Winchester, KY MLS# 26003583
$359,000
3

Beds

2.0

Baths

2,080

Sq.Ft.

175 Overlooking Drive

Winchester, KY

Bluegrass
View 1270 Sewell Shop Road Winchester, KY MLS# 26000914
    1 of 34
    OPEN HOUSE: Saturday 3/21 10:00 AM - 12:00 PM
    $354,900
    5

    Beds

    2.0

    Baths

    1,952

    Sq.Ft.

    1270 Sewell Shop Road

    Winchester, KY

    Bluegrass
    View 538 S Maple Street Winchester, KY MLS# 26000925
    • New Construction
    1 of 32
    $354,900
    3

    Beds

    2.1

    Baths

    1,628

    Sq.Ft.

    538 S Maple Street

    Winchester, KY

    Bluegrass
    The time to sell is now! THE TIME TO SELL IS NOW!
    View 1128-1130 Dale Drive Winchester, KY MLS# 26000922
    $345,000
    4

    Beds

    2.2

    Baths

    2,072

    Sq.Ft.

    1128-1130 Dale Drive

    Winchester, KY

    Bluegrass
    View 1128-1130 Dale Drive Winchester, KY MLS# 26005390
    • Recently Listed
    1 of 12
    $345,000
    4

    Beds

    2.2

    Baths

    1,682

    Sq.Ft.

    1128-1130 Dale Drive

    Winchester, KY

    Bluegrass
    View 215 Old Log Lick Road Winchester, KY MLS# 26003717
    • Recently Listed
    1 of 84
    $343,000
    3

    Beds

    2.0

    Baths

    1,450

    Sq.Ft.

    215 Old Log Lick Road

    Winchester, KY

    Bluegrass
    View 322 S Burns Avenue Winchester, KY MLS# 26004053
    • Recently Listed
    1 of 97
    $339,900
    3

    Beds

    2.1

    Baths

    1,794

    Sq.Ft.

    322 S Burns Avenue

    Winchester, KY

    Bluegrass
    View 1291-1299 Muddy Creek Road Winchester, KY MLS# 26005152
    $339,900
    3

    Beds

    2.0

    Baths

    1,222

    Sq.Ft.

    1291-1299 Muddy Creek Road

    Winchester, KY

    Bluegrass
    View 297 S Main Street Winchester, KY MLS# 25501793
    $335,000
    6

    Beds

    4.0

    Baths

    3,544

    Sq.Ft.

    297 S Main Street

    Winchester, KY

    Bluegrass
    View 120 Pilot View Road Winchester, KY MLS# 26003979
    $334,000
    3

    Beds

    2.1

    Baths

    1,900

    Sq.Ft.

    120 Pilot View Road

    Winchester, KY

    Bluegrass
    View 225 Plantations Drive Winchester, KY MLS# 25506523
    $332,700
    3

    Beds

    2.1

    Baths

    3,868

    Sq.Ft.

    225 Plantations 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 3622 Stamper Drive Winchester, KY MLS# 26003842
    • Recently Listed
    1 of 67
    $325,000
    3

    Beds

    3.0

    Baths

    2,821

    Sq.Ft.

    3622 Stamper Drive

    Winchester, KY

    Bluegrass
    View 128 Cherokee Drive Winchester, KY MLS# 26003806
    • Recently Listed
    1 of 36
    $319,900
    5

    Beds

    2.0

    Baths

    2,082

    Sq.Ft.

    128 Cherokee Drive

    Winchester, KY

    Bluegrass
    View 144 Holly Avenue Winchester, KY MLS# 26002633
    $319,500
    8

    Beds

    5.0

    Baths

    3,637

    Sq.Ft.

    144 Holly Avenue

    Winchester, KY

    Bluegrass
    View 55 Hillcrest Drive Winchester, KY MLS# 26004166
    • Recently Listed
    1 of 12
    OPEN HOUSE: Saturday 3/21 11:00 AM - 1:00 PM
    $305,000
    5

    Beds

    2.0

    Baths

    2,214

    Sq.Ft.

    55 Hillcrest 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 1508 Ford Hampton Road Winchester, KY MLS# 25503339
    $300,000
    2

    Beds

    1.0

    Baths

    1,531

    Sq.Ft.

    1508 Ford Hampton Road

    Winchester, KY

    Bluegrass
    View 3811 Combs Ferry Road Winchester, KY MLS# 26004722
    $300,000
    Studio

    Beds

    0.0

    Baths

    3811 Combs Ferry Road

    Winchester, KY

    Bluegrass

    About Winchester

    Listings in Winchester, KY

    266

    Estimated median home price

    $285,000
    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 - 100K30
    $100K - 200K54
    $200K - 300K61
    $300K - 400K37
    $400K - 500K18
    $500K - 600K13
    $600K - 700K11
    $700K - 800K11
    $800K - 900K7
    $900K - 1M4
    $1M - Max20

    Homes for Sale by Type in Winchester, KY

    Property TypeCount
    Single Family145
    Townhouse5
    Condo0
    Commercial13
    Rental15
    Lots and Land78
    Condo/Town/CoOp0
    CoOp0
    Multi Family13
    Mobile Home0
    Farms12

    (Data as of 3/18/2026)

    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 3/20/2026.