251 total properties
Did you mean the neighborhood Winchester?
View 265 S Highland Street Winchester, KY MLS# 26004961
  • Recently Listed
1 of 31
$505,000
8

Beds

4.0

Baths

5,058

Sq.Ft.

265 S Highland Street

Winchester, KY

Bluegrass
View 327 Newcastle Lane Winchester, KY MLS# 26004861
  • Recently Listed
1 of 12
$297,000
4

Beds

2.1

Baths

1,693

Sq.Ft.

327 Newcastle Lane

Winchester, KY

Bluegrass
View 20 Stoney Brook Drive Winchester, KY MLS# 26004633
  • Recently Listed
1 of 65
$667,700
5

Beds

4.1

Baths

4,712

Sq.Ft.

20 Stoney Brook Drive

Winchester, KY

Bluegrass
The time to sell is now! THE TIME TO SELL IS NOW!
View 1911 Trapp-Goffs Cor Road Winchester, KY MLS# 26004732
$460,000
3

Beds

2.0

Baths

1,288

Sq.Ft.

1911 Trapp-Goffs Cor Road

Winchester, KY

Bluegrass
View 613 Bunker Hill Drive Winchester, KY MLS# 26004036
$135,000
3

Beds

2.0

Baths

1,152

Sq.Ft.

613 Bunker Hill Drive

Winchester, KY

Bluegrass
View 601 Gilbert Court Winchester, KY MLS# 26004646
    1 of 62
    OPEN HOUSE: Saturday 3/14 1:00 PM - 3:00 PM
    $399,900
    3

    Beds

    3.0

    Baths

    2,475

    Sq.Ft.

    601 Gilbert Court

    Winchester, KY

    Bluegrass
    View 218 S Maple Street Winchester, KY MLS# 26004697
    • Recently Listed
    1 of 25
    $825,000
    6,110

    Sq.Ft.

    218 S Maple Street

    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
    View 23 Kittison Drive Winchester, KY MLS# 25503252
    $235,000
    3

    Beds

    2.0

    Baths

    1,346

    Sq.Ft.

    23 Kittison Drive

    Winchester, KY

    Bluegrass
    View 240 Athens Boonesboro Road Winchester, KY MLS# 26004512
    $429,900
    4

    Beds

    2.1

    Baths

    1,500

    Sq.Ft.

    240 Athens Boonesboro Road

    Winchester, KY

    Bluegrass
    View 5127 Combs Ferry Road Winchester, KY MLS# 26004544
    $450,000
    Studio

    Beds

    0.0

    Baths

    5127 Combs Ferry Road

    Winchester, KY

    Bluegrass
    View 221 Moundale Avenue Winchester, KY MLS# 26004551
    • Recently Listed
    1 of 49
    $360,000
    3

    Beds

    2.1

    Baths

    2,628

    Sq.Ft.

    221 Moundale Avenue

    Winchester, KY

    Bluegrass
    View 225 Buffalo Trace Winchester, KY MLS# 26004556
    • Recently Listed
    1 of 24
    $209,900
    3

    Beds

    2.0

    Baths

    915

    Sq.Ft.

    225 Buffalo Trace

    Winchester, KY

    Bluegrass
    View 221 W Hickman Street Winchester, KY MLS# 26004557
    • Recently Listed
    1 of 44
    OPEN HOUSE: Sunday 3/15 1:00 PM - 3:00 PM
    $360,000
    4

    Beds

    3.0

    Baths

    3,440

    Sq.Ft.

    221 W Hickman Street

    Winchester, KY

    Bluegrass
    View 1450 Ford Road Winchester, KY MLS# 26004572
    • Recently Listed
    1 of 51
    $69,900
    Studio

    Beds

    0.0

    Baths

    1450 Ford Road

    Winchester, KY

    Bluegrass
    View 1407 Ironworks Road Winchester, KY MLS# 26004591
    • Recently Listed
    1 of 25
    $259,900
    3

    Beds

    2.0

    Baths

    1,530

    Sq.Ft.

    1407 Ironworks Road

    Winchester, KY

    Bluegrass
    View 1860 Ford Road Winchester, KY MLS# 26004497
    • Recently Listed
    1 of 58
    $89,900
    2

    Beds

    1.0

    Baths

    825

    Sq.Ft.

    1860 Ford Road

    Winchester, KY

    Bluegrass
    View 104 Colby Hills Drive Winchester, KY MLS# 25004009
    $429,000
    4

    Beds

    2.0

    Baths

    1,950

    Sq.Ft.

    104 Colby Hills Drive

    Winchester, KY

    Bluegrass
    View 7919 Mt Sterling Road Winchester, KY MLS# 26004302
    • Recently Listed
    1 of 54
    $700,000
    4

    Beds

    3.1

    Baths

    3,431

    Sq.Ft.

    7919 Mt Sterling Road

    Winchester, KY

    Bluegrass
    View 130 E Broadway Street Winchester, KY MLS# 26004331
    • Recently Listed
    1 of 19
    $265,000
    4

    Beds

    3.0

    Baths

    2,445

    Sq.Ft.

    130 E Broadway Street

    Winchester, KY

    Bluegrass

    About Winchester

    Listings in Winchester, KY

    270

    Estimated median home price

    $275,350
    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 - 200K57
    $200K - 300K64
    $300K - 400K36
    $400K - 500K18
    $500K - 600K12
    $600K - 700K11
    $700K - 800K11
    $800K - 900K7
    $900K - 1M3
    $1M - Max20

    Homes for Sale by Type in Winchester, KY

    Property TypeCount
    Single Family147
    Townhouse5
    Condo0
    Commercial13
    Rental15
    Lots and Land81
    Condo/Town/CoOp0
    CoOp0
    Multi Family12
    Mobile Home0
    Farms12

    (Data as of 3/13/2026)

    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 3/14/2026.