250 total properties
Did you mean the neighborhood Winchester?
View 220 Athens Boonsboro Road Winchester, KY MLS# 25012986
$531,000
5,012

Sq.Ft.

220 Athens Boonsboro Road

Winchester, KY

Bluegrass
View 110 White Conkwright Road Winchester, KY MLS# 26007022
$525,000
5

Beds

3.0

Baths

3,102

Sq.Ft.

110 White Conkwright Road

Winchester, KY

Bluegrass
View 35-37 Hays Street Winchester, KY MLS# 26002170
$515,000
1,440

Sq.Ft.

35-37 Hays Street

Winchester, KY

Bluegrass
The time to sell is now! THE TIME TO SELL IS NOW!
View 935 Stoner-Ephesus Road Winchester, KY MLS# 26009385
$515,000
3

Beds

2.0

Baths

2,563

Sq.Ft.

935 Stoner-Ephesus Road

Winchester, KY

Bluegrass
View 1005 Early Drive Winchester, KY MLS# 20111871
$500,000
Studio

Beds

0.0

Baths

1005 Early Drive

Winchester, KY

Bluegrass
View 808 Bypass Road Winchester, KY MLS# 26008729
$500,000
1.0

Baths

5,054

Sq.Ft.

808 Bypass Road

Winchester, KY

Bluegrass
View 16 Manor Drive Winchester, KY MLS# 26010312
$499,900
4

Beds

3.0

Baths

5,646

Sq.Ft.

16 Manor Drive

Winchester, KY

Bluegrass
View 182 Chardonnay Court Winchester, KY MLS# 26013305
$499,000
5

Beds

2.1

Baths

3,097

Sq.Ft.

182 Chardonnay Court

Winchester, KY

Bluegrass
View 33-41 Winn Avenue Winchester, KY MLS# 25508043
$490,000
Studio

Beds

0.0

Baths

33-41 Winn Avenue

Winchester, KY

Bluegrass
View 414 Fairholme Way Winchester, KY MLS# 26011136
  • New Construction
1 of 38
$484,900
4

Beds

3.0

Baths

2,418

Sq.Ft.

414 Fairholme Way

Winchester, KY

Bluegrass
View 265 S Highland Street Winchester, KY MLS# 26004961
$479,000
8

Beds

4.0

Baths

5,058

Sq.Ft.

265 S Highland Street

Winchester, KY

Bluegrass
View 287 Logan Lick Road Winchester, KY MLS# 26011126
$465,000
3

Beds

2.0

Baths

1,680

Sq.Ft.

287 Logan Lick Road

Winchester, KY

Bluegrass
View 105 Monet Boulevard Winchester, KY MLS# 26013041
  • Recently Listed
1 of 49
$464,000
4

Beds

2.1

Baths

3,296

Sq.Ft.

105 Monet Boulevard

Winchester, KY

Bluegrass
View 207 Hibiscus Lane Winchester, KY MLS# 26013195
$449,900
4

Beds

3.0

Baths

3,126

Sq.Ft.

207 Hibiscus Lane

Winchester, KY

Bluegrass
View 42 Mockingbird Valley Road Winchester, KY MLS# 26009944
    1 of 49
    OPEN HOUSE: Sunday 7/5 1:45 PM - 4:00 PM
    $445,500
    3

    Beds

    2.1

    Baths

    2,961

    Sq.Ft.

    42 Mockingbird Valley Road

    Winchester, KY

    Bluegrass
    View 250 Evergreen Drive Winchester, KY MLS# 25009082
    • New Construction
    1 of 3
    $430,000
    3

    Beds

    2.0

    Baths

    1,855

    Sq.Ft.

    250 Evergreen 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 1661 Waterworks Road Winchester, KY MLS# 26015130
    $429,000
    4

    Beds

    2.1

    Baths

    2,793

    Sq.Ft.

    1661 Waterworks Road

    Winchester, KY

    Bluegrass
    View 20 Edgewood Drive Winchester, KY MLS# 26009517
    • Virtual Tour
    1 of 47
    $427,000
    3

    Beds

    2.1

    Baths

    2,288

    Sq.Ft.

    20 Edgewood Drive

    Winchester, KY

    Bluegrass
    View 2996/3056 Irvine Road Winchester, KY MLS# 26007128
    $425,000
    Studio

    Beds

    0.0

    Baths

    2996/3056 Irvine Road

    Winchester, KY

    Bluegrass

    About Winchester

    Listings in Winchester, KY

    296

    Estimated median home price

    $279,950
    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 - 100K30
    $100K - 200K63
    $200K - 300K71
    $300K - 400K49
    $400K - 500K18
    $500K - 600K17
    $600K - 700K10
    $700K - 800K10
    $800K - 900K3
    $900K - 1M2
    $1M - Max23

    Homes for Sale by Type in Winchester, KY

    Property TypeCount
    Single Family178
    Townhouse4
    Condo0
    Commercial12
    Rental18
    Lots and Land86
    Condo/Town/CoOp0
    CoOp0
    Multi Family9
    Mobile Home0
    Farms7

    (Data as of 6/30/2026)

    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 7/1/2026.