255 total properties
Did you mean the neighborhood Winchester?
View 808 Bypass Road Winchester, KY MLS# 25015851
$525,000
2

Beds

1.1

Baths

5,054

Sq.Ft.

808 Bypass Road

Winchester, KY

Bluegrass
View 35-37 Hays Street Winchester, KY MLS# 26002170
  • Recently Listed
1 of 18
$515,000
1,440

Sq.Ft.

35-37 Hays Street

Winchester, KY

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

Beds

0.0

Baths

1005 Early Drive

Winchester, KY

Bluegrass
The time to sell is now! THE TIME TO SELL IS NOW!
View 414 Fairholme Way Winchester, KY MLS# 25505996
  • New Construction
1 of 45
$499,900
4

Beds

3.0

Baths

2,300

Sq.Ft.

414 Fairholme Way

Winchester, KY

Bluegrass
View 595 Earlymeade Drive Winchester, KY MLS# 25506943
$499,000
5

Beds

3.1

Baths

3,823

Sq.Ft.

595 Earlymeade Drive

Winchester, KY

Bluegrass
View 2996/3056 Irvine Road Winchester, KY MLS# 25017324
$498,900
Studio

Beds

0.0

Baths

2996/3056 Irvine Road

Winchester, KY

Bluegrass
View 2996/3056 Irvine Road Winchester, KY MLS# 25500168
$498,900
Studio

Beds

0.0

Baths

2996/3056 Irvine Road

Winchester, KY

Bluegrass
View 42 Mockingbird Valley Road Winchester, KY MLS# 26000113
$452,500
3

Beds

2.1

Baths

2,961

Sq.Ft.

42 Mockingbird Valley Road

Winchester, KY

Bluegrass
View 550 E Broadway Street Winchester, KY MLS# 25018505
$450,000
Studio

Beds

0.0

Baths

550 E Broadway Street

Winchester, KY

Bluegrass
View 5127 Combs Ferry Road Winchester, KY MLS# 26002767
  • Recently Listed with Virtual Tour
1 of 5
$450,000
Studio

Beds

0.0

Baths

5127 Combs Ferry Road

Winchester, KY

Bluegrass
View 204 Delaplain Road Winchester, KY MLS# 26002697
  • Recently Listed
1 of 54
$434,900
3

Beds

2.0

Baths

3,563

Sq.Ft.

204 Delaplain Road

Winchester, KY

Bluegrass
View 104 Colby Hills Drive Winchester, KY MLS# 25004009
$432,000
4

Beds

2.0

Baths

1,950

Sq.Ft.

104 Colby Hills Drive

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 870 Pilot View Road Winchester, KY MLS# 26000270
$430,000
3

Beds

2.0

Baths

1,568

Sq.Ft.

870 Pilot View Road

Winchester, KY

Bluegrass
View 233 Cunningham Lane Winchester, KY MLS# 25507450
    1 of 39
    OPEN HOUSE: Sunday 3/8 1:00 PM - 3:00 PM
    $429,900
    3

    Beds

    2.1

    Baths

    2,258

    Sq.Ft.

    233 Cunningham Lane

    Winchester, KY

    Bluegrass
    View 107 Woodduck Court Winchester, KY MLS# 26001532
    $429,900
    3

    Beds

    2.1

    Baths

    2,652

    Sq.Ft.

    107 Woodduck Court

    Winchester, KY

    Bluegrass
    View 39 S Main Street Winchester, KY MLS# 25014867
    $429,000
    3,538

    Sq.Ft.

    39 S Main Street

    Winchester, KY

    Bluegrass
    View 1503 Schollsville Road Winchester, KY MLS# 25505942
    $425,000
    5

    Beds

    3.0

    Baths

    3,718

    Sq.Ft.

    1503 Schollsville Road

    Winchester, KY

    Bluegrass
    View 6504 Combs Ferry Road Winchester, KY MLS# 25506634
    $419,900
    5

    Beds

    3.1

    Baths

    2,564

    Sq.Ft.

    6504 Combs Ferry Road

    Winchester, KY

    Bluegrass
    View 145 Codella Drive Winchester, KY MLS# 22007107
    $400,000
    Studio

    Beds

    0.0

    Baths

    145 Codella Drive

    Winchester, KY

    Bluegrass

    About Winchester

    Listings in Winchester, KY

    255

    Estimated median home price

    $275,000
    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 - 100K29
    $100K - 200K55
    $200K - 300K58
    $300K - 400K34
    $400K - 500K17
    $500K - 600K12
    $600K - 700K9
    $700K - 800K10
    $800K - 900K8
    $900K - 1M3
    $1M - Max20

    Homes for Sale by Type in Winchester, KY

    Property TypeCount
    Single Family135
    Townhouse6
    Condo0
    Commercial13
    Rental18
    Lots and Land80
    Condo/Town/CoOp0
    CoOp0
    Multi Family11
    Mobile Home0
    Farms10

    (Data as of 3/3/2026)

    Information deemed reliable but not guaranteed.

    The data relating to real estate for sale on this web site comes in part from the Internet Data Exchange Program of Metro Search Multiple Listing Service. Real Estate listings held by IDX brokers (licensees) other than Weichert Realtors are marked with the IDX logo and detailed information about them includes the name of the IDX 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.

    © 2026 Metro Search Multiple Listing Service, Inc. All rights reserved.

    Data is updated as of 3/3/2026.

    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 3/3/2026.