40391 Homes for Sale

306 total properties
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 39 S Main Street Winchester, KY MLS# 25014867
$429,000
3,538

Sq.Ft.

39 S Main Street

Winchester, KY

Bluegrass
View 2996/3056 Irvine Road Winchester, KY MLS# 26007128
  • Recently Listed
1 of 25
$425,000
Studio

Beds

0.0

Baths

2996/3056 Irvine Road

Winchester, KY

Bluegrass
The time to sell is now! THE TIME TO SELL IS NOW!
View 104 Colby Hills Drive Winchester, KY MLS# 25004009
$420,000
4

Beds

2.0

Baths

1,950

Sq.Ft.

104 Colby Hills Drive

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 382 S Main Street Winchester, KY MLS# 26008931
  • Recently Listed
1 of 60
$415,000
4

Beds

3.0

Baths

3,310

Sq.Ft.

382 S Main Street

Winchester, KY

Bluegrass
View 505 LaSalle Court Winchester, KY MLS# 26008961
  • Recently Listed
1 of 34
$405,000
5

Beds

3.0

Baths

2,944

Sq.Ft.

505 LaSalle Court

Winchester, KY

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

Beds

0.0

Baths

145 Codella Drive

Winchester, KY

Bluegrass
View 1503 Schollsville Road Winchester, KY MLS# 25505942
$399,900
5

Beds

3.0

Baths

3,718

Sq.Ft.

1503 Schollsville Road

Winchester, KY

Bluegrass
View 205 Evergreen Drive Winchester, KY MLS# 25009077
  • New Construction
1 of 3
$395,000
3

Beds

2.0

Baths

1,855

Sq.Ft.

205 Evergreen Drive

Winchester, KY

Bluegrass
View 101 E Lexington Avenue Winchester, KY MLS# 25015191
$388,000
5

Beds

3.0

Baths

2,762

Sq.Ft.

101 E Lexington Avenue

Winchester, KY

Bluegrass
View 17 W Lexington Avenue Winchester, KY MLS# 26007617
  • Recently Listed
1 of 27
$388,000
8

Beds

8.0

Baths

4,000

Sq.Ft.

17 W Lexington Avenue

Winchester, KY

Bluegrass
View 270 Evergreen Drive Winchester, KY MLS# 25009085
  • New Construction
1 of 3
$380,000
3

Beds

2.0

Baths

1,677

Sq.Ft.

270 Evergreen Drive

Winchester, KY

Bluegrass
View 4305 Old Boonesboro Road Winchester, KY MLS# 26000275
$375,000
3

Beds

2.0

Baths

1,512

Sq.Ft.

4305 Old Boonesboro Road

Winchester, KY

Bluegrass
Courtesy of Lexington - WEICHERT, REALTORS® - ABG
View 137 East Broadway Street Winchester, KY MLS# 25508602
$374,000
1,536

Sq.Ft.

137 East Broadway Street

Winchester, KY

Bluegrass
View 206 Jett Drive Winchester, KY MLS# 24018286
  • New Construction
1 of 24
$369,900
3

Beds

2.0

Baths

1,635

Sq.Ft.

206 Jett Drive

Winchester, KY

Bluegrass
View 204 Jett Drive Winchester, KY MLS# 25507850
  • New Construction
1 of 5
$369,900
3

Beds

2.0

Baths

1,558

Sq.Ft.

204 Jett Drive

Winchester, KY

Bluegrass
View 614 Colby Ridge Boulevard Winchester, KY MLS# 26007904
  • Recently Listed
1 of 26
OPEN HOUSE: Sunday 4/26 2:00 PM - 4:00 PM
$369,900
4

Beds

2.1

Baths

2,100

Sq.Ft.

614 Colby Ridge Boulevard

Winchester, KY

Bluegrass
View 3600 Crowe Ridge Road Winchester, KY MLS# 25507522
  • New Construction
1 of 38
$359,900
4

Beds

4.1

Baths

3600 Crowe Ridge Road

Winchester, KY

Bluegrass
View 750 Providence Lane Winchester, KY MLS# 26006323
$359,900
Studio

Beds

0.0

Baths

750 Providence Lane

Winchester, KY

Bluegrass

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 4/25/2026.