199 total properties
Did you mean the neighborhood Winchester?
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 233 Cunningham Lane Winchester, KY MLS# 25507450
$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
The time to sell is now! THE TIME TO SELL IS NOW!
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 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 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
View 601 Gilbert Court Winchester, KY MLS# 26004646
  • Recently Listed
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 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 6239 Old Boonesboro Road Winchester, KY MLS# 25505595
$389,900
4

Beds

2.0

Baths

2,659

Sq.Ft.

6239 Old Boonesboro Road

Winchester, KY

Bluegrass
View 17 W Lexington Avenue Winchester, KY MLS# 26000777
$389,900
8

Beds

8.0

Baths

4,000

Sq.Ft.

17 W Lexington Avenue

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 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 300 Calmes Boulevard Winchester, KY MLS# 25504889
$379,717
3

Beds

2.1

Baths

2,636

Sq.Ft.

300 Calmes Boulevard

Winchester, KY

Bluegrass
View 137 East Broadway Street Winchester, KY MLS# 25508602
$379,000
1,536

Sq.Ft.

137 East Broadway Street

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 395 Croxton Way Winchester, KY MLS# 23015432
$374,900
Studio

Beds

0.0

Baths

395 Croxton Way

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

About Winchester

Listings in Winchester, KY

267

Estimated median home price

$269,900
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 - 100K32
$100K - 200K57
$200K - 300K64
$300K - 400K35
$400K - 500K17
$500K - 600K12
$600K - 700K10
$700K - 800K10
$800K - 900K7
$900K - 1M3
$1M - Max20

Homes for Sale by Type in Winchester, KY

Property TypeCount
Single Family144
Townhouse6
Condo0
Commercial13
Rental17
Lots and Land81
Condo/Town/CoOp0
CoOp0
Multi Family12
Mobile Home0
Farms11

(Data as of 3/11/2026)

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 3/12/2026.