182 total properties
Did you mean the neighborhood Winchester?
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
The time to sell is now! THE TIME TO SELL IS NOW!
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
View 204 Jett Drive Winchester, KY MLS# 25507850
  • New Construction
1 of 6
$369,900
3

Beds

2.0

Baths

1,558

Sq.Ft.

204 Jett Drive

Winchester, KY

Bluegrass
View 446 Tremont Lane Winchester, KY MLS# 25508633
$367,000
4

Beds

2.1

Baths

2,811

Sq.Ft.

446 Tremont Lane

Winchester, KY

Bluegrass
View 114 Mallard Lane Winchester, KY MLS# 25502189
$365,000
4

Beds

3.0

Baths

2,105

Sq.Ft.

114 Mallard Lane

Winchester, KY

Bluegrass
View 23 Windridge Drive Winchester, KY MLS# 26004120
  • Recently Listed
1 of 29
$364,900
3

Beds

2.0

Baths

1,858

Sq.Ft.

23 Windridge Drive

Winchester, KY

Bluegrass
View 1270 Sewell Shop Road Winchester, KY MLS# 26000914
$360,000
5

Beds

2.0

Baths

1,952

Sq.Ft.

1270 Sewell Shop 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 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 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 175 Overlooking Drive Winchester, KY MLS# 26003583
$359,000
3

Beds

2.0

Baths

2,080

Sq.Ft.

175 Overlooking Drive

Winchester, KY

Bluegrass
View 538 S Maple Street Winchester, KY MLS# 26000925
  • New Construction
1 of 32
$354,900
3

Beds

2.1

Baths

1,628

Sq.Ft.

538 S Maple Street

Winchester, KY

Bluegrass
View 1128-1130 Dale Drive Winchester, KY MLS# 26000922
$345,000
4

Beds

2.2

Baths

2,072

Sq.Ft.

1128-1130 Dale Drive

Winchester, KY

Bluegrass
View 215 Old Log Lick Road Winchester, KY MLS# 26003717
  • Recently Listed
1 of 84
$343,000
3

Beds

2.0

Baths

1,450

Sq.Ft.

215 Old Log Lick Road

Winchester, KY

Bluegrass
View 322 S Burns Avenue Winchester, KY MLS# 26004053
  • Recently Listed
1 of 97
$339,900
3

Beds

2.1

Baths

1,794

Sq.Ft.

322 S Burns Avenue

Winchester, KY

Bluegrass
View 297 S Main Street Winchester, KY MLS# 25501793
$335,000
6

Beds

4.0

Baths

3,544

Sq.Ft.

297 S Main 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 3/13/2026.