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 133 Shala-Mar Rue Winchester, KY MLS# 25507513
$379,000
3

Beds

2.0

Baths

2,000

Sq.Ft.

133 Shala-Mar Rue

Winchester, KY

Bluegrass
The time to sell is now! THE TIME TO SELL IS NOW!
View 395 Croxton Way Winchester, KY MLS# 23015432
$374,900
Studio

Beds

0.0

Baths

395 Croxton Way

Winchester, KY

Bluegrass
View 114 Mallard Lane Winchester, KY MLS# 25502189
$372,900
4

Beds

3.0

Baths

2,105

Sq.Ft.

114 Mallard Lane

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 2
$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 1270 Sewell Shop Road Winchester, KY MLS# 26000914
$365,000
5

Beds

2.0

Baths

1,952

Sq.Ft.

1270 Sewell Shop Road

Winchester, KY

Bluegrass
View 538 S Maple Street Winchester, KY MLS# 26000925
  • Recently Listed
1 of 32
OPEN HOUSE: Sunday 1/18 2:00 PM - 4:00 PM
$359,900
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
  • Recently Listed
1 of 12
$355,000
4

Beds

2.2

Baths

2,072

Sq.Ft.

1128-1130 Dale Drive

Winchester, KY

Bluegrass
View 3622 Stamper Drive Winchester, KY MLS# 25507430
$349,900
3

Beds

3.0

Baths

2,821

Sq.Ft.

3622 Stamper Drive

Winchester, KY

Bluegrass
View 121 Fitch Avenue Winchester, KY MLS# 25504324
  • Virtual Tour
1 of 35
$349,000
4

Beds

3.0

Baths

2,100

Sq.Ft.

121 Fitch Avenue

Winchester, KY

Bluegrass
View 212 Woodbine Court Winchester, KY MLS# 25505033
$349,000
3

Beds

2.1

Baths

2,475

Sq.Ft.

212 Woodbine Court

Winchester, KY

Bluegrass
View 225 Plantations Drive Winchester, KY MLS# 25506523
$345,900
3

Beds

2.1

Baths

3,868

Sq.Ft.

225 Plantations Drive

Winchester, KY

Bluegrass
View 215 Evergreen Drive Winchester, KY MLS# 25009078
  • New Construction
1 of 2
$345,000
3

Beds

2.0

Baths

1,800

Sq.Ft.

215 Evergreen Drive

Winchester, KY

Bluegrass
View 225 Evergreen Drive Winchester, KY MLS# 25009080
  • New Construction
1 of 3
$345,000
3

Beds

2.0

Baths

1,677

Sq.Ft.

225 Evergreen Drive

Winchester, KY

Bluegrass
View 208 Citation Court Winchester, KY MLS# 25017361
$345,000
2

Beds

2.0

Baths

1,568

Sq.Ft.

208 Citation Court

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
View 374 N Middletown Road Winchester, KY MLS# 25005575
$329,500
3

Beds

2.0

Baths

1,719

Sq.Ft.

374 N Middletown Road

Winchester, KY

Bluegrass

About Winchester

Listings in Winchester, KY

256

Estimated median home price

$299,000
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 - 100K22
$100K - 200K48
$200K - 300K63
$300K - 400K39
$400K - 500K23
$500K - 600K10
$600K - 700K11
$700K - 800K10
$800K - 900K8
$900K - 1M2
$1M - Max20

Homes for Sale by Type in Winchester, KY

Property TypeCount
Single Family152
Townhouse3
Condo0
Commercial11
Rental17
Lots and Land67
Condo/Town/CoOp0
CoOp0
Multi Family9
Mobile Home0
Farms14

(Data as of 1/16/2026)

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 1/18/2026.

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 1/18/2026.