View Lot 4 Plantations Drive Winchester, KY MLS# 25506248
$78,500
Studio

Beds

0.0

Baths

Lot 4 Plantations Drive

Winchester, KY

Bluegrass
View Lot 5 Plantations Drive Winchester, KY MLS# 25506250
$78,500
Studio

Beds

0.0

Baths

Lot 5 Plantations Drive

Winchester, KY

Bluegrass
View 410 Wellington Way Winchester, KY MLS# 25506265
$262,500
3

Beds

2.0

Baths

1,192

Sq.Ft.

410 Wellington Way

Winchester, KY

Bluegrass
The time to sell is now! THE TIME TO SELL IS NOW!
View 3166 Colby Road Winchester, KY MLS# 25505174
$1,789,000
3

Beds

2.1

Baths

4,518

Sq.Ft.

3166 Colby Road

Winchester, KY

Bluegrass
View 605 College Street Winchester, KY MLS# 25506124
$230,000
2

Beds

1.0

Baths

1,484

Sq.Ft.

605 College Street

Winchester, KY

Bluegrass
View 205 E Washington Street Winchester, KY MLS# 25506086
$115,000
4

Beds

2.1

Baths

2,131

Sq.Ft.

205 E Washington Street

Winchester, KY

Bluegrass
View 550-A Bullion Boulevard Winchester, KY MLS# 24020455
$200,000
Studio

Beds

0.0

Baths

550-A Bullion Boulevard

Winchester, KY

Bluegrass
View 222 Bracken Court Winchester, KY MLS# 25505927
$269,000
3

Beds

2.1

Baths

1,456

Sq.Ft.

222 Bracken Court

Winchester, KY

Bluegrass
View 300 W Broadway Street Winchester, KY MLS# 25505929
$249,000

300 W Broadway Street

Winchester, KY

Bluegrass
View 1503 Schollsville Road Winchester, KY MLS# 25505942
$450,000
5

Beds

3.0

Baths

3,718

Sq.Ft.

1503 Schollsville Road

Winchester, KY

Bluegrass
View 414 Fairholme Way Winchester, KY MLS# 25505996
  • New Construction
1 of 18
$499,900
4

Beds

3.0

Baths

2,300

Sq.Ft.

414 Fairholme Way

Winchester, KY

Bluegrass
View 1857 Ironworks Road Winchester, KY MLS# 25505808
$420,000
5

Beds

2.1

Baths

2,924

Sq.Ft.

1857 Ironworks Road

Winchester, KY

Bluegrass
View 101 S Burns Avenue 1 # 1,2,3,4 Winchester, KY MLS# 25505825
$600,000
8

Beds

4.0

Baths

5,046

Sq.Ft.

101 S Burns Avenue 1 # 1,2,3,4

Winchester, KY

Bluegrass
View 4074 Ironworks Road Winchester, KY MLS# 25505744
$299,000
3

Beds

1.1

Baths

1,356

Sq.Ft.

4074 Ironworks Road

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 218 E Washington Street Winchester, KY MLS# 25505534
$215,000
4

Beds

1.0

Baths

1,743

Sq.Ft.

218 E Washington Street

Winchester, KY

Bluegrass
View 612 Boone Avenue Winchester, KY MLS# 25505318
$200,000
2

Beds

2.0

Baths

1,262

Sq.Ft.

612 Boone Avenue

Winchester, KY

Bluegrass
View 404 Wellington Way Winchester, KY MLS# 25505330
$279,700
3

Beds

2.0

Baths

1,682

Sq.Ft.

404 Wellington Way

Winchester, KY

Bluegrass
View 228 Jackson Street Winchester, KY MLS# 25015194
$146,000
3

Beds

1.0

Baths

1,020

Sq.Ft.

228 Jackson Street

Winchester, KY

Bluegrass
View 250 Shoppers Drive Winchester, KY MLS# 25505209
$1,500,000

250 Shoppers Drive

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 1/17/2026.

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 1/17/2026.