View 400 Wexford Drive Winchester, KY MLS# 26000557
$110,000
3

Beds

2.0

Baths

1,260

Sq.Ft.

400 Wexford Drive

Winchester, KY

Bluegrass
View 1751 Little Stoner Road Winchester, KY MLS# 26000593
$74,900
Studio

Beds

0.0

Baths

1751 Little Stoner Road

Winchester, KY

Bluegrass
View 398 Pine Ridge Road Winchester, KY MLS# 26000601
  • Recently Listed
1 of 25
$310,000
2

Beds

1.0

Baths

1,170

Sq.Ft.

398 Pine Ridge Road

Winchester, KY

Bluegrass
The time to sell is now! THE TIME TO SELL IS NOW!
View 398 Pine Ridge Road Winchester, KY MLS# 26000610
  • Recently Listed
1 of 25
$310,000
Studio

Beds

0.0

Baths

398 Pine Ridge Road

Winchester, KY

Bluegrass
View 443 Jameson Way Winchester, KY MLS# 26000614
  • Recently Listed
1 of 22
$221,500
4

Beds

2.0

Baths

1,400

Sq.Ft.

443 Jameson Way

Winchester, KY

Bluegrass
View 521 Acadia Way Winchester, KY MLS# 26000616
  • Recently Listed
1 of 22
$221,500
4

Beds

2.0

Baths

1,370

Sq.Ft.

521 Acadia Way

Winchester, KY

Bluegrass
View 646 Laura Dr E Laura Drive Winchester, KY MLS# 26000619
$249,000
3

Beds

2.0

Baths

1,534

Sq.Ft.

646 Laura Dr E Laura Drive

Winchester, KY

Bluegrass
View 10 Upper Street Winchester, KY MLS# 25004895
$240,000
3

Beds

2.1

Baths

2,380

Sq.Ft.

10 Upper Street

Winchester, KY

Bluegrass
View 402 McDowell Drive Winchester, KY MLS# 26000341
  • Recently Listed with Virtual Tour
1 of 36
$299,500
4

Beds

2.1

Baths

2,136

Sq.Ft.

402 McDowell Drive

Winchester, KY

Bluegrass
View 104 Colby Hills Drive Winchester, KY MLS# 25004009
$439,000
4

Beds

2.0

Baths

1,950

Sq.Ft.

104 Colby Hills Drive

Winchester, KY

Bluegrass
View 104 Bella Shae Way Winchester, KY MLS# 26000264
  • New Construction
1 of 10
$591,650
3

Beds

2.1

Baths

2,200

Sq.Ft.

104 Bella Shae Way

Winchester, KY

Bluegrass
View 870 Pilot View Road Winchester, KY MLS# 26000270
  • Recently Listed
1 of 21
$440,000
3

Beds

2.0

Baths

1,568

Sq.Ft.

870 Pilot View Road

Winchester, KY

Bluegrass
View 113 Mimosa Drive Winchester, KY MLS# 26000273
  • Recently Listed
1 of 5
$95,000
3

Beds

2.0

Baths

750

Sq.Ft.

113 Mimosa Drive

Winchester, KY

Bluegrass
Courtesy of Lexington - WEICHERT, REALTORS® - ABG
View 4305 Old Boonesboro Road Winchester, KY MLS# 26000275
$425,000
3

Beds

2.0

Baths

1,512

Sq.Ft.

4305 Old Boonesboro Road

Winchester, KY

Bluegrass
Courtesy of Lexington - WEICHERT, REALTORS® - ABG
View 149 Winn Ave Winchester, KY MLS# 26000197
  • Recently Listed
1 of 24
$290,000
12

Beds

4.0

Baths

4,010

Sq.Ft.

149 Winn Ave

Winchester, KY

Bluegrass
View 122 Callaway Street SE Callaway Street Winchester, KY MLS# 26000228
$129,900
2

Beds

1.0

Baths

876

Sq.Ft.

122 Callaway Street SE Callaway Street

Winchester, KY

Bluegrass
View 100 Duclair Drive Winchester, KY MLS# 22024061
$100,000
Studio

Beds

0.0

Baths

100 Duclair Drive

Winchester, KY

Bluegrass
View 120 Knox Court Winchester, KY MLS# 22024088
$150,000
Studio

Beds

0.0

Baths

120 Knox Court

Winchester, KY

Bluegrass
View 125 Knox Court Winchester, KY MLS# 22024090
$150,000
Studio

Beds

0.0

Baths

125 Knox Court

Winchester, KY

Bluegrass
View 250 Duclair Drive Winchester, KY MLS# 22024097
$110,000
Studio

Beds

0.0

Baths

250 Duclair 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.