203 total properties
Did you mean the neighborhood Winchester?
View 280 Pine Ridge Road Winchester, KY MLS# 26004070
  • Recently Listed
1 of 18
$260,000
3

Beds

1.0

Baths

1,296

Sq.Ft.

280 Pine Ridge Road

Winchester, KY

Bluegrass
View 543 Cunningham Lane Winchester, KY MLS# 26004071
  • Recently Listed
1 of 35
$289,000
3

Beds

2.0

Baths

1,152

Sq.Ft.

543 Cunningham Lane

Winchester, KY

Bluegrass
View 23 Windridge Drive Winchester, KY MLS# 26004120
  • Recently Listed
1 of 29
OPEN HOUSE: Sunday 3/8 2:00 PM - 4:00 PM
$364,900
3

Beds

2.0

Baths

1,858

Sq.Ft.

23 Windridge Drive

Winchester, KY

Bluegrass
The time to sell is now! THE TIME TO SELL IS NOW!
View 59 Holiday Road Winchester, KY MLS# 26004165
  • Recently Listed
1 of 33
$209,900
3

Beds

1.0

Baths

1,050

Sq.Ft.

59 Holiday Road

Winchester, KY

Bluegrass
View 55 Hillcrest Drive Winchester, KY MLS# 26004166
$305,000
5

Beds

2.0

Baths

2,214

Sq.Ft.

55 Hillcrest Drive

Winchester, KY

Bluegrass
View 120 Pilot View Road Winchester, KY MLS# 26003979
  • Recently Listed
1 of 45
$325,000
3

Beds

2.1

Baths

1,900

Sq.Ft.

120 Pilot View Road

Winchester, KY

Bluegrass
View 500 Hidden Hills Way Winchester, KY MLS# 26004000
  • Recently Listed
1 of 6
$204,900
3

Beds

2.0

Baths

1,120

Sq.Ft.

500 Hidden Hills Way

Winchester, KY

Bluegrass
View 730 Byrd Avenue Winchester, KY MLS# 26004038
  • Recently Listed
1 of 31
$155,000
3

Beds

1.0

Baths

1,160

Sq.Ft.

730 Byrd Avenue

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 916 Stratton Lane Winchester, KY MLS# 26003907
$269,000
3

Beds

2.0

Baths

1,400

Sq.Ft.

916 Stratton Lane

Winchester, KY

Bluegrass
View 2465 Flanagan Station Road Winchester, KY MLS# 26003912
$85,000
Studio

Beds

0.0

Baths

2465 Flanagan Station Road

Winchester, KY

Bluegrass
View 120 Duclair Drive Winchester, KY MLS# 22024065
$110,000
Studio

Beds

0.0

Baths

120 Duclair Drive

Winchester, KY

Bluegrass
View 150 Duclair Drive Winchester, KY MLS# 22024072
$110,000
Studio

Beds

0.0

Baths

150 Duclair Drive

Winchester, KY

Bluegrass
View 160 Duclair Drive Winchester, KY MLS# 22024074
$110,000
Studio

Beds

0.0

Baths

160 Duclair Drive

Winchester, KY

Bluegrass
View 200 Duclair Drive Winchester, KY MLS# 22024092
$110,000
Studio

Beds

0.0

Baths

200 Duclair Drive

Winchester, KY

Bluegrass
View 270 Duclair Drive Winchester, KY MLS# 22024100
$100,000
Studio

Beds

0.0

Baths

270 Duclair Drive

Winchester, KY

Bluegrass
View 255 Duclair Drive Winchester, KY MLS# 22024102
$110,000
Studio

Beds

0.0

Baths

255 Duclair Drive

Winchester, KY

Bluegrass
View 135 Jacob Court Winchester, KY MLS# 22024112
$110,000
Studio

Beds

0.0

Baths

135 Jacob Court

Winchester, KY

Bluegrass
View 111 Jacob Court Winchester, KY MLS# 22024120
$100,000
Studio

Beds

0.0

Baths

111 Jacob Court

Winchester, KY

Bluegrass
View 225 Jacob Court Winchester, KY MLS# 22024121
$100,000
Studio

Beds

0.0

Baths

225 Jacob Court

Winchester, KY

Bluegrass

About Winchester

Listings in Winchester, KY

260

Estimated median home price

$269,950
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 - 100K30
$100K - 200K57
$200K - 300K61
$300K - 400K36
$400K - 500K15
$500K - 600K12
$600K - 700K9
$700K - 800K10
$800K - 900K7
$900K - 1M3
$1M - Max20

Homes for Sale by Type in Winchester, KY

Property TypeCount
Single Family139
Townhouse6
Condo0
Commercial13
Rental18
Lots and Land81
Condo/Town/CoOp0
CoOp0
Multi Family11
Mobile Home0
Farms10

(Data as of 3/5/2026)

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 3/6/2026.

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 3/6/2026.