View 140 Gibson Way Winchester, KY MLS# 26003011
$378,000
4

Beds

2.1

Baths

2,269

Sq.Ft.

140 Gibson Way

Winchester, KY

Bluegrass
View 701 Williamsburg Drive Winchester, KY MLS# 26002779
$97,000
2

Beds

1.0

Baths

996

Sq.Ft.

701 Williamsburg Drive

Winchester, KY

Bluegrass
View 190 Privacy Lane Winchester, KY MLS# 25501332
$260,000
Studio

Beds

0.0

Baths

190 Privacy Lane

Winchester, KY

Bluegrass
The time to sell is now! THE TIME TO SELL IS NOW!
View 1150 Craig Crossing Winchester, KY MLS# 26002724
  • Recently Listed
1 of 61
$925,000
5

Beds

3.1

Baths

2,842

Sq.Ft.

1150 Craig Crossing

Winchester, KY

Bluegrass
View 434 Paisley Court Winchester, KY MLS# 26002731
$275,000
3

Beds

2.1

Baths

1,678

Sq.Ft.

434 Paisley Court

Winchester, KY

Bluegrass
View 5127 Combs Ferry Road Winchester, KY MLS# 26002767
  • Recently Listed with Virtual Tour
1 of 5
$450,000
Studio

Beds

0.0

Baths

5127 Combs Ferry Road

Winchester, KY

Bluegrass
View 204 Delaplain Road Winchester, KY MLS# 26002697
  • Recently Listed
1 of 54
$434,900
3

Beds

2.0

Baths

3,563

Sq.Ft.

204 Delaplain Road

Winchester, KY

Bluegrass
View 144 Holly Avenue Winchester, KY MLS# 26002633
  • Recently Listed
1 of 62
$319,500
8

Beds

5.0

Baths

3,637

Sq.Ft.

144 Holly Avenue

Winchester, KY

Bluegrass
View 2 N Main Street Winchester, KY MLS# 25017572
$1,595,000
37

Beds

19.1

Baths

26,124

Sq.Ft.

2 N Main Street

Winchester, KY

Bluegrass
View 220 E Washington Street Winchester, KY MLS# 26002506
$169,900
3

Beds

1.0

Baths

1,097

Sq.Ft.

220 E Washington Street

Winchester, KY

Bluegrass
View 219 Woodbine Court Winchester, KY MLS# 26002508
  • Recently Listed
1 of 35
$329,900
4

Beds

2.0

Baths

1,751

Sq.Ft.

219 Woodbine Court

Winchester, KY

Bluegrass
View 600 Boone Avenue Winchester, KY MLS# 25018239
$589,900
4

Beds

3.2

Baths

4,374

Sq.Ft.

600 Boone Avenue

Winchester, KY

Bluegrass
View 35-37 Hays Street Winchester, KY MLS# 26002170
  • Recently Listed
1 of 18
$515,000
1,440

Sq.Ft.

35-37 Hays Street

Winchester, KY

Bluegrass
View 120 Windsor Drive Winchester, KY MLS# 26002472
  • Recently Listed
1 of 12
$269,900
4

Beds

1.0

Baths

1,610

Sq.Ft.

120 Windsor Drive

Winchester, KY

Bluegrass
View 616 Boone Avenue Winchester, KY MLS# 26002364
  • Recently Listed
1 of 27
$198,000
2

Beds

1.0

Baths

1,223

Sq.Ft.

616 Boone Avenue

Winchester, KY

Bluegrass
View 11 Shelley Dr Winchester, KY MLS# 26002369
  • Recently Listed
1 of 29
$234,900
3

Beds

2.0

Baths

1,188

Sq.Ft.

11 Shelley Dr

Winchester, KY

Bluegrass
View 233 E Washington Street Winchester, KY MLS# 26002299
$165,000
2

Beds

1.0

Baths

1,088

Sq.Ft.

233 E Washington Street

Winchester, KY

Bluegrass
View 115 Watercrest Circle Winchester, KY MLS# 26002338
  • Recently Listed
1 of 59
$279,950
4

Beds

3.0

Baths

2,112

Sq.Ft.

115 Watercrest Circle

Winchester, KY

Bluegrass
View 58 hughes Avenue Winchester, KY MLS# 26002214
  • Recently Listed
1 of 36
$199,000
3

Beds

2.0

Baths

1,456

Sq.Ft.

58 hughes Avenue

Winchester, KY

Bluegrass
View 220 Athens Boonsboro Road Winchester, KY MLS# 25012986
$531,000
5,012

Sq.Ft.

220 Athens Boonsboro Road

Winchester, KY

Bluegrass

About Winchester

Listings in Winchester, KY

246

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 - 100K21
$100K - 200K48
$200K - 300K58
$300K - 400K34
$400K - 500K22
$500K - 600K11
$600K - 700K9
$700K - 800K12
$800K - 900K8
$900K - 1M3
$1M - Max20

Homes for Sale by Type in Winchester, KY

Property TypeCount
Single Family140
Townhouse6
Condo0
Commercial13
Rental16
Lots and Land65
Condo/Town/CoOp0
CoOp0
Multi Family10
Mobile Home0
Farms12

(Data as of 2/20/2026)

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 2/20/2026.

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 2/20/2026.