174 total properties
Did you mean the neighborhood Winchester?
View 102 Augusta Drive Winchester, KY MLS# 24022901
$29,000
Studio

Beds

0.0

Baths

102 Augusta Drive

Winchester, KY

Bluegrass
View 312 Buffalo Trace Winchester, KY MLS# 26014058
  • Recently Listed
1 of 31
$249,900
3

Beds

2.0

Baths

1,284

Sq.Ft.

312 Buffalo Trace

Winchester, KY

Bluegrass
View 214 S Burns Avenue Winchester, KY MLS# 26014099
  • Recently Listed
1 of 29
$289,000
4

Beds

1.1

Baths

2,170

Sq.Ft.

214 S Burns Avenue

Winchester, KY

Bluegrass
The time to sell is now! THE TIME TO SELL IS NOW!
View 3150 Waterworks Road Winchester, KY MLS# 26013923
  • Recently Listed
1 of 31
$250,000
2,591

Sq.Ft.

3150 Waterworks Road

Winchester, KY

Bluegrass
View 65 Fitch Avenue Winchester, KY MLS# 26013935
  • Recently Listed
1 of 27
$152,500
3

Beds

1.1

Baths

1,680

Sq.Ft.

65 Fitch Avenue

Winchester, KY

Bluegrass
View 371 E Washington Street Winchester, KY MLS# 26013772
$180,000
3

Beds

1.0

Baths

1,198

Sq.Ft.

371 E Washington Street

Winchester, KY

Bluegrass
View 2 Western Avenue Winchester, KY MLS# 26013551
  • Recently Listed
1 of 22
$229,500
2

Beds

1.0

Baths

1,454

Sq.Ft.

2 Western Avenue

Winchester, KY

Bluegrass
View 119 Sunset Heights Winchester, KY MLS# 26012905
  • Recently Listed
1 of 21
OPEN HOUSE: Saturday 6/20 12:00 PM - 2:00 PM
$265,000
3

Beds

1.0

Baths

1,324

Sq.Ft.

119 Sunset Heights

Winchester, KY

Bluegrass
View 120 Windsor Drive Winchester, KY MLS# 26013563
  • Recently Listed
1 of 41
$235,000
4

Beds

1.0

Baths

1,609

Sq.Ft.

120 Windsor Drive

Winchester, KY

Bluegrass
View 30 Virginia Avenue Winchester, KY MLS# 26013434
  • Recently Listed
1 of 46
$247,000
3

Beds

1.0

Baths

1,050

Sq.Ft.

30 Virginia Avenue

Winchester, KY

Bluegrass
Courtesy of Lexington - WEICHERT, REALTORS® - ABG
View 17 Holiday Road Winchester, KY MLS# 26013480
$249,900
3

Beds

1.1

Baths

1,161

Sq.Ft.

17 Holiday Road

Winchester, KY

Bluegrass
View 750 Craig Crossing # Lot #7 Winchester, KY MLS# 26013322
$154,900
Studio

Beds

0.0

Baths

750 Craig Crossing # Lot #7

Winchester, KY

Bluegrass
View 377 Crescent Avenue Winchester, KY MLS# 26013350
  • Recently Listed
1 of 50
OPEN HOUSE: Saturday 6/20 1:00 PM - 3:00 PM
$254,500
3

Beds

1.1

Baths

1,533

Sq.Ft.

377 Crescent Avenue

Winchester, KY

Bluegrass
View 122 Callaway Street SE Callaway Street Winchester, KY MLS# 26000228
$124,500
2

Beds

1.0

Baths

876

Sq.Ft.

122 Callaway Street SE Callaway Street

Winchester, KY

Bluegrass
View 107 Patio Street Winchester, KY MLS# 26013181
$160,000
2

Beds

1.0

Baths

864

Sq.Ft.

107 Patio Street

Winchester, KY

Bluegrass
View 955 Right Angle Road Winchester, KY MLS# 26013194
  • Recently Listed
1 of 35
$274,900
2

Beds

1.0

Baths

849

Sq.Ft.

955 Right Angle Road

Winchester, KY

Bluegrass
View 14 Cook Avenue Winchester, KY MLS# 26011961
  • Recently Listed
1 of 37
$233,000
3

Beds

2.0

Baths

1,261

Sq.Ft.

14 Cook Avenue

Winchester, KY

Bluegrass
View 13 Long Avenue Winchester, KY MLS# 26013004
  • Recently Listed
1 of 27
$240,000
3

Beds

2.0

Baths

1,297

Sq.Ft.

13 Long Avenue

Winchester, KY

Bluegrass
View 310 W Hickman Street Winchester, KY MLS# 26012783
  • Recently Listed
1 of 13
$109,900
4

Beds

2.1

Baths

1,391

Sq.Ft.

310 W Hickman Street

Winchester, KY

Bluegrass
View 4100 Crowe Ridge Road Winchester, KY MLS# 26012816
$320,000
3

Beds

2.1

Baths

2,100

Sq.Ft.

4100 Crowe Ridge Road

Winchester, KY

Bluegrass

About Winchester

Listings in Winchester, KY

297

Estimated median home price

$274,900
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 - 200K65
$200K - 300K73
$300K - 400K47
$400K - 500K17
$500K - 600K16
$600K - 700K10
$700K - 800K11
$800K - 900K2
$900K - 1M3
$1M - Max23

Homes for Sale by Type in Winchester, KY

Property TypeCount
Single Family175
Townhouse4
Condo0
Commercial14
Rental18
Lots and Land91
Condo/Town/CoOp0
CoOp0
Multi Family9
Mobile Home0
Farms4

(Data as of 6/18/2026)

Information deemed reliable but not guaranteed.

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 6/18/2026.