45 total properties
Did you mean the neighborhood Winchester?
View 144 Holly Avenue Winchester, KY MLS# 26002633
$319,500
8

Beds

5.0

Baths

3,637

Sq.Ft.

144 Holly Avenue

Winchester, KY

Bluegrass
View 115 Watercrest Circle Winchester, KY MLS# 26002338
$279,950
4

Beds

3.0

Baths

2,112

Sq.Ft.

115 Watercrest Circle

Winchester, KY

Bluegrass
View 108 Ashley Drive Winchester, KY MLS# 26001564
$270,000
4

Beds

2.0

Baths

1,984

Sq.Ft.

108 Ashley Drive

Winchester, KY

Bluegrass
The time to sell is now! THE TIME TO SELL IS NOW!
View 1270 Sewell Shop Road Winchester, KY MLS# 26000914
$354,900
5

Beds

2.0

Baths

1,952

Sq.Ft.

1270 Sewell Shop Road

Winchester, KY

Bluegrass
View 1128-1130 Dale Drive Winchester, KY MLS# 26000922
$299,900
4

Beds

2.2

Baths

2,072

Sq.Ft.

1128-1130 Dale Drive

Winchester, KY

Bluegrass
View 538 S Maple Street Winchester, KY MLS# 26000925
  • New Construction
1 of 32
$354,900
3

Beds

2.1

Baths

1,628

Sq.Ft.

538 S Maple Street

Winchester, KY

Bluegrass
View 398 Pine Ridge Road Winchester, KY MLS# 26000601
$295,000
2

Beds

1.0

Baths

1,170

Sq.Ft.

398 Pine Ridge Road

Winchester, KY

Bluegrass
View 398 Pine Ridge Road Winchester, KY MLS# 26000610
$295,000
Studio

Beds

0.0

Baths

398 Pine Ridge Road

Winchester, KY

Bluegrass
View 149 Winn Ave Winchester, KY MLS# 26000197
$286,000
12

Beds

4.0

Baths

4,010

Sq.Ft.

149 Winn Ave

Winchester, KY

Bluegrass
View 446 Tremont Lane Winchester, KY MLS# 25508633
$367,000
4

Beds

2.1

Baths

2,811

Sq.Ft.

446 Tremont Lane

Winchester, KY

Bluegrass
View 204 Jett Drive Winchester, KY MLS# 25507850
  • New Construction
1 of 6
$369,900
3

Beds

2.0

Baths

1,558

Sq.Ft.

204 Jett Drive

Winchester, KY

Bluegrass
View 3600 Crowe Ridge Road Winchester, KY MLS# 25507522
  • New Construction
1 of 38
$359,900
4

Beds

4.1

Baths

3600 Crowe Ridge Road

Winchester, KY

Bluegrass
View 24 N Burns Avenue Winchester, KY MLS# 25507536
$298,900
3

Beds

3.1

Baths

2,526

Sq.Ft.

24 N Burns Avenue

Winchester, KY

Bluegrass
View 404 Wellington Way Winchester, KY MLS# 25505330
$275,700
3

Beds

2.0

Baths

1,682

Sq.Ft.

404 Wellington Way

Winchester, KY

Bluegrass
View 1508 Ford Hampton Road Winchester, KY MLS# 25503339
$300,000
2

Beds

1.0

Baths

1,531

Sq.Ft.

1508 Ford Hampton Road

Winchester, KY

Bluegrass
View 114 Mallard Lane Winchester, KY MLS# 25502189
$365,000
4

Beds

3.0

Baths

2,105

Sq.Ft.

114 Mallard Lane

Winchester, KY

Bluegrass
View 297 S Main Street Winchester, KY MLS# 25501793
$335,000
6

Beds

4.0

Baths

3,544

Sq.Ft.

297 S Main Street

Winchester, KY

Bluegrass
View 3056 Irvine Road Winchester, KY MLS# 25500166
$285,000
Studio

Beds

0.0

Baths

3056 Irvine Road

Winchester, KY

Bluegrass
View 206 Jett Drive Winchester, KY MLS# 24018286
  • New Construction
1 of 24
$369,900
3

Beds

2.0

Baths

1,635

Sq.Ft.

206 Jett Drive

Winchester, KY

Bluegrass
View 550 E Broadway Street Winchester, KY MLS# 25018505
$299,000
Studio

Beds

0.0

Baths

550 E Broadway Street

Winchester, KY

Bluegrass

About Winchester

Listings in Winchester, KY

266

Estimated median home price

$285,000
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 - 100K30
$100K - 200K54
$200K - 300K61
$300K - 400K37
$400K - 500K18
$500K - 600K13
$600K - 700K11
$700K - 800K11
$800K - 900K7
$900K - 1M4
$1M - Max20

Homes for Sale by Type in Winchester, KY

Property TypeCount
Single Family145
Townhouse5
Condo0
Commercial13
Rental15
Lots and Land78
Condo/Town/CoOp0
CoOp0
Multi Family13
Mobile Home0
Farms12

(Data as of 3/18/2026)

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 3/23/2026.