132 total properties
Did you mean the neighborhood Winchester?
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
View 426 Paisley Court Winchester, KY MLS# 26001596
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1 of 35
$244,900
3

Beds

2.1

Baths

1,641

Sq.Ft.

426 Paisley Court

Winchester, KY

Bluegrass
View 5434 Pine Ridge Road Winchester, KY MLS# 26001199
$215,000
2

Beds

2.0

Baths

1,000

Sq.Ft.

5434 Pine Ridge Road

Winchester, KY

Bluegrass
The time to sell is now! THE TIME TO SELL IS NOW!
View 564 Trapp-Goffs Cor Road Winchester, KY MLS# 26000897
$269,000
3

Beds

2.0

Baths

1,960

Sq.Ft.

564 Trapp-Goffs Cor Road

Winchester, KY

Bluegrass
View 17 Euclid Avenue Winchester, KY MLS# 26000917
$249,900
3

Beds

2.0

Baths

1,656

Sq.Ft.

17 Euclid Avenue

Winchester, KY

Bluegrass
View 357 E Washington Street Winchester, KY MLS# 26000958
$189,900
3

Beds

2.0

Baths

1,328

Sq.Ft.

357 E Washington Street

Winchester, KY

Bluegrass
View 37 7th Street Winchester, KY MLS# 24025642
$220,000
3

Beds

2.0

Baths

1,680

Sq.Ft.

37 7th Street

Winchester, KY

Bluegrass
View 221 S Highland Street Winchester, KY MLS# 26000780
$246,400
5

Beds

3.0

Baths

3,007

Sq.Ft.

221 S Highland Street

Winchester, KY

Bluegrass
View 111 Quail Ridge Road Winchester, KY MLS# 26000646
$189,500
2

Beds

2.1

Baths

1,197

Sq.Ft.

111 Quail Ridge Road

Winchester, KY

Bluegrass
View 109 Quail Ridge Road Winchester, KY MLS# 26000647
$189,500
2

Beds

2.1

Baths

1,197

Sq.Ft.

109 Quail Ridge Road

Winchester, KY

Bluegrass
View 6699 Boonesboro Road Winchester, KY MLS# 25000480
$195,000
Studio

Beds

0.0

Baths

6699 Boonesboro Road

Winchester, KY

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

Beds

1.1

Baths

1,260

Sq.Ft.

400 Wexford Drive

Winchester, KY

Bluegrass
View 443 Jameson Way Winchester, KY MLS# 26000614
$221,500
4

Beds

2.0

Baths

1,400

Sq.Ft.

443 Jameson 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 113 Mimosa Drive Winchester, KY MLS# 26000273
$92,000
3

Beds

2.0

Baths

750

Sq.Ft.

113 Mimosa Drive

Winchester, KY

Bluegrass
Courtesy of Lexington - WEICHERT, REALTORS® - ABG
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

About Winchester

Listings in Winchester, KY

255

Estimated median home price

$275,000
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 - 100K29
$100K - 200K55
$200K - 300K58
$300K - 400K34
$400K - 500K17
$500K - 600K12
$600K - 700K9
$700K - 800K10
$800K - 900K8
$900K - 1M3
$1M - Max20

Homes for Sale by Type in Winchester, KY

Property TypeCount
Single Family135
Townhouse6
Condo0
Commercial13
Rental18
Lots and Land80
Condo/Town/CoOp0
CoOp0
Multi Family11
Mobile Home0
Farms10

(Data as of 3/3/2026)

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 3/3/2026.