View 808 Bypass Road Winchester, KY MLS# 25015851
$525,000
2

Beds

1.1

Baths

5,054

Sq.Ft.

808 Bypass 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 100 Spencer Lane Winchester, KY MLS# 25016234
$100,000
Studio

Beds

0.0

Baths

100 Spencer Lane

Winchester, KY

Bluegrass
The time to sell is now! THE TIME TO SELL IS NOW!
View 271 April Way Winchester, KY MLS# 25016184
$215,000
2

Beds

1.1

Baths

1,120

Sq.Ft.

271 April Way

Winchester, KY

Bluegrass
View 838 Bypass Road Winchester, KY MLS# 25015909
$614,900
2,906

Sq.Ft.

838 Bypass Road

Winchester, KY

Bluegrass
View 152 W Broadway Street Winchester, KY MLS# 25015809
$199,900
2,844

Sq.Ft.

152 W Broadway Street

Winchester, KY

Bluegrass
View 160 Agawam Road Winchester, KY MLS# 25015815
$524,000
3

Beds

2.1

Baths

4,933

Sq.Ft.

160 Agawam Road

Winchester, KY

Bluegrass
View 2395 Paris Road Winchester, KY MLS# 25015654
$14,100,000
Studio

Beds

0.0

Baths

2395 Paris Road

Winchester, KY

Bluegrass
View 118 Windridge Drive Winchester, KY MLS# 25015387
$318,000
3

Beds

2.0

Baths

1,617

Sq.Ft.

118 Windridge Drive

Winchester, KY

Bluegrass
View 101 E Lexington Avenue Winchester, KY MLS# 25015191
$388,000
5

Beds

3.0

Baths

2,762

Sq.Ft.

101 E Lexington Avenue

Winchester, KY

Bluegrass
View 150 Cook Avenue Winchester, KY MLS# 25015192
$144,000
3

Beds

1.0

Baths

805

Sq.Ft.

150 Cook Avenue

Winchester, KY

Bluegrass
View 39 S Highland Street Winchester, KY MLS# 25015196
$102,000
2

Beds

1.0

Baths

552

Sq.Ft.

39 S Highland Street

Winchester, KY

Bluegrass
View 39 S Main Street Winchester, KY MLS# 25014867
$429,000
3,538

Sq.Ft.

39 S Main Street

Winchester, KY

Bluegrass
View 13015 Irvine Road Winchester, KY MLS# 25014720
$219,000
Studio

Beds

0.0

Baths

13015 Irvine Road

Winchester, KY

Bluegrass
View 700 Nick Lane Winchester, KY MLS# 25013735
$949,950
3

Beds

2.1

Baths

2,400

Sq.Ft.

700 Nick Lane

Winchester, KY

Bluegrass
View 5045 Van Meter Road Winchester, KY MLS# 25013058
$2,650,000
6

Beds

5.1

Baths

7,274

Sq.Ft.

5045 Van Meter Road

Winchester, KY

Bluegrass
View 5515 Van Meter Road Winchester, KY MLS# 25012984
$524,900
4

Beds

2.0

Baths

2,940

Sq.Ft.

5515 Van Meter Road

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
View 6237 Bybee Road Winchester, KY MLS# 25012707
$1,200,000
5

Beds

5.2

Baths

8,236

Sq.Ft.

6237 Bybee Road

Winchester, KY

Bluegrass
View 1940 Athens Boonesboro Road Winchester, KY MLS# 25012636
$125,000
Studio

Beds

0.0

Baths

1940 Athens Boonesboro Road

Winchester, KY

Bluegrass

About Winchester

Listings in Winchester, KY

276

Estimated median home price

$274,950
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 - 100K38
$100K - 200K56
$200K - 300K56
$300K - 400K41
$400K - 500K24
$500K - 600K11
$600K - 700K11
$700K - 800K8
$800K - 900K8
$900K - 1M2
$1M - Max21

Homes for Sale by Type in Winchester, KY

Property TypeCount
Single Family142
Townhouse4
Condo0
Commercial12
Rental19
Lots and Land94
Condo/Town/CoOp0
CoOp0
Multi Family10
Mobile Home0
Farms14

(Data as of 12/27/2025)

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 12/28/2025.