112 total properties
Did you mean the neighborhood Winchester?
View 18 N Main Street Winchester, KY MLS# 26014568
$199,900
4,300

Sq.Ft.

18 N Main Street

Winchester, KY

Bluegrass
View 122 Spruce Court Winchester, KY MLS# 26014330
$228,500
3

Beds

2.0

Baths

1,210

Sq.Ft.

122 Spruce Court

Winchester, KY

Bluegrass
View 102 Augusta Drive Winchester, KY MLS# 24022901
$29,000
Studio

Beds

0.0

Baths

102 Augusta Drive

Winchester, KY

Bluegrass
The time to sell is now! THE TIME TO SELL IS NOW!
View 65 Fitch Avenue Winchester, KY MLS# 26013935
$149,900
3

Beds

1.1

Baths

1,680

Sq.Ft.

65 Fitch Avenue

Winchester, KY

Bluegrass
View 2 Western Avenue Winchester, KY MLS# 26013551
$221,500
2

Beds

1.0

Baths

1,454

Sq.Ft.

2 Western Avenue

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 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 14 Cook Avenue Winchester, KY MLS# 26011961
$225,000
3

Beds

2.0

Baths

1,261

Sq.Ft.

14 Cook Avenue

Winchester, KY

Bluegrass
View 563 Constitution Drive Winchester, KY MLS# 26012893
$99,500
2

Beds

2.0

Baths

924

Sq.Ft.

563 Constitution Drive

Winchester, KY

Bluegrass
View 104 Bay Hill Drive Winchester, KY MLS# 26012179
$199,000
2

Beds

2.0

Baths

1,200

Sq.Ft.

104 Bay Hill Drive

Winchester, KY

Bluegrass
View 86 Brink Avenue Winchester, KY MLS# 26011897
$225,000
3

Beds

2.0

Baths

1,136

Sq.Ft.

86 Brink Avenue

Winchester, KY

Bluegrass
View 590 Craig Crossing Winchester, KY MLS# 25506729
$152,500
Studio

Beds

0.0

Baths

590 Craig Crossing

Winchester, KY

Bluegrass
View 225 Buffalo Trace Winchester, KY MLS# 26011564
$199,900
3

Beds

2.0

Baths

915

Sq.Ft.

225 Buffalo Trace

Winchester, KY

Bluegrass
View 2799 Pine Ridge Road Winchester, KY MLS# 26011430
$99,900
3

Beds

2.0

Baths

675

Sq.Ft.

2799 Pine Ridge Road

Winchester, KY

Bluegrass
View Lot 3 Plantations Drive Winchester, KY MLS# 26011487
$78,500
Studio

Beds

0.0

Baths

Lot 3 Plantations Drive

Winchester, KY

Bluegrass
View Lot 4 Plantations Drive Winchester, KY MLS# 26011488
$78,500
Studio

Beds

0.0

Baths

Lot 4 Plantations Drive

Winchester, KY

Bluegrass
View 5127 Combs Ferry Road Winchester, KY MLS# 26011064
$225,000
Studio

Beds

0.0

Baths

5127 Combs Ferry Road

Winchester, KY

Bluegrass
View 301 Snowden Drive Winchester, KY MLS# 26010643
$210,000
3

Beds

1.0

Baths

1,386

Sq.Ft.

301 Snowden Drive

Winchester, KY

Bluegrass
View 103 Yorktowne Court Winchester, KY MLS# 25500573
$130,000
3

Beds

1.0

Baths

1,150

Sq.Ft.

103 Yorktowne Court

Winchester, KY

Bluegrass
View 108 Spruce Court Winchester, KY MLS# 26009399
$230,000
4

Beds

2.0

Baths

2,106

Sq.Ft.

108 Spruce Court

Winchester, KY

Bluegrass

About Winchester

Listings in Winchester, KY

296

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 - 100K39
$100K - 200K55
$200K - 300K71
$300K - 400K48
$400K - 500K19
$500K - 600K16
$600K - 700K11
$700K - 800K11
$800K - 900K4
$900K - 1M2
$1M - Max20

Homes for Sale by Type in Winchester, KY

Property TypeCount
Single Family167
Townhouse4
Condo0
Commercial14
Rental20
Lots and Land96
Condo/Town/CoOp0
CoOp0
Multi Family7
Mobile Home0
Farms8

(Data as of 7/18/2026)

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 7/19/2026.