167 total properties
Did you mean the neighborhood Winchester?
View 17 Holiday Road Winchester, KY MLS# 26013480
  • Recently Listed
1 of 60
$249,900
3

Beds

1.1

Baths

1,161

Sq.Ft.

17 Holiday Road

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 3614 Stamper Drive Winchester, KY MLS# 25017189
$249,500
3

Beds

2.0

Baths

1,247

Sq.Ft.

3614 Stamper Drive

Winchester, KY

Bluegrass
The time to sell is now! THE TIME TO SELL IS NOW!
View 377 Crescent Avenue Winchester, KY MLS# 26013350
  • Recently Listed
1 of 49
$249,500
3

Beds

1.1

Baths

1,533

Sq.Ft.

377 Crescent Avenue

Winchester, KY

Bluegrass
View 407 Pueblo Court Winchester, KY MLS# 26010046
$240,000
3

Beds

2.0

Baths

1,244

Sq.Ft.

407 Pueblo Court

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 30 Virginia Avenue Winchester, KY MLS# 26013434
  • Recently Listed
1 of 46
OPEN HOUSE: Sunday 6/28 2:00 PM - 4:00 PM
$239,000
3

Beds

1.0

Baths

1,050

Sq.Ft.

30 Virginia Avenue

Winchester, KY

Bluegrass
Courtesy of Lexington - WEICHERT, REALTORS® - ABG
View 125 Kittison Drive Winchester, KY MLS# 26011953
$237,500
3

Beds

1.0

Baths

1,100

Sq.Ft.

125 Kittison Drive

Winchester, KY

Bluegrass
View 190 Privacy Lane Winchester, KY MLS# 25501332
$237,000
Studio

Beds

0.0

Baths

190 Privacy Lane

Winchester, KY

Bluegrass
View 13 Arlington Road Winchester, KY MLS# 26005875
$235,000
4

Beds

2.0

Baths

1,431

Sq.Ft.

13 Arlington Road

Winchester, KY

Bluegrass
View 5127 Combs Ferry Road Winchester, KY MLS# 26011064
$235,000
Studio

Beds

0.0

Baths

5127 Combs Ferry Road

Winchester, KY

Bluegrass
View 120 Windsor Drive Winchester, KY MLS# 26013563
$235,000
4

Beds

1.0

Baths

1,609

Sq.Ft.

120 Windsor Drive

Winchester, KY

Bluegrass
View 122 Spruce Court Winchester, KY MLS# 26014330
  • Recently Listed
1 of 20
$235,000
3

Beds

2.0

Baths

1,210

Sq.Ft.

122 Spruce Court

Winchester, KY

Bluegrass
View 5127 Combs Ferry Road Winchester, KY MLS# 26014732
$235,000
Studio

Beds

0.0

Baths

5127 Combs Ferry Road

Winchester, KY

Bluegrass
View 528 Estes Drive Winchester, KY MLS# 26012351
$234,900
3

Beds

2.0

Baths

1,904

Sq.Ft.

528 Estes Drive

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

Beds

2.0

Baths

2,106

Sq.Ft.

108 Spruce Court

Winchester, KY

Bluegrass
View 217 Short Street Winchester, KY MLS# 26012199
$229,900
3

Beds

1.0

Baths

1,042

Sq.Ft.

217 Short 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 2110 Athens Boonesboro Road Winchester, KY MLS# 25500014
$225,000
Studio

Beds

0.0

Baths

2110 Athens Boonesboro Road

Winchester, KY

Bluegrass

About Winchester

Listings in Winchester, KY

297

Estimated median home price

$277,500
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 - 100K31
$100K - 200K65
$200K - 300K71
$300K - 400K49
$400K - 500K17
$500K - 600K17
$600K - 700K10
$700K - 800K9
$800K - 900K2
$900K - 1M3
$1M - Max23

Homes for Sale by Type in Winchester, KY

Property TypeCount
Single Family173
Townhouse4
Condo0
Commercial12
Rental18
Lots and Land92
Condo/Town/CoOp0
CoOp0
Multi Family9
Mobile Home0
Farms7

(Data as of 6/25/2026)

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 6/25/2026.