165 total properties
Did you mean the neighborhood Winchester?
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 265 Cunningham Lane Winchester, KY MLS# 26010094
$199,900
3

Beds

2.0

Baths

1,140

Sq.Ft.

265 Cunningham Lane

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
The time to sell is now! THE TIME TO SELL IS NOW!
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 22 Magnolia Street Winchester, KY MLS# 26009730
$160,900
2

Beds

1.0

Baths

842

Sq.Ft.

22 Magnolia Street

Winchester, KY

Bluegrass
View 17 Holiday Road Winchester, KY MLS# 26009671
$259,900
3

Beds

1.1

Baths

1,161

Sq.Ft.

17 Holiday Road

Winchester, KY

Bluegrass
View 123 Sunset Heights Winchester, KY MLS# 26009360
$249,900
3

Beds

2.0

Baths

1,446

Sq.Ft.

123 Sunset Heights

Winchester, KY

Bluegrass
View 618 Westmeade Drive Winchester, KY MLS# 26009371
$289,900
4

Beds

2.0

Baths

2,116

Sq.Ft.

618 Westmeade Drive

Winchester, KY

Bluegrass
View 164 Buckingham Lane Winchester, KY MLS# 26009383
$270,000
3

Beds

2.0

Baths

1,190

Sq.Ft.

164 Buckingham Lane

Winchester, KY

Bluegrass
View 86 Bon-Haven Avenue Winchester, KY MLS# 26009398
$269,000
4

Beds

2.0

Baths

2,295

Sq.Ft.

86 Bon-Haven Avenue

Winchester, KY

Bluegrass
View 2697 Pine Ridge Road Winchester, KY MLS# 26009146
$209,000
Studio

Beds

0.0

Baths

2697 Pine Ridge Road

Winchester, KY

Bluegrass
View 54 Locust Drive Winchester, KY MLS# 26007779
$289,000
3

Beds

2.0

Baths

1,692

Sq.Ft.

54 Locust Drive

Winchester, KY

Bluegrass
View 363 S Main Street Winchester, KY MLS# 26009123
$250,000
3

Beds

2.0

Baths

2,142

Sq.Ft.

363 S Main Street

Winchester, KY

Bluegrass
View 720 Terry Drive Winchester, KY MLS# 26009068
$275,000
3

Beds

2.0

Baths

1,779

Sq.Ft.

720 Terry Drive

Winchester, KY

Bluegrass
View 414 Pueblo Court Winchester, KY MLS# 26008330
$289,999
3

Beds

2.1

Baths

2,648

Sq.Ft.

414 Pueblo Court

Winchester, KY

Bluegrass
View 11 Taylor Avenue Winchester, KY MLS# 26008944
$149,900
3

Beds

1.0

Baths

1,362

Sq.Ft.

11 Taylor Avenue

Winchester, KY

Bluegrass
View 148 W Lexington Avenue Winchester, KY MLS# 26008946
$199,900
5

Beds

2.0

Baths

2,444

Sq.Ft.

148 W Lexington Avenue

Winchester, KY

Bluegrass
View 9 Linden Avenue Winchester, KY MLS# 25007762
$139,000
2

Beds

1.0

Baths

886

Sq.Ft.

9 Linden Avenue

Winchester, KY

Bluegrass
View 110 Buckingham Lane Winchester, KY MLS# 26008814
$275,000
3

Beds

2.0

Baths

1,240

Sq.Ft.

110 Buckingham Lane

Winchester, KY

Bluegrass
View 229 S Highland Street Winchester, KY MLS# 26008701
$180,000
4

Beds

3.0

Baths

3,462

Sq.Ft.

229 S Highland Street

Winchester, KY

Bluegrass

About Winchester

Listings in Winchester, KY

280

Estimated median home price

$269,950
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 - 100K29
$100K - 200K62
$200K - 300K74
$300K - 400K42
$400K - 500K17
$500K - 600K14
$600K - 700K5
$700K - 800K10
$800K - 900K1
$900K - 1M3
$1M - Max23

Homes for Sale by Type in Winchester, KY

Property TypeCount
Single Family160
Townhouse4
Condo0
Commercial13
Rental18
Lots and Land89
Condo/Town/CoOp0
CoOp0
Multi Family10
Mobile Home0
Farms4

(Data as of 6/7/2026)

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 6/8/2026.