132 total properties
Did you mean the neighborhood Winchester?
View 250 Duclair Drive Winchester, KY MLS# 22024097
$110,000
Studio

Beds

0.0

Baths

250 Duclair Drive

Winchester, KY

Bluegrass
View 260 Duclair Drive Winchester, KY MLS# 22024098
$110,000
Studio

Beds

0.0

Baths

260 Duclair Drive

Winchester, KY

Bluegrass
View 139 Jacob Court Winchester, KY MLS# 22024111
$110,000
Studio

Beds

0.0

Baths

139 Jacob Court

Winchester, KY

Bluegrass
The time to sell is now! THE TIME TO SELL IS NOW!
View 125 Jacob Court Winchester, KY MLS# 22024114
$110,000
Studio

Beds

0.0

Baths

125 Jacob Court

Winchester, KY

Bluegrass
View 115 Jacob Court Winchester, KY MLS# 22024116
$110,000
Studio

Beds

0.0

Baths

115 Jacob Court

Winchester, KY

Bluegrass
View 41 7th Street Winchester, KY MLS# 25506758
$188,900
3

Beds

2.0

Baths

1,116

Sq.Ft.

41 7th Street

Winchester, KY

Bluegrass
View 20 Bon-Haven Avenue Winchester, KY MLS# 25500083
$275,000
4

Beds

3.0

Baths

1,850

Sq.Ft.

20 Bon-Haven Avenue

Winchester, KY

Bluegrass
View 417 Mt Vernon Drive Winchester, KY MLS# 25508464
$145,000
3

Beds

2.0

Baths

1,300

Sq.Ft.

417 Mt Vernon Drive

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 146 W Lexington Avenue Winchester, KY MLS# 25508389
$269,900
8

Beds

3.0

Baths

3,393

Sq.Ft.

146 W Lexington Avenue

Winchester, KY

Bluegrass
View 146 W Lexington Avenue Winchester, KY MLS# 25508390
$269,900
8

Beds

3.0

Baths

3,393

Sq.Ft.

146 W Lexington Avenue

Winchester, KY

Bluegrass
View 313 S Burns Avenue Winchester, KY MLS# 25508192
$230,000
3

Beds

2.0

Baths

1,518

Sq.Ft.

313 S Burns Avenue

Winchester, KY

Bluegrass
View 35 Cherokee Court Winchester, KY MLS# 25508113
$260,000
4

Beds

2.0

Baths

2,332

Sq.Ft.

35 Cherokee Court

Winchester, KY

Bluegrass
View 217 S Highland Street Winchester, KY MLS# 25507680
$249,900
4

Beds

2.0

Baths

2,683

Sq.Ft.

217 S Highland Street

Winchester, KY

Bluegrass
View 314 E Broadway Street Winchester, KY MLS# 25507471
$219,000
3

Beds

1.0

Baths

1,188

Sq.Ft.

314 E Broadway Street

Winchester, KY

Bluegrass
View 2721 Pretty Run Road Winchester, KY MLS# 24025198
$215,000
3

Beds

2.0

Baths

1,456

Sq.Ft.

2721 Pretty Run Road

Winchester, KY

Bluegrass
View 720 Estes Drive Winchester, KY MLS# 25506836
$249,900
3

Beds

1.1

Baths

1,494

Sq.Ft.

720 Estes Drive

Winchester, KY

Bluegrass
View 21 Virginia Avenue Winchester, KY MLS# 25506127
$255,000
3

Beds

2.0

Baths

1,749

Sq.Ft.

21 Virginia Avenue

Winchester, KY

Bluegrass
View 590 Craig Crossing Winchester, KY MLS# 25506729
$159,900
Studio

Beds

0.0

Baths

590 Craig Crossing

Winchester, KY

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

Beds

0.0

Baths

102 Augusta Drive

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.