View 35 Cherokee Court Winchester, KY MLS# 25508113
$265,000
4

Beds

2.0

Baths

2,332

Sq.Ft.

35 Cherokee Court

Winchester, KY

Bluegrass
View 394 S Main Street Winchester, KY MLS# 25507786
$229,000
4

Beds

2.0

Baths

1,858

Sq.Ft.

394 S Main Street

Winchester, KY

Bluegrass
View 217 S Highland Street Winchester, KY MLS# 25507680
$259,900
4

Beds

2.0

Baths

2,683

Sq.Ft.

217 S Highland Street

Winchester, KY

Bluegrass
The time to sell is now! THE TIME TO SELL IS NOW!
View 117 Buffalo Trace Winchester, KY MLS# 25507380
$199,900
3

Beds

2.0

Baths

1,072

Sq.Ft.

117 Buffalo Trace

Winchester, KY

Bluegrass
View 314 E Broadway Street Winchester, KY MLS# 25507471
$224,000
3

Beds

1.0

Baths

1,188

Sq.Ft.

314 E Broadway Street

Winchester, KY

Bluegrass
View 120 Jackson Street Winchester, KY MLS# 25507377
$248,000
3

Beds

2.1

Baths

1,342

Sq.Ft.

120 Jackson Street

Winchester, KY

Bluegrass
View 19 Cherokee Court Winchester, KY MLS# 25507379
$230,000
3

Beds

1.0

Baths

1,134

Sq.Ft.

19 Cherokee Court

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 208 Watercrest Way Winchester, KY MLS# 25507056
$255,000
3

Beds

2.1

Baths

1,416

Sq.Ft.

208 Watercrest Way

Winchester, KY

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

Beds

1.0

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 8 Village Drive Winchester, KY MLS# 25506553
$295,000
3

Beds

2.0

Baths

1,979

Sq.Ft.

8 Village Drive

Winchester, KY

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

Beds

0.0

Baths

102 Augusta Drive

Winchester, KY

Bluegrass
View 3208 Ford Hampton Road Winchester, KY MLS# 25506476
$147,000
2

Beds

1.0

Baths

807

Sq.Ft.

3208 Ford Hampton Road

Winchester, KY

Bluegrass
Courtesy of Lexington - WEICHERT, REALTORS® - ABG
View 125 Summerhill Way Winchester, KY MLS# 25506492
$259,900
3

Beds

2.0

Baths

1,333

Sq.Ft.

125 Summerhill Way

Winchester, KY

Bluegrass
View 114 Magnolia Street Winchester, KY MLS# 25506511
$99,000
2

Beds

1.0

Baths

910

Sq.Ft.

114 Magnolia Street

Winchester, KY

Bluegrass
View 368 Flanagan Station Road Winchester, KY MLS# 25009200
$206,000
Studio

Beds

0.0

Baths

368 Flanagan Station Road

Winchester, KY

Bluegrass
View 12541 Ironworks Road Winchester, KY MLS# 25506465
$70,000
Studio

Beds

0.0

Baths

12541 Ironworks Road

Winchester, KY

Bluegrass
View 12 Linden Avenue Winchester, KY MLS# 25506319
$235,000
3

Beds

2.0

Baths

1,050

Sq.Ft.

12 Linden Avenue

Winchester, KY

Bluegrass

About Winchester

Listings in Winchester, KY

262

Estimated median home price

$292,500
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 - 100K29
$100K - 200K48
$200K - 300K62
$300K - 400K37
$400K - 500K24
$500K - 600K10
$600K - 700K11
$700K - 800K10
$800K - 900K9
$900K - 1M2
$1M - Max20

Homes for Sale by Type in Winchester, KY

Property TypeCount
Single Family151
Townhouse3
Condo0
Commercial12
Rental18
Lots and Land74
Condo/Town/CoOp0
CoOp0
Multi Family8
Mobile Home0
Farms14

(Data as of 1/14/2026)

Information deemed reliable but not guaranteed.

The data relating to real estate for sale on this web site comes in part from the Internet Data Exchange Program of Metro Search Multiple Listing Service. Real Estate listings held by IDX brokers (licensees) other than Weichert Realtors are marked with the IDX logo and detailed information about them includes the name of the IDX 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.

© 2026 Metro Search Multiple Listing Service, Inc. All rights reserved.

Data is updated as of 1/14/2026.

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 1/14/2026.