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
7

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
7

Beds

3.0

Baths

3,393

Sq.Ft.

146 W Lexington Avenue

Winchester, KY

Bluegrass
The time to sell is now! THE TIME TO SELL IS NOW!
View 420 Willowbrook Road Winchester, KY MLS# 25508189
  • Recently Listed with Virtual Tour
1 of 31
$295,000
3

Beds

3.0

Baths

1,738

Sq.Ft.

420 Willowbrook Road

Winchester, KY

Bluegrass
View 313 S Burns Avenue Winchester, KY MLS# 25508192
  • Recently Listed with Virtual Tour
1 of 23
$250,000
3

Beds

2.0

Baths

1,518

Sq.Ft.

313 S Burns Avenue

Winchester, KY

Bluegrass
View 424 Waycross Drive Winchester, KY MLS# 25508213
$289,900
4

Beds

3.0

Baths

1,944

Sq.Ft.

424 Waycross Drive

Winchester, KY

Bluegrass
View 35 Cherokee Court Winchester, KY MLS# 25508113
  • Recently Listed
1 of 22
$270,000
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
  • Recently Listed
1 of 30
$259,900
4

Beds

2.0

Baths

2,683

Sq.Ft.

217 S Highland Street

Winchester, KY

Bluegrass
View 24 N Burns Avenue Winchester, KY MLS# 25507536
  • Recently Listed
1 of 28
$309,900
3

Beds

3.1

Baths

2,526

Sq.Ft.

24 N Burns Avenue

Winchester, KY

Bluegrass
View 117 Buffalo Trace Winchester, KY MLS# 25507380
  • Recently Listed
1 of 19
$199,900
3

Beds

2.0

Baths

1,072

Sq.Ft.

117 Buffalo Trace

Winchester, KY

Bluegrass
View 22 N Bloomfield Road Winchester, KY MLS# 25507403
$318,000
3

Beds

2.0

Baths

1,913

Sq.Ft.

22 N Bloomfield Road

Winchester, KY

Bluegrass
View 314 E Broadway Street Winchester, KY MLS# 25507471
  • Recently Listed with Virtual Tour
1 of 37
$229,000
3

Beds

1.0

Baths

1,188

Sq.Ft.

314 E Broadway Street

Winchester, KY

Bluegrass
View 443 Jameson Way Winchester, KY MLS# 25507351
$225,000
4

Beds

2.0

Baths

1,400

Sq.Ft.

443 Jameson Way

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
$220,000
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 214 S Burns Avenue Winchester, KY MLS# 25506625
$318,500
4

Beds

1.1

Baths

2,170

Sq.Ft.

214 S Burns Avenue

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

About Winchester

Listings in Winchester, KY

276

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 - 100K38
$100K - 200K55
$200K - 300K57
$300K - 400K41
$400K - 500K24
$500K - 600K11
$600K - 700K11
$700K - 800K8
$800K - 900K8
$900K - 1M2
$1M - Max21

Homes for Sale by Type in Winchester, KY

Property TypeCount
Single Family142
Townhouse4
Condo0
Commercial12
Rental19
Lots and Land94
Condo/Town/CoOp0
CoOp0
Multi Family10
Mobile Home0
Farms14

(Data as of 12/24/2025)

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 12/25/2025.