223 total properties
Did you mean the neighborhood Winchester?
View 508 Acadia Way Winchester, KY MLS# 26003275
$224,500
4

Beds

2.0

Baths

1,400

Sq.Ft.

508 Acadia Way

Winchester, KY

Bluegrass
View 443 Jameson Way Winchester, KY MLS# 26000614
$221,500
4

Beds

2.0

Baths

1,400

Sq.Ft.

443 Jameson Way

Winchester, KY

Bluegrass
View 37 7th Street Winchester, KY MLS# 24025642
$220,000
3

Beds

2.0

Baths

1,680

Sq.Ft.

37 7th Street

Winchester, KY

Bluegrass
The time to sell is now! THE TIME TO SELL IS NOW!
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 334 S Burns Avenue Winchester, KY MLS# 26003334
$219,000
3

Beds

1.1

Baths

1,636

Sq.Ft.

334 S Burns Avenue

Winchester, KY

Bluegrass
View 271 April Way Winchester, KY MLS# 25016184
$215,000
2

Beds

1.1

Baths

1,120

Sq.Ft.

271 April Way

Winchester, KY

Bluegrass
View 218 E Washington Street Winchester, KY MLS# 25505534
$215,000
4

Beds

1.0

Baths

1,743

Sq.Ft.

218 E Washington Street

Winchester, KY

Bluegrass
View 313 S Burns Avenue Winchester, KY MLS# 25508192
$215,000
3

Beds

2.0

Baths

1,518

Sq.Ft.

313 S Burns Avenue

Winchester, KY

Bluegrass
View 707 Estes Drive Winchester, KY MLS# 26004204
$212,000
3

Beds

1.0

Baths

1,053

Sq.Ft.

707 Estes Drive

Winchester, KY

Bluegrass
View 59 Holiday Road Winchester, KY MLS# 26004165
  • Recently Listed
1 of 33
$209,900
3

Beds

1.0

Baths

1,050

Sq.Ft.

59 Holiday Road

Winchester, KY

Bluegrass
View 225 Buffalo Trace Winchester, KY MLS# 26004556
  • Recently Listed
1 of 24
$209,900
3

Beds

2.0

Baths

915

Sq.Ft.

225 Buffalo Trace

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 10 Upper Street Winchester, KY MLS# 25004895
$205,000
3

Beds

2.1

Baths

2,380

Sq.Ft.

10 Upper Street

Winchester, KY

Bluegrass
View 5434 Pine Ridge Road Winchester, KY MLS# 26001199
$205,000
2

Beds

2.0

Baths

1,000

Sq.Ft.

5434 Pine Ridge Road

Winchester, KY

Bluegrass
View 500 Hidden Hills Way Winchester, KY MLS# 26004000
$204,900
3

Beds

2.0

Baths

1,120

Sq.Ft.

500 Hidden Hills Way

Winchester, KY

Bluegrass
View 128 Bay Hill Drive Winchester, KY MLS# 26005243
$200,000
3

Beds

2.0

Baths

1,289

Sq.Ft.

128 Bay Hill Drive

Winchester, KY

Bluegrass
View 605 College Street Winchester, KY MLS# 25506124
$199,900
2

Beds

1.0

Baths

1,484

Sq.Ft.

605 College Street

Winchester, KY

Bluegrass
View 58 hughes Avenue Winchester, KY MLS# 26002214
$199,000
3

Beds

2.0

Baths

1,456

Sq.Ft.

58 hughes Avenue

Winchester, KY

Bluegrass
View 319 Essex Court Winchester, KY MLS# 26003610
  • Virtual Tour
1 of 21
$199,000
3

Beds

2.1

Baths

1,224

Sq.Ft.

319 Essex Court

Winchester, KY

Bluegrass
View 616 Boone Avenue Winchester, KY MLS# 26002364
$198,000
2

Beds

1.0

Baths

1,223

Sq.Ft.

616 Boone Avenue

Winchester, KY

Bluegrass

About Winchester

Listings in Winchester, KY

266

Estimated median home price

$285,000
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 - 100K30
$100K - 200K54
$200K - 300K61
$300K - 400K37
$400K - 500K18
$500K - 600K13
$600K - 700K11
$700K - 800K11
$800K - 900K7
$900K - 1M4
$1M - Max20

Homes for Sale by Type in Winchester, KY

Property TypeCount
Single Family145
Townhouse5
Condo0
Commercial13
Rental15
Lots and Land78
Condo/Town/CoOp0
CoOp0
Multi Family13
Mobile Home0
Farms12

(Data as of 3/18/2026)

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 3/20/2026.