302 total properties
Did you mean the neighborhood Winchester?
View 3934 Trapp-Goffs Corner Road Winchester, KY MLS# 26005737
$225,000
Studio

Beds

0.0

Baths

3934 Trapp-Goffs Corner Road

Winchester, KY

Bluegrass
View 11 Shelley Drive Winchester, KY MLS# 26007607
$224,900
3

Beds

2.0

Baths

1,188

Sq.Ft.

11 Shelley Drive

Winchester, KY

Bluegrass
View 2366 Ironworks Road Winchester, KY MLS# 26005485
$220,000
3

Beds

2.0

Baths

1,530

Sq.Ft.

2366 Ironworks Road

Winchester, KY

Bluegrass
The time to sell is now! THE TIME TO SELL IS NOW!
View 21 Kentucky Street Winchester, KY MLS# 26007124
$219,900
3

Beds

2.0

Baths

1,340

Sq.Ft.

21 Kentucky Street

Winchester, KY

Bluegrass
View 7 Hiawatha Trail Winchester, KY MLS# 26008410
  • Recently Listed
1 of 20
OPEN HOUSE: Saturday 5/2 12:00 PM - 2:00 PM
$217,500
3

Beds

1.0

Baths

1,190

Sq.Ft.

7 Hiawatha Trail

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 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 218 E Washington Street Winchester, KY MLS# 25505534
$210,000
4

Beds

1.0

Baths

1,743

Sq.Ft.

218 E Washington Street

Winchester, KY

Bluegrass
View 34 Hays Street Winchester, KY MLS# 26007612
  • Recently Listed
1 of 31
$210,000
4

Beds

1.1

Baths

2,450

Sq.Ft.

34 Hays Street

Winchester, KY

Bluegrass
View 59 Holiday Road Winchester, KY MLS# 26004165
$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
$209,900
3

Beds

2.0

Baths

915

Sq.Ft.

225 Buffalo Trace

Winchester, KY

Bluegrass
View 217 S Highland Street Winchester, KY MLS# 25507680
$209,000
4

Beds

2.0

Baths

2,683

Sq.Ft.

217 S Highland Street

Winchester, KY

Bluegrass
View 2697 Pine Ridge Road Winchester, KY MLS# 26009146
  • Recently Listed
1 of 19
$209,000
Studio

Beds

0.0

Baths

2697 Pine Ridge Road

Winchester, KY

Bluegrass
View 415 L E Junction Road Winchester, KY MLS# 26006620
$205,000
3

Beds

2.0

Baths

1,152

Sq.Ft.

415 L E Junction 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 60 Hiawatha Trail Winchester, KY MLS# 26006850
$204,900
3

Beds

1.0

Baths

1,290

Sq.Ft.

60 Hiawatha Trail

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 215 Short Street Winchester, KY MLS# 26007746
  • Virtual Tour
1 of 27
$199,900
3

Beds

1.0

Baths

1,036

Sq.Ft.

215 Short Street

Winchester, KY

Bluegrass
View 368 Flanagan Station Road Winchester, KY MLS# 25009200
$199,500
Studio

Beds

0.0

Baths

368 Flanagan Station Road

Winchester, KY

Bluegrass

About Winchester

Listings in Winchester, KY

308

Estimated median home price

$264,950
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 - 100K36
$100K - 200K74
$200K - 300K72
$300K - 400K40
$400K - 500K23
$500K - 600K12
$600K - 700K10
$700K - 800K15
$800K - 900K3
$900K - 1M2
$1M - Max21

Homes for Sale by Type in Winchester, KY

Property TypeCount
Single Family175
Townhouse4
Condo0
Commercial15
Rental18
Lots and Land96
Condo/Town/CoOp0
CoOp0
Multi Family12
Mobile Home0
Farms6

(Data as of 4/27/2026)

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 4/28/2026.