119 total properties
Did you mean the neighborhood Winchester?
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 34 Hays Street Winchester, KY MLS# 26007612
  • Recently Listed
1 of 32
$222,500
4

Beds

1.1

Baths

2,450

Sq.Ft.

34 Hays Street

Winchester, KY

Bluegrass
View 101 Alabama Street Winchester, KY MLS# 26007407
  • Recently Listed
1 of 41
$169,900
1

Beds

2.0

Baths

1,056

Sq.Ft.

101 Alabama Street

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 3991 Jackson Ferry Road Winchester, KY MLS# 26007285
$97,500
Studio

Beds

0.0

Baths

3991 Jackson Ferry Road

Winchester, KY

Bluegrass
View 3961 Jackson Ferry Road Winchester, KY MLS# 26007286
$97,500
Studio

Beds

0.0

Baths

3961 Jackson Ferry Road

Winchester, KY

Bluegrass
View 3925 Jackson Ferry Road Winchester, KY MLS# 26007287
$180,000
Studio

Beds

0.0

Baths

3925 Jackson Ferry Road

Winchester, KY

Bluegrass
View 3821 Jackson Ferry Road Winchester, KY MLS# 26007288
$150,000
Studio

Beds

0.0

Baths

3821 Jackson Ferry Road

Winchester, KY

Bluegrass
View 3759 Jackson Ferry Road Winchester, KY MLS# 26007289
$105,000
Studio

Beds

0.0

Baths

3759 Jackson Ferry Road

Winchester, KY

Bluegrass
View 2996 Irvine Road Winchester, KY MLS# 26007067
  • Recently Listed
1 of 20
$175,000
Studio

Beds

0.0

Baths

2996 Irvine Road

Winchester, KY

Bluegrass
View 403 Country Club Drive Winchester, KY MLS# 26007069
$174,900
2

Beds

2.0

Baths

1,122

Sq.Ft.

403 Country Club Drive

Winchester, KY

Bluegrass
View 41 Hiawatha Trail Winchester, KY MLS# 26006789
  • Recently Listed
1 of 14
$189,999
3

Beds

1.0

Baths

950

Sq.Ft.

41 Hiawatha Trail

Winchester, KY

Bluegrass
View 150 Spencer Lane Winchester, KY MLS# 26006848
  • Recently Listed
1 of 4
$137,500
Studio

Beds

0.0

Baths

150 Spencer Lane

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 308 Duclair Drive Winchester, KY MLS# 25018185
$50,000
Studio

Beds

0.0

Baths

308 Duclair Drive

Winchester, KY

Bluegrass
View 47 Buckner Street Winchester, KY MLS# 26006752
  • Recently Listed
1 of 16
$179,900
3

Beds

2.0

Baths

1,635

Sq.Ft.

47 Buckner Street

Winchester, KY

Bluegrass
View 37 Ashland Avenue Winchester, KY MLS# 26006776
$139,000
2

Beds

1.0

Baths

904

Sq.Ft.

37 Ashland Avenue

Winchester, KY

Bluegrass
View 415 L E Junction Road Winchester, KY MLS# 26006620
  • Recently Listed
1 of 36
$225,000
3

Beds

2.0

Baths

1,152

Sq.Ft.

415 L E Junction Road

Winchester, KY

Bluegrass
View 117 4th Street Winchester, KY MLS# 25501219
$10,000
Studio

Beds

0.0

Baths

117 4th Street

Winchester, KY

Bluegrass
View 174 Cook Avenue 174 # 174 Winchester, KY MLS# 26006389
$139,900
2

Beds

1.0

Baths

986

Sq.Ft.

174 Cook Avenue 174 # 174

Winchester, KY

Bluegrass

About Winchester

Listings in Winchester, KY

290

Estimated median home price

$269,000
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 - 100K36
$100K - 200K66
$200K - 300K68
$300K - 400K37
$400K - 500K17
$500K - 600K14
$600K - 700K11
$700K - 800K14
$800K - 900K5
$900K - 1M3
$1M - Max19

Homes for Sale by Type in Winchester, KY

Property TypeCount
Single Family159
Townhouse6
Condo0
Commercial12
Rental15
Lots and Land95
Condo/Town/CoOp0
CoOp0
Multi Family11
Mobile Home0
Farms7

(Data as of 4/12/2026)

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 4/12/2026.