View 219 Bartram Court Winchester, KY MLS# 26009207
$310,000
3

Beds

2.1

Baths

1,696

Sq.Ft.

219 Bartram Court

Winchester, KY

Bluegrass
View 363 S Main Street Winchester, KY MLS# 26009123
$250,000
3

Beds

2.0

Baths

2,142

Sq.Ft.

363 S Main Street

Winchester, KY

Bluegrass
View 720 Terry Drive Winchester, KY MLS# 26009068
  • Recently Listed
1 of 57
$275,000
3

Beds

2.0

Baths

1,779

Sq.Ft.

720 Terry Drive

Winchester, KY

Bluegrass
The time to sell is now! THE TIME TO SELL IS NOW!
View 382 S Main Street Winchester, KY MLS# 26008931
  • Recently Listed
1 of 60
$395,000
4

Beds

3.0

Baths

3,310

Sq.Ft.

382 S Main Street

Winchester, KY

Bluegrass
View 414 Pueblo Court Winchester, KY MLS# 26008330
  • Recently Listed
1 of 33
$309,999
3

Beds

2.1

Baths

2,648

Sq.Ft.

414 Pueblo Court

Winchester, KY

Bluegrass
View 11 Taylor Avenue Winchester, KY MLS# 26008944
  • Recently Listed
1 of 18
$149,900
3

Beds

1.0

Baths

1,362

Sq.Ft.

11 Taylor Avenue

Winchester, KY

Bluegrass
View 148 W Lexington Avenue Winchester, KY MLS# 26008946
$199,900
5

Beds

2.0

Baths

2,444

Sq.Ft.

148 W Lexington Avenue

Winchester, KY

Bluegrass
View 505 LaSalle Court Winchester, KY MLS# 26008961
$405,000
5

Beds

3.0

Baths

2,944

Sq.Ft.

505 LaSalle Court

Winchester, KY

Bluegrass
View 310 Essex Court Winchester, KY MLS# 26009036
$192,500
2

Beds

2.1

Baths

1,188

Sq.Ft.

310 Essex Court

Winchester, KY

Bluegrass
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 412 Pueblo Court Winchester, KY MLS# 26008794
  • Virtual Tour
1 of 30
OPEN HOUSE: Sunday 5/17 1:00 PM - 3:00 PM
$312,000
3

Beds

2.1

Baths

2,648

Sq.Ft.

412 Pueblo Court

Winchester, KY

Bluegrass
View 28 Churchill Drive Winchester, KY MLS# 26008797
  • Virtual Tour
1 of 31
OPEN HOUSE: Saturday 5/16 3:00 PM - 5:00 PM
$320,000
5

Beds

3.0

Baths

2,624

Sq.Ft.

28 Churchill Drive

Winchester, KY

Bluegrass
View 110 Buckingham Lane Winchester, KY MLS# 26008814
$275,000
3

Beds

2.0

Baths

1,240

Sq.Ft.

110 Buckingham Lane

Winchester, KY

Bluegrass
View 39 Casa Landa Way Winchester, KY MLS# 26008661
$125,000
Studio

Beds

0.0

Baths

39 Casa Landa Way

Winchester, KY

Bluegrass
View 229 S Highland Street Winchester, KY MLS# 26008701
$180,000
4

Beds

3.0

Baths

3,462

Sq.Ft.

229 S Highland Street

Winchester, KY

Bluegrass
View 808 Bypass Road Winchester, KY MLS# 26008729
$500,000
1.0

Baths

5,054

Sq.Ft.

808 Bypass Road

Winchester, KY

Bluegrass
View 175 Magnolia Street Winchester, KY MLS# 26008759
$179,000
3

Beds

1.0

Baths

1,046

Sq.Ft.

175 Magnolia Street

Winchester, KY

Bluegrass
View 110 Knox Court Winchester, KY MLS# 26008587
$129,300
Studio

Beds

0.0

Baths

110 Knox Court

Winchester, KY

Bluegrass
View 213 Short Street Winchester, KY MLS# 26008598
$229,000
3

Beds

2.0

Baths

1,068

Sq.Ft.

213 Short Street

Winchester, KY

Bluegrass
View 697 Goose Creek Road Winchester, KY MLS# 26008440
$180,000
3

Beds

2.0

Baths

1,848

Sq.Ft.

697 Goose Creek Road

Winchester, KY

Bluegrass

About Winchester

Listings in Winchester, KY

307

Estimated median home price

$275,000
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 - 400K43
$400K - 500K24
$500K - 600K16
$600K - 700K12
$700K - 800K13
$800K - 900K4
$900K - 1M2
$1M - Max23

Homes for Sale by Type in Winchester, KY

Property TypeCount
Single Family176
Townhouse2
Condo0
Commercial16
Rental18
Lots and Land95
Condo/Town/CoOp0
CoOp0
Multi Family11
Mobile Home0
Farms7

(Data as of 5/14/2026)

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 5/15/2026.