301 total properties
Did you mean the neighborhood Winchester?
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
  • Recently Listed with Virtual Tour
1 of 30
$322,500
3

Beds

2.1

Baths

2,648

Sq.Ft.

412 Pueblo Court

Winchester, KY

Bluegrass
View 28 Churchill Drive Winchester, KY MLS# 26008797
  • Recently Listed with Virtual Tour
1 of 31
OPEN HOUSE: Sunday 4/26 1:00 PM - 3:00 PM
$330,000
5

Beds

3.0

Baths

2,624

Sq.Ft.

28 Churchill Drive

Winchester, KY

Bluegrass
The time to sell is now! THE TIME TO SELL IS NOW!
View 110 Buckingham Lane Winchester, KY MLS# 26008814
  • Recently Listed
1 of 15
$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
  • Recently Listed
1 of 2
$125,000
Studio

Beds

0.0

Baths

39 Casa Landa Way

Winchester, KY

Bluegrass
View 229 S Highland Street Winchester, KY MLS# 26008701
  • Recently Listed
1 of 14
$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
  • Recently Listed
1 of 48
$500,000
1.0

Baths

5,054

Sq.Ft.

808 Bypass Road

Winchester, KY

Bluegrass
View 175 Magnolia Street Winchester, KY MLS# 26008759
  • Recently Listed
1 of 12
$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
  • Recently Listed
1 of 14
$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
  • Recently Listed
1 of 16
$180,000
3

Beds

2.0

Baths

1,848

Sq.Ft.

697 Goose Creek Road

Winchester, KY

Bluegrass
View 306 Trapp-Goffs Cor Road Winchester, KY MLS# 26008462
$299,900
4

Beds

2.0

Baths

1,840

Sq.Ft.

306 Trapp-Goffs Cor Road

Winchester, KY

Bluegrass
View 17 Holiday Road Winchester, KY MLS# 26008222
  • Recently Listed
1 of 62
$264,900
3

Beds

1.1

Baths

1,161

Sq.Ft.

17 Holiday Road

Winchester, KY

Bluegrass
View 409 N Main Street Winchester, KY MLS# 26008406
  • Recently Listed with Virtual Tour
1 of 32
$199,000
300

Sq.Ft.

409 N Main Street

Winchester, KY

Bluegrass
View 411 N Main Street Winchester, KY MLS# 26008407
  • Recently Listed with Virtual Tour
1 of 34
$99,000
600

Sq.Ft.

411 N Main Street

Winchester, KY

Bluegrass
View 7 Hiawatha Trail Winchester, KY MLS# 26008410
  • Recently Listed
1 of 20
$225,000
3

Beds

1.0

Baths

1,190

Sq.Ft.

7 Hiawatha Trail

Winchester, KY

Bluegrass
View 443 S Maple Street Winchester, KY MLS# 26008225
  • Recently Listed
1 of 57
$350,000
4

Beds

2.0

Baths

3,261

Sq.Ft.

443 S Maple Street

Winchester, KY

Bluegrass
View 2 Stoney Brook Drive Winchester, KY MLS# 26008275
$435,000
3

Beds

3.1

Baths

3,633

Sq.Ft.

2 Stoney Brook Drive

Winchester, KY

Bluegrass
View 13 Maryland Avenue Winchester, KY MLS# 26008307
  • Recently Listed
1 of 4
$179,000
3

Beds

1.0

Baths

1,472

Sq.Ft.

13 Maryland Avenue

Winchester, KY

Bluegrass
View 142 Clubhouse Drive Winchester, KY MLS# 26008332
  • Recently Listed
1 of 90
$650,000
6

Beds

4.0

Baths

4,351

Sq.Ft.

142 Clubhouse Drive

Winchester, KY

Bluegrass

About Winchester

Listings in Winchester, KY

298

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 - 200K72
$200K - 300K66
$300K - 400K38
$400K - 500K20
$500K - 600K13
$600K - 700K12
$700K - 800K15
$800K - 900K4
$900K - 1M2
$1M - Max20

Homes for Sale by Type in Winchester, KY

Property TypeCount
Single Family163
Townhouse5
Condo0
Commercial14
Rental14
Lots and Land97
Condo/Town/CoOp0
CoOp0
Multi Family12
Mobile Home0
Farms7

(Data as of 4/23/2026)

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 4/24/2026.