286 total properties
Did you mean the neighborhood Winchester?
View 1509 Boonesboro Road Winchester, KY MLS# 20101924
$1,850,000
Studio

Beds

0.0

Baths

1509 Boonesboro Road

Winchester, KY

Bluegrass
View 722 Colby Road # #1 Winchester, KY MLS# 26008233
$1,800,000
Studio

Beds

0.0

Baths

722 Colby Road # #1

Winchester, KY

Bluegrass
View 4578 Combs Ferry Road Winchester, KY MLS# 26011707
$1,750,000
3

Beds

2.0

Baths

1,860

Sq.Ft.

4578 Combs Ferry Road

Winchester, KY

Bluegrass
The time to sell is now! THE TIME TO SELL IS NOW!
View 3166 Colby Road Winchester, KY MLS# 26011538
$1,695,000
3

Beds

2.1

Baths

4,518

Sq.Ft.

3166 Colby Road

Winchester, KY

Bluegrass
View 599 BLT Way Winchester, KY MLS# 26012007
$1,599,900
20,252

Sq.Ft.

599 BLT Way

Winchester, KY

Bluegrass
View 2 N Main Street Winchester, KY MLS# 25017572
$1,575,000
37

Beds

19.1

Baths

26,124

Sq.Ft.

2 N Main Street

Winchester, KY

Bluegrass
View 1015 Old Stone Church Road Winchester, KY MLS# 25502084
$1,500,000
Studio

Beds

0.0

Baths

1015 Old Stone Church Road

Winchester, KY

Bluegrass
View 155 April Way Winchester, KY MLS# 23015568
$1,350,000
Studio

Beds

0.0

Baths

155 April Way

Winchester, KY

Bluegrass
View 1200 Craig Crossing Winchester, KY MLS# 26013734
  • Recently Listed with Virtual Tour
1 of 76
$1,349,000
4

Beds

4.1

Baths

3,350

Sq.Ft.

1200 Craig Crossing

Winchester, KY

Bluegrass
View 1395 Two Mile Road Winchester, KY MLS# 23018853
$1,200,000
Studio

Beds

0.0

Baths

1395 Two Mile Road

Winchester, KY

Bluegrass
View 101 Jefferson Street Winchester, KY MLS# 25502866
$1,200,000
7,744

Sq.Ft.

101 Jefferson Street

Winchester, KY

Bluegrass
View 16 Linden Avenue Winchester, KY MLS# 26007993
$1,200,000
16

Beds

16.0

Baths

7,480

Sq.Ft.

16 Linden Avenue

Winchester, KY

Bluegrass
View 2100 Irvine Road # 40391 Winchester, KY MLS# 25018600
$1,149,000
3

Beds

3.1

Baths

3,672

Sq.Ft.

2100 Irvine Road # 40391

Winchester, KY

Bluegrass
View 345 Providence Lane Winchester, KY MLS# 26005598
$1,115,000
Studio

Beds

0.0

Baths

345 Providence Lane

Winchester, KY

Bluegrass
View 330 Spencer Lane Winchester, KY MLS# 26013217
  • Recently Listed
1 of 46
$949,000
3

Beds

3.0

Baths

2,200

Sq.Ft.

330 Spencer Lane

Winchester, KY

Bluegrass
View 200 Old Log Lick Road Winchester, KY MLS# 26013036
  • Recently Listed
1 of 89
$939,000
3

Beds

2.0

Baths

4,019

Sq.Ft.

200 Old Log Lick Road

Winchester, KY

Bluegrass
View 300 Rolling Hills Lane Winchester, KY MLS# 1805484
$925,000
Studio

Beds

0.0

Baths

300 Rolling Hills Lane

Winchester, KY

Bluegrass
View Lot 1 - 7 Plantations Drive Winchester, KY MLS# 26011486
$882,000
Studio

Beds

0.0

Baths

Lot 1 - 7 Plantations Drive

Winchester, KY

Bluegrass
View 111 Bella Shae Way Winchester, KY MLS# 24025579
  • New Construction
1 of 3
$825,000
3

Beds

2.1

Baths

2,995

Sq.Ft.

111 Bella Shae Way

Winchester, KY

Bluegrass
View 1108 W Lexington Avenue Winchester, KY MLS# 26010978
$800,000
Studio

Beds

0.0

Baths

1108 W Lexington Avenue

Winchester, KY

Bluegrass

About Winchester

Listings in Winchester, KY

296

Estimated median home price

$274,700
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 - 200K65
$200K - 300K73
$300K - 400K47
$400K - 500K18
$500K - 600K16
$600K - 700K10
$700K - 800K9
$800K - 900K2
$900K - 1M3
$1M - Max23

Homes for Sale by Type in Winchester, KY

Property TypeCount
Single Family175
Townhouse4
Condo0
Commercial13
Rental18
Lots and Land91
Condo/Town/CoOp0
CoOp0
Multi Family9
Mobile Home0
Farms4

(Data as of 6/19/2026)

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 6/19/2026.