300 total properties
Did you mean the neighborhood Winchester?
View 3049 Ironworks Road Winchester, KY MLS# 25507142
$2,999,000
6

Beds

5.0

Baths

3,693

Sq.Ft.

3049 Ironworks Road

Winchester, KY

Bluegrass
View 3049 Ironworks Road Winchester, KY MLS# 25507353
$2,999,000
6

Beds

5.0

Baths

3,693

Sq.Ft.

3049 Ironworks Road

Winchester, KY

Bluegrass
View 5045 Van Meter Road Winchester, KY MLS# 25013058
$2,650,000
6

Beds

5.1

Baths

7,274

Sq.Ft.

5045 Van Meter Road

Winchester, KY

Bluegrass
The time to sell is now! THE TIME TO SELL IS NOW!
View 1395 Two Mile Road Winchester, KY MLS# 23018755
$2,500,000
Studio

Beds

0.0

Baths

1395 Two Mile Road

Winchester, KY

Bluegrass
View 1395 Two Mile Road Winchester, KY MLS# 23018756
$2,500,000
Studio

Beds

0.0

Baths

1395 Two Mile Road

Winchester, KY

Bluegrass
View 5039 Combs Ferry Road Winchester, KY MLS# 25504793
$2,399,000
5

Beds

3.2

Baths

6,284

Sq.Ft.

5039 Combs Ferry Road

Winchester, KY

Bluegrass
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 599 BLT Way Winchester, KY MLS# 25506547
$1,799,900
20,252

Sq.Ft.

599 BLT Way

Winchester, KY

Bluegrass
View 3166 Colby Road Winchester, KY MLS# 25505174
$1,695,000
3

Beds

2.1

Baths

4,518

Sq.Ft.

3166 Colby Road

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 250 Shoppers Drive Winchester, KY MLS# 25505209
$1,500,000

250 Shoppers Drive

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 3760 Old Boonesboro Road Winchester, KY MLS# 26006697
$1,290,000
5

Beds

5.0

Baths

5,666

Sq.Ft.

3760 Old Boonesboro Road

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
  • Recently Listed
1 of 16
$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 300 Rolling Hills Lane Winchester, KY MLS# 1805484
$925,000
Studio

Beds

0.0

Baths

300 Rolling Hills Lane

Winchester, KY

Bluegrass

About Winchester

Listings in Winchester, KY

302

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 - 200K70
$200K - 300K71
$300K - 400K39
$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 Family171
Townhouse4
Condo0
Commercial15
Rental18
Lots and Land96
Condo/Town/CoOp0
CoOp0
Multi Family10
Mobile Home0
Farms6

(Data as of 4/28/2026)

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.