View 1509 Boonesboro Road Winchester, KY MLS# 20101924
$2,000,000
Studio

Beds

0.0

Baths

1509 Boonesboro Road

Winchester, KY

Bluegrass
View 3166 Colby Road Winchester, KY MLS# 25505174
$1,889,000
3

Beds

2.1

Baths

4,518

Sq.Ft.

3166 Colby Road

Winchester, KY

Bluegrass
View 599 BLT Way Winchester, KY MLS# 25506547
  • Recently Listed
1 of 57
$1,799,900
20,252

Sq.Ft.

599 BLT Way

Winchester, KY

Bluegrass
The time to sell is now! THE TIME TO SELL IS NOW!
View 2 N Main Street Winchester, KY MLS# 25017572
$1,595,000
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 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 345 Providence Lane Winchester, KY MLS# 25504563
$1,300,000
Studio

Beds

0.0

Baths

345 Providence Lane

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 6237 Bybee Road Winchester, KY MLS# 25012707
$1,200,000
5

Beds

5.2

Baths

8,236

Sq.Ft.

6237 Bybee 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 2100 Irvine Road 40391 # 40391 Winchester, KY MLS# 25018600
$1,149,000
3

Beds

3.1

Baths

3,672

Sq.Ft.

2100 Irvine Road 40391 # 40391

Winchester, KY

Bluegrass
View 700 Nick Lane Winchester, KY MLS# 25013735
$949,950
3

Beds

2.1

Baths

2,400

Sq.Ft.

700 Nick 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
View 1150 Craig Crossing Winchester, KY MLS# 25009722
  • New Construction
1 of 69
$925,000
5

Beds

3.1

Baths

2,842

Sq.Ft.

1150 Craig Crossing

Winchester, KY

Bluegrass
View 2447 Clintonville Road Winchester, KY MLS# 25003433
$899,000
5

Beds

4.0

Baths

4,058

Sq.Ft.

2447 Clintonville Road

Winchester, KY

Bluegrass
View Lot 1 - 12 Plantations Drive Winchester, KY MLS# 25506246
$882,000
Studio

Beds

0.0

Baths

Lot 1 - 12 Plantations Drive

Winchester, KY

Bluegrass
View 2509 Mount Sterling Road Winchester, KY MLS# 25018118
$849,900
4

Beds

3.1

Baths

4,922

Sq.Ft.

2509 Mount Sterling Road

Winchester, KY

Bluegrass
View 4040 Muddy Creek Road Winchester, KY MLS# 25018691
$849,900
4

Beds

3.1

Baths

4,584

Sq.Ft.

4040 Muddy Creek Road

Winchester, KY

Bluegrass
View 1701 Gay Evans Road Winchester, KY MLS# 25500860
$829,000
4

Beds

3.1

Baths

4,345

Sq.Ft.

1701 Gay Evans Road

Winchester, KY

Bluegrass

About Winchester

Listings in Winchester, KY

281

Estimated median home price

$300,000
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 - 100K32
$100K - 200K58
$200K - 300K51
$300K - 400K54
$400K - 500K24
$500K - 600K12
$600K - 700K14
$700K - 800K9
$800K - 900K6
$900K - 1M3
$1M - Max18

Homes for Sale by Type in Winchester, KY

Property TypeCount
Single Family154
Townhouse6
Condo0
Commercial14
Rental17
Lots and Land85
Condo/Town/CoOp0
CoOp0
Multi Family8
Mobile Home0
Farms14

(Data as of 11/11/2025)

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 12/9/2025.