277 total properties
Did you mean the neighborhood Winchester?
View 128 Cherokee Drive Winchester, KY MLS# 26003806
$319,900
5

Beds

2.0

Baths

2,082

Sq.Ft.

128 Cherokee Drive

Winchester, KY

Bluegrass
View 3622 Stamper Drive Winchester, KY MLS# 26003842
$325,000
3

Beds

3.0

Baths

2,821

Sq.Ft.

3622 Stamper Drive

Winchester, KY

Bluegrass
View 374 N Middletown Road Winchester, KY MLS# 25005575
$329,500
3

Beds

2.0

Baths

1,719

Sq.Ft.

374 N Middletown Road

Winchester, KY

Bluegrass
The time to sell is now! THE TIME TO SELL IS NOW!
View 360 N Middletown Road Winchester, KY MLS# 25005577
$329,500
3

Beds

2.0

Baths

1,792

Sq.Ft.

360 N Middletown Road

Winchester, KY

Bluegrass
View 225 Plantations Drive Winchester, KY MLS# 25506523
$329,900
3

Beds

2.1

Baths

3,868

Sq.Ft.

225 Plantations Drive

Winchester, KY

Bluegrass
View 120 Pilot View Road Winchester, KY MLS# 26003979
$334,000
3

Beds

2.1

Baths

1,900

Sq.Ft.

120 Pilot View Road

Winchester, KY

Bluegrass
View 1291-1299 Muddy Creek Road Winchester, KY MLS# 26005152
$334,900
3

Beds

2.0

Baths

1,222

Sq.Ft.

1291-1299 Muddy Creek Road

Winchester, KY

Bluegrass
View 297 S Main Street Winchester, KY MLS# 25501793
$335,000
6

Beds

4.0

Baths

3,544

Sq.Ft.

297 S Main Street

Winchester, KY

Bluegrass
View 322 S Burns Avenue Winchester, KY MLS# 26004053
$339,900
3

Beds

2.1

Baths

1,794

Sq.Ft.

322 S Burns Avenue

Winchester, KY

Bluegrass
View 168 Buckingham Lane Winchester, KY MLS# 26006049
  • Recently Listed
1 of 38
$339,900
4

Beds

2.1

Baths

2,358

Sq.Ft.

168 Buckingham Lane

Winchester, KY

Bluegrass
View 215 Old Log Lick Road Winchester, KY MLS# 26003717
$343,000
3

Beds

2.0

Baths

1,450

Sq.Ft.

215 Old Log Lick Road

Winchester, KY

Bluegrass
View 1270 Sewell Shop Road Winchester, KY MLS# 26000914
$354,900
5

Beds

2.0

Baths

1,952

Sq.Ft.

1270 Sewell Shop Road

Winchester, KY

Bluegrass
View 538 S Maple Street Winchester, KY MLS# 26000925
  • New Construction
1 of 32
$354,900
3

Beds

2.1

Baths

1,628

Sq.Ft.

538 S Maple Street

Winchester, KY

Bluegrass
View 221 Moundale Avenue Winchester, KY MLS# 26004551
  • Recently Listed
1 of 49
OPEN HOUSE: Sunday 3/29 2:00 PM - 4:00 PM
$355,000
3

Beds

2.1

Baths

2,628

Sq.Ft.

221 Moundale Avenue

Winchester, KY

Bluegrass
View 175 Overlooking Drive Winchester, KY MLS# 26003583
$359,000
3

Beds

2.0

Baths

2,080

Sq.Ft.

175 Overlooking Drive

Winchester, KY

Bluegrass
View 3600 Crowe Ridge Road Winchester, KY MLS# 25507522
  • New Construction
1 of 38
$359,900
4

Beds

4.1

Baths

3600 Crowe Ridge Road

Winchester, KY

Bluegrass
View 23 Windridge Drive Winchester, KY MLS# 26004120
$359,900
3

Beds

2.0

Baths

1,858

Sq.Ft.

23 Windridge Drive

Winchester, KY

Bluegrass
View 221 W Hickman Street Winchester, KY MLS# 26004557
  • Recently Listed
1 of 44
$360,000
4

Beds

3.0

Baths

3,440

Sq.Ft.

221 W Hickman Street

Winchester, KY

Bluegrass
View 114 Mallard Lane Winchester, KY MLS# 25502189
$365,000
4

Beds

3.0

Baths

2,105

Sq.Ft.

114 Mallard Lane

Winchester, KY

Bluegrass
View 446 Tremont Lane Winchester, KY MLS# 25508633
$367,000
4

Beds

2.1

Baths

2,811

Sq.Ft.

446 Tremont Lane

Winchester, KY

Bluegrass

About Winchester

Listings in Winchester, KY

272

Estimated median home price

$279,475
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 - 200K55
$200K - 300K67
$300K - 400K34
$400K - 500K19
$500K - 600K14
$600K - 700K11
$700K - 800K12
$800K - 900K5
$900K - 1M4
$1M - Max19

Homes for Sale by Type in Winchester, KY

Property TypeCount
Single Family143
Townhouse5
Condo0
Commercial14
Rental15
Lots and Land86
Condo/Town/CoOp0
CoOp0
Multi Family13
Mobile Home0
Farms11

(Data as of 3/24/2026)

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 3/27/2026.