View 38 N Burns Avenue Winchester, KY MLS# 26009835
  • Recently Listed
1 of 27
$350,000
4

Beds

2.1

Baths

2,310

Sq.Ft.

38 N Burns Avenue

Winchester, KY

Bluegrass
View 538 S Maple Street Winchester, KY MLS# 26000925
  • New Construction
1 of 32
$349,900
3

Beds

2.1

Baths

1,628

Sq.Ft.

538 S Maple Street

Winchester, KY

Bluegrass
View 221 W Hickman Street Winchester, KY MLS# 26004557
$349,500
4

Beds

3.0

Baths

3,440

Sq.Ft.

221 W Hickman Street

Winchester, KY

Bluegrass
The time to sell is now! THE TIME TO SELL IS NOW!
View 221 Moundale Avenue Winchester, KY MLS# 26004551
$345,000
3

Beds

2.1

Baths

2,628

Sq.Ft.

221 Moundale Avenue

Winchester, KY

Bluegrass
View 23 Windridge Drive Winchester, KY MLS# 26004120
$344,900
3

Beds

2.0

Baths

1,858

Sq.Ft.

23 Windridge Drive

Winchester, KY

Bluegrass
View 228 Holiday Road Winchester, KY MLS# 26006679
$339,900
4

Beds

2.0

Baths

1,843

Sq.Ft.

228 Holiday Road

Winchester, KY

Bluegrass
View 740 Pilot Ridge Lane Winchester, KY MLS# 26006680
$339,900
3

Beds

2.1

Baths

1,608

Sq.Ft.

740 Pilot Ridge Lane

Winchester, KY

Bluegrass
View 110 Powe Drive Winchester, KY MLS# 26008249
  • Recently Listed
1 of 31
$339,900
4

Beds

2.1

Baths

2,010

Sq.Ft.

110 Powe Drive

Winchester, KY

Bluegrass
View 201 Boone Avenue Winchester, KY MLS# 26007703
$335,000
4

Beds

2.1

Baths

2,513

Sq.Ft.

201 Boone Avenue

Winchester, KY

Bluegrass
View 414 Pueblo Court Winchester, KY MLS# 26008330
  • Recently Listed
1 of 32
$329,999
3

Beds

2.1

Baths

2,648

Sq.Ft.

414 Pueblo Court

Winchester, KY

Bluegrass
View 1291-1299 Muddy Creek Road Winchester, KY MLS# 26005152
$329,900
3

Beds

2.0

Baths

1,222

Sq.Ft.

1291-1299 Muddy Creek Road

Winchester, KY

Bluegrass
View 162 French Avenue Winchester, KY MLS# 26009734
  • Recently Listed
1 of 38
$329,900
4

Beds

1.0

Baths

2,327

Sq.Ft.

162 French Avenue

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
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 322 S Burns Avenue Winchester, KY MLS# 26004053
$327,500
3

Beds

2.1

Baths

1,794

Sq.Ft.

322 S Burns Avenue

Winchester, KY

Bluegrass
View 215 Old Log Lick Road Winchester, KY MLS# 26003717
$325,000
3

Beds

2.0

Baths

1,450

Sq.Ft.

215 Old Log Lick Road

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 225 Plantations Drive Winchester, KY MLS# 25506523
$324,900
3

Beds

2.1

Baths

3,868

Sq.Ft.

225 Plantations Drive

Winchester, KY

Bluegrass
View 412 Pueblo Court Winchester, KY MLS# 26008794
  • Recently Listed with Virtual Tour
1 of 30
$320,500
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
$320,000
5

Beds

3.0

Baths

2,624

Sq.Ft.

28 Churchill Drive

Winchester, KY

Bluegrass

About Winchester

Listings in Winchester, KY

300

Estimated median home price

$269,500
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 - 100K37
$100K - 200K68
$200K - 300K68
$300K - 400K39
$400K - 500K22
$500K - 600K13
$600K - 700K10
$700K - 800K16
$800K - 900K4
$900K - 1M2
$1M - Max21

Homes for Sale by Type in Winchester, KY

Property TypeCount
Single Family172
Townhouse3
Condo0
Commercial14
Rental17
Lots and Land95
Condo/Town/CoOp0
CoOp0
Multi Family10
Mobile Home0
Farms6

(Data as of 5/4/2026)

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 5/4/2026.