View 601 Hollingsworth Drive Winchester, VA MLS# VAWI2010058
$335,000
2

Beds

1.1

Baths

1,684

Sq.Ft.

601 Hollingsworth Drive

Winchester, VA

Bright
Courtesy of COLDWELL BANKER PREMIER
View 320 E Piccadilly Street Winchester, VA MLS# VAWI2010018
$409,900
3

Beds

2.0

Baths

1,764

Sq.Ft.

320 E Piccadilly Street

Winchester, VA

Bright
Courtesy of COLONY REALTY
View Lot 7 Graywolf Trail Winchester, VA MLS# VAFV2039722
$399,900
3

Beds

3.0

Baths

1,850

Sq.Ft.

Lot 7 Graywolf Trail

Winchester, VA

Bright
Courtesy of REALTY ONE GROUP OLD TOWNE
The time to sell is now! THE TIME TO SELL IS NOW!
View 720 Panther Drive Winchester, VA MLS# VAFV2039676
  • New Construction
1 of 6
$350,000
3

Beds

2.0

Baths

1,344

Sq.Ft.

720 Panther Drive

Winchester, VA

Bright
Courtesy of PRESLEE REAL ESTATE
View 115 Dogwood Trail Winchester, VA MLS# VAFV2039682
  • Recently Listed
1 of 21
$359,017
3

Beds

2.1

Baths

1,660

Sq.Ft.

115 Dogwood Trail

Winchester, VA

Bright
Courtesy of Bowie - Weichert, Realtors - Blue Ribbon
View 234 Monteith Drive Winchester, VA MLS# VAWI2009986
  • Recently Listed with Virtual Tour
1 of 25
OPEN HOUSE: Saturday 3/7 12:00 PM - 3:00 PM
$399,990
3

Beds

3.1

Baths

1,784

Sq.Ft.

234 Monteith Drive

Winchester, VA

Bright
Courtesy of DRB GROUP REALTY, LLC
View 433-435 Bryarly Road Winchester, VA MLS# VAFV2039646
$325,000
4

Beds

0.0

Baths

433-435 Bryarly Road

Winchester, VA

Bright
Courtesy of MINT REALTY
View 215 Cochise Trail Winchester, VA MLS# VAFV2039592
$410,000
3

Beds

2.1

Baths

1,608

Sq.Ft.

215 Cochise Trail

Winchester, VA

Bright
Courtesy of RE/MAX ROOTS
View 105 Castaway Winchester, VA MLS# VAFV2039606
  • Recently Listed
1 of 27
$374,990
3

Beds

2.1

Baths

1,784

Sq.Ft.

105 Castaway

Winchester, VA

Bright
Courtesy of BROOKFIELD MID-ATLANTIC BROKERAGE, LLC
View 108 Senseny Glen Drive Winchester, VA MLS# VAFV2039554
$423,000
3

Beds

2.0

Baths

1,397

Sq.Ft.

108 Senseny Glen Drive

Winchester, VA

Bright
Courtesy of PEARSON SMITH REALTY, LLC
View 431 Jefferson Street Winchester, VA MLS# VAWI2009944
$419,900
3

Beds

1.1

Baths

1,632

Sq.Ft.

431 Jefferson Street

Winchester, VA

Bright
Courtesy of COLONY REALTY
View 218 Monteith Drive Winchester, VA MLS# VAWI2009978
  • Recently Listed with Virtual Tour
1 of 24
$389,990
3

Beds

3.1

Baths

1,784

Sq.Ft.

218 Monteith Drive

Winchester, VA

Bright
Courtesy of DRB GROUP REALTY, LLC
View 213 Woodrow Road Winchester, VA MLS# VAFV2039552
  • Recently Listed
1 of 50
$355,000
3

Beds

2.0

Baths

1,416

Sq.Ft.

213 Woodrow Road

Winchester, VA

Bright
Courtesy of SAMSON PROPERTIES
View 221 Cobble Stone Drive Winchester, VA MLS# VAFV2039498
$435,000
4

Beds

3.1

Baths

2,413

Sq.Ft.

221 Cobble Stone Drive

Winchester, VA

Bright
Courtesy of REALTY ONE GROUP OLD TOWNE
View 128 Killbuck Trail Winchester, VA MLS# VAFV2039474
$410,000
3

Beds

4.0

Baths

2,100

Sq.Ft.

128 Killbuck Trail

Winchester, VA

Bright
Courtesy of RE/MAX ROOTS
View 19 W Germain Street Winchester, VA MLS# VAWI2009802
$337,000
3

Beds

1.1

Baths

1,280

Sq.Ft.

19 W Germain Street

Winchester, VA

Bright
Courtesy of COTTAGE STREET REALTY LLC
View 1821 Harvest Drive Winchester, VA MLS# VAWI2009960
  • Recently Listed
1 of 40
$399,990
4

Beds

3.1

Baths

1,920

Sq.Ft.

1821 Harvest Drive

Winchester, VA

Bright
Courtesy of D R HORTON REALTY OF VIRGINIA LLC
View 1809 Harvest Drive Winchester, VA MLS# VAWI2009962
  • Recently Listed
1 of 40
$419,990
4

Beds

3.1

Baths

1,939

Sq.Ft.

1809 Harvest Drive

Winchester, VA

Bright
Courtesy of D R HORTON REALTY OF VIRGINIA LLC
View 1813 Harvest Drive Winchester, VA MLS# VAWI2009964
  • Recently Listed
1 of 39
$419,990
4

Beds

3.1

Baths

1,920

Sq.Ft.

1813 Harvest Drive

Winchester, VA

Bright
Courtesy of D R HORTON REALTY OF VIRGINIA LLC
View 109 Boone Court Winchester, VA MLS# VAFV2039494
  • Recently Listed
1 of 22
OPEN HOUSE: Monday 3/2 11:00 AM - 3:00 PM
$389,880
3

Beds

2.2

Baths

1,989

Sq.Ft.

109 Boone Court

Winchester, VA

Bright
Courtesy of NEW HOME STAR VIRGINIA, LLC

About Winchester

Listings in Winchester, VA

480

Estimated median home price

$449,000
Winchester VA Homes for Sale & Properties

Weichert Realtors is one of the nation's leading providers of Winchester, Virginia real estate for sale and home ownership services. Contact Weichert today to buy or sell real estate in Winchester, VA.

Homes for Sale by Price in Winchester, VA

PriceCount
$0 - 100K44
$100K - 200K20
$200K - 300K46
$300K - 400K92
$400K - 500K81
$500K - 600K56
$600K - 700K39
$700K - 800K16
$800K - 900K12
$900K - 1M13
$1M - Max61

Homes for Sale by Type in Winchester, VA

Property TypeCount
Single Family248
Townhouse50
Condo24
Commercial46
Rental143
Lots and Land106
Condo/Town/CoOp0
CoOp0
Multi Family6
Mobile Home0
Farms0

(Data as of 3/1/2026)

Information deemed reliable but not guaranteed.

Information Deemed Reliable But Not Guaranteed. The data relating to real estate for sale on this website appears in part through the BrightMLS Broker ReciprocitySM program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms in which Weichert, Realtors® participates, and is provided by BrightMLS through a licensing agreement.

Real estate listings held by brokerage firms other than Weichert, Realtors® are marked with the Broker Reciprocity icon (a little black house) and detailed information about each listing includes the name of the listing broker.

The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

Some properties which appear for sale on this website may no longer be available because they are under contract, have sold or are no longer being offered for sale.

© 2026 BrightMLS. All Rights Reserved.