View 105 Parkside Drive Winchester, VA MLS# VAFV2039526
$269,900
2

Beds

1.1

Baths

1,385

Sq.Ft.

105 Parkside Drive

Winchester, VA

Bright
Courtesy of LONG & FOSTER REAL ESTATE, INC.
View 320 Bethel Grange Road Winchester, VA MLS# VAFV2039596
$199,900
3

Beds

1.0

Baths

1,032

Sq.Ft.

320 Bethel Grange Road

Winchester, VA

Bright
Courtesy of SAMSON PROPERTIES
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
The time to sell is now! THE TIME TO SELL IS NOW!
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 15.63 Acres, 52-2-B Winchester, VA MLS# VAFV2039232
  • Recently Listed
1 of 8
$250,000
Studio

Beds

0.0

Baths

15.63 Acres, 52-2-B

Winchester, VA

Bright
Courtesy of COLONY REALTY
View 19 W Germain Street Winchester, VA MLS# VAWI2009802
  • Recently Listed
1 of 10
$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 376 Charles Street Winchester, VA MLS# VAWI2009942
  • Virtual Tour
1 of 30
$185,000
3

Beds

1.0

Baths

1,232

Sq.Ft.

376 Charles Street

Winchester, VA

Bright
Courtesy of REAL BROKER, LLC
View 513 Pheasant Drive Winchester, VA MLS# VAFV2039468
  • Recently Listed
1 of 36
$365,000
3

Beds

2.0

Baths

1,368

Sq.Ft.

513 Pheasant Drive

Winchester, VA

Bright
Courtesy of MARKETPLACE REALTY
View 407 Van Fossen Street Winchester, VA MLS# VAWI2009922
$279,999
2

Beds

1.1

Baths

954

Sq.Ft.

407 Van Fossen Street

Winchester, VA

Bright
Courtesy of SAMSON PROPERTIES
View Lot 5 Snake Dr. Winchester, VA MLS# VAFV2039136
  • Recently Listed
1 of 7
$235,000
Studio

Beds

0.0

Baths

Lot 5 Snake Dr.

Winchester, VA

Bright
Courtesy of HUNT COUNTRY SOTHEBY'S INTERNATIONAL REALTY
View Lot 7 Oak Drive Winchester, VA MLS# VAFV2039448
$250,000
Studio

Beds

0.0

Baths

Lot 7 Oak Drive

Winchester, VA

Bright
Courtesy of REALTY ONE GROUP OLD TOWNE
View 181 Oak Drive Winchester, VA MLS# VAFV2039452
$250,000
Studio

Beds

0.0

Baths

181 Oak Drive

Winchester, VA

Bright
Courtesy of REALTY ONE GROUP OLD TOWNE
View 580 York Avenue Winchester, VA MLS# VAWI2009852
  • Recently Listed
1 of 12
$290,000
2

Beds

1.0

Baths

817

Sq.Ft.

580 York Avenue

Winchester, VA

Bright
Courtesy of THE VASQUEZ GROUP LLC
View 177 Dicks Hollow Road Winchester, VA MLS# VAFV2039402
$245,000
2

Beds

1.0

Baths

650

Sq.Ft.

177 Dicks Hollow Road

Winchester, VA

Bright
Courtesy of RE/MAX ROOTS
View Lot 18 Pheasant Drive Winchester, VA MLS# VAFV2039430
$18,800
Studio

Beds

0.0

Baths

Lot 18 Pheasant Drive

Winchester, VA

Bright
Courtesy of MARKETPLACE REALTY
View 249 West Street Street Winchester, VA MLS# VAWI2009908
$349,900
3

Beds

1.0

Baths

1,196

Sq.Ft.

249 West Street Street

Winchester, VA

Bright
Courtesy of LONG & FOSTER REAL ESTATE, INC.
View 114 Harrison Lane Winchester, VA MLS# VAFV2039356
$335,000
2

Beds

1.0

Baths

1,111

Sq.Ft.

114 Harrison Lane

Winchester, VA

Bright
Courtesy of ERA OAKCREST REALTY, INC.
View 107 Smith Dr Winchester, VA MLS# VAFV2039342
$79,900
3

Beds

2.0

Baths

1,118

Sq.Ft.

107 Smith Dr

Winchester, VA

Bright
Courtesy of SAMSON PROPERTIES
View 520 Highland Avenue Winchester, VA MLS# VAWI2009882
$80,000
Studio

Beds

0.0

Baths

520 Highland Avenue

Winchester, VA

Bright
Courtesy of SAMSON PROPERTIES
View 24 N Pleasant Valley Road Winchester, VA MLS# VAWI2009884
$80,000
Studio

Beds

0.0

Baths

24 N Pleasant Valley Road

Winchester, VA

Bright
Courtesy of SAMSON PROPERTIES

About Winchester

Listings in Winchester, VA

479

Estimated median home price

$439,900
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

Price Count
$0 - 100K 45
$100K - 200K 21
$200K - 300K 45
$300K - 400K 94
$400K - 500K 78
$500K - 600K 56
$600K - 700K 39
$700K - 800K 16
$800K - 900K 12
$900K - 1M 14
$1M - Max 59

Homes for Sale by Type in Winchester, VA

Property Type Count
Single Family 247
Townhouse 50
Condo 24
Commercial 45
Rental 147
Lots and Land 107
Condo/Town/CoOp 0
CoOp 0
Multi Family 6
Mobile Home 0
Farms 0

(Data as of 2/28/2026)

Information deemed reliable but not guaranteed.

The data relating to real estate for sale on this web site comes in part from the Internet Data Exchange Program of the Harrisonburg-Rockingham Association of 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 reproduced or redistribute. Its sole purpose is to be used for no other purpose than to identify prospective properties consumers may be interested in purchasing. p>

Data is updated as of 3/1/2026.

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.