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 111 Genesee Trail Winchester, VA MLS# VAFV2039668
  • Recently Listed
1 of 25
$279,900
2

Beds

1.0

Baths

924

Sq.Ft.

111 Genesee Trail

Winchester, VA

Bright
Courtesy of MARKETPLACE REALTY
View 20 E Hart Street Winchester, VA MLS# VAWI2008932
$279,000
2

Beds

1.0

Baths

950

Sq.Ft.

20 E Hart Street

Winchester, VA

Bright
Courtesy of LINK REALTY SERVICES LLC
The time to sell is now! THE TIME TO SELL IS NOW!
View 239 Chestnut Street Winchester, VA MLS# VAFV2037798
$279,000
2

Beds

1.0

Baths

1,176

Sq.Ft.

239 Chestnut Street

Winchester, VA

Bright
Courtesy of WILDHAWKS REALTY LLC
View 208 Shenandoah Avenue Winchester, VA MLS# VAWI2009462
$279,000
3

Beds

1.0

Baths

907

Sq.Ft.

208 Shenandoah Avenue

Winchester, VA

Bright
Courtesy of COLONY REALTY
View 106 W Southwerk Street Winchester, VA MLS# VAWI2009996
  • Recently Listed with Virtual Tour
1 of 47
$279,000
3

Beds

1.1

Baths

1,144

Sq.Ft.

106 W Southwerk Street

Winchester, VA

Bright
Courtesy of ERA OAKCREST REALTY, INC.
View 424 Highland Avenue Winchester, VA MLS# VAWI2010002
$279,000
2

Beds

1.0

Baths

759

Sq.Ft.

424 Highland Avenue

Winchester, VA

Bright
Courtesy of LONG & FOSTER REAL ESTATE, INC.
View LOT 1 - Handley Drive Winchester, VA MLS# VAFV2038132
$275,000
Studio

Beds

0.0

Baths

LOT 1 - Handley Drive

Winchester, VA

Bright
Courtesy of MERRIFIELD REALTY, LLC
View LOT 27A - Handley Drive Winchester, VA MLS# VAFV2039092
$275,000
Studio

Beds

0.0

Baths

LOT 27A - Handley Drive

Winchester, VA

Bright
Courtesy of MERRIFIELD REALTY, LLC
View 719 Smithfield Avenue Winchester, VA MLS# VAFV2039748
$275,000
2

Beds

1.0

Baths

720

Sq.Ft.

719 Smithfield Avenue

Winchester, VA

Bright
Courtesy of NEXTHOME REALTY SELECT
View 354 Valley Mill Road Winchester, VA MLS# VAFV2038696
$274,000
2

Beds

1.1

Baths

1,200

Sq.Ft.

354 Valley Mill Road

Winchester, VA

Bright
Courtesy of PRIME PROPERTIES DMV, LLC.
View 1125 Conway Street Winchester, VA MLS# VAWI2009200
$269,900
2

Beds

1.0

Baths

870

Sq.Ft.

1125 Conway Street

Winchester, VA

Bright
Courtesy of ERA OAKCREST REALTY, INC.
View 403 Tudor Drive Winchester, VA MLS# VAFV2038568
$269,900
2

Beds

1.1

Baths

1,200

Sq.Ft.

403 Tudor Drive

Winchester, VA

Bright
Courtesy of JIM BARB REALTY INC.
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 939 Woodland Avenue Winchester, VA MLS# VAWI2010076
$269,000
2

Beds

2.0

Baths

897

Sq.Ft.

939 Woodland Avenue

Winchester, VA

Bright
Courtesy of ROBERTS REALTY GROUP, LLC
View 204 Shenandoah Avenue Winchester, VA MLS# VAWI2009534
$265,000
2

Beds

1.0

Baths

882

Sq.Ft.

204 Shenandoah Avenue

Winchester, VA

Bright
Courtesy of KELLER WILLIAMS REALTY
View 803 Tomahawk Trail Winchester, VA MLS# VAFV2039034
$260,000
3

Beds

1.1

Baths

960

Sq.Ft.

803 Tomahawk Trail

Winchester, VA

Bright
Courtesy of RE/MAX ROOTS
View 1208 Rockwood Trl Winchester, VA MLS# VAFV2039648
$255,000
1

Beds

1.0

Baths

660

Sq.Ft.

1208 Rockwood Trl

Winchester, VA

Bright
Courtesy of LONG & FOSTER REAL ESTATE, INC.
View 115 Brookland Terrace # 12 Winchester, VA MLS# VAFV2037862
$250,000
2

Beds

2.0

Baths

1,173

Sq.Ft.

115 Brookland Terrace # 12

Winchester, VA

Bright
Courtesy of COLONY 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

About Winchester

Listings in Winchester, VA

485

Estimated median home price

$450,000
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 - 100K47
$100K - 200K18
$200K - 300K41
$300K - 400K97
$400K - 500K78
$500K - 600K58
$600K - 700K41
$700K - 800K16
$800K - 900K13
$900K - 1M13
$1M - Max63

Homes for Sale by Type in Winchester, VA

Property TypeCount
Single Family255
Townhouse47
Condo24
Commercial45
Rental151
Lots and Land108
Condo/Town/CoOp0
CoOp0
Multi Family6
Mobile Home0
Farms0

(Data as of 3/7/2026)

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 3/8/2026.

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.

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