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 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
The time to sell is now! THE TIME TO SELL IS NOW!
View 106 W Southwerk Street Winchester, VA MLS# VAWI2009996
$265,000
3

Beds

1.1

Baths

1,144

Sq.Ft.

106 W Southwerk Street

Winchester, VA

Bright
Courtesy of ERA OAKCREST REALTY, INC.
View 109 Ash Hollow Drive Winchester, VA MLS# VAFV2040096
$259,000
3

Beds

1.1

Baths

1,160

Sq.Ft.

109 Ash Hollow Drive

Winchester, VA

Bright
Courtesy of ELCY & CO. REALTY, LLC.
View 138 Parkside Drive Winchester, VA MLS# VAFV2040364
  • Recently Listed
1 of 32
OPEN HOUSE: Saturday 3/28 12:00 PM - 2:00 PM
$255,000
3

Beds

1.1

Baths

1,200

Sq.Ft.

138 Parkside Drive

Winchester, VA

Bright
Courtesy of PRIME PROPERTIES DMV, LLC.
View 803 Tomahawk Trail Winchester, VA MLS# VAFV2039034
$250,000
3

Beds

1.1

Baths

960

Sq.Ft.

803 Tomahawk Trail

Winchester, VA

Bright
Courtesy of RE/MAX ROOTS
View 2519 Hockman Avenue Winchester, VA MLS# VAWI2009854
$250,000
2

Beds

2.0

Baths

780

Sq.Ft.

2519 Hockman Avenue

Winchester, VA

Bright
Courtesy of HOFFMAN 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 15.63 Acres, 52-2-B Winchester, VA MLS# VAFV2039232
$250,000
Studio

Beds

0.0

Baths

15.63 Acres, 52-2-B

Winchester, VA

Bright
Courtesy of COLONY REALTY
View 523 Monticello Street Winchester, VA MLS# VAWI2010120
$250,000
2

Beds

1.1

Baths

1,064

Sq.Ft.

523 Monticello Street

Winchester, VA

Bright
Courtesy of BERKSHIRE HATHAWAY HOMESERVICES PENFED REALTY
View 136 Brookland Court # 2 Winchester, VA MLS# VAFV2040300
  • Virtual Tour
1 of 31
OPEN HOUSE: Saturday 3/28 11:00 AM - 1:00 PM
$250,000
2

Beds

2.0

Baths

1,173

Sq.Ft.

136 Brookland Court # 2

Winchester, VA

Bright
Courtesy of SAMSON PROPERTIES
View 514 Cather Avenue Winchester, VA MLS# VAWI2010238
$250,000
3

Beds

2.0

Baths

1,008

Sq.Ft.

514 Cather Avenue

Winchester, VA

Bright
Courtesy of EXP REALTY, LLC
View 815 Pheasant Drive Winchester, VA MLS# VAFV2035952
$245,000
2

Beds

1.0

Baths

960

Sq.Ft.

815 Pheasant Drive

Winchester, VA

Bright
Courtesy of RE/MAX ROOTS
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 2967 Sorrell Court Winchester, VA MLS# VAWI2010008
$245,000
2

Beds

2.1

Baths

1,280

Sq.Ft.

2967 Sorrell Court

Winchester, VA

Bright
Courtesy of TRECK REALTY LLC
View 139 Little River Drive Winchester, VA MLS# VAFV2040398
$239,900
2

Beds

1.0

Baths

900

Sq.Ft.

139 Little River Drive

Winchester, VA

Bright
Courtesy of CENTURY 21 REDWOOD REALTY
View Lot 5 Snake Dr. Winchester, VA MLS# VAFV2039136
$235,000
Studio

Beds

0.0

Baths

Lot 5 Snake Dr.

Winchester, VA

Bright
Courtesy of HUNT COUNTRY SOTHEBY'S INTERNATIONAL REALTY
View 228 Graywolf Trail Winchester, VA MLS# VAFV2040314
$235,000
2

Beds

1.0

Baths

640

Sq.Ft.

228 Graywolf Trail

Winchester, VA

Bright
Courtesy of COLDWELL BANKER REALTY

About Winchester

Listings in Winchester, VA

531

Estimated median home price

$435,000
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

Price Count
$0 - 100K 52
$100K - 200K 26
$200K - 300K 44
$300K - 400K 111
$400K - 500K 79
$500K - 600K 60
$600K - 700K 44
$700K - 800K 19
$800K - 900K 15
$900K - 1M 15
$1M - Max 66

Homes for Sale by Type in Winchester, VA

Property Type Count
Single Family 280
Townhouse 55
Condo 24
Commercial 48
Rental 164
Lots and Land 118
Condo/Town/CoOp 0
CoOp 0
Multi Family 5
Mobile Home 0
Farms 1

(Data as of 3/27/2026)

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 3/27/2026.

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.