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 Heirloom Way Winchester, VA MLS# VAFV2038026
  • Adult Community
1 of 17
$389,990
3

Beds

2.1

Baths

1,752

Sq.Ft.

106 Heirloom Way

Winchester, VA

Bright
Courtesy of BROOKFIELD MID-ATLANTIC BROKERAGE, LLC
View 166 Graywolf Trail Winchester, VA MLS# VAFV2038002
$369,900
4

Beds

3.0

Baths

1,840

Sq.Ft.

166 Graywolf Trail

Winchester, VA

Bright
Courtesy of EXP REALTY, LLC
The time to sell is now! THE TIME TO SELL IS NOW!
View 117 W Oates Avenue Winchester, VA MLS# VAWI2009446
$330,000
3

Beds

1.0

Baths

1,237

Sq.Ft.

117 W Oates Avenue

Winchester, VA

Bright
Courtesy of REALTY ONE GROUP OLD TOWNE
View 0 Hedrick Ln Winchester, VA MLS# VAFV2037912
$135,000
Studio

Beds

0.0

Baths

0 Hedrick Ln

Winchester, VA

Bright
Courtesy of ERA VALLEY REALTY
View Lots 11 & 12 Glen Ridge Road Winchester, VA MLS# VAFV2037934
$61,900
Studio

Beds

0.0

Baths

Lots 11 & 12 Glen Ridge Road

Winchester, VA

Bright
Courtesy of ERA OAKCREST REALTY, INC.
View Lots 14 & 15 Glen Ridge Road Winchester, VA MLS# VAFV2037936
$61,900
Studio

Beds

0.0

Baths

Lots 14 & 15 Glen Ridge Road

Winchester, VA

Bright
Courtesy of ERA OAKCREST REALTY, INC.
View Lot 10 Glen Ridge Road Winchester, VA MLS# VAFV2037938
$51,900
Studio

Beds

0.0

Baths

Lot 10 Glen Ridge Road

Winchester, VA

Bright
Courtesy of ERA OAKCREST REALTY, INC.
View 627 Watson Avenue Winchester, VA MLS# VAWI2009434
$294,990
3

Beds

1.0

Baths

1,205

Sq.Ft.

627 Watson Avenue

Winchester, VA

Bright
Courtesy of SAMSON PROPERTIES
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 157 Brookland Terrace # 11 Winchester, VA MLS# VAFV2037772
$235,000
2

Beds

2.0

Baths

1,173

Sq.Ft.

157 Brookland Terrace # 11

Winchester, VA

Bright
Courtesy of SAMSON PROPERTIES
View 21 E Germain Street Winchester, VA MLS# VAWI2009356
$250,000
3

Beds

2.0

Baths

1,682

Sq.Ft.

21 E Germain Street

Winchester, VA

Bright
Courtesy of CENTURY 21 ENVISION
View 127 Shirley Street Winchester, VA MLS# VAWI2009378
$365,000
4

Beds

2.0

Baths

1,780

Sq.Ft.

127 Shirley Street

Winchester, VA

Bright
Courtesy of ERA OAKCREST REALTY, INC.
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 151 Mccormick Circle # 201 Winchester, VA MLS# VAFV2037732
$385,000
2

Beds

2.0

Baths

1,554

Sq.Ft.

151 Mccormick Circle # 201

Winchester, VA

Bright
Courtesy of ERA OAKCREST REALTY, INC.
View Lot 9 Dogwood Trail Winchester, VA MLS# VAFV2037742
$23,900
Studio

Beds

0.0

Baths

Lot 9 Dogwood Trail

Winchester, VA

Bright
Courtesy of MARKETPLACE REALTY
View Lot 101 Dogwood Trail Winchester, VA MLS# VAFV2037748
$23,900
Studio

Beds

0.0

Baths

Lot 101 Dogwood Trail

Winchester, VA

Bright
Courtesy of MARKETPLACE REALTY
View Lot 102 Dogwood Trail Winchester, VA MLS# VAFV2037750
$23,900
Studio

Beds

0.0

Baths

Lot 102 Dogwood Trail

Winchester, VA

Bright
Courtesy of MARKETPLACE REALTY
View Lot 56 Bear Trail Winchester, VA MLS# VAFV2037756
$9,997
Studio

Beds

0.0

Baths

Lot 56 Bear Trail

Winchester, VA

Bright
Courtesy of ROBERTS REALTY GROUP, LLC
View Lot 132 Tomahawk Trail Winchester, VA MLS# VAFV2037696
$23,900
Studio

Beds

0.0

Baths

Lot 132 Tomahawk Trail

Winchester, VA

Bright
Courtesy of MARKETPLACE REALTY

About Winchester

Listings in Winchester, VA

474

Estimated median home price

$449,990
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 - 100K45
$100K - 200K19
$200K - 300K43
$300K - 400K91
$400K - 500K80
$500K - 600K56
$600K - 700K39
$700K - 800K16
$800K - 900K12
$900K - 1M13
$1M - Max60

Homes for Sale by Type in Winchester, VA

Property TypeCount
Single Family245
Townhouse47
Condo25
Commercial45
Rental143
Lots and Land106
Condo/Town/CoOp0
CoOp0
Multi Family6
Mobile Home0
Farms0

(Data as of 3/3/2026)

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 3/3/2026.

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.