View 113 Christopher Drive Winchester, VA MLS# VAWI2010188
$349,900
3

Beds

1.1

Baths

1,890

Sq.Ft.

113 Christopher Drive

Winchester, VA

Bright
Courtesy of ERA OAKCREST REALTY, INC.
View 113 Deer Trail Winchester, VA MLS# VAFV2040322
$370,000
3

Beds

2.0

Baths

1,592

Sq.Ft.

113 Deer Trail

Winchester, VA

Bright
Courtesy of SAMSON PROPERTIES
View 523 Monticello Street Winchester, VA MLS# VAWI2010120
$220,000
2

Beds

1.1

Baths

1,064

Sq.Ft.

523 Monticello Street

Winchester, VA

Bright
Courtesy of BERKSHIRE HATHAWAY HOMESERVICES PENFED REALTY
The time to sell is now! THE TIME TO SELL IS NOW!
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 16 S Pleasant Valley Road Winchester, VA MLS# VAWI2010240
$349,900
3

Beds

2.1

Baths

1,600

Sq.Ft.

16 S Pleasant Valley Road

Winchester, VA

Bright
Courtesy of SAMSON PROPERTIES
View 83 Bobcat Trail Winchester, VA MLS# VAFV2040318
$130,000
Studio

Beds

0.0

Baths

83 Bobcat Trail

Winchester, VA

Bright
Courtesy of SAMSON PROPERTIES
View 1033 Sunnyside Drive Winchester, VA MLS# VAFV2040250
$386,000
3

Beds

2.0

Baths

1,365

Sq.Ft.

1033 Sunnyside Drive

Winchester, VA

Bright
Courtesy of REDFIN CORPORATION
View Fox Trail Winchester, VA MLS# VAFV2040348
$6,500
Studio

Beds

0.0

Baths

Fox Trail

Winchester, VA

Bright
Courtesy of SAMSON PROPERTIES
View LOTS 8 & 9 Elk Trail Winchester, VA MLS# VAFV2040350
$9,500
Studio

Beds

0.0

Baths

LOTS 8 & 9 Elk Trail

Winchester, VA

Bright
Courtesy of SAMSON PROPERTIES
View Rockwood Trail # 49.61 ACRES Winchester, VA MLS# VAFV2040340
$169,900
Studio

Beds

0.0

Baths

Rockwood Trail # 49.61 ACRES

Winchester, VA

Bright
Courtesy of CEDAR CREEK REAL ESTATE
View 208 Beaver Trail Winchester, VA MLS# VAFV2040342
  • New Construction
1 of 30
$399,900
3

Beds

3.0

Baths

1,914

Sq.Ft.

208 Beaver Trail

Winchester, VA

Bright
Courtesy of REALTY ONE GROUP OLD TOWNE
View 2956 Grace Street Winchester, VA MLS# VAWI2010184
$319,900
4

Beds

1.0

Baths

1,699

Sq.Ft.

2956 Grace Street

Winchester, VA

Bright
Courtesy of SAMSON PROPERTIES
View 520 N Braddock Street Winchester, VA MLS# VAWI2010142
$365,000
3

Beds

2.0

Baths

1,999

Sq.Ft.

520 N Braddock Street

Winchester, VA

Bright
Courtesy of MARKETPLACE REALTY
View 616 Cardinal Drive Winchester, VA MLS# VAFV2040274
$349,900
3

Beds

2.0

Baths

1,510

Sq.Ft.

616 Cardinal Drive

Winchester, VA

Bright
Courtesy of SAMSON PROPERTIES
View 704 Watson Avenue Winchester, VA MLS# VAWI2010194
$280,000
2

Beds

2.0

Baths

864

Sq.Ft.

704 Watson Avenue

Winchester, VA

Bright
Courtesy of SAMSON PROPERTIES
View 303 Fox Winchester, VA MLS# VAFV2040160
$240,000
2

Beds

1.0

Baths

960

Sq.Ft.

303 Fox

Winchester, VA

Bright
Courtesy of JOHNSTON AND RHODES REAL ESTATE
View 102 Stribling Way Winchester, VA MLS# VAFV2040206
$355,000
3

Beds

2.1

Baths

1,710

Sq.Ft.

102 Stribling Way

Winchester, VA

Bright
Courtesy of MARKETPLACE REALTY
View 951 Bobcat Trl Winchester, VA MLS# VAFV2040270
$199,000
Studio

Beds

0.0

Baths

951 Bobcat Trl

Winchester, VA

Bright
Courtesy of REALTY ONE GROUP OLD TOWNE
View 224 Doe Trail Winchester, VA MLS# VAFV2040182
  • Virtual Tour
1 of 56
$349,900
4

Beds

2.1

Baths

2,348

Sq.Ft.

224 Doe Trail

Winchester, VA

Bright
Courtesy of SAMSON PROPERTIES
View 307 Fox Run Lane Winchester, VA MLS# VAFV2040196
$399,000
3

Beds

1.0

Baths

1,260

Sq.Ft.

307 Fox Run Lane

Winchester, VA

Bright
Courtesy of CORCORAN MCENEARNEY

About Winchester

Listings in Winchester, VA

601

Estimated median home price

$444,990
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 - 100K61
$100K - 200K35
$200K - 300K46
$300K - 400K126
$400K - 500K76
$500K - 600K74
$600K - 700K68
$700K - 800K20
$800K - 900K17
$900K - 1M13
$1M - Max65

Homes for Sale by Type in Winchester, VA

Property TypeCount
Single Family348
Townhouse57
Condo16
Commercial42
Rental162
Lots and Land131
Condo/Town/CoOp0
CoOp0
Multi Family4
Mobile Home0
Farms3

(Data as of 6/1/2026)

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 6/1/2026.

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.

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