View 1885 Rosser Lane Winchester, VA MLS# VAWI2009918
  • Recently Listed
1 of 20
$389,900
2

Beds

2.0

Baths

1,550

Sq.Ft.

1885 Rosser Lane

Winchester, VA

Bright
Courtesy of OLIVETREE PROPERTY GROUP
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
The time to sell is now! THE TIME TO SELL IS NOW!
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
  • Recently Listed
1 of 45
$245,000
2

Beds

1.0

Baths

650

Sq.Ft.

177 Dicks Hollow Road

Winchester, VA

Bright
Courtesy of RE/MAX ROOTS
View 232 Myrtle Avenue Winchester, VA MLS# VAWI2009914
$389,900
4

Beds

2.0

Baths

1,949

Sq.Ft.

232 Myrtle Avenue

Winchester, VA

Bright
Courtesy of LONG & FOSTER REAL ESTATE, INC.
View Lot 18 Pheasant Drive Winchester, VA MLS# VAFV2039430
  • Recently Listed
1 of 10
$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 415 Fortress Drive Winchester, VA MLS# VAFV2038786
$430,000
3

Beds

2.0

Baths

1,710

Sq.Ft.

415 Fortress Drive

Winchester, VA

Bright
Courtesy of LPT REALTY, LLC
View 105 Keller Court Winchester, VA MLS# VAFV2033426
$410,000
4

Beds

3.1

Baths

2,250

Sq.Ft.

105 Keller Court

Winchester, VA

Bright
Courtesy of SKYLINE TEAM REAL ESTATE
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 4403 Back Mountain Road Winchester, VA MLS# VAFV2039282
$415,000
3

Beds

2.1

Baths

2,012

Sq.Ft.

4403 Back Mountain Road

Winchester, VA

Bright
Courtesy of RE/MAX ROOTS
View 137 Woodrow Road Winchester, VA MLS# VAFV2039288
$405,990
3

Beds

2.0

Baths

1,763

Sq.Ft.

137 Woodrow Road

Winchester, VA

Bright
Courtesy of COLDWELL BANKER PREMIER
View 139 Biscane Court Winchester, VA MLS# VAFV2039270
  • Virtual Tour
1 of 60
OPEN HOUSE: Sunday 3/1 1:00 PM - 4:00 PM
$414,900
3

Beds

3.1

Baths

2,250

Sq.Ft.

139 Biscane Court

Winchester, VA

Bright
Courtesy of PEARSON SMITH REALTY, LLC
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
View 611 Tudor Drive Winchester, VA MLS# VAFV2039200
$285,000
3

Beds

2.1

Baths

2,000

Sq.Ft.

611 Tudor Drive

Winchester, VA

Bright
Courtesy of SAMSON PROPERTIES
View 1806 Blythe Way Winchester, VA MLS# VAWI2009856
  • New Construction with Virtual Tour
1 of 40
$409,990
4

Beds

3.1

Baths

1,889

Sq.Ft.

1806 Blythe Way

Winchester, VA

Bright
Courtesy of D R HORTON REALTY OF VIRGINIA LLC

About Winchester

Listings in Winchester, VA

485

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 44
$100K - 200K 21
$200K - 300K 44
$300K - 400K 97
$400K - 500K 86
$500K - 600K 56
$600K - 700K 39
$700K - 800K 14
$800K - 900K 11
$900K - 1M 14
$1M - Max 59

Homes for Sale by Type in Winchester, VA

Property Type Count
Single Family 248
Townhouse 51
Condo 27
Commercial 46
Rental 143
Lots and Land 106
Condo/Town/CoOp 0
CoOp 0
Multi Family 7
Mobile Home 0
Farms 0

(Data as of 2/26/2026)

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 2/27/2026.

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.

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