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 Webster Court # SIERRA 39-F2 Winchester, VA MLS# VAFV2039358
$593,790
3

Beds

3.0

Baths

3,200

Sq.Ft.

Webster Court # SIERRA 39-F2

Winchester, VA

Bright
Courtesy of PEARSON SMITH REALTY, LLC
The time to sell is now! THE TIME TO SELL IS NOW!
View Wagtail Lane # VALE 34-F2 Winchester, VA MLS# VAFV2039360
  • Adult Community with Virtual Tour
1 of 52
$480,290
3

Beds

2.1

Baths

2,257

Sq.Ft.

Wagtail Lane # VALE 34-F2

Winchester, VA

Bright
Courtesy of PEARSON SMITH REALTY, LLC
View 133 Mascouten Street Winchester, VA MLS# VAFV2039376
  • New Construction with Virtual Tour
1 of 34
OPEN HOUSE: Sunday 3/1 12:00 PM - 3:00 PM
$597,990
6

Beds

4.0

Baths

3,127

Sq.Ft.

133 Mascouten Street

Winchester, VA

Bright
Courtesy of D R HORTON REALTY OF VIRGINIA LLC
View 137 Mascouten Street Winchester, VA MLS# VAFV2039380
  • New Construction with Virtual Tour
1 of 34
$604,990
6

Beds

4.0

Baths

3,127

Sq.Ft.

137 Mascouten Street

Winchester, VA

Bright
Courtesy of D R HORTON REALTY OF VIRGINIA LLC
View 123 Wappinger Terrace Winchester, VA MLS# VAFV2039382
  • New Construction with Virtual Tour
1 of 57
$619,990
6

Beds

4.1

Baths

3,619

Sq.Ft.

123 Wappinger Terrace

Winchester, VA

Bright
Courtesy of D R HORTON REALTY OF VIRGINIA LLC
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 105 Seminole Drive Winchester, VA MLS# VAFV2039384
  • New Construction
1 of 28
$519,990
4

Beds

3.1

Baths

2,216

Sq.Ft.

105 Seminole Drive

Winchester, VA

Bright
Courtesy of D R HORTON REALTY OF VIRGINIA LLC
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 101 Delaware Trail Winchester, VA MLS# VAFV2039152
$475,000
3

Beds

2.0

Baths

2,094

Sq.Ft.

101 Delaware Trail

Winchester, VA

Bright
Courtesy of EXP REALTY, LLC
View 132 Amherst Street Winchester, VA MLS# VAWI2009872
  • Virtual Tour
1 of 73
$650,000
4

Beds

3.1

Baths

3,474

Sq.Ft.

132 Amherst Street

Winchester, VA

Bright
Courtesy of COLONY REALTY
View 308 Lehigh Drive Winchester, VA MLS# VAFV2039278
  • Virtual Tour
1 of 62
OPEN HOUSE: Sunday 3/1 12:00 PM - 2:00 PM
$549,990
4

Beds

3.1

Baths

3,132

Sq.Ft.

308 Lehigh Drive

Winchester, VA

Bright
Courtesy of REAL BROKER, LLC
View 124 Lenore Winchester, VA MLS# VAFV2039294
$550,000
4

Beds

2.1

Baths

2,439

Sq.Ft.

124 Lenore

Winchester, VA

Bright
Courtesy of EXP REALTY, LLC
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 116 Wickham Terrace Winchester, VA MLS# VAFV2039246
$649,000
4

Beds

3.1

Baths

2,864

Sq.Ft.

116 Wickham Terrace

Winchester, VA

Bright
Courtesy of HUNT COUNTRY SOTHEBY'S INTERNATIONAL REALTY
View Apple Pie Ridge Road Winchester, VA MLS# VAFV2039276
  • New Construction
1 of 8
$785,000
3

Beds

3.0

Baths

2,548

Sq.Ft.

Apple Pie Ridge Road

Winchester, VA

Bright
Courtesy of PEARSON SMITH REALTY, LLC

About Winchester

Listings in Winchester, VA

480

Estimated median home price

$449,000
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 20
$200K - 300K 46
$300K - 400K 92
$400K - 500K 81
$500K - 600K 56
$600K - 700K 39
$700K - 800K 16
$800K - 900K 12
$900K - 1M 13
$1M - Max 61

Homes for Sale by Type in Winchester, VA

Property Type Count
Single Family 248
Townhouse 50
Condo 24
Commercial 46
Rental 143
Lots and Land 106
Condo/Town/CoOp 0
CoOp 0
Multi Family 6
Mobile Home 0
Farms 0

(Data as of 3/1/2026)

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 3/2/2026.

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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