View 1044 Orchard Avenue Winchester, VA MLS# VAWI2010904
  • Recently Listed with Virtual Tour
1 of 24
$329,000
4

Beds

2.0

Baths

1,163

Sq.Ft.

1044 Orchard Avenue

Winchester, VA

Bright
Courtesy of COLDWELL BANKER REALTY
View 703 S Loudoun Street Winchester, VA MLS# VAWI2010922
$450,000
3

Beds

2.1

Baths

1,992

Sq.Ft.

703 S Loudoun Street

Winchester, VA

Bright
Courtesy of SAMSON PROPERTIES
View 160 Shirley Court Winchester, VA MLS# VAFV2042368
$639,900
3

Beds

3.1

Baths

3,246

Sq.Ft.

160 Shirley Court

Winchester, VA

Bright
Courtesy of CENTURY 21 REDWOOD REALTY
The time to sell is now! THE TIME TO SELL IS NOW!
View 314 Greenfield Avenue Winchester, VA MLS# VAFV2041140
$550,000
4

Beds

2.1

Baths

2,520

Sq.Ft.

314 Greenfield Avenue

Winchester, VA

Bright
Courtesy of RE/MAX ROOTS
View 140 Cahille Drive Winchester, VA MLS# VAFV2042186
  • Recently Listed
1 of 54
OPEN HOUSE: Sunday 6/7 1:00 PM - 3:00 PM
$649,000
4

Beds

3.0

Baths

3,005

Sq.Ft.

140 Cahille Drive

Winchester, VA

Bright
Courtesy of KELLER WILLIAMS REALTY
View 527 Grouse Drive Winchester, VA MLS# VAFV2042220
  • Recently Listed
1 of 30
$399,000
3

Beds

2.1

Baths

1,909

Sq.Ft.

527 Grouse Drive

Winchester, VA

Bright
Courtesy of RE/MAX ROOTS
View 528 Battle Avenue Winchester, VA MLS# VAWI2010886
  • Recently Listed
1 of 39
$320,000
3

Beds

1.0

Baths

1,988

Sq.Ft.

528 Battle Avenue

Winchester, VA

Bright
Courtesy of CARTER BRAXTON PREFERRED PROPERTIES
View 1709 Brandon Drive Winchester, VA MLS# VAWI2010678
$425,000
4

Beds

3.0

Baths

2,157

Sq.Ft.

1709 Brandon Drive

Winchester, VA

Bright
Courtesy of COLONY REALTY
View 1317 Caroline Street Winchester, VA MLS# VAWI2010866
  • Recently Listed
1 of 67
OPEN HOUSE: Saturday 6/6 12:00 PM - 2:00 PM
$519,000
4

Beds

2.0

Baths

2,837

Sq.Ft.

1317 Caroline Street

Winchester, VA

Bright
Courtesy of Front Royal - Weichert, Realtors - Blue Ribbon
View 440 Bristol Drive Winchester, VA MLS# VAFV2042310
  • Recently Listed
1 of 128
$849,000
5

Beds

3.0

Baths

3,816

Sq.Ft.

440 Bristol Drive

Winchester, VA

Bright
Courtesy of REALTY ONE GROUP OLD TOWNE
View 431 Wembley Court Winchester, VA MLS# VAFV2042370
  • Recently Listed
1 of 18
$315,000
Studio

Beds

0.0

Baths

431 Wembley Court

Winchester, VA

Bright
Courtesy of REALTY ONE GROUP OLD TOWNE
View 2294 Welltown Road Winchester, VA MLS# VAFV2042382
$370,000
3

Beds

1.1

Baths

1,408

Sq.Ft.

2294 Welltown Road

Winchester, VA

Bright
Courtesy of REALTY ONE GROUP OLD TOWNE
View LOT 159-140 Hawk Trail Winchester, VA MLS# VAFV2041966
$55,000
Studio

Beds

0.0

Baths

LOT 159-140 Hawk Trail

Winchester, VA

Bright
Courtesy of VAZE REALTY
View LOT 160-142 Hawk Trail Winchester, VA MLS# VAFV2042246
$55,000
Studio

Beds

0.0

Baths

LOT 160-142 Hawk Trail

Winchester, VA

Bright
Courtesy of VAZE REALTY
View 188 Sioux Loop Winchester, VA MLS# VAFV2042312
  • Recently Listed with Virtual Tour
1 of 44
OPEN HOUSE: Saturday 6/6 12:00 PM - 3:00 PM
$388,990
4

Beds

3.1

Baths

1,889

Sq.Ft.

188 Sioux Loop

Winchester, VA

Bright
Courtesy of D R HORTON REALTY OF VIRGINIA LLC
View 108 Magpie Lane # HOMESITE 1035 Winchester, VA MLS# VAFV2042316
  • Recently Listed with Virtual Tour
1 of 44
$590,259
3

Beds

3.0

Baths

3,200

Sq.Ft.

108 Magpie Lane # HOMESITE 1035

Winchester, VA

Bright
Courtesy of PEARSON SMITH REALTY, LLC
View 2532 Middle Road Winchester, VA MLS# VAWI2010874
  • Recently Listed
1 of 42
$579,000
4

Beds

2.1

Baths

2,108

Sq.Ft.

2532 Middle Road

Winchester, VA

Bright
Courtesy of COLONY REALTY
View 801 Armistead Street Winchester, VA MLS# VAWI2010892
$1,150,000
5

Beds

3.2

Baths

5,695

Sq.Ft.

801 Armistead Street

Winchester, VA

Bright
Courtesy of SAMSON PROPERTIES
View 304 Ash Hollow Drive Winchester, VA MLS# VAFV2042334
$240,000
3

Beds

1.1

Baths

1,148

Sq.Ft.

304 Ash Hollow Drive

Winchester, VA

Bright
Courtesy of PEARSON SMITH REALTY, LLC
View 300 Tavistock Drive Winchester, VA MLS# VAFV2042352
$999,990
4

Beds

3.1

Baths

3,803

Sq.Ft.

300 Tavistock Drive

Winchester, VA

Bright
Courtesy of COLDWELL BANKER PREMIER

About Winchester

Listings in Winchester, VA

622

Estimated median home price

$439,532
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 - 100K62
$100K - 200K34
$200K - 300K51
$300K - 400K132
$400K - 500K77
$500K - 600K84
$600K - 700K67
$700K - 800K20
$800K - 900K17
$900K - 1M14
$1M - Max64

Homes for Sale by Type in Winchester, VA

Property TypeCount
Single Family366
Townhouse59
Condo16
Commercial42
Rental163
Lots and Land132
Condo/Town/CoOp0
CoOp0
Multi Family5
Mobile Home0
Farms2

(Data as of 6/6/2026)

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 6/6/2026.

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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