View 136 Wappinger Terrace Winchester, VA MLS# VAFV2040006
$449,990
3

Beds

2.1

Baths

1,657

Sq.Ft.

136 Wappinger Terrace

Winchester, VA

Bright
Courtesy of D R HORTON REALTY OF VIRGINIA LLC
View 142 Sequoia Drive Winchester, VA MLS# VAFV2040156
  • Recently Listed with Virtual Tour
1 of 54
$449,990
3

Beds

3.1

Baths

2,239

Sq.Ft.

142 Sequoia Drive

Winchester, VA

Bright
Courtesy of REAL BROKER, LLC
View 25 W Southwerk Street Winchester, VA MLS# VAWI2009902
$449,000
3

Beds

2.1

Baths

1,904

Sq.Ft.

25 W Southwerk Street

Winchester, VA

Bright
Courtesy of COLONY REALTY
The time to sell is now! THE TIME TO SELL IS NOW!
View 154 Montague Avenue Winchester, VA MLS# VAWI2010086
$449,000
3

Beds

1.1

Baths

2,303

Sq.Ft.

154 Montague Avenue

Winchester, VA

Bright
Courtesy of COLONY REALTY
View 108 Keystone # HOMESITE 1094 Winchester, VA MLS# VAFV2039166
  • Adult Community with Virtual Tour
1 of 49
$448,119
3

Beds

2.1

Baths

2,181

Sq.Ft.

108 Keystone # HOMESITE 1094

Winchester, VA

Bright
Courtesy of PEARSON SMITH REALTY, LLC
View 117 Wagtail Lane Winchester, VA MLS# VAFV2039080
  • Adult Community with Virtual Tour
1 of 40
$444,990
3

Beds

2.1

Baths

2,195

Sq.Ft.

117 Wagtail Lane

Winchester, VA

Bright
Courtesy of REAL BROKER, LLC
View 110 Shouner Court Winchester, VA MLS# VAFV2040288
  • Recently Listed
1 of 21
$444,990
4

Beds

3.1

Baths

1,989

Sq.Ft.

110 Shouner Court

Winchester, VA

Bright
Courtesy of NEW HOME STAR VIRGINIA, LLC
View 110 Elaine Drive Winchester, VA MLS# VAFV2039216
$439,990
3

Beds

2.0

Baths

2,080

Sq.Ft.

110 Elaine Drive

Winchester, VA

Bright
Courtesy of CENTURY 21 REDWOOD REALTY
View 109 Glen Ridge Road Winchester, VA MLS# VAFV2038356
  • New Construction
1 of 20
$439,900
3

Beds

3.0

Baths

1,935

Sq.Ft.

109 Glen Ridge Road

Winchester, VA

Bright
Courtesy of CENTURY 21 NEW MILLENNIUM
View 1105 Henry Drive Winchester, VA MLS# VAFV2038626
$439,900
4

Beds

2.1

Baths

2,850

Sq.Ft.

1105 Henry Drive

Winchester, VA

Bright
Courtesy of RE/MAX ROOTS
View 1025 S Loudoun Street Winchester, VA MLS# VAWI2009836
    1 of 31
    OPEN HOUSE: Sunday 3/22 1:00 PM - 3:00 PM
    $439,900
    3

    Beds

    2.1

    Baths

    2,100

    Sq.Ft.

    1025 S Loudoun Street

    Winchester, VA

    Bright
    Courtesy of SAMSON PROPERTIES
    View 743 Berryville Avenue Winchester, VA MLS# VAWI2010062
    $439,000
    4

    Beds

    2.0

    Baths

    1,400

    Sq.Ft.

    743 Berryville Avenue

    Winchester, VA

    Bright
    Courtesy of PEARSON SMITH REALTY, LLC
    View 122 Cherry Hill Circle Winchester, VA MLS# VAFV2036714
    $435,000
    5

    Beds

    4.0

    Baths

    2,014

    Sq.Ft.

    122 Cherry Hill Circle

    Winchester, VA

    Bright
    Courtesy of ERA OAKCREST REALTY, INC.
    View 221 Cobble Stone Drive Winchester, VA MLS# VAFV2039498
    $435,000
    4

    Beds

    3.1

    Baths

    2,413

    Sq.Ft.

    221 Cobble Stone Drive

    Winchester, VA

    Bright
    Courtesy of REALTY ONE GROUP OLD TOWNE
    View 17 E Leicester Street Winchester, VA MLS# VAWI2009350
    $430,000
    4

    Beds

    2.0

    Baths

    2,100

    Sq.Ft.

    17 E Leicester Street

    Winchester, VA

    Bright
    Courtesy of MARKETPLACE REALTY
    View 1822 Blythe Way Winchester, VA MLS# VAWI2009206
    • New Construction with Virtual Tour
    1 of 44
    $429,990
    4

    Beds

    3.1

    Baths

    1,889

    Sq.Ft.

    1822 Blythe Way

    Winchester, VA

    Bright
    Courtesy of D R HORTON REALTY OF VIRGINIA LLC
    View 570 Welltown Road Winchester, VA MLS# VAFV2039004
      1 of 34
      OPEN HOUSE: Saturday 3/21 1:00 PM - 3:00 PM
      $429,000
      4

      Beds

      3.0

      Baths

      1,783

      Sq.Ft.

      570 Welltown Road

      Winchester, VA

      Bright
      Courtesy of KELLER WILLIAMS REALTY
      View 1332 Ramseur Lane Winchester, VA MLS# VAWI2010104
      • Recently Listed with Virtual Tour
      1 of 43
      $429,000
      3

      Beds

      2.0

      Baths

      2,648

      Sq.Ft.

      1332 Ramseur Lane

      Winchester, VA

      Bright
      Courtesy of RE/MAX ROOTS
      View 115 E Monmouth Street Winchester, VA MLS# VAWI2010138
      $429,000
      4

      Beds

      2.0

      Baths

      1,432

      Sq.Ft.

      115 E Monmouth Street

      Winchester, VA

      Bright
      Courtesy of INMOBILIARIA DE LAS CASAS LLC
      View 209 Wood Avenue Winchester, VA MLS# VAWI2010178
      • Recently Listed
      1 of 36
      $429,000
      3

      Beds

      2.1

      Baths

      1,528

      Sq.Ft.

      209 Wood Avenue

      Winchester, VA

      Bright
      Courtesy of COLONY REALTY

      About Winchester

      Listings in Winchester, VA

      518

      Estimated median home price

      $449,995
      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 - 100K50
      $100K - 200K21
      $200K - 300K41
      $300K - 400K104
      $400K - 500K84
      $500K - 600K58
      $600K - 700K45
      $700K - 800K21
      $800K - 900K15
      $900K - 1M13
      $1M - Max66

      Homes for Sale by Type in Winchester, VA

      Property TypeCount
      Single Family281
      Townhouse50
      Condo22
      Commercial47
      Rental160
      Lots and Land112
      Condo/Town/CoOp0
      CoOp0
      Multi Family5
      Mobile Home0
      Farms1

      (Data as of 3/18/2026)

      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 3/20/2026.

      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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