View 105 Castaway Winchester, VA MLS# VAFV2039606
  • Recently Listed
1 of 27
$374,990
3

Beds

2.1

Baths

1,784

Sq.Ft.

105 Castaway

Winchester, VA

Bright
Courtesy of BROOKFIELD MID-ATLANTIC BROKERAGE, LLC
View 2643 Middle Road Winchester, VA MLS# VAWI2009924
$500,000
4

Beds

3.1

Baths

2,524

Sq.Ft.

2643 Middle Road

Winchester, VA

Bright
Courtesy of BERKSHIRE HATHAWAY HOMESERVICES PENFED REALTY
View 108 Senseny Glen Drive Winchester, VA MLS# VAFV2039554
    1 of 28
    OPEN HOUSE: Saturday 2/28 2:00 PM - 4:00 PM
    $423,000
    3

    Beds

    2.0

    Baths

    1,397

    Sq.Ft.

    108 Senseny Glen Drive

    Winchester, VA

    Bright
    Courtesy of PEARSON SMITH REALTY, LLC
    The time to sell is now! THE TIME TO SELL IS NOW!
    View 431 Jefferson Street Winchester, VA MLS# VAWI2009944
    $419,900
    3

    Beds

    1.1

    Baths

    1,632

    Sq.Ft.

    431 Jefferson Street

    Winchester, VA

    Bright
    Courtesy of COLONY REALTY
    View 118 Trellis View Lane Winchester, VA MLS# VAFV2039558
    • Recently Listed with Virtual Tour
    1 of 40
    $449,990
    3

    Beds

    2.0

    Baths

    1,492

    Sq.Ft.

    118 Trellis View Lane

    Winchester, VA

    Bright
    Courtesy of D R HORTON REALTY OF VIRGINIA LLC
    View 218 Monteith Drive Winchester, VA MLS# VAWI2009978
    • Recently Listed with Virtual Tour
    1 of 24
    $389,990
    3

    Beds

    3.1

    Baths

    1,784

    Sq.Ft.

    218 Monteith Drive

    Winchester, VA

    Bright
    Courtesy of DRB GROUP REALTY, LLC
    View 213 Woodrow Road Winchester, VA MLS# VAFV2039552
    • Recently Listed
    1 of 50
    $374,900
    3

    Beds

    2.0

    Baths

    1,416

    Sq.Ft.

    213 Woodrow Road

    Winchester, VA

    Bright
    Courtesy of SAMSON PROPERTIES
    View 221 Cobble Stone Drive Winchester, VA MLS# VAFV2039498
    • Recently Listed with Virtual Tour
    1 of 73
    $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 128 Killbuck Trail Winchester, VA MLS# VAFV2039474
    • Recently Listed
    1 of 52
    $410,000
    3

    Beds

    4.0

    Baths

    2,100

    Sq.Ft.

    128 Killbuck Trail

    Winchester, VA

    Bright
    Courtesy of RE/MAX ROOTS
    View 15.63 Acres, 52-2-B Winchester, VA MLS# VAFV2039232
    $250,000
    Studio

    Beds

    0.0

    Baths

    15.63 Acres, 52-2-B

    Winchester, VA

    Bright
    Courtesy of COLONY REALTY
    View 19 W Germain Street Winchester, VA MLS# VAWI2009802
    $337,000
    3

    Beds

    1.1

    Baths

    1,280

    Sq.Ft.

    19 W Germain Street

    Winchester, VA

    Bright
    Courtesy of COTTAGE STREET REALTY LLC
    View 1821 Harvest Drive Winchester, VA MLS# VAWI2009960
    • Recently Listed
    1 of 40
    $414,990
    4

    Beds

    3.1

    Baths

    1,920

    Sq.Ft.

    1821 Harvest Drive

    Winchester, VA

    Bright
    Courtesy of D R HORTON REALTY OF VIRGINIA LLC
    View 1809 Harvest Drive Winchester, VA MLS# VAWI2009962
    • Recently Listed
    1 of 40
    $449,990
    4

    Beds

    3.1

    Baths

    1,939

    Sq.Ft.

    1809 Harvest Drive

    Winchester, VA

    Bright
    Courtesy of D R HORTON REALTY OF VIRGINIA LLC
    View 1813 Harvest Drive Winchester, VA MLS# VAWI2009964
    • Recently Listed
    1 of 39
    $449,990
    4

    Beds

    3.1

    Baths

    1,920

    Sq.Ft.

    1813 Harvest Drive

    Winchester, VA

    Bright
    Courtesy of D R HORTON REALTY OF VIRGINIA LLC
    View 109 Boone Court Winchester, VA MLS# VAFV2039494
    • Recently Listed
    1 of 22
    OPEN HOUSE: Tuesday 2/24 12:00 PM - 4:00 PM
    $389,880
    3

    Beds

    2.2

    Baths

    1,989

    Sq.Ft.

    109 Boone Court

    Winchester, VA

    Bright
    Courtesy of NEW HOME STAR VIRGINIA, LLC
    View 108 Webster Court # HOMESITE 1048 Winchester, VA MLS# VAFV2039488
    • Recently Listed with Virtual Tour
    1 of 48
    $480,724
    3

    Beds

    2.1

    Baths

    2,263

    Sq.Ft.

    108 Webster Court # HOMESITE 1048

    Winchester, VA

    Bright
    Courtesy of PEARSON SMITH REALTY, LLC
    View 376 Charles Street Winchester, VA MLS# VAWI2009942
    $185,000
    3

    Beds

    1.0

    Baths

    1,232

    Sq.Ft.

    376 Charles Street

    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
    View 513 Pheasant Drive Winchester, VA MLS# VAFV2039468
    • Recently Listed
    1 of 36
    $365,000
    3

    Beds

    2.0

    Baths

    1,368

    Sq.Ft.

    513 Pheasant Drive

    Winchester, VA

    Bright
    Courtesy of MARKETPLACE REALTY
    View 407 Van Fossen Street Winchester, VA MLS# VAWI2009922
    $279,999
    2

    Beds

    1.1

    Baths

    954

    Sq.Ft.

    407 Van Fossen Street

    Winchester, VA

    Bright
    Courtesy of SAMSON PROPERTIES

    About Winchester

    Listings in Winchester, VA

    484

    Estimated median home price

    $442,445
    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 - 100K44
    $100K - 200K19
    $200K - 300K43
    $300K - 400K98
    $400K - 500K87
    $500K - 600K57
    $600K - 700K37
    $700K - 800K15
    $800K - 900K11
    $900K - 1M14
    $1M - Max59

    Homes for Sale by Type in Winchester, VA

    Property TypeCount
    Single Family250
    Townhouse53
    Condo27
    Commercial44
    Rental138
    Lots and Land103
    Condo/Town/CoOp0
    CoOp0
    Multi Family7
    Mobile Home0
    Farms0

    (Data as of 2/23/2026)

    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 2/23/2026.

    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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