View 107 Pinto Trail Winchester, VA MLS# VAFV2038456
  • New Construction
1 of 20
$389,900
3

Beds

3.0

Baths

1,850

Sq.Ft.

107 Pinto Trail

Winchester, VA

Bright
Courtesy of REALTY ONE GROUP OLD TOWNE
View 1619 Tomahawk Trail Winchester, VA MLS# VAFV2038460
  • New Construction
1 of 19
$349,900
3

Beds

3.0

Baths

1,850

Sq.Ft.

1619 Tomahawk Trail

Winchester, VA

Bright
Courtesy of REALTY ONE GROUP OLD TOWNE
View 126 N Euclid Avenue Winchester, VA MLS# VAWI2009594
$370,000
4

Beds

3.0

Baths

1,868

Sq.Ft.

126 N Euclid Avenue

Winchester, VA

Bright
Courtesy of REAL BROKER, LLC
The time to sell is now! THE TIME TO SELL IS NOW!
View 405 1/2 Elm Street Winchester, VA MLS# VAWI2009592
$299,990
3

Beds

2.0

Baths

1,152

Sq.Ft.

405 1/2 Elm Street

Winchester, VA

Bright
Courtesy of THE VASQUEZ GROUP LLC
View 318 E Piccadilly Street Winchester, VA MLS# VAWI2009582
$399,000
4

Beds

1.1

Baths

1,953

Sq.Ft.

318 E Piccadilly Street

Winchester, VA

Bright
Courtesy of COLONY REALTY
View 534 N Kent Street Winchester, VA MLS# VAWI2009588
$300,000
3

Beds

1.1

Baths

1,152

Sq.Ft.

534 N Kent Street

Winchester, VA

Bright
Courtesy of SAMSON PROPERTIES
View 133 Meade Drive Winchester, VA MLS# VAFV2038412
$400,000
3

Beds

3.0

Baths

2,550

Sq.Ft.

133 Meade Drive

Winchester, VA

Bright
Courtesy of RE/MAX ROOTS
View 103 Castaway Place Winchester, VA MLS# VAFV2038396
  • Adult Community
1 of 29
$374,990
3

Beds

2.1

Baths

1,752

Sq.Ft.

103 Castaway Place

Winchester, VA

Bright
Courtesy of BROOKFIELD MID-ATLANTIC BROKERAGE, LLC
View 415 Quail Drive Winchester, VA MLS# VAFV2037052
$359,000
3

Beds

2.1

Baths

1,719

Sq.Ft.

415 Quail Drive

Winchester, VA

Bright
Courtesy of RE/MAX ROOTS
View 126 Plainfield Drive Winchester, VA MLS# VAFV2038270
$329,900
4

Beds

1.1

Baths

1,456

Sq.Ft.

126 Plainfield Drive

Winchester, VA

Bright
Courtesy of RE/MAX ROOTS
View 203 Crestwood Lane Winchester, VA MLS# VAFV2038228
  • Adult Community
1 of 32
$379,000
2

Beds

2.0

Baths

1,590

Sq.Ft.

203 Crestwood Lane

Winchester, VA

Bright
Courtesy of MARKETPLACE REALTY
View 207 Eastside Winchester, VA MLS# VAFV2037926
$314,000
4

Beds

3.1

Baths

1,840

Sq.Ft.

207 Eastside

Winchester, VA

Bright
Courtesy of COLDWELL BANKER PREMIER
View 209 Monteith Drive Winchester, VA MLS# VAWI2009524
  • New Construction with Virtual Tour
1 of 29
$379,990
3

Beds

3.1

Baths

1,784

Sq.Ft.

209 Monteith Drive

Winchester, VA

Bright
Courtesy of DRB GROUP REALTY, LLC
View 222 Monteith Drive Winchester, VA MLS# VAWI2009526
  • New Construction with Virtual Tour
1 of 27
$369,990
3

Beds

3.1

Baths

1,784

Sq.Ft.

222 Monteith Drive

Winchester, VA

Bright
Courtesy of DRB GROUP REALTY, LLC
View 230 Monteith Drive Winchester, VA MLS# VAWI2009528
  • New Construction with Virtual Tour
1 of 23
$369,990
3

Beds

3.1

Baths

1,784

Sq.Ft.

230 Monteith Drive

Winchester, VA

Bright
Courtesy of DRB GROUP REALTY, LLC
View 3221 Laurel Grove Road Winchester, VA MLS# VAFV2038200
$325,000
4

Beds

2.0

Baths

1,450

Sq.Ft.

3221 Laurel Grove Road

Winchester, VA

Bright
Courtesy of KELLER WILLIAMS REALTY CENTRE
View 111 Meadowview Court Winchester, VA MLS# VAFV2038234
    1 of 29
    OPEN HOUSE: Sunday 1/11 12:00 PM - 2:00 PM
    $356,000
    3

    Beds

    1.1

    Baths

    1,164

    Sq.Ft.

    111 Meadowview Court

    Winchester, VA

    Bright
    Courtesy of ERA OAKCREST REALTY, INC.
    View 414 S Cameron Street Winchester, VA MLS# VAWI2009506
    • Virtual Tour
    1 of 65
    OPEN HOUSE: Saturday 1/10 11:00 AM - 1:00 PM
    $405,000
    3

    Beds

    2.0

    Baths

    1,802

    Sq.Ft.

    414 S Cameron Street

    Winchester, VA

    Bright
    Courtesy of REALTY ONE GROUP OLD TOWNE
    View 100 Maury Way Winchester, VA MLS# VAFV2038220
    • Adult Community with Virtual Tour
    1 of 39
    $385,000
    3

    Beds

    2.1

    Baths

    1,678

    Sq.Ft.

    100 Maury Way

    Winchester, VA

    Bright
    Courtesy of KELLER WILLIAMS REALTY
    View 7 N Purcell Avenue Winchester, VA MLS# VAWI2009512
    $375,000
    3

    Beds

    3.0

    Baths

    2,016

    Sq.Ft.

    7 N Purcell Avenue

    Winchester, VA

    Bright
    Courtesy of REALTY ONE GROUP OLD TOWNE

    About Winchester

    Listings in Winchester, VA

    446

    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

    PriceCount
    $0 - 100K49
    $100K - 200K17
    $200K - 300K41
    $300K - 400K90
    $400K - 500K72
    $500K - 600K51
    $600K - 700K38
    $700K - 800K12
    $800K - 900K11
    $900K - 1M12
    $1M - Max53

    Homes for Sale by Type in Winchester, VA

    Property TypeCount
    Single Family233
    Townhouse45
    Condo20
    Commercial39
    Rental147
    Lots and Land103
    Condo/Town/CoOp0
    CoOp0
    Multi Family6
    Mobile Home0
    Farms0

    (Data as of 1/9/2026)

    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 1/9/2026.

    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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