View 236 Bentley Avenue Winchester, VA MLS# VAFV2038404
$419,000
3

Beds

2.0

Baths

1,791

Sq.Ft.

236 Bentley Avenue

Winchester, VA

Bright
Courtesy of COLONY REALTY
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 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
The time to sell is now! THE TIME TO SELL IS NOW!
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
    View 105 Boone Court Winchester, VA MLS# VAFV2038140
    • New Construction
    1 of 21
    $384,880
    3

    Beds

    2.2

    Baths

    1,989

    Sq.Ft.

    105 Boone Court

    Winchester, VA

    Bright
    Courtesy of NEW HOME STAR VIRGINIA, LLC
    View 109 Boone Court Winchester, VA MLS# VAFV2038142
    • New Construction
    1 of 22
    $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 117 Boone Ct Winchester, VA MLS# VAFV2038144
    • New Construction
    1 of 21
    $389,880
    3

    Beds

    2.2

    Baths

    1,989

    Sq.Ft.

    117 Boone Ct

    Winchester, VA

    Bright
    Courtesy of NEW HOME STAR VIRGINIA, LLC
    View 138 Windstone Drive Winchester, VA MLS# VAFV2038094
    $340,000
    3

    Beds

    2.1

    Baths

    1,488

    Sq.Ft.

    138 Windstone Drive

    Winchester, VA

    Bright
    Courtesy of ERA OAKCREST REALTY, INC.

    About Winchester

    Listings in Winchester, VA

    448

    Estimated median home price

    $434,995
    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 - 200K17
    $200K - 300K41
    $300K - 400K94
    $400K - 500K66
    $500K - 600K51
    $600K - 700K40
    $700K - 800K12
    $800K - 900K12
    $900K - 1M11
    $1M - Max54

    Homes for Sale by Type in Winchester, VA

    Property TypeCount
    Single Family233
    Townhouse46
    Condo19
    Commercial40
    Rental146
    Lots and Land104
    Condo/Town/CoOp0
    CoOp0
    Multi Family6
    Mobile Home0
    Farms0

    (Data as of 1/5/2026)

    Information deemed reliable but not guaranteed.

    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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