View 135 Gregory Place Winchester, VA MLS# VAFV2040136
$110,000
3

Beds

2.0

Baths

1,495

Sq.Ft.

135 Gregory Place

Winchester, VA

Bright
Courtesy of KELLER WILLIAMS REALTY
View 104 Inca Trail Winchester, VA MLS# VAFV2039390
$155,000
2

Beds

1.0

Baths

900

Sq.Ft.

104 Inca Trail

Winchester, VA

Bright
Courtesy of KELLER WILLIAMS REALTY
View 142 Sequoia Drive Winchester, VA MLS# VAFV2040156
$449,990
3

Beds

3.1

Baths

2,239

Sq.Ft.

142 Sequoia Drive

Winchester, VA

Bright
Courtesy of REAL BROKER, LLC
The time to sell is now! THE TIME TO SELL IS NOW!
View Lot 115 Rockwood Trail Winchester, VA MLS# VAFV2040164
$165,000
Studio

Beds

0.0

Baths

Lot 115 Rockwood Trail

Winchester, VA

Bright
Courtesy of COLDWELL BANKER PREMIER
View 154 Nevermore Dr Winchester, VA MLS# VAFV2040166
$579,000
3

Beds

2.0

Baths

1,839

Sq.Ft.

154 Nevermore Dr

Winchester, VA

Bright
Courtesy of SAMSON PROPERTIES
View 123 Castaway Place Winchester, VA MLS# VAFV2040172
  • Adult Community
1 of 14
$349,990
3

Beds

2.1

Baths

1,752

Sq.Ft.

123 Castaway Place

Winchester, VA

Bright
Courtesy of BROOKFIELD MID-ATLANTIC BROKERAGE, LLC
View 320 Opequon Avenue Winchester, VA MLS# VAWI2010088
$280,000
3

Beds

2.0

Baths

1,020

Sq.Ft.

320 Opequon Avenue

Winchester, VA

Bright
Courtesy of RE/MAX ROOTS
View 221 Broad Avenue Winchester, VA MLS# VAFV2040030
$325,000
3

Beds

3.0

Baths

800

Sq.Ft.

221 Broad Avenue

Winchester, VA

Bright
Courtesy of KELLER WILLIAMS REALTY
View 111 Asbury Road Winchester, VA MLS# VAFV2040120
$425,000
4

Beds

2.1

Baths

2,353

Sq.Ft.

111 Asbury Road

Winchester, VA

Bright
Courtesy of REALTY ONE GROUP OLD TOWNE
View LOT 136 Senseny Road Winchester, VA MLS# VAFV2039792
$499,000
Studio

Beds

0.0

Baths

LOT 136 Senseny Road

Winchester, VA

Bright
Courtesy of COLONY REALTY
View 201 Monteith Drive Winchester, VA MLS# VAWI2010156
  • New Construction
1 of 30
$389,990
3

Beds

3.1

Baths

1,784

Sq.Ft.

201 Monteith Drive

Winchester, VA

Bright
Courtesy of DRB GROUP REALTY, LLC
View 221 Monteith Drive Winchester, VA MLS# VAWI2010162
  • New Construction with Virtual Tour
1 of 30
$389,990
3

Beds

3.1

Baths

1,784

Sq.Ft.

221 Monteith Drive

Winchester, VA

Bright
Courtesy of DRB GROUP REALTY, LLC
View Lot 58 Timber Ridge Trail Winchester, VA MLS# VAFV2040090
$19,500
Studio

Beds

0.0

Baths

Lot 58 Timber Ridge Trail

Winchester, VA

Bright
Courtesy of SAMSON PROPERTIES
View 135 Meade Drive Winchester, VA MLS# VAFV2040144
$360,000
3

Beds

2.1

Baths

1,852

Sq.Ft.

135 Meade Drive

Winchester, VA

Bright
Courtesy of RE/MAX ROOTS
View 1851 Melvor Lane Winchester, VA MLS# VAWI2010102
  • Adult Community with Virtual Tour
1 of 43
$399,900
2

Beds

2.0

Baths

1,405

Sq.Ft.

1851 Melvor Lane

Winchester, VA

Bright
Courtesy of RE/MAX ROOTS
View 1317 Caroline Street Winchester, VA MLS# VAWI2010126
    1 of 46
    OPEN HOUSE: Sunday 4/19 12:00 PM - 2:00 PM
    $550,000
    4

    Beds

    2.0

    Baths

    2,837

    Sq.Ft.

    1317 Caroline Street

    Winchester, VA

    Bright
    Courtesy of COLONY REALTY
    View 103 Fenwick Court Winchester, VA MLS# VAFV2040028
    $425,000
    5

    Beds

    3.1

    Baths

    1,776

    Sq.Ft.

    103 Fenwick Court

    Winchester, VA

    Bright
    Courtesy of KELLER WILLIAMS REALTY
    View 506 Fairmont Avenue Winchester, VA MLS# VAWI2010144
    $215,000
    Studio

    Beds

    0.0

    Baths

    506 Fairmont Avenue

    Winchester, VA

    Bright
    Courtesy of COLONY REALTY
    View 101 Molden Drive Winchester, VA MLS# VAWI2009338
    $360,000
    3

    Beds

    2.0

    Baths

    1,260

    Sq.Ft.

    101 Molden Drive

    Winchester, VA

    Bright
    Courtesy of MARKETPLACE REALTY
    View 2510 Windwood Drive Winchester, VA MLS# VAWI2010122
    $499,000
    4

    Beds

    2.1

    Baths

    2,068

    Sq.Ft.

    2510 Windwood Drive

    Winchester, VA

    Bright
    Courtesy of REALTY ONE GROUP OLD TOWNE

    About Winchester

    Listings in Winchester, VA

    558

    Estimated median home price

    $450,000
    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 - 100K51
    $100K - 200K27
    $200K - 300K49
    $300K - 400K110
    $400K - 500K76
    $500K - 600K76
    $600K - 700K51
    $700K - 800K21
    $800K - 900K13
    $900K - 1M14
    $1M - Max70

    Homes for Sale by Type in Winchester, VA

    Property TypeCount
    Single Family302
    Townhouse66
    Condo18
    Commercial47
    Rental162
    Lots and Land118
    Condo/Town/CoOp0
    CoOp0
    Multi Family5
    Mobile Home0
    Farms2

    (Data as of 4/15/2026)

    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 4/16/2026.

    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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