View 436 Westside Station Drive Winchester, VA MLS# VAFV2038424
$569,900
4

Beds

3.0

Baths

2,644

Sq.Ft.

436 Westside Station Drive

Winchester, VA

Bright
Courtesy of SAMSON PROPERTIES
View Bobcat Trail LOT 152 Winchester, VA MLS# VAFV2038190
$55,000
Studio

Beds

0.0

Baths

Bobcat Trail LOT 152

Winchester, VA

Bright
Courtesy of LONG & FOSTER REAL ESTATE, INC.
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
The time to sell is now! THE TIME TO SELL IS NOW!
View 107 Fox Trail Winchester, VA MLS# VAFV2038406
$3,500
Studio

Beds

0.0

Baths

107 Fox Trail

Winchester, VA

Bright
Courtesy of VENTURE 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 146 Beeler Lane Winchester, VA MLS# VAFV2038360
$499,000
3

Beds

2.0

Baths

2,940

Sq.Ft.

146 Beeler Lane

Winchester, VA

Bright
Courtesy of MARKETPLACE REALTY
View 534 N Kent Street Winchester, VA MLS# VAWI2009588
$295,000
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 518 Yorktowne Place Winchester, VA MLS# VAWI2009522
$269,000
2

Beds

1.1

Baths

1,116

Sq.Ft.

518 Yorktowne Place

Winchester, VA

Bright
Courtesy of PIFER REALTY, LLC
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 218 Flanagan Drive Winchester, VA MLS# VAFV2038366
    1 of 50
    OPEN HOUSE: Saturday 1/17 12:00 PM - 2:00 PM
    $650,000
    4

    Beds

    4.1

    Baths

    4,354

    Sq.Ft.

    218 Flanagan Drive

    Winchester, VA

    Bright
    Courtesy of BURCH REAL ESTATE GROUP, LLC
    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 Lot 57, 58, 59 Iroquois Trail Winchester, VA MLS# VAFV2038324
    $19,500
    Studio

    Beds

    0.0

    Baths

    Lot 57, 58, 59 Iroquois Trail

    Winchester, VA

    Bright
    Courtesy of MARKETPLACE REALTY
    View Lot 12 Crow Drive Winchester, VA MLS# VAFV2038336
    $7,900
    Studio

    Beds

    0.0

    Baths

    Lot 12 Crow Drive

    Winchester, VA

    Bright
    Courtesy of MARKETPLACE REALTY
    View Lot 13 Crow Drive Winchester, VA MLS# VAFV2038340
    $7,900
    Studio

    Beds

    0.0

    Baths

    Lot 13 Crow Drive

    Winchester, VA

    Bright
    Courtesy of MARKETPLACE REALTY
    View Lot 16 Crow Drive Winchester, VA MLS# VAFV2038342
    $7,900
    Studio

    Beds

    0.0

    Baths

    Lot 16 Crow Drive

    Winchester, VA

    Bright
    Courtesy of MARKETPLACE REALTY
    View Lot 8 Crow Drive Winchester, VA MLS# VAFV2038344
    $7,900
    Studio

    Beds

    0.0

    Baths

    Lot 8 Crow Drive

    Winchester, VA

    Bright
    Courtesy of MARKETPLACE REALTY
    View 92 Bobcat Trail Winchester, VA MLS# VAFV2038326
    $450,000
    Studio

    Beds

    0.0

    Baths

    92 Bobcat Trail

    Winchester, VA

    Bright
    Courtesy of RE/MAX REAL ESTATE CONNECTIONS
    View 108 Martin Drive Winchester, VA MLS# VAFV2038282
    $285,000
    2

    Beds

    1.0

    Baths

    997

    Sq.Ft.

    108 Martin Drive

    Winchester, VA

    Bright
    Courtesy of SAMSON PROPERTIES
    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

    About Winchester

    Listings in Winchester, VA

    442

    Estimated median home price

    $439,995
    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 - 100K49
    $100K - 200K16
    $200K - 300K40
    $300K - 400K88
    $400K - 500K75
    $500K - 600K45
    $600K - 700K39
    $700K - 800K13
    $800K - 900K11
    $900K - 1M12
    $1M - Max54

    Homes for Sale by Type in Winchester, VA

    Property TypeCount
    Single Family235
    Townhouse44
    Condo20
    Commercial39
    Rental145
    Lots and Land99
    Condo/Town/CoOp0
    CoOp0
    Multi Family5
    Mobile Home0
    Farms0

    (Data as of 1/14/2026)

    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 1/15/2026.

    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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