View 2250 Roosevelt Boulevard Winchester, VA MLS# VAWI2009326
$455,000
6

Beds

3.0

Baths

1,552

Sq.Ft.

2250 Roosevelt Boulevard

Winchester, VA

Bright
Courtesy of SPRING HILL REAL ESTATE, LLC.
View 115 Alpine Meadow Road Winchester, VA MLS# VAFV2038222
$450,000
3

Beds

3.1

Baths

2,486

Sq.Ft.

115 Alpine Meadow Road

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
The time to sell is now! THE TIME TO SELL IS NOW!
View 129 Doonbeg Court Winchester, VA MLS# VAFV2038410
  • Recently Listed with Virtual Tour
1 of 51
$450,000
4

Beds

2.1

Baths

2,072

Sq.Ft.

129 Doonbeg Court

Winchester, VA

Bright
Courtesy of ERA OAKCREST REALTY, INC.
View 139 Bryarly Road Winchester, VA MLS# VAFV2038700
  • Recently Listed
1 of 59
$450,000
3

Beds

2.0

Baths

1,585

Sq.Ft.

139 Bryarly Road

Winchester, VA

Bright
Courtesy of REAL BROKER, LLC
View 364 Bethel Grange Road Winchester, VA MLS# VAFV2038802
  • Recently Listed with Virtual Tour
1 of 52
$450,000
2

Beds

2.0

Baths

2,448

Sq.Ft.

364 Bethel Grange Road

Winchester, VA

Bright
Courtesy of SAMSON PROPERTIES
View 104 Primrose Place Winchester, VA MLS# VAFV2035982
$449,900
3

Beds

2.1

Baths

2,250

Sq.Ft.

104 Primrose Place

Winchester, VA

Bright
Courtesy of LONG & FOSTER REAL ESTATE, INC.
View 1105 Henry Drive Winchester, VA MLS# VAFV2038626
  • Recently Listed
1 of 52
$449,900
4

Beds

2.1

Baths

2,850

Sq.Ft.

1105 Henry Drive

Winchester, VA

Bright
Courtesy of RE/MAX ROOTS
View 1420 Fishel Road Winchester, VA MLS# VAFV2038746
$449,900
3

Beds

2.0

Baths

1,680

Sq.Ft.

1420 Fishel Road

Winchester, VA

Bright
Courtesy of CENTURY 21 REDWOOD REALTY
View 207 Trefoil Court Winchester, VA MLS# VAFV2038808
  • Recently Listed
1 of 61
$449,900
3

Beds

3.0

Baths

2,150

Sq.Ft.

207 Trefoil Court

Winchester, VA

Bright
Courtesy of COLONY REALTY
View 4403 Back Mountain Road Winchester, VA MLS# VAFV2037762
$444,900
3

Beds

2.1

Baths

2,012

Sq.Ft.

4403 Back Mountain Road

Winchester, VA

Bright
Courtesy of RE/MAX ROOTS
View 421 Superior Ave Winchester, VA MLS# VAWI2009092
$441,700
3

Beds

2.0

Baths

1,800

Sq.Ft.

421 Superior Ave

Winchester, VA

Bright
Courtesy of CENTURY 21 NEW MILLENNIUM
View 519 Whitacre Street Winchester, VA MLS# VAWI2009672
    1 of 1
    OPEN HOUSE: Saturday 1/17 1:00 PM - 3:00 PM
    $440,000
    4

    Beds

    2.0

    Baths

    2,408

    Sq.Ft.

    519 Whitacre Street

    Winchester, VA

    Bright
    Courtesy of SAMSON PROPERTIES
    View 123 Lakota Street Winchester, VA MLS# VAFV2038530
    • New Construction with Virtual Tour
    1 of 55
    $439,990
    4

    Beds

    3.1

    Baths

    1,889

    Sq.Ft.

    123 Lakota Street

    Winchester, VA

    Bright
    Courtesy of D R HORTON REALTY OF VIRGINIA 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 122 Cherry Hill Circle Winchester, VA MLS# VAFV2036714
    $435,000
    5

    Beds

    4.0

    Baths

    2,014

    Sq.Ft.

    122 Cherry Hill Circle

    Winchester, VA

    Bright
    Courtesy of ERA OAKCREST REALTY, INC.
    View 1818 Blythe Way Winchester, VA MLS# VAWI2009210
    • New Construction with Virtual Tour
    1 of 45
    $434,990
    4

    Beds

    3.1

    Baths

    1,923

    Sq.Ft.

    1818 Blythe Way

    Winchester, VA

    Bright
    Courtesy of D R HORTON REALTY OF VIRGINIA LLC
    View 127 Lakota Street Winchester, VA MLS# VAFV2038816
    • Recently Listed with Virtual Tour
    1 of 44
    $434,990
    4

    Beds

    3.1

    Baths

    1,889

    Sq.Ft.

    127 Lakota Street

    Winchester, VA

    Bright
    Courtesy of D R HORTON REALTY OF VIRGINIA LLC
    View 113 Williamson Road Winchester, VA MLS# VAFV2038542
    $434,900
    3

    Beds

    2.1

    Baths

    2,547

    Sq.Ft.

    113 Williamson Road

    Winchester, VA

    Bright
    Courtesy of RE/MAX ROOTS
    View 17 E Leicester Street Winchester, VA MLS# VAWI2009350
    $430,000
    4

    Beds

    2.0

    Baths

    2,100

    Sq.Ft.

    17 E Leicester Street

    Winchester, VA

    Bright
    Courtesy of MARKETPLACE REALTY

    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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