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Homes Under $400K in Winchester, VA
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161 listings
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3 bedsNew construction

Homes Under $400K in Winchester, VA

Homes Under $400K in Winchester, VA

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24 of 161 Listings
Map

Homes Under $400K in Winchester, VA

24 of 161 Listings

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #0225245042

Call Thomas
  1. 121 Duwamish Trl — photoNew34Active

    $339,900

    3 bd · 2 ba · 1,570 sqft

    121 Duwamish Trl, Winchester, VA

    Harry T Hamilton · CENTURY 21 New Millennium

  2. 1308 Commerce — photo44Active

    $299,900

    3 bd · 1 ba · 2,228 sqft

    1308 Commerce, Winchester, VA

    Jeanne Mezzatesta · Colony Realty

  3. 828 Woodland Ave — photo40Active

    $298,900

    2 bd · 2 ba · 1,079 sqft

    828 Woodland Ave, Winchester, VA

    Sylvia R Stoneberger · Samson Properties

  4. 111 Glendale Cir — photo40Active

    $399,900

    4 bd · 3 ba · 1,932 sqft

    111 Glendale Cir, Winchester, VA

    Josh W Feltner · Realty ONE Group Old Towne

  5. 118 Shuoner Ct — photo26Active

    $374,990

    3 bd · 3 ba · 2,000 sqft

    118 Shuoner Ct, Winchester, VA

    James Thomas · New Home Star Virginia, LLC

  6. Homesite 40 Shuoner Ct — photo22Active

    $399,999

    4 bd · 4 ba · 2,250 sqft

    Homesite 40 Shuoner Ct, Winchester, VA

    James Thomas · New Home Star Virginia, LLC

  7. 136-9 Brookland Ct #9 — photo32Active

    $249,900

    2 bd · 2 ba · 1,173 sqft

    136-9 Brookland Ct #9, Winchester, VA

    Daniel J Whitacre · Colony Realty

  8. 1013 Orchard Hill Dr — photo33Active

    $299,900

    3 bd · 2 ba · 1,648 sqft

    1013 Orchard Hill Dr, Winchester, VA

    Josh W Feltner · Realty ONE Group Old Towne

  9. Homesite 3 Monteith Dr — photo36Active

    $376,990

    3 bd · 4 ba · 1,806 sqft

    Homesite 3 Monteith Dr, Winchester, VA

    Brittany Newman · DRB Group Realty, LLC

  10. 132 White Pine Ln — photo30Active

    $225,000

    2 bd · 1 ba · 0 sqft

    132 White Pine Ln, Winchester, VA

    Shannon N Willett · Long & Foster Real Estate, Inc.

  11. 5 E Hart St — photo29Active

    $284,900

    2 bd · 3 ba · 1,540 sqft

    5 E Hart St, Winchester, VA

    Leah Stafford Marabella · Realty ONE Group Old Towne

  12. 3 S Euclid Ave — photo11Active

    $305,500

    3 bd · 2 ba · 1,350 sqft

    3 S Euclid Ave, Winchester, VA

    Tina Marie Jacobin · Main Street Realty

  13. 1 E Hart St — photo25Active

    $299,900

    4 bd · 3 ba · 1,680 sqft

    1 E Hart St, Winchester, VA

    Leah Stafford Marabella · Realty ONE Group Old Towne

  14. 129 Rappahannock Trl — photo36Active

    $329,000

    3 bd · 2 ba · 2,103 sqft

    129 Rappahannock Trl, Winchester, VA

    Alexandra H Chism · Loudoun Ridge Realty, LLC

  15. 621 Patterson Ave — photoPrice Reduced34Active

    $357,000

    4 bd · 3 ba · 2,050 sqft

    621 Patterson Ave, Winchester, VA

    Leslie A. Webb · Long & Foster Real Estate, Inc.

  16. 245 Glenridge Drive — photo52Active

    $379,900

    4 bd · 3 ba · 1,572 sqft

    245 Glenridge Drive, Winchester, VA

    Susan Susan Raburn · Long & Foster Real Estate, Inc.

  17. 208 Lauck Dr — photoPrice Reduced17Active

    $378,000

    3 bd · 2 ba · 1,486 sqft

    208 Lauck Dr, Winchester, VA

    Richard L Guthrie · Keller Williams Realty

  18. 103 Elaine Dr — photo44Active

    $379,900

    3 bd · 2 ba · 1,452 sqft

    103 Elaine Dr, Winchester, VA

    Pamela Baber · Coldwell Banker Premier

  19. 302 Doe Trl Trl SW — photo15Active

    $235,000

    2 bd · 1 ba · 2,335 sqft

    302 Doe Trl Trl SW, Winchester, VA

    Avis Drummond · Long & Foster Real Estate, Inc.

  20. 123 Averrell Ave — photo50Active

    $139,000

    3 bd · 3 ba · 2,016 sqft

    123 Averrell Ave, Winchester, VA

    mazin A abdelhameid · Spring Hill Real Estate, LLC.

  21. 422 Granite Ridge Dr — photo42Active

    $394,990

    3 bd · 3 ba · 1,752 sqft

    422 Granite Ridge Dr, Winchester, VA

    Elizabeth Ellis · Brookfield Mid-Atlantic Brokerage, LLC

  22. 310 Bellview Ave — photo26Active

    $300,000

    2 bd · 1 ba · 1,097 sqft

    310 Bellview Ave, Winchester, VA

    Cynthia K. Greenya · Keller Williams Realty

  23. 141 Sioux Loop — photo44Active

    $389,160

    4 bd · 4 ba · 1,889 sqft

    141 Sioux Loop, Winchester, VA

    Victoria Jane Clark · D R Horton Realty of Virginia LLC

  24. Homesite 126 Monteith Dr — photo39Active

    $384,990

    3 bd · 4 ba · 1,756 sqft

    Homesite 126 Monteith Dr, Winchester, VA

    Brittany Newman · DRB Group Realty, LLC

12…7

About Homes Under $400K in Winchester, VA

Homes Under $400K in Winchester, VA: 161 active listings as of October 1, 2026, 20:16 UTC.

Property types among these 161 listings, by the property type each listing’s MLS reports, spelled as the MLS spells it. Types with fewer than 5 listings, and listings whose MLS reports no type, are not shown, so the shares can total less than 100%.
Property typeListingsShare
Single Family Residence8552.8%
Townhouse3421.1%
Condominium138.1%

Explore Winchester homes

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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. Listing data is derived from various Multiple Listing Services; each source MLS and its required disclaimer are shown with the listings on the applicable page. Realty.com is an independently owned and operated brokerage.

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Listing data & MLS disclosures

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The data relating to real estate for sale on this website appears in part through the BRIGHT Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms in which Realty.com participates, and is provided by BRIGHT through a licensing agreement. 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 Closed or are no longer being offered for sale.
Listing information ©2026 BRIGHT MLS®. All Rights Reserved, Information deemed reliable but not guaranteed. Data Last Updated: 2026-10-01 17:17:15 UTC
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    Thomas O'Leary

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    Lic. #0225245042

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    Winchester, VA community profile

    Population
    27,805
    Median income
    $66,091
    Housing units
    12,270
    People per sq. mi.
    128.8
    Area
    215.8 sq. mi.

    Source: HJN community data

    Winchester housing market

    September 2026 · This period is still settling

    Winchester 12-month median sale price trend

    Selling at 100.0% of asking price

    Sales here are closing essentially at asking. MLS · 77 sales · as of Sep 28, 2026

    Homes that sold · County records, as of Sep 11, 2026

    Median sale price
    $386,773$287,500–$523,750 typical range
    Price per sq. ft.
    $255
    Sales
    34
    Paid in cash
    29.4%

    Homes on the market · MLS, as of Sep 27, 2026–Sep 28, 2026

    Median list price
    $422,495
    Homes for sale
    334
    Median days on market
    28 days

    Price trend · Assessor repeat sales, as of Sep 30, 2026

    Year-over-year
    -12.1%

    Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Sep 2, 2026

    Median home size
    1,620 sq. ft.