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3 bedsNew construction
Homes Under $300K in Winchester, VA
56 listings

Homes Under $300K in Winchester, VA

Homes Under $300K in Winchester, VA

Show Map
24 of 56 Listings
Map

Homes Under $300K in Winchester, VA

24 of 56 Listings

  1. 133 Blackfeet Trl — photo52Active

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #0225245042

Call Thomas

$249,000

2 bd · 1 ba · 756 sqft

133 Blackfeet Trl, Winchester, VA

Stephanie Feltner · Realty ONE Group Old Towne

  • 121 Lighthouse Ln — photo34Active

    $299,900

    2 bd · 2 ba · 1,254 sqft

    121 Lighthouse Ln, Winchester, VA

    Daniel J Whitacre · Colony Realty

  • 126 Marple Rd — photo42Active

    $275,000

    3 bd · 2 ba · 1,170 sqft

    126 Marple Rd, Winchester, VA

    Roxanna D Grimes · RE/MAX Roots

  • 23 Jigsaw Pl — photo21Active

    $229,000

    2 bd · 2 ba · 1,160 sqft

    23 Jigsaw Pl, Winchester, VA

    Wendy R Longerbeam · Coldwell Banker Elite

  • 611 Fawn Dr — photo31Active

    $289,900

    2 bd · 1 ba · 1,577 sqft

    611 Fawn Dr, Winchester, VA

    Kathrin Donovan · Keller Williams Realty

  • 508 Emily Ln — photo31Active

    $300,000

    3 bd · 3 ba · 1,296 sqft

    508 Emily Ln, Winchester, VA

    Keren Jayne · Pearson Smith Realty, LLC

  • 1591 Woodstock Ln — photo40Active

    $215,000

    2 bd · 1 ba · 1,535 sqft

    1591 Woodstock Ln, Winchester, VA

    Karen C Diggs · Real Broker LLC- Winchester

  • 329 Fairview Ave — photo13Active

    $255,000

    3 bd · 2 ba · 1,386 sqft

    329 Fairview Ave, Winchester, VA

    Verria Hairston · Open Door Brokerage, LLC

  • 606 Elk Trl — photo59Active

    $289,000

    2 bd · 2 ba · 1,580 sqft

    606 Elk Trl, Winchester, VA

    Philip Virgil Asper · Keller Williams Realty/Lee Beaver & Assoc.

  • 1308 Commerce — photo44Active

    $299,900

    3 bd · 1 ba · 2,228 sqft

    1308 Commerce, Winchester, VA

    Jeanne Mezzatesta · Colony Realty

  • 828 Woodland Ave — photo40Active

    $298,900

    2 bd · 2 ba · 1,079 sqft

    828 Woodland Ave, Winchester, VA

    Sylvia R Stoneberger · Samson Properties

  • 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

  • 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

  • 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

  • 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

  • 251 Waterford Ln — photo46Active

    $279,000

    3 bd · 2 ba · 1,120 sqft

    251 Waterford Ln, Winchester, VA

    Roxanna D Grimes · RE/MAX Roots

  • 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.

  • 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.

  • 310 Bellview Ave — photo26Active

    $300,000

    2 bd · 1 ba · 1,097 sqft

    310 Bellview Ave, Winchester, VA

    Cynthia K. Greenya · Keller Williams Realty

  • 132 Dogwood Trl — photo24Active

    $275,000

    3 bd · 1 ba · 1,296 sqft

    132 Dogwood Trl, Winchester, VA

    Sheila R Pack · RE/MAX Roots

  • 621 Watson Ave — photoPrice Reduced29Active

    $292,500

    3 bd · 2 ba · 1,138 sqft

    621 Watson Ave, Winchester, VA

    Caleb Christen Fowler · Samson Properties

  • 322 Highland Ave — photo35Active

    $289,900

    4 bd · 3 ba · 1,484 sqft

    322 Highland Ave, Winchester, VA

    James Michael Webber · EXP Realty, LLC

  • 107 Little River Dr — photo23Active

    $260,000

    2 bd · 1 ba · 900 sqft

    107 Little River Dr, Winchester, VA

    Erin M Kavanagh · EXP Realty, LLC

  • 114 Tudor Dr — photo42Active

    $289,900

    3 bd · 4 ba · 1,906 sqft

    114 Tudor Dr, Winchester, VA

    Bradley Comstock · ERA Oakcrest Realty, Inc.

  • 123

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    L. Custen Realty, Inc. d/b/a Realty.com/L. Custen Realty CT, LLC d/b/a Realty.com (Tom O’Leary-Broker)(CT properties only), 8323 Southwest Freeway, Suite 900, Houston, Texas 77074

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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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    Your local brokerage

    TO

    Thomas O'Leary

    Realty.com

    Lic. #0225245042

    Call Thomas

    Listing data & MLS disclosures

    Bright MLS
    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: 2026-10-10 00:37:43 UTC

    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 · 91 sales · as of Sep 30, 2026

    Homes that sold · County records, as of Sep 23, 2026

    Median sale price
    $400,000$304,350–$606,625 typical range
    Price per sq. ft.
    $254
    Sales
    87
    Paid in cash
    36.8%

    Homes on the market · MLS, as of Sep 27, 2026–Sep 30, 2026

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

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

    Year-over-year
    -5.4%

    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.