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2 Bedroom Homes in Winchester, VA
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3 bedsNew construction

2 Bedroom Homes in Winchester, VA

2 Bedroom Homes in Winchester, VA

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24 of 42 Listings
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2 Bedroom Homes in Winchester, VA

24 of 42 Listings

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Thomas O'Leary

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  1. 161 Brookland Ct #6 — photo1Active

    $244,900

    2 bd · 2 ba · 1,257 sqft

    161 Brookland Ct #6, Winchester, VA

    Paul J Gallagher Jr. · Colony Realty

  2. 133 Blackfeet Trl — photo52Active

    $249,000

    2 bd · 1 ba · 756 sqft

    133 Blackfeet Trl, Winchester, VA

    Stephanie Feltner · Realty ONE Group Old Towne

  3. 121 Lighthouse Ln — photo34Active

    $299,900

    2 bd · 2 ba · 1,254 sqft

    121 Lighthouse Ln, Winchester, VA

    Daniel J Whitacre · Colony Realty

  4. 23 Jigsaw Pl — photo21Active

    $229,000

    2 bd · 2 ba · 1,160 sqft

    23 Jigsaw Pl, Winchester, VA

    Wendy R Longerbeam · Coldwell Banker Elite

  5. 611 Fawn Dr — photo31Active

    $289,900

    2 bd · 1 ba · 1,577 sqft

    611 Fawn Dr, Winchester, VA

    Kathrin Donovan · Keller Williams Realty

  6. 451 Lake Serene Dr — photoPrice Reduced102Active

    $759,000

    2 bd · 4 ba · 3,900 sqft

    451 Lake Serene Dr, Winchester, VA

    John S Scully IV · Colony Realty

  7. 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.

  8. 316 Crow Dr — photo16Active

    $240,000

    2 bd · 1 ba · 906 sqft

    316 Crow Dr, Winchester, VA

    Matthew Peter Streiff · Keller Williams Realty

  9. 3016 Siler Rd — photo80Active

    $649,900

    2 bd · 1 ba · 825 sqft

    3016 Siler Rd, Winchester, VA

    Edward L Beightol III · Cedar Creek Real Estate

  10. 828 Woodland Ave — photo40Active

    $298,900

    2 bd · 2 ba · 1,079 sqft

    828 Woodland Ave, Winchester, VA

    Sylvia R Stoneberger · Samson Properties

  11. 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

  12. 2660 Daniel Ter — photo20Active

    $335,000

    2 bd · 2 ba · 1,352 sqft

    2660 Daniel Ter, Winchester, VA

    Elizabeth P Boxwell · MarketPlace REALTY

  13. 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

  14. 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.

  15. 310 Bellview Ave — photo26Active

    $300,000

    2 bd · 1 ba · 1,097 sqft

    310 Bellview Ave, Winchester, VA

    Cynthia K. Greenya · Keller Williams Realty

  16. 102 Buckwood Ln — photo24Active

    $368,000

    2 bd · 2 ba · 1,424 sqft

    102 Buckwood Ln, Winchester, VA

    Kathryn A Symenow · CENTURY 21 New Millennium

  17. 107 Little River Dr — photoPrice Reduced23Active

    $250,000

    2 bd · 1 ba · 900 sqft

    107 Little River Dr, Winchester, VA

    Erin M Kavanagh · EXP Realty, LLC

  18. 100 Gooseberry Dr — photoPrice Reduced30Active

    $499,000

    2 bd · 3 ba · 2,679 sqft

    100 Gooseberry Dr, Winchester, VA

    Lisa A Behr · Hunt Country Sotheby's International Realty

  19. 531 Cedar Grove Rd — photoPrice Reduced83Active

    $659,900

    2 bd · 1 ba · 1,540 sqft

    531 Cedar Grove Rd, Winchester, VA

    Tyler Franklin Hazelwood · Virginia Real Estate

  20. 1847 Melvor Ln — photoPrice Reduced98Active

    $339,900

    2 bd · 2 ba · 1,234 sqft

    1847 Melvor Ln, Winchester, VA

    Lisette B. Turner · Century 21 Redwood Realty

  21. 1125 Conway St — photo25Active

    $250,000

    2 bd · 1 ba · 870 sqft

    1125 Conway St, Winchester, VA

    Curtis W Siever · NextHome Realty Select

  22. 187 Valley Mill Rd — photoPrice Reduced17Active

    $220,000

    2 bd · 1 ba · 997 sqft

    187 Valley Mill Rd, Winchester, VA

    Heloisa P Amar · Samson Properties

  23. 103 E Germain St — photoPrice Reduced78Active

    $240,000

    2 bd · 2 ba · 1,068 sqft

    103 E Germain St, Winchester, VA

    Roxanna D Grimes · RE/MAX Roots

  24. 123 Harvest Ridge Dr — photoPrice Reduced62Active

    $549,000

    2 bd · 2 ba · 2,205 sqft

    123 Harvest Ridge Dr, Winchester, VA

    Brian Keith Yoder · Realty ONE Group Old Towne

12

About 2 Bedroom Homes in Winchester, VA

2 Bedroom Homes in Winchester, VA: 42 active listings as of October 23, 2026, 07:06 UTC.

Property types among these 42 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 Residence2559.5%
Townhouse921.4%
Condominium614.3%

Explore Winchester homes

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  • Homes Under $300K
  • Homes Under $400K
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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: 2026-10-23 04:12:23 UTC
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    TO

    Thomas O'Leary

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    Lic. #0225245042

    Call Thomas

    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

    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 30, 2026

    Median sale price
    $399,000$306,725–$581,250 typical range
    Price per sq. ft.
    $252
    Sales
    119
    Paid in cash
    36.1%

    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
    -6.3%

    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.