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Single-Family Homes in Winchester, VA
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259 listings
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3 bedsNew construction

Single-Family Homes in Winchester, VA

Single-Family Homes in Winchester, VA

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24 of 259 Listings
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Single-Family Homes in Winchester, VA

24 of 259 Listings

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Thomas O'Leary

Realty.com

Lic. #0225245042

Call Thomas
  1. 134 Wilkins Dr — photoNew67Active

    $399,900

    4 bd · 2 ba · 2,886 sqft

    134 Wilkins Dr, Winchester, VA

    Justin Mistretta · Berkshire Hathaway HomeServices PenFed Realty

  2. 15 W Germain St — photoNew15Active

    $219,000

    4 bd · 2 ba · 1,251 sqft

    15 W Germain St, Winchester, VA

    Minh-Thieng T. Le · Levi Clarke, LLC

  3. 2691 Senseny Rd — photo46Active

    $359,900

    3 bd · 1 ba · 1,120 sqft

    2691 Senseny Rd, Winchester, VA

    Daniel J Whitacre · Colony Realty

  4. 18 Williamson Rd — photo25Active

    $598,990

    3 bd · 2 ba · 3,056 sqft

    18 Williamson Rd, Winchester, VA

    Cindy Lorena Gomez · New Home Star Virginia, LLC

  5. 602 Patterson Ave — photo12Active

    $295,000

    3 bd · 1 ba · 1,066 sqft

    602 Patterson Ave, Winchester, VA

    Steven Koleno · BEYCOME BROKERAGE REALTY LLC

  6. 694 Round Hill Rd — photo49Active

    $300,000

    3 bd · 1 ba · 816 sqft

    694 Round Hill Rd, Winchester, VA

    Cynthia Lee · RE/MAX Roots

  7. 113 Malbec Ct — photo28Active

    $677,130

    4 bd · 3 ba · 3,397 sqft

    113 Malbec Ct, Winchester, VA

    Cindy Lorena Gomez · New Home Star Virginia, LLC

  8. 29 Williamson Rd — photo21Active

    $549,990

    4 bd · 3 ba · 3,747 sqft

    29 Williamson Rd, Winchester, VA

    Cindy Lorena Gomez · New Home Star Virginia, LLC

  9. 230 Crinoline Ln — photo7Active

    $479,777

    3 bd · 2 ba · 1,232 sqft

    230 Crinoline Ln, Winchester, VA

    Leo J Smith · CENTURY 21 New Millennium

  10. 508 Lanny Dr — photo40Active

    $400,000

    3 bd · 2 ba · 2,185 sqft

    508 Lanny Dr, Winchester, VA

    Marcella S Cantatore · Corcoran McEnearney

  11. 381 Hidden Valley Ln — photo98Active

    $699,000

    3 bd · 2 ba · 1,778 sqft

    381 Hidden Valley Ln, Winchester, VA

    Daniel J Whitacre · Colony Realty

  12. 2018 Colin Dr — photo54Active

    $499,000

    3 bd · 3 ba · 2,510 sqft

    2018 Colin Dr, Winchester, VA

    Angela R. Duncan · MarketPlace REALTY

  13. 134 Hudson Ave — photo52Active

    $375,000

    4 bd · 2 ba · 2,322 sqft

    134 Hudson Ave, Winchester, VA

    Cara L Wilkins · MarketPlace REALTY

  14. 1785 Berryville Pike — photo7Active

    $199,000

    2 bd · 1 ba · 718 sqft

    1785 Berryville Pike, Winchester, VA

    Meridee A Powars · Link Realty Services LLC

  15. 117 Amberfield Ct — photo18Active

    $493,000

    3 bd · 2 ba · 1,784 sqft

    117 Amberfield Ct, Winchester, VA

    Verria Hairston · Open Door Brokerage, LLC

  16. 1281 Merrimans Ln — photo107Active

    $2,500,000

    4 bd · 7 ba · 6,219 sqft

    1281 Merrimans Ln, Winchester, VA

    Dallas D Croft · Samson Properties

  17. 460 Cattail Rd — photo78Active

    $624,000

    4 bd · 4 ba · 3,290 sqft

    460 Cattail Rd, Winchester, VA

    Ned S Stock · Berkshire Hathaway HomeServices PenFed Realty

  18. 757 Seldon Dr — photo53Active

    $867,500

    4 bd · 4 ba · 3,057 sqft

    757 Seldon Dr, Winchester, VA

    Kara Koonce · Weichert, REALTORS

  19. 127 Wappinger Ter — photo34Active

    $559,990

    6 bd · 4 ba · 3,127 sqft

    127 Wappinger Ter, Winchester, VA

    Victoria Jane Clark · D R Horton Realty of Virginia LLC

  20. 827 Buckner Dr — photo41Active

    $610,000

    3 bd · 2 ba · 1,951 sqft

    827 Buckner Dr, Winchester, VA

    Stuart A Sinclair · Coldwell Banker Premier

  21. 3298 Shawnee Dr — photo40Active

    $395,000

    3 bd · 2 ba · 1,368 sqft

    3298 Shawnee Dr, Winchester, VA

    Harry T Hamilton · CENTURY 21 New Millennium

  22. 125 Fox Dr — photo56Active

    $419,000

    3 bd · 2 ba · 2,228 sqft

    125 Fox Dr, Winchester, VA

    Dana J Ashlock · Samson Properties

  23. 338 E Piccadilly St — photo73Active

    $399,900

    3 bd · 2 ba · 1,422 sqft

    338 E Piccadilly St, Winchester, VA

    Daniel J Whitacre · Colony Realty

  24. 1151 Wardensville Grade — photo93Active

    $700,000

    4 bd · 5 ba · 3,365 sqft

    1151 Wardensville Grade, Winchester, VA

    Leah R REALTOR · Re/Max Roots

12…11

About Single-Family Homes in Winchester, VA

Single-Family Homes in Winchester, VA: 259 active listings as of November 1, 2026, 02:49 UTC.

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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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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: 2026-10-31 21:59:41 UTC
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    Thomas O'Leary

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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

    Winchester 12-month median sale price trend

    Selling at 100.0% of asking price

    Sales here are closing essentially at asking. MLS · 92 sales · as of Sep 30, 2026

    Homes that sold · County records, as of Sep 30, 2026

    Median sale price
    $399,500$307,713–$580,625 typical range
    Price per sq. ft.
    $252
    Sales
    120
    Paid in cash
    35.8%

    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
    32 days

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

    Year-over-year
    -6.1%

    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.