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Single-Family Homes in Winchester, VA
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3 bedsNew constructionWith a pool

Single-Family Homes in Winchester, VA

Single-Family Homes in Winchester, VA

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24 of 168 Listings
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Single-Family Homes in Winchester, VA

24 of 168 Listings

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #0225245042

Call Thomas
  1. 131 Shirley St — photoNew13Active

    $419,000

    3 bd · 3 ba · 1,453 sqft

    131 Shirley St, Winchester, VA

    Brandon W Pifer · Pifer Realty, LLC

  2. 1748 Handley Ave — photoNew58Active

    $735,000

    3 bd · 3 ba · 2,572 sqft

    1748 Handley Ave, Winchester, VA

    Barbara Jane Smith · RE/MAX Real Estate Connections

  3. 144 Apple Valley Rd — photoNew44Active

    $350,000

    3 bd · 2 ba · 1,317 sqft

    144 Apple Valley Rd, Winchester, VA

    Julie M Teets · ERA Oakcrest Realty, Inc.

  4. 610 Puma Trl — photoNew27Active

    $220,000

    2 bd · 1 ba · 560 sqft

    610 Puma Trl, Winchester, VA

    James Podoley · EXP Realty, LLC

  5. 120 Comanche Trl — photo47Active

    $349,999

    4 bd · 2 ba · 1,812 sqft

    120 Comanche Trl, Winchester, VA

    Michelle L Belford · NextHome Realty Select

  6. 114 Nassau Dr — photo67Active

    $525,000

    4 bd · 4 ba · 3,829 sqft

    114 Nassau Dr, Winchester, VA

    Angela Kim · RE/MAX Galaxy

  7. 178 Payne Rd — photo99Active

    $395,600

    4 bd · 2 ba · 1,860 sqft

    178 Payne Rd, Winchester, VA

    Wanda Garris Miller · Century 21 Redwood Realty

  8. 100 Winns Cir — photo33Active

    $552,000

    4 bd · 3 ba · 2,636 sqft

    100 Winns Cir, Winchester, VA

    Thomas S Hennerty · NetRealtyNow.com, LLC

  9. 314 Huntersridge Rd — photo75Active

    $634,900

    5 bd · 4 ba · 3,856 sqft

    314 Huntersridge Rd, Winchester, VA

    Laura D White · ERA Oakcrest Realty, Inc.

  10. 223 Asbury Rd — photo57Active

    $549,900

    5 bd · 4 ba · 2,824 sqft

    223 Asbury Rd, Winchester, VA

    Mark S Francis · Real Broker LLC- Winchester

  11. 265 McDonald Rd — photo19Active

    $375,000

    3 bd · 2 ba · 1,452 sqft

    265 McDonald Rd, Winchester, VA

    Verria Hairston · Open Door Brokerage, LLC

  12. 991 Front Royal Pike — photo54Active

    $459,900

    3 bd · 2 ba · 1,834 sqft

    991 Front Royal Pike, Winchester, VA

    James W. King, Jr. · Re/Max Roots

  13. 100 Gooseberry Dr — photo67Active

    $515,000

    2 bd · 3 ba · 2,679 sqft

    100 Gooseberry Dr, Winchester, VA

    Lisa A Behr · Hunt Country Sotheby's International Realty

  14. 2700 Loyalty Ct — photo63Active

    $699,000

    7 bd · 5 ba · 4,736 sqft

    2700 Loyalty Ct, Winchester, VA

    Daniel J Whitacre · Colony Realty

  15. 1960 Siler Rd — photo59Active

    $499,900

    3 bd · 2 ba · 1,479 sqft

    1960 Siler Rd, Winchester, VA

    Natasha Roberts · Realty ONE Group Old Towne

  16. 110 Bentpath Ct — photo37Active

    $710,000

    5 bd · 4 ba · 3,946 sqft

    110 Bentpath Ct, Winchester, VA

    Xinli Ji · Realty Aspire

  17. 300 Pembridge Dr — photo48Active

    $439,000

    5 bd · 3 ba · 2,508 sqft

    300 Pembridge Dr, Winchester, VA

    Magnolia L Halkowitz · ERA Oakcrest Realty, Inc.

  18. 128 Alliance Ct — photo32Active

    $550,000

    4 bd · 4 ba · 2,149 sqft

    128 Alliance Ct, Winchester, VA

    Emily Elizabeth Hink · Samson Properties

  19. 900 Enfield Dr — photo56Active

    $380,000

    4 bd · 3 ba · 2,243 sqft

    900 Enfield Dr, Winchester, VA

    Alexandra Lilian Brown · Spring Hill Real Estate, LLC.

  20. 111 Haven Ter — photo2Active

    $300,000

    3 bd · 1 ba · 1,008 sqft

    111 Haven Ter, Winchester, VA

    Erin M Kavanagh · EXP Realty, LLC

  21. 159 Aspen Trl — photo54Active

    $295,000

    2 bd · 3 ba · 2,148 sqft

    159 Aspen Trl, Winchester, VA

    Kimberly C Baggett · EXP Realty, LLC

  22. 127 Mountain View Rd — photo58Active

    $549,900

    4 bd · 3 ba · 2,208 sqft

    127 Mountain View Rd, Winchester, VA

    Josh W Feltner · Realty ONE Group Old Towne

  23. 308 Fawn Dr — photo22Active

    $334,000

    3 bd · 3 ba · 1,680 sqft

    308 Fawn Dr, Winchester, VA

    Steve A DuBrueler · Coldwell Banker Premier

  24. 700 Tomahawk Trl — photo15Active

    $287,000

    3 bd · 1 ba · 1,104 sqft

    700 Tomahawk Trl, Winchester, VA

    Stacy Priddy · Berkshire Hathaway HomeServices PenFed Realty

12…7

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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.
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    Your local brokerage

    TO

    Thomas O'Leary

    Realty.com

    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

    August 2026 · This period is still settling

    Winchester 12-month median sale price trend

    Selling at 99.0% of asking price

    Buyers here are paying below asking. MLS · 86 sales · as of Aug 31, 2026

    Homes that sold · County records, as of Aug 26, 2026

    Median sale price
    $387,990$285,000–$541,000 typical range
    Price per sq. ft.
    $236
    Sales
    85
    Paid in cash
    31.8%

    Homes on the market · MLS, as of Aug 31, 2026

    Median list price
    $429,450
    Homes for sale
    326
    Median days on market
    37 days

    Price trend · Assessor repeat sales, as of Aug 31, 2026

    Year-over-year
    -2.5%

    Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Jul 29, 2026

    Median home size
    1,620 sq. ft.