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5 Bedroom Homes in Winston-Salem, NC
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3 bedsNew constructionWith a pool

5 Bedroom Homes in Winston-Salem, NC

5 Bedroom Homes in Winston-Salem, NC

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23 of 58 Listings
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5 Bedroom Homes in Winston-Salem, NC

23 of 58 Listings

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Thomas O'Leary

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Lic. #300693

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  1. 4362 Eland Court — photoNew40Active

    $399,000

    5 bd · 4 ba · 2,899 sqft

    4362 Eland Court, Winston-Salem, NC

    Tim Russell · Epique Realty

  2. 816 Quail Meadow Drive — photo26Active

    $335,000

    5 bd · 3 ba · 2,511 sqft

    816 Quail Meadow Drive, Winston-Salem, NC

    Elizabeth Ward · DR Horton

  3. 3915 Chadwyck Court — photo49Active

    $439,990

    5 bd · 4 ba · 2,769 sqft

    3915 Chadwyck Court, Winston-Salem, NC

    Helen Howard · KELLER WILLIAMS REALTY

  4. 1893 Latchkey Drive #17 — photo22Active

    $397,625

    5 bd · 3 ba · 2,982 sqft

    1893 Latchkey Drive #17, Winston-Salem, NC

    Kaylee Wilson · TLS Realty LLC

  5. 1875 Paragon Drive — photo43Active

    $499,000

    5 bd · 4 ba · 3,335 sqft

    1875 Paragon Drive, Winston-Salem, NC

    Sophia Karageorgos · World Headquarters of Awesome Inc. DBA Dash Carolina

  6. 337 E Rhyne Avenue — photo30Active

    $299,000

    5 bd · 3 ba · 2,672 sqft

    337 E Rhyne Avenue, Winston-Salem, NC

    Briana Portillo · R&B Legacy Group

  7. 805 Chartwell Circle — photo43Active

    $518,000

    5 bd · 4 ba · 3,362 sqft

    805 Chartwell Circle, Winston-Salem, NC

    Zach Dawson · Mitchell Prime Properties

  8. 4209 Hollowoak Court — photo35Active

    $725,000

    5 bd · 4 ba · 4,351 sqft

    4209 Hollowoak Court, Winston-Salem, NC

    Blake Ginther · Keller Williams Realty Elite

  9. 880 Osprey Ridge Road — photo46Active

    $1,395,000

    5 bd · 5 ba · 5,072 sqft

    880 Osprey Ridge Road, Winston-Salem, NC

    Deana Browder · Leonard Ryden Burr Real Estate

  10. 3773 Quail Haven Drive — photo26Active

    $339,000

    5 bd · 3 ba · 2,511 sqft

    3773 Quail Haven Drive, Winston-Salem, NC

    Elizabeth Ward · DR Horton

  11. 210 Surrey Path Court — photo36Active

    $1,050,000

    5 bd · 4 ba · 4,922 sqft

    210 Surrey Path Court, Winston-Salem, NC

    Blake Ginther · Keller Williams Realty Elite

  12. 4620 Cherryhill Lane — photo45Active

    $1,695,000

    5 bd · 8 ba · 9,404 sqft

    4620 Cherryhill Lane, Winston-Salem, NC

    Melissa Parker · Leonard Ryden Burr Real Estate

  13. 3828 Robbins Brook Drive — photo38Active

    $349,900

    5 bd · 3 ba · 2,402 sqft

    3828 Robbins Brook Drive, Winston-Salem, NC

    Kristi Idol · RE/MAX Preferred Properties

  14. 3055 Scarlet Tanager Drive — photo7Active

    $1,215,000

    5 bd · 4 ba · 3,418 sqft

    3055 Scarlet Tanager Drive, Winston-Salem, NC

    Courtney Pizzitola · Berkshire Hathaway HomeServices Carolinas Realty

  15. 2862 Robinhood Road — photo50Active

    $995,000

    5 bd · 5 ba · 6,032 sqft

    2862 Robinhood Road, Winston-Salem, NC

    Debbie DeBruhl Burns · Leonard Ryden Burr Real Estate

  16. 5603 Hundley Road — photo44Active

    $1,795,000

    5 bd · 5 ba · 4,864 sqft

    5603 Hundley Road, Winston-Salem, NC

    Lloyd Dillon, III · Berkshire Hathaway HomeServices Carolinas Realty

  17. 1708 Indigo Bunting Court — photo32Active

    $1,300,000

    5 bd · 4 ba · 4,161 sqft

    1708 Indigo Bunting Court, Winston-Salem, NC

    Tara Haymore · ERA Live Moore

  18. 3790 Spring Willow Way — photo39Active

    $349,750

    5 bd · 3 ba · 2,890 sqft

    3790 Spring Willow Way, Winston-Salem, NC

    Spencer Harrell · Real Broker LLC

  19. 4926 Leinbach Drive — photo50Active

    $443,900

    5 bd · 3 ba · 2,508 sqft

    4926 Leinbach Drive, Winston-Salem, NC

    Lanisha Haithcock · Triangle Door

  20. 5330 Summer Hill Lane — photo50Active

    $1,275,000

    5 bd · 5 ba · 5,312 sqft

    5330 Summer Hill Lane, Winston-Salem, NC

    Jessica Zombek Ferris · Keller Williams Realty Elite

  21. 727 Royal Jasmine Court — photo48Active

    $1,499,900

    5 bd · 6 ba · 5,101 sqft

    727 Royal Jasmine Court, Winston-Salem, NC

    Victoria L. Boysen · Berkshire Hathaway HomeServices Carolinas Realty

  22. 739 Petree Road — photo44Active

    $418,500

    5 bd · 3 ba · 2,736 sqft

    739 Petree Road, Winston-Salem, NC

    Milly Khowala · Fathom Realty

  23. 709 Royal Jasmine Court — photo49Active

    $2,309,000

    5 bd · 6 ba · 5,831 sqft

    709 Royal Jasmine Court, Winston-Salem, NC

    Emily Dunlap · Berkshire Hathaway HomeServices Carolinas Realty

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About 5 Bedroom Homes in Winston-Salem, NC

5 Bedroom Homes in Winston-Salem, NC: 58 active listings as of November 1, 2026, 08:09 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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Listing information © 2026 Triad MLS, Inc. of North Carolina. All rights reserved. The data relating to real estate for sale on this web site comes in part from the Internet Data Exchange (IDX) Program of the Triad MLS, Inc. of High Point, NC. Real estate listings held by brokerage firms other than Realty.com are marked with the Internet Data Exchange logo or the Internet Data Exchange (IDX) thumbnail logo (the TRIAD MLS logo) and detailed information about them includes the name of the listing brokers. IDX information provided is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information deemed reliable but not guaranteed. Data last updated 2026-10-31 18:51:00 UTC
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    Thomas O'Leary

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    Winston-Salem, NC community profile

    Population
    260,950
    Median income
    $57,150
    Housing units
    114,072
    People per sq. mi.
    1,934.4
    Area
    134.9 sq. mi.

    Source: HJN community data

    Winston-Salem housing market

    October 2026 · This period is still settling

    Winston-Salem 12-month median sale price trend

    Selling at 98.4% of asking price

    Buyers here are paying below asking. MLS · 147 sales · as of Oct 23, 2026

    Homes that sold · County records, as of Oct 8, 2026

    Median sale price
    $250,000$180,500–$387,500 typical range
    Price per sq. ft.
    $143
    Sales
    79
    Paid in cash
    36.7%

    Homes on the market · MLS, as of Oct 18, 2026–Oct 23, 2026

    Median list price
    $285,000
    Homes for sale
    861
    Median days on market
    29 days

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

    Year-over-year
    -1.9%

    Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Sep 30, 2026

    Median home size
    2,040 sq. ft.