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Homes Under $500K in Winthrop, MA
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3 bedsNew constructionWith a pool

Homes Under $500K in Winthrop, MA

Homes Under $500K in Winthrop, MA

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15 Listings
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Homes Under $500K in Winthrop, MA

15 Listings

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #1000018

Call Thomas
  1. 43 Sagamore Ave #1 — photo25Active

    $459,900

    2 bd · 1 ba · 805 sqft

    43 Sagamore Ave #1, Winthrop, MA

    Katelyn E. Sullivan · Coldwell Banker Realty - Boston

  2. 483 Shirley St. #6a — photo10Active

    $309,900

    1 bd · 1 ba · 720 sqft

    483 Shirley St. #6a, Winthrop, MA

    Sharon Tallent · Compass

  3. 34 Underhill Street #4 — photo17Active

    $475,000

    2 bd · 2 ba · 903 sqft

    34 Underhill Street #4, Winthrop, MA

    Reserve Team · Reference Real Estate

  4. 130 Shirley Street #330 — photo18Active

    $499,900

    1 bd · 1 ba · 623 sqft

    130 Shirley Street #330, Winthrop, MA

  5. 10 Somerset U.305 — photo18Active

    $473,900

    1 bd · 1 ba · 693 sqft

    10 Somerset U.305, Winthrop, MA

  6. 22 Pauline St. #3 — photo19Active

    $399,900

    1 bd · 1 ba · 500 sqft

    22 Pauline St. #3, Winthrop, MA

    Highland Group · Compass

  7. 22 Pauline St. #5 — photo20Active

    $419,900

    1 bd · 1 ba · 525 sqft

    22 Pauline St. #5, Winthrop, MA

    Highland Group · Compass

  8. 175 Shirley Street #5 — photo14Active

    $350,000

    2 bd · 1 ba · 649 sqft

    175 Shirley Street #5, Winthrop, MA

  9. 229 Washington Ave #3a — photo7Active

    $219,999

    1 bd · 1 ba · 350 sqft

    229 Washington Ave #3a, Winthrop, MA

  10. 10 Somerset #U304 — photoPrice Reduced10Active

    $397,900

    1 bd · 1 ba · 546 sqft

    10 Somerset #U304, Winthrop, MA

  11. 1 Seal Harbor #210 — photoPrice Reduced39Active

    $479,900

    1 bd · 1 ba · 947 sqft

    1 Seal Harbor #210, Winthrop, MA

    Rita Angelesco · LAER Realty Partners

  12. 600 Shirley St # 7 — photo20Active

    $485,000

    1 bd · 2 ba · 591 sqft

    600 Shirley St # 7, Winthrop, MA

  13. 53 Trident Ave #301 — photoPrice Reduced26Active

    $365,000

    2 bd · 1 ba · 677 sqft

    53 Trident Ave #301, Winthrop, MA

    Amanda Woodward · Coldwell Banker Realty - Boston

  14. 800 Governors Dr #6 — photo3Active

    $340,000

    2 bd · 1 ba · 772 sqft

    800 Governors Dr #6, Winthrop, MA

  15. 600 Shirley #4 — photoPrice Reduced29Active

    $384,888

    1 bd · 2 ba · 585 sqft

    600 Shirley #4, Winthrop, MA

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Listing information ©2026 MLS Property Information Network, Inc®. All Rights Reserved. Last Updated: 2026-09-28 07:05:00 UTC
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    Your local brokerage

    TO

    Thomas O'Leary

    Realty.com

    Lic. #1000018

    Call Thomas

    Winthrop, MA community profile

    Area
    3.2 sq. mi.

    Source: HJN community data

    Winthrop housing market

    August 2026 · This period is still settling

    Selling at 100.0% of asking price

    Sales here are closing essentially at asking. MLS · 11 sales · as of Aug 31, 2026

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

    Median list price
    $607,500
    Homes for sale
    64
    Median days on market
    30 days

    Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Aug 13, 2026

    Median home size
    1,880 sq. ft.