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2 Bedroom Homes in Winthrop, MA
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3 bedsNew constructionWith a pool

2 Bedroom Homes in Winthrop, MA

2 Bedroom Homes in Winthrop, MA

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23 Listings
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2 Bedroom Homes in Winthrop, MA

23 Listings

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Thomas O'Leary

Realty.com

Lic. #1000018

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  1. 194 Washington Ave #2 — photo21Active

    $600,000

    2 bd · 2 ba · 912 sqft

    194 Washington Ave #2, Winthrop, MA

  2. 550 Pleasant St #201 — photo29Active

    $710,000

    2 bd · 2 ba · 1,192 sqft

    550 Pleasant St #201, Winthrop, MA

  3. 194 Washington Ave #4 — photo18Active

    $550,000

    2 bd · 2 ba · 756 sqft

    194 Washington Ave #4, Winthrop, MA

  4. 10 Somerset #402U — photo35Active

    $606,900

    2 bd · 2 ba · 1,024 sqft

    10 Somerset #402U, Winthrop, MA

  5. 1001 Shirley St #3 — photo14Active

    $775,000

    2 bd · 3 ba · 1,551 sqft

    1001 Shirley St #3, Winthrop, MA

  6. 15 Ocean Ave #203 — photo32Active

    $524,900

    2 bd · 3 ba · 1,210 sqft

    15 Ocean Ave #203, Winthrop, MA

  7. 35 Somerset #3a — photo18Active

    $549,900

    2 bd · 2 ba · 969 sqft

    35 Somerset #3a, Winthrop, MA

  8. 1001 Shirley St #2 — photo22Active

    $865,000

    2 bd · 3 ba · 1,806 sqft

    1001 Shirley St #2, Winthrop, MA

  9. 1 Seal Harbor Rd #413 — photoPrice Reduced40Active

    $549,999

    2 bd · 2 ba · 1,205 sqft

    1 Seal Harbor Rd #413, Winthrop, MA

  10. 21 Hutchinson St #2 — photo25Active

    $629,000

    2 bd · 3 ba · 1,463 sqft

    21 Hutchinson St #2, Winthrop, MA

  11. 175 Shirley Street #5 — photo14Active

    $350,000

    2 bd · 1 ba · 649 sqft

    175 Shirley Street #5, Winthrop, MA

  12. 12 Sewall Ave #2B — photo27Active

    $555,000

    2 bd · 2 ba · 874 sqft

    12 Sewall Ave #2B, Winthrop, MA

  13. 1 Seal Harbor Rd. #615 — photoPrice Reduced36Active

    $585,000

    2 bd · 2 ba · 1,203 sqft

    1 Seal Harbor Rd. #615, Winthrop, MA

  14. 16 Billows Street #B — photo15Active

    $549,000

    2 bd · 1 ba · 928 sqft

    16 Billows Street #B, Winthrop, MA

  15. 3 Seal Harbor #336 — photo42Active

    $859,900

    2 bd · 2 ba · 1,674 sqft

    3 Seal Harbor #336, Winthrop, MA

  16. 1 Seal Harbor Rd #815 — photoPrice Reduced24Active

    $615,000

    2 bd · 2 ba · 1,203 sqft

    1 Seal Harbor Rd #815, Winthrop, MA

  17. 53 Trident Ave #301 — photoPrice Reduced26Active

    $379,000

    2 bd · 1 ba · 677 sqft

    53 Trident Ave #301, Winthrop, MA

  18. 52 Trident Ave #52 — photoPrice Reduced27Active

    $495,000

    2 bd · 1 ba · 1,006 sqft

    52 Trident Ave #52, Winthrop, MA

  19. 53 Trident # 303 — photoPrice Reduced17Active

    $399,900

    2 bd · 1 ba · 664 sqft

    53 Trident # 303, Winthrop, MA

  20. 800 Governors Dr #6 — photo3Active

    $340,000

    2 bd · 1 ba · 772 sqft

    800 Governors Dr #6, Winthrop, MA

  21. 43 Sagamore Ave #1a — photoPrice Reduced21Active

    $485,000

    2 bd · 1 ba · 913 sqft

    43 Sagamore Ave #1a, Winthrop, MA

  22. 142 Pleasant Street #12 — photoPrice Reduced33Active

    $585,000

    2 bd · 2 ba · 1,141 sqft

    142 Pleasant Street #12, Winthrop, MA

  23. 3 Seal Harbor Road #342 — photoPrice Reduced42Active

    $639,000

    2 bd · 2 ba · 1,302 sqft

    3 Seal Harbor Road #342, Winthrop, MA

Explore Winthrop homes

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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

    July 2026

    Winthrop 12-month median sale price trend

    Selling at 100.0% of asking price

    Sales here are closing essentially at asking. MLS · 10 sales · as of Jul 31, 2026

    Homes that sold · County records, as of Jul 31, 2026

    Median sale price
    $725,000$467,500–$947,000 typical range
    Price per sq. ft.
    $372
    Sales
    15
    Paid in cash
    26.7%

    Homes on the market · MLS, as of Jul 21, 2026–Jul 31, 2026

    Median list price
    $649,000
    Homes for sale
    60
    Median days on market
    24 days

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

    Year-over-year
    -14.6%

    Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Jul 14, 2026

    Median home size
    1,715 sq. ft.