7,545

Winthrop, MA Homes

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  • 142 Pleasant St Unit 5, Winthrop, MA 02152
    142 Pleasant St Unit 5, Winthrop, MA 02152
    142 Pleasant St Unit 5, Winthrop, MA 02152
    /23

    $665,000 Sold Aug 27, 2025

    142 Pleasant St Unit 5, Winthrop, MA 02152

    • 2 Beds
    • 2.5 Baths
    • 1,404 Sq Ft
    • Built 1968

    Last Sold Summary

    • 2% Above List Price
    • $474/SF
    • 2 Days On Market

    Current Estimated Value $658,923

    Last Listing Agent Felicia Giuliano Classified Realty Group

    142 Pleasant St Unit 5, Winthrop, MA 02152
    • 162 Circuit Rd, Winthrop, MA 02152
      162 Circuit Rd, Winthrop, MA 02152
      162 Circuit Rd, Winthrop, MA 02152
      /42

      Est $956,635 Not Listed For Sale

      • 6 Beds
      • 2.5 Baths
      • 2,649 Sq Ft

      162 Circuit Rd, Winthrop, MA 02152

      162 Circuit Rd, Winthrop, MA 02152
  • 67 Bay View Ave Unit 1L, Winthrop, MA 02152
    67 Bay View Ave Unit 1L, Winthrop, MA 02152
    67 Bay View Ave Unit 1L, Winthrop, MA 02152
    /27

    $635,000 Sold May 09, 2025

    67 Bay View Ave Unit 1L, Winthrop, MA 02152

    • 2 Beds
    • 2 Baths
    • 1,200 Sq Ft
    • Built 1910

    Last Sold Summary

    • $529/SF
    • 4 Days On Market

    Last Listing Agent The Reference Group Reference Real Estate

    67 Bay View Ave Unit 1L, Winthrop, MA 02152
    • 65 Beacon St, Winthrop, MA 02152
      65 Beacon St, Winthrop, MA 02152
      65 Beacon St, Winthrop, MA 02152
      /22

      Est $890,501 Not Listed For Sale

      • 6 Beds
      • 4 Baths
      • 3,360 Sq Ft

      65 Beacon St, Winthrop, MA 02152

      65 Beacon St, Winthrop, MA 02152
  • 550 Pleasant St Unit 209, Winthrop, MA 02152
    550 Pleasant St Unit 209, Winthrop, MA 02152
    550 Pleasant St Unit 209, Winthrop, MA 02152
    /31

    $545,000 Sold Jun 04, 2025

    550 Pleasant St Unit 209, Winthrop, MA 02152

    • 1 Bed
    • 1 Bath
    • 999 Sq Ft
    • Built 2006

    Last Sold Summary

    • 1% Below List Price
    • $546/SF
    • 3 Days On Market

    Current Estimated Value $533,761

    Last Listing Agent The Reference Group Reference Real Estate

    550 Pleasant St Unit 209, Winthrop, MA 02152
    • 73 Crystal Cove Ave, Winthrop, MA 02152
      73 Crystal Cove Ave, Winthrop, MA 02152
      73 Crystal Cove Ave, Winthrop, MA 02152
      /17

      Est $762,872 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 1,542 Sq Ft

      73 Crystal Cove Ave, Winthrop, MA 02152

      73 Crystal Cove Ave, Winthrop, MA 02152
    • 39 Cottage Ave, Winthrop, MA 02152
      39 Cottage Ave, Winthrop, MA 02152
      39 Cottage Ave, Winthrop, MA 02152
      /38

      Est $840,271 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 4,345 Sq Ft

      39 Cottage Ave, Winthrop, MA 02152

      39 Cottage Ave, Winthrop, MA 02152
    • 59 Cottage Ave, Winthrop, MA 02152
      59 Cottage Ave, Winthrop, MA 02152
      59 Cottage Ave, Winthrop, MA 02152
      /25

      Est $960,444 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 1,818 Sq Ft

      59 Cottage Ave, Winthrop, MA 02152

      59 Cottage Ave, Winthrop, MA 02152
    • 106 Cottage Ave, Winthrop, MA 02152
      106 Cottage Ave, Winthrop, MA 02152
      106 Cottage Ave, Winthrop, MA 02152
      /34

      Est $940,868 Not Listed For Sale

      • 5 Beds
      • 1.5 Baths
      • 3,000 Sq Ft

      106 Cottage Ave, Winthrop, MA 02152

      106 Cottage Ave, Winthrop, MA 02152
    • 31 Prospect Ave, Winthrop, MA 02152
      31 Prospect Ave, Winthrop, MA 02152
      31 Prospect Ave, Winthrop, MA 02152
      /30

      Est $599,532 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 1,657 Sq Ft

      31 Prospect Ave, Winthrop, MA 02152

      31 Prospect Ave, Winthrop, MA 02152
    • 46 Orlando Ave, Winthrop, MA 02152
      46 Orlando Ave, Winthrop, MA 02152
      46 Orlando Ave, Winthrop, MA 02152
      /25

      Est $1,067,618 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 2,044 Sq Ft

      46 Orlando Ave, Winthrop, MA 02152

      46 Orlando Ave, Winthrop, MA 02152
    • 124 Terrace Ave, Winthrop, MA 02152
      124 Terrace Ave, Winthrop, MA 02152
      124 Terrace Ave, Winthrop, MA 02152
      /42

      Est $721,600 Not Listed For Sale

      • 4 Beds
      • 1.5 Baths
      • 1,866 Sq Ft

      124 Terrace Ave, Winthrop, MA 02152

      124 Terrace Ave, Winthrop, MA 02152
    • 90 Terrace Ave Unit 1, Winthrop, MA 02152
      90 Terrace Ave Unit 1, Winthrop, MA 02152
      90 Terrace Ave Unit 1, Winthrop, MA 02152
      /22

      Est $532,751 Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 1,228 Sq Ft

      90 Terrace Ave Unit 1, Winthrop, MA 02152

      90 Terrace Ave Unit 1, Winthrop, MA 02152
    • 799 Shirley St, Winthrop, MA 02152
      799 Shirley St, Winthrop, MA 02152
      799 Shirley St, Winthrop, MA 02152
      /22

      Est $1,224,257 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 3,115 Sq Ft

      799 Shirley St, Winthrop, MA 02152

      799 Shirley St, Winthrop, MA 02152
    • 829 Shirley St, Winthrop, MA 02152
      829 Shirley St, Winthrop, MA 02152
      829 Shirley St, Winthrop, MA 02152
      /42

      Est $692,290 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 1,456 Sq Ft

      829 Shirley St, Winthrop, MA 02152

      829 Shirley St, Winthrop, MA 02152
    • 885 Shirley St, Winthrop, MA 02152
      885 Shirley St, Winthrop, MA 02152
      885 Shirley St, Winthrop, MA 02152
      /34

      Est $725,649 Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 1,211 Sq Ft

      885 Shirley St, Winthrop, MA 02152

      885 Shirley St, Winthrop, MA 02152
    • 921 Shirley St, Winthrop, MA 02152
      921 Shirley St, Winthrop, MA 02152
      921 Shirley St, Winthrop, MA 02152
      /39

      Est $787,033 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,786 Sq Ft

      921 Shirley St, Winthrop, MA 02152

      921 Shirley St, Winthrop, MA 02152
    • 29 Brewster Ave, Winthrop, MA 02152
      29 Brewster Ave, Winthrop, MA 02152
      29 Brewster Ave, Winthrop, MA 02152
      /34

      Est $1,007,113 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 2,464 Sq Ft

      29 Brewster Ave, Winthrop, MA 02152

      29 Brewster Ave, Winthrop, MA 02152
    • 33 Bay View Ave, Winthrop, MA 02152
      33 Bay View Ave, Winthrop, MA 02152
      33 Bay View Ave, Winthrop, MA 02152
      /33

      Est $574,875 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 931 Sq Ft

      33 Bay View Ave, Winthrop, MA 02152

      33 Bay View Ave, Winthrop, MA 02152
    • 29 Undine Ave Unit 31, Winthrop, MA 02152
      29 Undine Ave Unit 31, Winthrop, MA 02152
      29 Undine Ave Unit 31, Winthrop, MA 02152
      /22

      Est $553,327 Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 1,300 Sq Ft

      29 Undine Ave Unit 31, Winthrop, MA 02152

      29 Undine Ave Unit 31, Winthrop, MA 02152
    • 97 Triton Ave Unit 99, Winthrop, MA 02152
      97 Triton Ave Unit 99, Winthrop, MA 02152
      97 Triton Ave Unit 99, Winthrop, MA 02152
      /42

      Est $664,339 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 1,496 Sq Ft

      97 Triton Ave Unit 99, Winthrop, MA 02152

      97 Triton Ave Unit 99, Winthrop, MA 02152
    • 9 Elliot St, Winthrop, MA 02152
      9 Elliot St, Winthrop, MA 02152
      9 Elliot St, Winthrop, MA 02152
      /25

      Est $729,200 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 1,736 Sq Ft

      9 Elliot St, Winthrop, MA 02152

      9 Elliot St, Winthrop, MA 02152
    • 23 Tafts Ave, Winthrop, MA 02152
      23 Tafts Ave, Winthrop, MA 02152
      23 Tafts Ave, Winthrop, MA 02152
      /42

      Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 1,851 Sq Ft

      23 Tafts Ave, Winthrop, MA 02152

      23 Tafts Ave, Winthrop, MA 02152
    • 95 Bay View Ave, Winthrop, MA 02152
      95 Bay View Ave, Winthrop, MA 02152
      95 Bay View Ave, Winthrop, MA 02152
      /40

      Est $651,586 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,171 Sq Ft

      95 Bay View Ave, Winthrop, MA 02152

      95 Bay View Ave, Winthrop, MA 02152
    • 51 Undine Ave, Winthrop, MA 02152
      51 Undine Ave, Winthrop, MA 02152
      51 Undine Ave, Winthrop, MA 02152
      /20

      Est $507,860 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 1,064 Sq Ft

      51 Undine Ave, Winthrop, MA 02152

      51 Undine Ave, Winthrop, MA 02152
    • 55 Undine Ave, Winthrop, MA 02152
      55 Undine Ave, Winthrop, MA 02152
      55 Undine Ave, Winthrop, MA 02152
      /20

      Est $565,034 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,020 Sq Ft

      55 Undine Ave, Winthrop, MA 02152

      55 Undine Ave, Winthrop, MA 02152
    • 91 Undine Ave, Winthrop, MA 02152
      91 Undine Ave, Winthrop, MA 02152
      91 Undine Ave, Winthrop, MA 02152
      /27

      Est $731,757 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 1,586 Sq Ft

      91 Undine Ave, Winthrop, MA 02152

      91 Undine Ave, Winthrop, MA 02152
    • 7 Siren St, Winthrop, MA 02152
      7 Siren St, Winthrop, MA 02152
      7 Siren St, Winthrop, MA 02152
      /40

      Est $918,739 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 2,708 Sq Ft

      7 Siren St, Winthrop, MA 02152

      7 Siren St, Winthrop, MA 02152
    • 27 Siren St, Winthrop, MA 02152
      27 Siren St, Winthrop, MA 02152
      27 Siren St, Winthrop, MA 02152
      /42

      Est $819,020 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 2,934 Sq Ft

      27 Siren St, Winthrop, MA 02152

      27 Siren St, Winthrop, MA 02152
    • 35 Siren St, Winthrop, MA 02152
      35 Siren St, Winthrop, MA 02152
      35 Siren St, Winthrop, MA 02152
      /7

      Est $754,803 Not Listed For Sale

      • 5 Beds
      • 2 Baths
      • 2,280 Sq Ft

      35 Siren St, Winthrop, MA 02152

      35 Siren St, Winthrop, MA 02152
    • 34 Siren St Unit 42, Winthrop, MA 02152
      34 Siren St Unit 42, Winthrop, MA 02152
      34 Siren St Unit 42, Winthrop, MA 02152
      /42

      Est $729,291 Not Listed For Sale

      • 5 Beds
      • 2 Baths
      • 2,032 Sq Ft

      34 Siren St Unit 42, Winthrop, MA 02152

      34 Siren St Unit 42, Winthrop, MA 02152
    • 60 Grand View Ave, Winthrop, MA 02152
      60 Grand View Ave, Winthrop, MA 02152
      60 Grand View Ave, Winthrop, MA 02152
      /35

      Est $709,009 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 1,428 Sq Ft

      60 Grand View Ave, Winthrop, MA 02152

      60 Grand View Ave, Winthrop, MA 02152
    • 70 Triton Ave, Winthrop, MA 02152
      70 Triton Ave, Winthrop, MA 02152
      70 Triton Ave, Winthrop, MA 02152
      /42

      Est $666,823 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,421 Sq Ft

      70 Triton Ave, Winthrop, MA 02152

      70 Triton Ave, Winthrop, MA 02152
    • 151 Strandway, Winthrop, MA 02152
      151 Strandway, Winthrop, MA 02152
      151 Strandway, Winthrop, MA 02152
      /36

      Est $837,462 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,900 Sq Ft

      151 Strandway, Winthrop, MA 02152

      151 Strandway, Winthrop, MA 02152
    • 84 Tafts Ave, Winthrop, MA 02152
      84 Tafts Ave, Winthrop, MA 02152
      84 Tafts Ave, Winthrop, MA 02152
      /15

      Est $585,888 Not Listed For Sale

      • 2 Beds
      • 1.5 Baths
      • 1,200 Sq Ft

      84 Tafts Ave, Winthrop, MA 02152

      84 Tafts Ave, Winthrop, MA 02152
    • 121 Strandway, Winthrop, MA 02152
      121 Strandway, Winthrop, MA 02152
      121 Strandway, Winthrop, MA 02152
      /13

      Est $821,845 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 2,099 Sq Ft

      121 Strandway, Winthrop, MA 02152

      121 Strandway, Winthrop, MA 02152
    • 30 Townsend St, Winthrop, MA 02152
      30 Townsend St, Winthrop, MA 02152
      30 Townsend St, Winthrop, MA 02152
      /34

      Est $658,458 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 1,652 Sq Ft

      30 Townsend St, Winthrop, MA 02152

      30 Townsend St, Winthrop, MA 02152
    • 14 Townsend St, Winthrop, MA 02152
      14 Townsend St, Winthrop, MA 02152
      14 Townsend St, Winthrop, MA 02152
      /21

      Est $609,313 Not Listed For Sale

      • 4 Beds
      • 1 Bath
      • 1,008 Sq Ft

      14 Townsend St, Winthrop, MA 02152

      14 Townsend St, Winthrop, MA 02152
    • 37 Underhill St Unit 1, Winthrop, MA 02152
      37 Underhill St Unit 1, Winthrop, MA 02152
      37 Underhill St Unit 1, Winthrop, MA 02152
      /20

      Est $509,308 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 1,248 Sq Ft

      37 Underhill St Unit 1, Winthrop, MA 02152

      37 Underhill St Unit 1, Winthrop, MA 02152
    • 47 Tileston Rd Unit 47, Winthrop, MA 02152
      47 Tileston Rd Unit 47, Winthrop, MA 02152
      47 Tileston Rd Unit 47, Winthrop, MA 02152
      /38

      Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 1,980 Sq Ft

      47 Tileston Rd Unit 47, Winthrop, MA 02152

      47 Tileston Rd Unit 47, Winthrop, MA 02152

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Massachusetts Suffolk County Winthrop

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