3,427

Downtown Winthrop Homes

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    • 106 Centre St, Winthrop, MA 02152
      106 Centre St, Winthrop, MA 02152
      106 Centre St, Winthrop, MA 02152
      /39

      Est $607,367 Not Listed For Sale

      • 4 Beds
      • 1 Bath
      • 1,053 Sq Ft

      106 Centre St, Winthrop, MA 02152

      106 Centre St, Winthrop, MA 02152
  • 700 Governors Dr Unit 38, Winthrop, MA 02152
    700 Governors Dr Unit 38, Winthrop, MA 02152
    700 Governors Dr Unit 38, Winthrop, MA 02152
    /14

    $392,000 Sold Mar 14, 2025

    • 989 Sq Ft
    • $396/SF
    • 20 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1971

    700 Governors Dr Unit 38, Winthrop, MA 02152

    This top-floor 2-bedroom, 1-bath unit offers an open living/dining area with sliders to a private balcony. The updated kitchen features granite countertops, and the spacious bedrooms are complemented by large full bath. Crown molding and custom-built shelving add charm to the living space. Situated in one of Governors Park’s desirable front buildings, this home comes with great amenities:

    Elizabeth Ferrara Cottage Hill Real Estate

    700 Governors Dr Unit 38, Winthrop, MA 02152
    • 208 Lincoln St, Winthrop, MA 02152
      208 Lincoln St, Winthrop, MA 02152
      208 Lincoln St, Winthrop, MA 02152
      /34

      Est $596,680 Not Listed For Sale

      • 2 Beds
      • 1.5 Baths
      • 1,226 Sq Ft

      208 Lincoln St, Winthrop, MA 02152

      208 Lincoln St, Winthrop, MA 02152
  • 19 Oceanview Way, Winthrop, MA 02152
    19 Oceanview Way, Winthrop, MA 02152
    19 Oceanview Way, Winthrop, MA 02152
    /42

    $960,000 Sold Mar 14, 2025

    • 3,749 Sq Ft
    • $256/SF
    • 6 Days On Market
    • 5 Beds
    • 2 Baths
    • Built 1953

    19 Oceanview Way, Winthrop, MA 02152

    Spectacular 2-Family Home Near the Ocean!Located in a fantastic neighborhood close to the ocean, this freshly updated 2-family home offers both charm and modern convenience. Recent updates include fresh paint, new windows, renovated kitchens, updated bathrooms, new floors, and appliances, plus a newer roof.The upper unit spans two floors, featuring a spacious living room, dining area, three

    Ella Goren Sunrise Realty & Investment LLC

    19 Oceanview Way, Winthrop, MA 02152
    • 81 Hermon St, Winthrop, MA 02152
      81 Hermon St, Winthrop, MA 02152
      81 Hermon St, Winthrop, MA 02152
      /24

      Est $760,973 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,488 Sq Ft

      81 Hermon St, Winthrop, MA 02152

      81 Hermon St, Winthrop, MA 02152
  • 1100 Governors Dr Unit 24, Winthrop, MA 02152
    1100 Governors Dr Unit 24, Winthrop, MA 02152
    1100 Governors Dr Unit 24, Winthrop, MA 02152
    /11

    $332,000 Sold Feb 21, 2025

    • 782 Sq Ft
    • $425/SF
    • 29 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1971

    1100 Governors Dr Unit 24, Winthrop, MA 02152

    This 2 bedroom/1 bath corner unit offers an open living room/dining room with new sliders to a balcony for outdoor space. A nice galley kitchen, two good size bedrooms and a recently renovated full bath. The Governors Park complex has lots of amenities including a laundry room in each building, heat and hot water included in the condo fee, parking for 2 cars and visitor parking too, in-ground

    Quinn Nguyen Engel & Volkers Boston

    1100 Governors Dr Unit 24, Winthrop, MA 02152
    • 42 Centre St, Winthrop, MA 02152
      42 Centre St, Winthrop, MA 02152
      42 Centre St, Winthrop, MA 02152
      /40

      Est $622,517 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 1,258 Sq Ft

      42 Centre St, Winthrop, MA 02152

      42 Centre St, Winthrop, MA 02152
  • 51 Paine St, Winthrop, MA 02152
    51 Paine St, Winthrop, MA 02152
    51 Paine St, Winthrop, MA 02152
    /12

    $605,000 Sold Feb 20, 2025

    • 1,445 Sq Ft
    • $419/SF
    • 5 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1931

    51 Paine St, Winthrop, MA 02152

    New to the market - a spacious single family home in a desirable Winthrop location with an unbeatable price point and no flood insurance. This three bedroom, one bath is the perfect starter home, for those downsizing and everyone in-between. Needs some TLC, but offers plenty of original charm, hardwood floors, off-street parking and more! Updated utilities. Tons of potential - including a large

    Liliana Monroy Century 21 Mario Real Estate

    51 Paine St, Winthrop, MA 02152
    • 26 Centre St, Winthrop, MA 02152
      26 Centre St, Winthrop, MA 02152
      26 Centre St, Winthrop, MA 02152
      /24

      Est $888,744 Not Listed For Sale

      • 6 Beds
      • 4 Baths
      • 3,232 Sq Ft

      26 Centre St, Winthrop, MA 02152

      26 Centre St, Winthrop, MA 02152
  • 19 Buchanan St, Winthrop, MA 02152
    19 Buchanan St, Winthrop, MA 02152
    19 Buchanan St, Winthrop, MA 02152
    /34

    $735,000 Sold Jan 31, 2025

    • 1,563 Sq Ft
    • $470/SF
    • 13 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1900

    19 Buchanan St, Winthrop, MA 02152

    Just steps from Winthrop Center, this charming 3-bedroom 2- bath home offers convenience and character. Enjoy an open-concept living space with hardwood floors and recessed lighting. Upon entry, you’re greeted by a cozy sitting room with a gas fireplace, leading to a spacious living room that flows into an eat-in kitchen with exposed brick, granite countertops, stainless steel appliances, and a

    Elizabeth Ferrara Cottage Hill Real Estate

    19 Buchanan St, Winthrop, MA 02152
    • 41 Beal St, Winthrop, MA 02152
      41 Beal St, Winthrop, MA 02152
      41 Beal St, Winthrop, MA 02152
      /42

      Est $648,161 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,260 Sq Ft

      41 Beal St, Winthrop, MA 02152

      41 Beal St, Winthrop, MA 02152
  • 28 Thornton Park, Winthrop, MA 02152
    28 Thornton Park, Winthrop, MA 02152
    28 Thornton Park, Winthrop, MA 02152
    /6

    $800,000 Sold Dec 30, 2024

    • 3,769 Sq Ft
    • $212/SF
    • 15 Days On Market
    • 7 Beds
    • 3 Baths
    • Built 1900

    28 Thornton Park, Winthrop, MA 02152

    This is a one-of-a-kind opportunity for a savvy developer to restore the grandeur of this expansive, sun-drenched two-unit Victorian gem located in the heart of Thornton Park. With 3,769+ square feet of living space, this 1900-built beauty boasts six spacious bedrooms and overlooks the picturesque, tree-lined Thornton Park. This property requires extensive rehabilitation and is not eligible for

    Brian Perrin Brian J. Perrin Real Estate

    28 Thornton Park, Winthrop, MA 02152
    • 12 Lincoln St, Winthrop, MA 02152
      12 Lincoln St, Winthrop, MA 02152
      12 Lincoln St, Winthrop, MA 02152
      /27

      Est $810,501 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 1,641 Sq Ft

      12 Lincoln St, Winthrop, MA 02152

      12 Lincoln St, Winthrop, MA 02152
  • 209 River Rd, Winthrop, MA 02152
    209 River Rd, Winthrop, MA 02152
    209 River Rd, Winthrop, MA 02152
    /41

    $729,000 Sold Dec 23, 2024

    • 1,715 Sq Ft
    • $425/SF
    • 6 Days On Market
    • 3 Beds
    • 1.5 Baths
    • Built 1939

    209 River Rd, Winthrop, MA 02152

    Discover the allure and serenity of 209 River Road, situated in one of the most sought-after neighborhoods in Winthrop, MA. This inviting home promises both comfort and sophistication. Featuring three bedrooms, a versatile bonus office space, and 1.5 meticulously maintained baths. It marries style with functionality beautifully. The high-efficiency heating system, updated in 2021, promises warmth

    Helen Sullivan Chinatti Realty Group, Inc.

    209 River Rd, Winthrop, MA 02152
    • 35 Lincoln St, Winthrop, MA 02152
      35 Lincoln St, Winthrop, MA 02152
      35 Lincoln St, Winthrop, MA 02152
      /22

      Est $994,637 Not Listed For Sale

      • 8 Beds
      • 2.5 Baths
      • 3,799 Sq Ft

      35 Lincoln St, Winthrop, MA 02152

      35 Lincoln St, Winthrop, MA 02152
  • 257 Bowdoin St, Winthrop, MA 02152
    257 Bowdoin St, Winthrop, MA 02152
    257 Bowdoin St, Winthrop, MA 02152
    /41

    $1,100,000 Sold Dec 23, 2024

    • 2,936 Sq Ft
    • $375/SF
    • 6 Days On Market
    • 8 Beds
    • 2 Baths
    • Built 1920

    257 Bowdoin St, Winthrop, MA 02152

    Interior photos coming soon. This substantial 2 family duplex. 7/7 is a rare find in Winthrop. It's like having two single family homes. This property is very suitable for the owner occupant who wants privacy and where the rental side helps pay a substantial part of the mortgage, the investor where the rents pay the mortgage or the condo developer who will renovate and sell for profit. The units

    James Polino Compass

    257 Bowdoin St, Winthrop, MA 02152
    • 83 Lincoln St, Winthrop, MA 02152
      83 Lincoln St, Winthrop, MA 02152
      83 Lincoln St, Winthrop, MA 02152
      /40

      Est $887,262 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 2,022 Sq Ft

      83 Lincoln St, Winthrop, MA 02152

      83 Lincoln St, Winthrop, MA 02152
  • 1100 Governors Dr Unit 4, Winthrop, MA 02152
    1100 Governors Dr Unit 4, Winthrop, MA 02152
    1100 Governors Dr Unit 4, Winthrop, MA 02152
    /12

    $322,000 Sold Dec 20, 2024

    • 977 Sq Ft
    • $330/SF
    • 19 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1971

    1100 Governors Dr Unit 4, Winthrop, MA 02152

    Discover a fantastic opportunity to own a well-maintained condo unit featuring two spacious bedrooms, a generous entertainment area and a cozy kitchen nook. This is one of the bigger two bedroom units in the building. The unit showcases a sizable open-concept living room. Residents enjoy access to various complex amenities, including a fitness room and swimming pool. The location is ideal for

    Zina Glikberg Conway - Swampscott

    1100 Governors Dr Unit 4, Winthrop, MA 02152
    • 36 Beal St Unit 2, Winthrop, MA 02152
      36 Beal St Unit 2, Winthrop, MA 02152
      36 Beal St Unit 2, Winthrop, MA 02152
      /42

      Est $468,371 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,256 Sq Ft

      36 Beal St Unit 2, Winthrop, MA 02152

      36 Beal St Unit 2, Winthrop, MA 02152
  • 15 Almont St Unit 17, Winthrop, MA 02152
    15 Almont St Unit 17, Winthrop, MA 02152
    /2

    $849,000 Sold Jun 06, 2025

    • 2,200 Sq Ft
    • $386/SF
    • 6 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 1965

    15 Almont St Unit 17, Winthrop, MA 02152

    Welcome to this beautifully renovated 4 bedroom, 2.5 bath home with a large fenced in yard. This home offers an open-concept main living area including an updated kitchen with quartz countertops, stainless steel appliances, gas stove top, and a large island with plenty of storage. The living room offers a large picture window that brings in lots of natural light and a pretty fireplace. On the

    Judy Pagano Gibson Sotheby's International Realty

    15 Almont St Unit 17, Winthrop, MA 02152
    • 550 Pleasant St Unit 501, Winthrop, MA 02152
      550 Pleasant St Unit 501, Winthrop, MA 02152
      550 Pleasant St Unit 501, Winthrop, MA 02152
      /28

      Est $649,102 Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 1,192 Sq Ft

      550 Pleasant St Unit 501, Winthrop, MA 02152

      550 Pleasant St Unit 501, Winthrop, MA 02152
    • 550 Pleasant St Unit 410, Winthrop, MA 02152
      550 Pleasant St Unit 410, Winthrop, MA 02152
      550 Pleasant St Unit 410, Winthrop, MA 02152
      /28

      Est $661,719 Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 1,472 Sq Ft

      550 Pleasant St Unit 410, Winthrop, MA 02152

      550 Pleasant St Unit 410, Winthrop, MA 02152
    • 550 Pleasant St Unit 208, Winthrop, MA 02152
      550 Pleasant St Unit 208, Winthrop, MA 02152
      550 Pleasant St Unit 208, Winthrop, MA 02152
      /32

      Est $531,137 Not Listed For Sale

      • 1 Bed
      • 1 Bath
      • 988 Sq Ft

      550 Pleasant St Unit 208, Winthrop, MA 02152

      550 Pleasant St Unit 208, Winthrop, MA 02152
    • 550 Pleasant St Unit 205, Winthrop, MA 02152
      550 Pleasant St Unit 205, Winthrop, MA 02152
      550 Pleasant St Unit 205, Winthrop, MA 02152
      /34

      Est $859,796 Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 1,972 Sq Ft

      550 Pleasant St Unit 205, Winthrop, MA 02152

      550 Pleasant St Unit 205, Winthrop, MA 02152
    • 36 River Rd, Winthrop, MA 02152
      36 River Rd, Winthrop, MA 02152
      36 River Rd, Winthrop, MA 02152
      /39

      Est $716,930 Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 1,781 Sq Ft

      36 River Rd, Winthrop, MA 02152

      36 River Rd, Winthrop, MA 02152
    • 270 Winthrop St Unit 3, Winthrop, MA 02152
      270 Winthrop St Unit 3, Winthrop, MA 02152
      270 Winthrop St Unit 3, Winthrop, MA 02152
      /40

      Est $660,529 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 2,160 Sq Ft

      270 Winthrop St Unit 3, Winthrop, MA 02152

      270 Winthrop St Unit 3, Winthrop, MA 02152
    • 19 Belcher St, Winthrop, MA 02152
      19 Belcher St, Winthrop, MA 02152
      19 Belcher St, Winthrop, MA 02152
      /33

      Est $615,502 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,232 Sq Ft

      19 Belcher St, Winthrop, MA 02152

      19 Belcher St, Winthrop, MA 02152
    • 47 Edgehill Rd, Winthrop, MA 02152
      47 Edgehill Rd, Winthrop, MA 02152
      47 Edgehill Rd, Winthrop, MA 02152
      /35

      Est $1,104,262 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 2,610 Sq Ft

      47 Edgehill Rd, Winthrop, MA 02152

      47 Edgehill Rd, Winthrop, MA 02152
    • 56 Willow Ave, Winthrop, MA 02152
      56 Willow Ave, Winthrop, MA 02152
      56 Willow Ave, Winthrop, MA 02152
      /34

      Est $866,091 Not Listed For Sale

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

      56 Willow Ave, Winthrop, MA 02152

      56 Willow Ave, Winthrop, MA 02152
    • 45 Chester Ave, Winthrop, MA 02152
      45 Chester Ave, Winthrop, MA 02152
      45 Chester Ave, Winthrop, MA 02152
      /42

      Est $942,536 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,359 Sq Ft

      45 Chester Ave, Winthrop, MA 02152

      45 Chester Ave, Winthrop, MA 02152
    • 260 Bowdoin St, Winthrop, MA 02152
      260 Bowdoin St, Winthrop, MA 02152
      260 Bowdoin St, Winthrop, MA 02152
      /19

      Est $866,470 Not Listed For Sale

      • 5 Beds
      • 2 Baths
      • 2,220 Sq Ft

      260 Bowdoin St, Winthrop, MA 02152

      260 Bowdoin St, Winthrop, MA 02152
    • 158 Winthrop St, Winthrop, MA 02152
      158 Winthrop St, Winthrop, MA 02152
      158 Winthrop St, Winthrop, MA 02152
      /38

      Est $1,107,156 Not Listed For Sale

      • 4 Beds
      • 4 Baths
      • 3,051 Sq Ft

      158 Winthrop St, Winthrop, MA 02152

      158 Winthrop St, Winthrop, MA 02152
    • 10 Putnam Place, Winthrop, MA 02152
      10 Putnam Place, Winthrop, MA 02152
      10 Putnam Place, Winthrop, MA 02152
      /38

      Est $666,770 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 2,100 Sq Ft

      10 Putnam Place, Winthrop, MA 02152

      10 Putnam Place, Winthrop, MA 02152
    • 23 Fremont St Unit 25, Winthrop, MA 02152
      23 Fremont St Unit 25, Winthrop, MA 02152
      23 Fremont St Unit 25, Winthrop, MA 02152
      /40

      Est $1,048,343 Not Listed For Sale

      • 6 Beds
      • 3 Baths
      • 3,420 Sq Ft

      23 Fremont St Unit 25, Winthrop, MA 02152

      23 Fremont St Unit 25, Winthrop, MA 02152
    • 25 Somerset Ave Unit 2, Winthrop, MA 02152
      25 Somerset Ave Unit 2, Winthrop, MA 02152
      25 Somerset Ave Unit 2, Winthrop, MA 02152
      /23

      Est $505,985 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,203 Sq Ft

      25 Somerset Ave Unit 2, Winthrop, MA 02152

      25 Somerset Ave Unit 2, Winthrop, MA 02152
    • 142 Pauline St, Winthrop, MA 02152
      142 Pauline St, Winthrop, MA 02152
      142 Pauline St, Winthrop, MA 02152
      /20

      Est $903,536 Not Listed For Sale

      • 3 Beds
      • 3.5 Baths
      • 2,600 Sq Ft

      142 Pauline St, Winthrop, MA 02152

      142 Pauline St, Winthrop, MA 02152
    • 194 Washington Ave, Winthrop, MA 02152
      194 Washington Ave, Winthrop, MA 02152
      194 Washington Ave, Winthrop, MA 02152
      /9

      Est $930,000 Not Listed For Sale

      • 6 Beds
      • 4 Baths
      • 3,600 Sq Ft

      194 Washington Ave, Winthrop, MA 02152

      194 Washington Ave, Winthrop, MA 02152
    • 26 Elmwood Ave, Winthrop, MA 02152
      26 Elmwood Ave, Winthrop, MA 02152
      26 Elmwood Ave, Winthrop, MA 02152
      /29

      Est $895,178 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 2,248 Sq Ft

      26 Elmwood Ave, Winthrop, MA 02152

      26 Elmwood Ave, Winthrop, MA 02152
    • 20 Elmwood Ave, Winthrop, MA 02152
      20 Elmwood Ave, Winthrop, MA 02152
      20 Elmwood Ave, Winthrop, MA 02152
      /39

      Est $872,239 Not Listed For Sale

      • 5 Beds
      • 1.5 Baths
      • 1,920 Sq Ft

      20 Elmwood Ave, Winthrop, MA 02152

      20 Elmwood Ave, Winthrop, MA 02152
    • 59 Lewis Ave, Winthrop, MA 02152
      59 Lewis Ave, Winthrop, MA 02152
      59 Lewis Ave, Winthrop, MA 02152
      /42

      Est $876,296 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 1,884 Sq Ft

      59 Lewis Ave, Winthrop, MA 02152

      59 Lewis Ave, Winthrop, MA 02152

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