7,650

Winthrop, MA Homes

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  • /38

    $739,000

    Pending
    • 3 Beds
    • 2 Baths
    • 1,428 Sq Ft

    8 Siren St, Winthrop, MA 02152

    This meticulously maintained 3-bedroom, 2 full bath home sits on a private corner lot in Winthrop's coveted Point Shirley neighborhood. The main level offers two distinct living areas, a fireplace, eat-in kitchen, a full bathroom and a bedroom or home office. Featuring two spacious bedrooms, the upper level also provides a generous walk-in closet, a second full bath and glimpses of the ocean and

    Agent Photo

    Nicole Bettano

    Real Broker MA, LLC

    8 Siren St, Winthrop, MA 02152
  • /14

    $3,000 Per Month

    • 3 Beds
    • 1 Bath
    • 1,300 Sq Ft
    • Apartment for Rent

    411 Shirley St Unit 2, Winthrop, MA 02152

    Welcome home to this very clean, move-in-ready three-bedroom, one-bath apartment in Winthrop! Conveniently located near a playground, the beach, and a neighborhood ice cream shop, this home offers comfortable coastal living with everyday conveniences close by. One parking spot is included. Available for $3,000 per month.

    Agent Photo

    Nicole Bettano

    Real Broker MA, LLC

    411 Shirley St Unit 2, Winthrop, MA 02152
  • /26

    $949,000

    Sold Oct 03, 2025

    26 Sargent St, Winthrop, MA 02152

    • 5 Beds
    • 2.5 Baths
    • 2,237 Sq Ft
    • Built 1887

    Last Sold Summary

    • 14% Below List Price
    • $424/SF
    • 27 Days On Market

    Current Estimated Value $933,003

    Last Listing Agent Mike Wetherbee Cameron Real Estate Group

    26 Sargent St, Winthrop, MA 02152
    • /41

      Est $1,172,407

      Not Listed For Sale

      72 Sewall Ave, Winthrop, MA 02152

      • 4 Beds
      • 3.5 Baths
      • 2,214 Sq Ft
      • Built 2009
      72 Sewall Ave, Winthrop, MA 02152

      Last Sold Summary

      • 15 Days On Market

      Last Listing Agent Elizabeth Ferrara Cottage Hill Real Estate

  • /14

    $350,000

    $25K PRICE INCREASE
    • 2 Beds
    • 1 Bath
    • 649 Sq Ft

    175 Shirley St Unit 5, Winthrop, MA 02152

    If you are a beach person or enjoy a short commute to the city you've come to the right place. Take this opportunity to live in the perfect location at a price that is ideal. Your two bedroom one bath is the perfect size at just under 700 square feet with an additional 300 square feet in the attic that is deeded exclusively to you to use as you like. Enjoy fresh air on your roof deck or a view of

    Tammy Merk Lantern Residential

    175 Shirley St Unit 5, Winthrop, MA 02152
  • /16

    Starting at $1,795

    Total Monthly Price

    • Studio - 2 Beds

    91 Veterans Rd, Winthrop, MA 02152

    Welcome to The Abby at 91 Veterans Road in Winthrop, MA, where city-access meets coastal charm. Nestled just steps from the beach and the Winthrop Golf Club, this professionally managed community offers modern, pet-friendly apartments with reserved parking, in-unit laundry, and easy highway and public-transit access to Boston.Walkable town, breeze-filled viewsResidents love Winthrop’s

    The Abby

    91 Veterans Rd, Winthrop, MA 02152
  • /42

    $855,000

    Sold Aug 10, 2026

    18-20 Fairview St, Winthrop, MA 02152

    • 5 Beds
    • 3 Baths
    • 3,035 Sq Ft
    • Built 1950

    Last Sold Summary

    • 1% Above List Price
    • $282/SF
    • 7 Days On Market

    Last Listing Agent Laura Baliestiero Coldwell Banker Realty - Concord

    18-20 Fairview St, Winthrop, MA 02152
    • /23

      Est $362,599

      Not Listed For Sale

      500 Governors Dr Unit 9, Winthrop, MA 02152

      • 3 Beds
      • 1 Bath
      • 772 Sq Ft
      • Built 1971
      500 Governors Dr Unit 9, Winthrop, MA 02152

      Last Sold Summary

      • 7 Days On Market

      Last Listing Agent Juan Cano Broad Sound Real Estate, LLC

  • /41

    $779,986

    $50K PRICE DROP
    • 6 Beds
    • 2 Baths
    • 2,560 Sq Ft

    50 Main St, Winthrop, MA 02152

    PRICE REDUCTION! Excellent opportunity to own a well-maintained 2-family property in the highly desirable seaside community of Winthrop! Perfect for investors, owner-occupants or multi-generational living, this spacious property offers two large units featuring 3 bedrooms,1 full bathroom, hardwood floors, generous living areas and a bonus office room! Separate utilities and washer/dryer hookups

    Matt Tasgin United Brokers

    50 Main St, Winthrop, MA 02152
  • /20

    $2,100 Plus Fees

    • 1 Bed
    • 1 Bath
    • Condo for Rent

    87 Winthrop Shore Dr Unit 1, Winthrop, MA 02152

    Awesome this nice 1 Bed 1 Bath place in the WINTHROP area is available for Sep 1, 2019. Included Features are: Gas Heat, and Gas Hot Water. Boston Pads is not responsible for any errors, omissions and change in price, prior sale, rent and withdrawal without notice. All information from sources reliable but not guaranteed. Photographs, videos, description and information about the properties

    87 Winthrop Shore Dr Unit 1, Winthrop, MA 02152
  • /42

    $900,000

    Sold Sep 15, 2026

    126 Brookfield Rd, Winthrop, MA 02152

    • 4 Beds
    • 3 Baths
    • 2,016 Sq Ft
    • Built 1951

    Last Sold Summary

    • 3% Above List Price
    • $446/SF
    • 7 Days On Market

    Current Estimated Value $808,067

    Last Listing Agent Marissa Amin Amo Realty - Boston City Properties

    126 Brookfield Rd, Winthrop, MA 02152
    • /25

      Est $693,942

      Not Listed For Sale

      162 Shirley St Unit 164, Winthrop, MA 02152

      • 3 Beds
      • 2 Baths
      • 1,413 Sq Ft
      • Built 1884
      162 Shirley St Unit 164, Winthrop, MA 02152

      Last Sold Summary

      • 76 Days On Market

      Last Listing Agent Jenny Golic Bowdoin Real Estate Partners

  • /42

    $639,000

    $40K PRICE DROP Pending
    • 2 Beds
    • 2 Baths
    • 1,302 Sq Ft

    3 Seal Harbor Rd Unit 342, Winthrop, MA 02152

    Seal Harbor in Winthrop offers an elevated coastal living experience that is unparalleled. Timeless detail inside & out of this building is complemented by white-glove concierge service. Unit 342 is a luxury residence with ocean & pool views from every window. It is conveniently located a few steps from the new elevators & welcomes you into an open floor plan with striking natural sunlight;

    Nancy McLaughlin Redfin Corp.

    3 Seal Harbor Rd Unit 342, Winthrop, MA 02152
  • /16

    $2,600 Plus Fees

    • 2 Beds
    • 1 Bath
    • 772 Sq Ft
    • Condo for Rent

    200 Governors Dr, Winthrop, MA 02152

    Property Id: 2107749 Hii! This is a newly renovated 2 bedroom apartment, 1 bath, with hardwood floors, renovated kitchen appliances, in the 1st floor of the building. The building in located at Governor's Park Condominium. Offering a great, convenient location! Just minutes from downtown Boston, 15 mins from Logan international Airport, 10 mins walk to Winthrop beach shoreline, and 5 mins to

    200 Governors Dr, Winthrop, MA 02152
  • /40

    $560,000

    Sold Oct 30, 2025

    41 Sargent St, Winthrop, MA 02152

    • 3 Beds
    • 2 Baths
    • 1,724 Sq Ft
    • Built 1925

    Last Sold Summary

    • $325/SF
    • 2 Days On Market

    Current Estimated Value $650,534

    Last Listing Agent Erin Dinsmoor Keller Williams Realty Metropolitan

    41 Sargent St, Winthrop, MA 02152
    • /30

      Est $929,511

      Not Listed For Sale

      94 Circuit Rd, Winthrop, MA 02152

      • 3 Beds
      • 2 Baths
      • 1,831 Sq Ft
      • Built 1925
      94 Circuit Rd, Winthrop, MA 02152

      Last Sold Summary

      • 40 Days On Market

      Last Listing Agent Leighann Eruzione Bowdoin Real Estate Partners

  • /35

    $606,900

    Open Wed 5PM - 6:30PM Pending
    • 2 Beds
    • 2 Baths
    • 1,024 Sq Ft

    10 Somerset Ave Unit 402, Winthrop, MA 02152

    Unit 402 at The Somerset is a bright and spacious top-floor 2-bedroom, 2-bath condo in the heart of Winthrop. Designed for modern living, this move-in-ready home features an open-concept layout, a primary bedroom with a private en-suite bath, two private balconies, quartz countertops, stainless steel appliances, central A/C, and generous closet space. Garage parking is included, along with access

    Charlesgate New Development Team Charlesgate Realty Group, llc

    10 Somerset Ave Unit 402, Winthrop, MA 02152
  • /8

    $3,200 Per Month

    • 3 Beds
    • 1 Bath
    • 1,800 Sq Ft
    • Condo for Rent

    28 Beach Rd Unit Beach Rd, Winthrop, MA 02152

    Recently remodeled 3 bedroom apartment. Unit features 3 spacious bedrooms, bathroom, open concept living room, and parking for 1 vehicle available. +++ CATS are WELCOME+++

    28 Beach Rd Unit Beach Rd, Winthrop, MA 02152
  • /35

    $605,000

    Sold Dec 19, 2025

    88 Grand View Ave, Winthrop, MA 02152

    • 2 Beds
    • 1 Bath
    • 1,262 Sq Ft
    • Built 1945

    Last Sold Summary

    • 9% Below List Price
    • $479/SF
    • 153 Days On Market

    Current Estimated Value $638,170

    Last Listing Agent Elizabeth Ferrara Cottage Hill Real Estate

    88 Grand View Ave, Winthrop, MA 02152
    • /26

      Est $513,976

      Not Listed For Sale

      600 Shirley St Unit 16, Winthrop, MA 02152

      • 2 Beds
      • 2 Baths
      • 865 Sq Ft
      • Built 1999
      600 Shirley St Unit 16, Winthrop, MA 02152

      Last Sold Summary

      • 117 Days On Market

      Last Listing Agent Elizabeth Crowley William Raveis R.E. & Home Services

  • /37

    $829,900

    $20K PRICE DROP
    • 5 Beds
    • 2.5 Baths
    • 2,437 Sq Ft

    43 Dolphin Ave, Winthrop, MA 02152

    Welcome to 43 Dolphin Ave, a charming, move-in-ready Colonial offering ocean views in a desirable Winthrop location just moments from the newly renovated Winthrop Beach. The inviting main level features a sun-filled living room with a gas fireplace and classic arched doorways, a spacious kitchen overlooking the covered deck and fenced backyard, a formal dining room, a half bath, and a versatile

    Patricia Nunez Redfin Corp.

    43 Dolphin Ave, Winthrop, MA 02152
  • /13

    $2,950 Plus Fees

    • 2 Beds
    • 1 Bath
    • 1,062 Sq Ft
    • Condo for Rent

    98 Woodside Ave, Winthrop, MA 02152

    Spacious 2-bedroom, 1-bath apartment with a versatile bonus room that can be used as a home office, den, or potential third bedroom. This well-maintained home features a bright and functional layout, hardwood floors, abundant natural light, and generous living space. Ideally located on a quiet residential street just minutes from Winthrop's beaches, restaurants, parks, shopping, public

    98 Woodside Ave, Winthrop, MA 02152
  • /34

    $722,000

    Sold Sep 25, 2025

    41 Centre St, Winthrop, MA 02152

    • 5 Beds
    • 1.5 Baths
    • 1,776 Sq Ft
    • Built 1910

    Last Sold Summary

    • 2% Below List Price
    • $407/SF
    • 12 Days On Market

    Current Estimated Value $740,370

    Last Listing Agent Leighann Eruzione Bowdoin Real Estate Partners

    41 Centre St, Winthrop, MA 02152
    • /16

      Est $488,614

      Not Listed For Sale

      62 Park Ave Unit 1, Winthrop, MA 02152

      • 3 Beds
      • 1 Bath
      • 1,050 Sq Ft
      • Built 1884
      62 Park Ave Unit 1, Winthrop, MA 02152

      Last Sold Summary

      • 34 Days On Market

      Last Listing Agent Jaime Venezia Real Estate Pros Inc.

  • /42

    $1,499,000

    $101K PRICE DROP Pending
    • 5 Beds
    • 3 Baths
    • 2,889 Sq Ft

    516 Pleasant St, Winthrop, MA 02152

    Every evening, the harbor turns amber from the west, 516 Pleasant Street has a front-row seat. A one-of-a-kind home set along Winthrop's harbor front with direct water access, a concrete seawall, and a private boat launch, (all outside the flood-zone by the way!!) this residence offers a lifestyle that cannot be assembled from scratch in today's coastal market. The rights to rebuild a pier remain

    Amanda George Lamacchia Realty, Inc.

    516 Pleasant St, Winthrop, MA 02152
  • /2

    $2,100 Per Month

    • 1 Bed
    • 1 Bath
    • 999 Sq Ft
    • Condo for Rent

    25 Pratt St Unit 1, Boston, MA 02134

    If you are looking to move into the Allston area next fall, look no further! This 1 bed and 1 bath apartment is perfect with the amount of natural light as well as close connection to public transportation. The apartment comes with an eat in kitchen, dishwasher, a porch, ceramic tiles, and also has laundry in the building. The local area is also filled with numerous restaurants and shops for all

    25 Pratt St Unit 1, Boston, MA 02134
  • /33

    $760,000

    Sold Sep 03, 2026

    55 Banks St Unit 2, Winthrop, MA 02152

    • 3 Beds
    • 3 Baths
    • 1,996 Sq Ft
    • Built 2022

    Last Sold Summary

    • 8% Below List Price
    • $381/SF
    • 94 Days On Market

    Current Estimated Value $773,196

    Last Listing Agent Cheng Liang CWQ Realty Group LLC

    55 Banks St Unit 2, Winthrop, MA 02152
    • /20

      Est $427,578

      Not Listed For Sale

      148 Winthrop Shore Dr Unit 2, Winthrop, MA 02152

      • 1 Bed
      • 1 Bath
      • 738 Sq Ft
      • Built 1900
      148 Winthrop Shore Dr Unit 2, Winthrop, MA 02152

      Last Sold Summary

      • 53 Days On Market

      Last Listing Agent Robert Bennett Dream Seekers Realty, LLC

  • /21

    $949,000

    • 7 Beds
    • 4 Baths
    • 4,251 Sq Ft

    190 Pleasant St, Winthrop, MA 02152

    Welcome to 190 Pleasant Street, a spacious two-family home offering approximately 4,251 square feet of living space across three levels. Featuring 13 total rooms,seven bedrooms, two full bathrooms and two half bathrooms, this property presents an excellent opportunity for an owner-occupant, investor or multigenerational household. Each unit offers generous living space, while the home’s flexible

    Michael MacDonald REMAX Andrew Realty Services

    190 Pleasant St, Winthrop, MA 02152
  • /30

    $2,695 Plus Fees

    • 2 Beds
    • 1 Bath
    • Condo for Rent

    87 Winthrop Shore Dr Unit 2, Winthrop, MA 02152

    This nice 2 Bedrooms 1 Bath place in the Winthrop area is available for Now. Included Features are: Front Porch, and Laundry in Common Area. Boston Pads is not responsible for any errors, omissions and change in price, prior sale, rent and withdrawal without notice. All information from sources reliable but not guaranteed. Photographs, videos, description and information about the

    87 Winthrop Shore Dr Unit 2, Winthrop, MA 02152
  • /22

    $380,000

    Sold Oct 15, 2025

    200 Governors Dr Unit 39, Winthrop, MA 02152

    • 2 Beds
    • 1 Bath
    • 782 Sq Ft
    • Built 1971

    Last Sold Summary

    • $486/SF
    • 7 Days On Market

    Current Estimated Value $382,667

    Last Listing Agent The Movement Group Compass

    200 Governors Dr Unit 39, Winthrop, MA 02152
    • /37

      Est $592,917

      Not Listed For Sale

      46 Jefferson St Unit 1, Winthrop, MA 02152

      • 3 Beds
      • 2 Baths
      • 1,320 Sq Ft
      • Built 1900
      46 Jefferson St Unit 1, Winthrop, MA 02152

      Last Sold Summary

      • 35 Days On Market

      Last Listing Agent Nicole Bettano Real Broker MA, LLC

  • /10

    $309,900

    Open Wed 5:30PM - 6:30PM
    • 1 Bed
    • 1 Bath
    • 720 Sq Ft

    483 Shirley St Unit 6A, Winthrop, MA 02152

    HERE IS A GREAT INVESTMENT OPPORTUNITY OR OWNER OCCUPY.....Why rent when this updated seaside condo can give you a start to have a place of your own? Conveniently located on the Bus Line to the Blue Line and just steps to the beach. This unit has been freshly painted, new grey vinyl flooring throughout, new updated fully applianced kitchen with white cabinets, quartz counters and good size rooms.

    Sharon Tallent Compass

    483 Shirley St Unit 6A, Winthrop, MA 02152
  • /16

    $2,950 Plus Fees

    • 2 Beds
    • 1 Bath
    • Condo for Rent

    70 Cottage Park Rd Unit 1, Winthrop, MA 02152

    Photos coming soon! Central AC & Heat Private laundry in basement Modern Kitchen w/ all new stainless steel appliances Dishwasher & Disposal Large open living room & dining room w/ wall mounted 70' smart TV Sun room/ office nook Pets are negotiable Off Street parking is negotiable Boston Pads is not responsible for any errors, omissions and change in

    70 Cottage Park Rd Unit 1, Winthrop, MA 02152
  • /42

    $1,650,000

    Sold May 29, 2026

    201 Cliff Ave, Winthrop, MA 02152

    • 8 Beds
    • 6.5 Baths
    • 5,362 Sq Ft
    • Built 1978

    Last Sold Summary

    • 8% Below List Price
    • $308/SF
    • 100 Days On Market

    Current Estimated Value $1,595,960

    Last Listing Agent Connie Doto Connie Doto Realty Group

    201 Cliff Ave, Winthrop, MA 02152
    • /42

      Est $926,077

      Not Listed For Sale

      211 Cliff Ave Unit 2, Winthrop, MA 02152

      • 3 Beds
      • 2 Baths
      • 2,600 Sq Ft
      • Built 1910
      211 Cliff Ave Unit 2, Winthrop, MA 02152

      Last Sold Summary

      • 7 Days On Market

      Last Listing Agent Mike Hayes Century 21 North East

  • /42

    $859,900

    • 2 Beds
    • 1.5 Baths
    • 1,674 Sq Ft

    3 Seal Harbor Rd Unit 336, Winthrop, MA 02152

    A rare offering at the prestigious Seal Harbor III, this exceptional corner residence captures breathtaking panoramic water views from an expansive, light filled interior and a private balcony - perfect for enjoying morning coffee, evening sunsets, or simply taking in the every changing waterfront scenery. Completely reimagined with a full gut reno in 2010, the home showcases timeless design, an

    Cathie Curran Charlesgate Realty Group, llc

    3 Seal Harbor Rd Unit 336, Winthrop, MA 02152
  • /20

    $6,500 Plus Fees

    • 4 Beds
    • 3.5 Baths
    • 2,359 Sq Ft
    • Townhouse for Rent

    170 Cliff Ave, Winthrop, MA 02152

    Welcome to your new home in the charming district of Winthrop, Massachusetts! This inviting rental property is ideally situated for those seeking both comfort and convenience. With nearby restaurants and department stores, everything you need is just a stone's throw away. This property features spacious living accommodations with a layout designed for relaxation. Enjoy the comfort of central

    170 Cliff Ave, Winthrop, MA 02152
  • /4

    $450,000

    Sold Apr 23, 2026

    86 Undine Ave, Winthrop, MA 02152

    • 1 Bed
    • 1 Bath
    • 620 Sq Ft
    • Built 1900

    Last Sold Summary

    • 10% Below List Price
    • $726/SF
    • 97 Days On Market

    Current Estimated Value $455,079

    Last Listing Agent Reserve Team Reference Real Estate

    86 Undine Ave, Winthrop, MA 02152
    • /14

      Est $393,220

      Not Listed For Sale

      308 Shirley St Unit 2, Winthrop, MA 02152

      • 2 Beds
      • 1 Bath
      • 890 Sq Ft
      • Built 1900
      308 Shirley St Unit 2, Winthrop, MA 02152

      Last Sold Summary

      • 3 Days On Market

      Last Listing Agent Maria Mainini JDS Realty Group

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