7,647

Winthrop, MA Homes

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  • /40

    $855,000

    Pending
    • 4 Beds
    • 2.5 Baths
    • 2,447 Sq Ft

    143 Morton St, Winthrop, MA 02152

    Spacious 4-bed, 2.5-bath single-family home in Winthrop—where coastal living meets effortless access to Boston. Set near Belle Isle Marsh, enjoy kayaking in calm waters, nearby ocean beaches, yacht clubs, and a scenic seaside golf course—all part of Winthrop’s rare small-town feel. Easy access to the major route in town means smoother, lower-traffic commutes in and out of the city. Inside,

    Alla Rossi Coldwell Banker Realty - Boston

    143 Morton St, Winthrop, MA 02152
  • /18

    $3,200 Per Month

    • 3 Beds
    • 1 Bath
    • 1,113 Sq Ft
    • Apartment for Rent

    180 Shirley St Unit 3, Winthrop, MA 02152

    Beautifully renovated 3-bedroom apartment available now, offering generous space and modern finishes throughout. This bright and spacious home features gorgeous hardwood floors, updated fixtures, and a fresh contemporary design that blends comfort with style. The layout includes a large living room plus an additional flexible room perfect for a formal dining area, home office, or play space—ideal

    Jenny Golic Lantern Residential

    180 Shirley St Unit 3, Winthrop, MA 02152
  • /27

    $720,000

    Sold Aug 29, 2025

    12 Park Ave, Winthrop, MA 02152

    • 3 Beds
    • 1.5 Baths
    • 1,172 Sq Ft
    • Built 1890

    Last Sold Summary

    • 3% Above List Price
    • $614/SF
    • 14 Days On Market

    Current Estimated Value $689,119

    Last Listing Agent Mary Ann Cash Charlesgate Realty Group, llc

    12 Park Ave, Winthrop, MA 02152
    • /24

      Est $906,747

      Not Listed For Sale

      44 Fairview St, Winthrop, MA 02152

      • 5 Beds
      • 2 Baths
      • 2,413 Sq Ft
      • Built 1911
      44 Fairview St, Winthrop, MA 02152

      Last Sold Summary

      • 12 Days On Market

  • /15

    $359,999

    $5K PRICE DROP Pending
    • 2 Beds
    • 1 Bath
    • 723 Sq Ft

    300 Governors Dr Unit 21, Winthrop, MA 02152

    Open House Sunday 04/26 1-2pm. Rarely available corner-unit condo offering exceptional privacy and abundant natural light. (Situated at the corner of the building, this home benefits from a side entrance that feels like private access). Freshly painted, the unit features a well-designed layout with comfortable living spaces and a seamless flow ideal for everyday living or entertaining.Located in

    Alla Rossi Coldwell Banker Realty - Boston

    300 Governors Dr Unit 21, Winthrop, MA 02152
  • /26

    $2,550 Per Month

    • 2 Beds
    • 1 Bath
    • 700 Sq Ft
    • Apartment for Rent

    46 Washington Ave Unit 1, Winthrop, MA 02152

    $2550! Available SEPTEMBER 1! Spacious and sunny 1.5 bedroom 1bath apartment in beautiful Winthrop by the sea! Upon entry find an open living room or living and dining room with gorgeous character with wood beam and stone fireplace (non working). Eat in kitchen with dishwasher and gas cooking, ample storage space with large pantry closet. Large king sized master bedroom with ample closet space.

    Katerina Patras Anzalone Realty

    46 Washington Ave Unit 1, Winthrop, MA 02152
  • /18

    $265,000

    Sold Aug 18, 2025

    265 Washington Ave Unit 2A, Winthrop, MA 02152

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

    Last Sold Summary

    • 12% Below List Price
    • $662/SF
    • 54 Days On Market

    Current Estimated Value $256,250

    Last Listing Agent Pareene Group EXIT Premier Real Estate

    265 Washington Ave Unit 2A, Winthrop, MA 02152
    • /28

      Est $553,705

      Not Listed For Sale

      26 Amelia Ave, Winthrop, MA 02152

      • 2 Beds
      • 1 Bath
      • 1,100 Sq Ft
      • Built 1953
      26 Amelia Ave, Winthrop, MA 02152

      Last Sold Summary

      • 23 Days On Market

  • /34

    $4,724,900

    Open Sat 11AM - 1:30PM
    • 10 Beds
    • 15 Baths
    • 9,156 Sq Ft

    1001 Shirley St, Winthrop, MA 02152

    Rooted in history & reimagined with intention, The Pearl is a one-of-a-kind five-unit multifamily property by the coast in Winthrop. Formerly a church, the building has been thoughtfully transformed into five distinct loft-style residences, each with its own layout, character & design identity. Original architectural details including exposed beams, hardwood floors, oversized windows & dramatic

    The Legacy Group Serhant

    1001 Shirley St, Winthrop, MA 02152
  • /14

    $2,100 Per Month

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

    267 Washington Ave Unit 5, Winthrop, MA 02152

    This top floor 2 bedroom and 1 bath condo can be rented furnished or unfurnished. If it is rented furnished the rent is $2,500 a month. It is equipped with a modern kitchen, gas stove, dishwasher, microwave and hardwood floors throughout. The unit is very conveniently located across from bus stop to Orient Heights and a very short walk to Winthrop Beach. There are several fine restaurants around

    James Polino Compass

    267 Washington Ave Unit 5, Winthrop, MA 02152
  • /42

    $545,000

    Sold Feb 13, 2026

    270 Winthrop St Unit 2, Winthrop, MA 02152

    • 2 Beds
    • 1.5 Baths
    • 1,421 Sq Ft
    • Built 1900

    Last Sold Summary

    • 1% Above List Price
    • $384/SF
    • 7 Days On Market

    Current Estimated Value $535,504

    Last Listing Agent Clara Arroyave eXp Realty LLC - Corporate Office

    270 Winthrop St Unit 2, Winthrop, MA 02152
    • /26

      Est $449,989

      Not Listed For Sale

      249 Winthrop Shore Dr Unit 1, Winthrop, MA 02152

      • 2 Beds
      • 1 Bath
      • 940 Sq Ft
      • Built 1900
      249 Winthrop Shore Dr Unit 1, Winthrop, MA 02152

      Last Sold Summary

      • 12 Days On Market

  • /26

    $849,900

    Open Sat 11AM - 1:30PM
    • 2 Beds
    • 2.5 Baths
    • 1,551 Sq Ft

    1001 Shirley St Unit 3, Winthrop, MA 02152

    Residence 3 at The Pearl offers a bright, refined take on loft living within a reimagined church conversion. Original hardwood floors, exposed beams, oversized windows, and 15’6” ceilings give the home rare scale and character. The kitchen features white cabinetry, Bosch appliances, green soapstone counters, a waterfall island with seating, farmhouse sink, and architectural hood. The living area

    The Legacy Group Serhant

    1001 Shirley St Unit 3, Winthrop, MA 02152
  • /12

    $2,200 Per Month

    • 2 Beds
    • 1 Bath
    • 800 Sq Ft
    • Apartment for Rent

    56 Park Ave Unit 2, Winthrop, MA 02152

    Spacious and bright 2 bedroom with bonus room/office, private front porch and rear enclosed porch just a block away from the Ocean. This building has a shared yard and coin op laundry in basement. Versatile space you can design your own layout!

    Josephine Marino DiMarzo Lyv Realty

    56 Park Ave Unit 2, Winthrop, MA 02152
  • /25

    $670,000

    Sold Sep 16, 2025

    162 Shirley St Unit 164, Winthrop, MA 02152

    • 3 Beds
    • 2 Baths
    • 1,413 Sq Ft
    • Built 1884

    Last Sold Summary

    • 8% Below List Price
    • $474/SF
    • 76 Days On Market

    Current Estimated Value $658,713

    Last Listing Agent Jenny Golic Lantern Residential

    162 Shirley St Unit 164, Winthrop, MA 02152
    • /29

      Est $789,817

      Not Listed For Sale

      239 Winthrop Shore Dr, Winthrop, MA 02152

      • 3 Beds
      • 2 Baths
      • 1,501 Sq Ft
      • Built 1880
      239 Winthrop Shore Dr, Winthrop, MA 02152

      Last Sold Summary

      • 1 Day On Market

  • /38

    $1,450,000

    • 6 Beds
    • 5.5 Baths
    • 5,278 Sq Ft

    100 Sargent St, Winthrop, MA 02152

    Set on a highly desirable corner lot at Sargent & Johnson Ave, this truly one of a kind home offers exceptional space and versatility. Welcoming foyer opens to a spacious living room, while the dining room features a covered porch with ocean views perfect for enjoying sunset evenings. The first floor also includes a bedroom and full bath, plus a kitchen with direct access to the backyard and one

    Elizabeth Ferrara Cottage Hill Real Estate

    100 Sargent St, Winthrop, MA 02152
  • /40

    $2,750 Per Month

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

    26 Forrest St Unit 2, Winthrop, MA 02152

    This fantastic second floor 2 bedroom, 1 bathroom apartment has SO MUCH to offer! There are beautiful hardwood floors and arched doorways throughout. There is also a den/office space for anyone who needs that. You will be steps from Winthrop Beach as well as having an ocean view from the front porch. There is a contemporary kitchen with a washer & dryer in the unit. It boasts a front AND back

    James Polino Compass

    26 Forrest St Unit 2, Winthrop, MA 02152
  • /15

    $357,000

    Sold Apr 24, 2026

    203 Winthrop Shore Dr Unit 2, Winthrop, MA 02152

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

    Last Sold Summary

    • 1% Below List Price
    • $492/SF
    • 13 Days On Market

    Current Estimated Value $353,000

    Last Listing Agent Molly Walker Coldwell Banker Realty - Scituate

    203 Winthrop Shore Dr Unit 2, Winthrop, MA 02152
    • /30

      Est $370,117

      Not Listed For Sale

      222 Winthrop Shore Dr Unit 3, Winthrop, MA 02152

      • 2 Beds
      • 1 Bath
      • 736 Sq Ft
      • Built 1964
      222 Winthrop Shore Dr Unit 3, Winthrop, MA 02152

      Last Sold Summary

      • 84 Days On Market

  • /32

    $750,000

    • 4 Beds
    • 2 Baths
    • 1,963 Sq Ft

    153 Locust St, Winthrop, MA 02152

    Charming 1930's two family, originally a seaside cottage, just steps to the beach. Family owned for over 70 years, it's now time for someone else to enjoy this coastal home. It offers off street parking and flexible living options. It could be a great single family. Unit 1 is a one bedroom while Unit 2 has three bedrooms. This property is brimming with potential and is priced to reflect the

    Mary Ann Cash Charlesgate Realty Group, llc

    153 Locust St, Winthrop, MA 02152
  • /11

    $2,100 Per Month

    • 1 Bed
    • 1 Bath
    • 760 Sq Ft
    • Apartment for Rent

    150 Locust St Unit 1, Winthrop, MA 02152

    JUST STEPS FROM THE BEACH IN WINTHROP by the SEA ........Freshly painted and nicely renovated, newer appliances, open floor plan, hardwood floors, very nice full bath and good size windows for natural light. This one bedroom plus den or home office has a generous living room/kitchen set up and large main bedroom. One car off street parking and on the bus line for easy public transportation to the

    Sharon Tallent Compass

    150 Locust St Unit 1, Winthrop, MA 02152
  • /20

    $625,000

    Sold Dec 03, 2025

    184 Woodside Ave Unit 1, Winthrop, MA 02152

    • 3 Beds
    • 1 Bath
    • 1,138 Sq Ft
    • Built 1880

    Last Sold Summary

    • 1% Below List Price
    • $549/SF
    • 12 Days On Market

    Current Estimated Value $617,286

    Last Listing Agent Michael Forcillo Coldwell Banker Peggy Carter Team

    184 Woodside Ave Unit 1, Winthrop, MA 02152
    • /39

      Est $747,036

      Not Listed For Sale

      41 Hawthorn Ave, Winthrop, MA 02152

      • 2 Beds
      • 2 Baths
      • 2,224 Sq Ft
      • Built 1954
      41 Hawthorn Ave, Winthrop, MA 02152

      Last Sold Summary

      • 3 Days On Market

  • /23

    $499,000

    Open Sat 12PM - 2PM
    • 1 Bed
    • 1 Bath
    • 683 Sq Ft

    10 Somerset Ave Unit 405, Winthrop, MA 02152

    Welcome to Unit 405 at The Somerset, Winthrop’s premier boutique condo community, where coastal charm meets modern design. This bright, open 1-bedroom, 1-bath home features a spacious living and dining area perfect for relaxing or entertaining plus a flex area for those who work from home. The kitchen blends style and functionality with quartz countertops and stainless steel appliances. Enjoy a

    Charlesgate New Development Team Charlesgate Realty Group, llc

    10 Somerset Ave Unit 405, Winthrop, MA 02152
  • /19

    $2,650 Per Month

    • 2 Beds
    • 1 Bath
    • 1,142 Sq Ft
    • Apartment for Rent

    19 Pearl Ave Unit 19, Winthrop, MA 02152

    Beautifully renovated and perfectly timed for summer, this inviting two bedroom apartment offers the ideal opportunity to enjoy life in Winthrop! This spacious second floor unit features a stunning modern kitchen fully equipped with gas cooking, ss appliances, quartz countertops, and peninsula for casual dining. A dedicated dining room, sun filled living room, along with a front deck, and rear

    Atiyeh Cassidy Blue Sky Realty

    19 Pearl Ave Unit 19, Winthrop, MA 02152
  • /22

    $570,000

    Sold Jan 20, 2026

    87 Hermon St, Winthrop, MA 02152

    • 3 Beds
    • 1 Bath
    • 1,182 Sq Ft
    • Built 1870

    Last Sold Summary

    • 4% Above List Price
    • $482/SF
    • 3 Days On Market

    Current Estimated Value $563,660

    Last Listing Agent James Polino Compass

    87 Hermon St, Winthrop, MA 02152
    • /24

      Est $758,614

      Not Listed For Sale

      15 Myrtle Ave, Winthrop, MA 02152

      • 3 Beds
      • 2 Baths
      • 1,687 Sq Ft
      • Built 1890
      15 Myrtle Ave, Winthrop, MA 02152

      Last Sold Summary

      • 8 Days On Market

  • /17

    $495,000

    $15K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 903 Sq Ft

    34 Underhill St Unit 4, Winthrop, MA 02152

    Gut renovated and converted in 2020, this upper-level 2-bedroom, 2-bath condo at 34 Underhill Street brings new construction finishes to one of Winthrop's most sought-after pockets. The white shaker kitchen is fitted with quartz countertops, blue glass tile backsplash, gold hardware, and stainless steel appliances including electric cooking. Wide plank hardwood floors & high ceilings run

    Reserve Team Reference Real Estate

    34 Underhill St Unit 4, Winthrop, MA 02152
  • /26

    $3,800 Per Month

    • 3 Beds
    • 1.5 Baths
    • 1,588 Sq Ft
    • House for Rent

    15 Wave Way, Winthrop, MA 02152

    RIGHT IN TIME FOR WINTHROP'S GREATEST WEEKEND!! Come experience coastal living and the 4TH of JULY at its finest in vibrant Winthrop!! This beautiful rental is just minutes from Boston! This seaside single-family home is ideally located just steps from picturesque Winthrop Beach. At the heart of the home is a stunning white quartz kitchen with SS appliances, vent hood, & rich espresso hardwood

    Atiyeh Cassidy Blue Sky Realty

    15 Wave Way, Winthrop, MA 02152
  • /27

    $800,000

    Sold Jul 14, 2025

    77 Otis St, Winthrop, MA 02152

    • 4 Beds
    • 2 Baths
    • 1,769 Sq Ft
    • Built 1912

    Last Sold Summary

    • 4% Below List Price
    • $452/SF
    • 41 Days On Market

    Current Estimated Value $781,219

    Last Listing Agent Molly Walker Coldwell Banker Realty - Scituate

    77 Otis St, Winthrop, MA 02152
    • /19

      Est $563,898

      Not Listed For Sale

      145 Locust St, Winthrop, MA 02152

      • 2 Beds
      • 1.5 Baths
      • 1,210 Sq Ft
      • Built 1900
      145 Locust St, Winthrop, MA 02152

      Last Sold Summary

      • 4 Days On Market

  • /17

    $749,000

    • 2 Beds
    • 2.5 Baths
    • 1,800 Sq Ft

    21 Hutchinson St Unit 1, Winthrop, MA 02152

    Welcome to 21 A Hutchison Street Condominium. This new construction 1800 sf unit has two levels of living space. Main level features open floor plan for kitchen, living area, dining and office. Kitchen is equipped with stainless steal appliances, island with built in drawer microwave, granite countertops and backsplash. Main bedroom has on-suite bathroom and walk-in closet. Convenient in unit

    Jason Saphire www.HomeZu.com

    21 Hutchinson St Unit 1, Winthrop, MA 02152
  • /12

    $2,300 Per Month

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

    900 Governors Dr Unit 22, Winthrop, MA 02152

    This great 2 bedroom and 1 bath condo is located in Governors Park. There is a new stove, newer kitchen. This comes with 2 car on-premises sticker parking. The bus stop is at the entrance to Governors Park to Orient Heights station. This condo complex is walking distance to Fort Banks school. Winthrop offers fine restaurants, and a center of town for your shopping needs.

    James Polino Compass

    900 Governors Dr Unit 22, Winthrop, MA 02152
  • /31

    $390,000

    Sold Sep 10, 2025

    23 Winthrop Shore Dr Unit 2, Winthrop, MA 02152

    • 2 Beds
    • 1 Bath
    • 679 Sq Ft
    • Built 1902

    Last Sold Summary

    • 2% Below List Price
    • $574/SF
    • 5 Days On Market

    Last Listing Agent Mariel Yovino Compass

    23 Winthrop Shore Dr Unit 2, Winthrop, MA 02152
    • /9

      Est $515,176

      Not Listed For Sale

      85 Beach Rd, Winthrop, MA 02152

      • 3 Beds
      • 1.5 Baths
      • 1,105 Sq Ft
      • Built 1900
      85 Beach Rd, Winthrop, MA 02152

      Last Sold Summary

      • 3 Days On Market

  • /28

    $839,000

    Pending
    • 3 Beds
    • 2 Baths
    • 1,736 Sq Ft

    70 Moore St Unit PH, Winthrop, MA 02152

    Set on coveted Winthrop Shore Drive, this meticulously maintained penthouse presents an opportunity for elevated, uncomplicated beachside living with breathtaking ocean views from nearly every window. The expansive one-level layout with 1,736 SF of polished living space offers flow and function, comprising three spacious bedrooms, two full baths, 360 degree exposure, three distinct living areas

    Cassie Comstock Compass

    70 Moore St Unit PH, Winthrop, MA 02152
  • /20

    $3,500 Per Month

    • 3 Beds
    • 2 Baths
    • 1,100 Sq Ft
    • Condo for Rent

    585 Shirley St Unit 1, Winthrop, MA 02152

    A waterfront living in the heart of Winthrop Harbor. This beautifully renovated ground-level apartment offers 3 bedrooms, 2 full bathrooms, and approximately 1,000 square feet of living space with breathtaking harbor, ocean, and city views. Features include hardwood flooring, updated kitchen with newer appliances, dishwasher, heat and hot water included, and a private ground-level patio

    Kevine Kakou Reference Real Estate

    585 Shirley St Unit 1, Winthrop, MA 02152
  • /21

    $650,000

    Sold May 12, 2026

    1080 Shirley St, Winthrop, MA 02152

    • 3 Beds
    • 2.5 Baths
    • 2,278 Sq Ft
    • Built 1930

    Last Sold Summary

    • 7% Below List Price
    • $285/SF
    • 18 Days On Market

    Last Listing Agent Reserve Team Reference Real Estate

    1080 Shirley St, Winthrop, MA 02152
    • /36

      Est $756,287

      Not Listed For Sale

      120 Almont St, Winthrop, MA 02152

      • 3 Beds
      • 2.5 Baths
      • 2,004 Sq Ft
      • Built 1986
      120 Almont St, Winthrop, MA 02152

      Last Sold Summary

      • 59 Days On Market

Showing Results 161 - 200, Page 5 of 18

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