7,650

Winthrop, MA Homes

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  • /26

    $365,000

    $35K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 677 Sq Ft

    53 Trident Ave Unit 301, Winthrop, MA 02152

    Welcome to coastal living at its best. HOA FEE INCLUDES HEAT & HOT WATER! This top-floor corner 2-bedroom condo offers ocean views & an ideal vantage point overlooking the water, bringing in incredible natural light throughout. Hardwood floors run throughout the living area, while the kitchen features granite countertops, stainless steel appliances, & ample storage. Recent upgrades include appx.

    Amanda Woodward Coldwell Banker Realty - Boston

    53 Trident Ave Unit 301, Winthrop, MA 02152
  • /10

    $2,200 Per Month

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

    200 Governors Dr Unit 13, Winthrop, MA 02152

    This is a bright 2 bedroom/1 bathroom unit with a balcony in a great building at Governor's Park in beautiful Winthrop, MA! It is a larger, cosmopolitan unit which also has an open dining room space as you enter the unit. The main bedroom has a separate vanity area as well as a walk-in closet. Laundry is in the building just one floor down and it also comes with a parking spot. The neighborhood

    Kenny Kelleher Compass

    200 Governors Dr Unit 13, Winthrop, MA 02152
  • /20

    $400,000

    Sold Apr 29, 2026

    53 Trident Ave Unit 204, Winthrop, MA 02152

    • 2 Beds
    • 1 Bath
    • 662 Sq Ft
    • Built 1920

    Last Sold Summary

    • $604/SF
    • 25 Days On Market

    Current Estimated Value $402,333

    Last Listing Agent Domenico Barbuto DJB Realty Corporation

    53 Trident Ave Unit 204, Winthrop, MA 02152
    • /26

      Est $447,130

      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

      Last Listing Agent Ryan Wilson Keller Williams Realty

  • /40

    $729,900

    Open Sat 12PM - 1:30PM $20K PRICE DROP
    • 5 Beds
    • 2.5 Baths
    • 3,000 Sq Ft

    180 Winthrop St, Winthrop, MA 02152

    HUGE 2-FAMILY HOME WITH LOTS OF CHARACTER! Great location close to Boston. You can even take the ferry to Boston! This large 2-family offers approximately 3,000+ square feet of living space.The 1st-floor unit features a modern kitchen with granite countertops, dishwasher, and refrigerator. There are 6 rooms, 3 bedrooms, a modern 1/2 bath and 3/4 bath, plus 2 wall A/C units. With Harwood floors

    Philip Consolo Century 21 North East

    180 Winthrop St, Winthrop, MA 02152
  • /28

    $3,000 Per Month

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

    6 Elmwood Ct Unit 2, Winthrop, MA 02152

    Your Harbor Front Apartment Home Awaits! Freshly Renovated 2 Bedroom / 1 Bath Apartment with 1 Off-Street Parking Spot located in an absolutely fantastic, stunning harbor front location in Winthrop. This meticulously refreshed, second floor residence was just renovated and offers a homey, flowing layout that is bright and airy and features spectacular harbor and ocean views. The newly renovated

    Matthew Giangregorio Charlesgate Realty Group, llc

    6 Elmwood Ct Unit 2, Winthrop, MA 02152
  • /30

    $610,000

    Sold Nov 14, 2025

    60 Waldemar Ave, Winthrop, MA 02152

    • 3 Beds
    • 1 Bath
    • 1,548 Sq Ft
    • Built 1900

    Last Sold Summary

    • 24% Below List Price
    • $394/SF
    • 114 Days On Market

    Current Estimated Value $664,038

    Last Listing Agent James Polino Compass

    60 Waldemar Ave, Winthrop, MA 02152
    • /29

      Est $816,401

      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

      Last Listing Agent The Reference Group Reference Real Estate

  • /18

    $549,900

    • 2 Beds
    • 1 Bath
    • 782 Sq Ft

    130 Shirley St Unit 220, Winthrop, MA 02152

    Discover the perfect blend of modern design and seaside charm at 140 Shirley Street, Winthrop’s newest boutique condominium residence—just steps from the shoreline of Winthrop Beach. This two-bedroom, one-bath home in a 10-unit building captures the essence of coastal living with its fresh, nautical-inspired style and high-end finishes. Inside, you’ll find engineered hardwood flooring, recessed

    Kovacs Team Compass

    130 Shirley St Unit 220, Winthrop, MA 02152
  • /18

    $2,875 Per Month

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

    583-585 Shirley St Unit 1, Winthrop, MA 02152

    Completely renovated waterfront three-bedroom in the heart of Winthrop Harbor. This ground-level home offers approximately 1,100 square feet with two full bathrooms, hardwood flooring throughout, and an updated kitchen with all-new appliances and a dishwasher. Harbor, ocean, and city views span the living space, and a private ground-level patio opens directly to the water. Heat and hot water are

    Reserve Team Reference Real Estate

    583-585 Shirley St Unit 1, Winthrop, MA 02152
  • /19

    $685,000

    Sold Jan 09, 2026

    34 Fremont St, Winthrop, MA 02152

    • 4 Beds
    • 2 Baths
    • 1,864 Sq Ft
    • Built 1886

    Last Sold Summary

    • 3% Above List Price
    • $367/SF
    • 3 Days On Market

    Current Estimated Value $700,025

    Last Listing Agent Reserve Team Reference Real Estate

    34 Fremont St, Winthrop, MA 02152
    • /39

      Est $717,233

      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

      Last Listing Agent Linda Calla Cottage Hill Real Estate

  • /31

    $585,000

    Open Sat 12PM - 1PM $30K PRICE DROP
    • 2 Beds
    • 1.5 Baths
    • 1,141 Sq Ft

    142 Pleasant St Unit 12, Winthrop, MA 02152

    Belle Mer is a Professionally managed boutique association. 15 of 16 units are owner occupied. Newer built condominium with 2 living levels in highly desired Winthrop Center location. Kitchen equipped with classic white shaker cabinetry, stainless Bosch appliances, wine cooler, + wonderful island to gather for enjoyment. Harbor views from main bedroom, inviting window seats, generous closet

    Stacey Steck Gibson Sotheby's International Realty

    142 Pleasant St Unit 12, Winthrop, MA 02152
  • /21

    $2,800 Per Month

    • 3 Beds
    • 1 Bath
    • 1,400 Sq Ft
    • Apartment for Rent

    81 Sunnyside Ave Unit 1, Winthrop, MA 02152

    SUNNY AND LARGE THREE-BEDROOM UNIT WITH HARDWOOD FLOORS THROUGHOUT, FULL SIZE FORMAL DINING ROOM WITH OPEN FLOOR PLAN EAT IN FULLY APPLIANCED KITCHEN, STORAGE IN BASEMENT AND WASHER AND DRYER HOOKUPS IN BASEMENT, DEAD END STREET WITH PRIVATE BEACH AT THE END IF THE ROAD ( five houses down from beach) quiet street with no constant traffic, across the street from a wild life sanctuary and walking

    Stephanie Macisaac East Coast Realty

    81 Sunnyside Ave Unit 1, Winthrop, MA 02152
  • /39

    $900,000

    Sold Jul 08, 2026

    44 Cottage Park Rd, Winthrop, MA 02152

    • 6 Beds
    • 2 Baths
    • 2,843 Sq Ft
    • Built 1925

    Last Sold Summary

    • 4% Above List Price
    • $317/SF
    • 3 Days On Market

    Current Estimated Value $858,990

    Last Listing Agent William McLaughlin Cameron Prestige, LLC

    44 Cottage Park Rd, Winthrop, MA 02152
    • /24

      Est $778,824

      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

      Last Listing Agent Leighann Eruzione Bowdoin Real Estate Partners

  • /26

    $1,650,000

    Pending
    • 6 Beds
    • 6 Baths
    • 4,122 Sq Ft

    304 Shirley St, Winthrop, MA 02152

    Situated just steps from the sand, 304 Shirley presents a rare opportunity to own a fully occupied 6-unit building in one of Winthrop's most desirable seaside neighborhoods. Each unit is a well-maintained 1-bedroom, offering consistent rental income and strong tenant demand. This beachside property is perfectly positioned near local shops, restaurants, and public transportation, making it a

    Reserve Team Reference Real Estate

    304 Shirley St, Winthrop, MA 02152
  • /18

    $4,000 Per Month

    • 3 Beds
    • 1.5 Baths
    • 1,600 Sq Ft
    • House for Rent

    393 Main St Unit house, Winthrop, MA 02152

    This is a custom built family owned single-family home in a part of town that's close to everything! The house has been renovated with a new kitchen and new 1/2 bath off of the primary bedroom. Gleaming hardwood floors throughout give the house a bright, streamlined look. The living room and dining room are open and connected for great entertaining and there are new windows throughout. The

    James Polino Compass

    393 Main St Unit house, Winthrop, MA 02152
  • /19

    $835,000

    Sold Jun 23, 2026

    108 Winthrop St, Winthrop, MA 02152

    • 5 Beds
    • 3 Baths
    • 4,768 Sq Ft
    • Built 1900

    Last Sold Summary

    • 8% Above List Price
    • $175/SF
    • 10 Days On Market

    Current Estimated Value $790,437

    Last Listing Agent Mark Mulkerrin Coldwell Banker Realty - Sharon

    108 Winthrop St, Winthrop, MA 02152
    • /9

      Est $525,081

      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

      Last Listing Agent Ricardo Rodriguez Coldwell Banker Realty - Boston

  • /42

    $979,000

    Pending
    • 4 Beds
    • 2 Baths
    • 2,126 Sq Ft

    41 Emerson Rd, Winthrop, MA 02152

    All offers due by Tuesday 9/15 at noon.Situated on one of Winthrops most desirable tree-lined streets in the most sought after neighborhood- the Maze, this charming four-bedroom home blends original character with thoughtful updates and inviting spaces for everyday living.The welcoming living room features a built-in window seat and wood-burning fireplace. An updated kitchen with butler’s pantry

    Christine D'Ambrosio Bowdoin Real Estate Partners

    41 Emerson Rd, Winthrop, MA 02152
  • /15

    $3,200 Per Month

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

    117 Revere St Unit 1, Winthrop, MA 02152

    Welcome to 117 Revere St. #3 in Winthrop! This recently renovated 3-bedroom, 1-bath apartment offers approximately 1,300 sq. ft. of bright and spacious living space. The unit features a large sun-filled living room with hardwood floors, a beautifully updated eat-in kitchen with granite countertops, stainless steel appliances, abundant cabinet space, and the convenience of an in-unit washer and

    Bruno Rodriguez Remmes & Co.

    117 Revere St Unit 1, Winthrop, MA 02152
  • /32

    $540,000

    Sold Mar 25, 2026

    600 Shirley St Unit 3, Winthrop, MA 02152

    • 2 Beds
    • 2 Baths
    • 773 Sq Ft
    • Built 1900

    Last Sold Summary

    • 2% Below List Price
    • $699/SF
    • 253 Days On Market

    Current Estimated Value $540,287

    Last Listing Agent Erika Leigh Pereira Keller Williams Realty Boston Northwest

    600 Shirley St Unit 3, Winthrop, MA 02152
    • /36

      Est $740,458

      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

      Last Listing Agent Elizabeth Ferrara Cottage Hill Real Estate

  • /25

    $629,000

    • 2 Beds
    • 2.5 Baths
    • 1,463 Sq Ft

    21 Hutchinson St Unit 2, Winthrop, MA 02152

    Completely renovated to the core with quality craftsmanship throughout, this exceptional property blends modern sophistication with the relaxed coastal lifestyle that makes Winthrop so special. This beautifully finished two-level unit offers a bright, open layout designed for comfortable everyday living and easy entertaining. The main level features a beautiful white kitchen with modern

    Atiyeh Cassidy Blue Sky Realty

    21 Hutchinson St Unit 2, Winthrop, MA 02152
  • /10

    $3,500 Per Month

    • 3 Beds
    • 1 Bath
    • 1,100 Sq Ft
    • Apartment for Rent

    78 Read St Unit 1, Winthrop, MA 02152

    A spacious & newly renovated 3-bedroom apartment with laundry with all new appliances... Dining room, living room, three bedrooms, full bath and parking for 1 car in driveway.... Utilities not included. Gas heat, Central Air. ***NO-FEE*** READY OCT 1 East to see. Just move in.

    John LaPlaca Benoit Real Estate Group ,LLC

    78 Read St Unit 1, Winthrop, MA 02152
  • /27

    $1,065,000

    Sold Feb 03, 2026

    41 Harbor View Ave, Winthrop, MA 02152

    • 4 Beds
    • 3 Baths
    • 2,028 Sq Ft
    • Built 1900

    Last Sold Summary

    • 1% Above List Price
    • $525/SF
    • 7 Days On Market

    Current Estimated Value $1,003,759

    Last Listing Agent Brian Perrin Brian J. Perrin Real Estate

    41 Harbor View Ave, Winthrop, MA 02152
    • /37

      Est $1,045,002

      Not Listed For Sale

      115 Almont St, Winthrop, MA 02152

      • 5 Beds
      • 3 Baths
      • 3,272 Sq Ft
      • Built 1967
      115 Almont St, Winthrop, MA 02152

      Last Sold Summary

      • 84 Days On Market

      Last Listing Agent Christine Goldstein Lyv Realty

  • /27

    $710,000

    • 4 Beds
    • 2 Baths
    • 1,193 Sq Ft

    542 Shirley St, Winthrop, MA 02152

    The perfect blend of comfort, convenience, and affordability! Whether you’re a first-time homebuyer, looking to downsize, or searching for an alternative to condo living, this charming 4-bedroom home offers the space you need with the low-maintenance lifestyle you want all just one block from the beach. The main level features a comfortable bedroom and full bathroom with a convenient walk-in

    Christine D'Ambrosio Bowdoin Real Estate Partners

    542 Shirley St, Winthrop, MA 02152
  • /15

    $3,400 Per Month

    • 2 Beds
    • 1 Bath
    • 1,376 Sq Ft
    • Apartment for Rent

    158 Highland Ave Unit 1, Winthrop, MA 02152

    Pristine apartment in desirable Winthrop Highlands is not your average rental. Featuring high ceilings and hardwood floors throughout, the home offers a spacious and elegant layout with a formal living room, formal dining room, and a sunroom that’s perfect as a home office. The fully applianced granite kitchen includes stainless steel appliances, ideal for both everyday cooking and entertaining.

    Erica Gore Century 21 Seaport

    158 Highland Ave Unit 1, Winthrop, MA 02152
  • /38

    $695,000

    Sold May 18, 2026

    960 Shirley St, Winthrop, MA 02152

    • 3 Beds
    • 1.5 Baths
    • 1,764 Sq Ft
    • Built 1910

    Last Sold Summary

    • 3% Below List Price
    • $394/SF
    • 148 Days On Market

    Current Estimated Value $700,247

    Last Listing Agent Bridget Conroy Coldwell Banker Realty - Milton

    960 Shirley St, Winthrop, MA 02152
    • /27

      Est $487,521

      Not Listed For Sale

      10 Beach Rd Unit 3, Winthrop, MA 02152

      • 3 Beds
      • 1 Bath
      • 1,361 Sq Ft
      • Built 1881
      10 Beach Rd Unit 3, Winthrop, MA 02152

      Last Sold Summary

      • 10 Days On Market

      Last Listing Agent Atiyeh Cassidy Blue Sky Realty

  • /19

    $515,000

    $4K PRICE DROP
    • 1 Bed
    • 1 Bath
    • 974 Sq Ft

    1 Seal Harbor Rd Unit 812, Winthrop, MA 02152

    Waterfront Living at Its Best! Enjoy breathtaking ocean views from this spacious 8th floor condominium offering 974 sq ft of comfortable living space. Relax on your private balcony overlooking the water, or good size bedroom including a large walk-in closet and a separate tub/shower room. This full service building offers outstanding amenities, including concierge service, an oceanside heated

    Peggie Gilbert Coldwell Banker Peggy Carter Team

    1 Seal Harbor Rd Unit 812, Winthrop, MA 02152
  • /6

    $3,500 Per Month

    • 4 Beds
    • 1 Bath
    • 999 Sq Ft
    • Apartment for Rent

    11 Pearl Ave Unit 3, Winthrop, MA 02152

    Move right into this bright and inviting four-bedroom apartment featuring a living room, eat-in kitchen, beautiful hardwood floors, and abundant natural light this apartment offers a comfortable and welcoming space. Enjoy a location within walking distance of the beach—perfect for enjoying the coastal surroundings. Available now

    Liliana Monroy Century 21 Mario Real Estate

    11 Pearl Ave Unit 3, Winthrop, MA 02152
  • /24

    $780,000

    Sold Dec 29, 2025

    62 Lowell Rd, Winthrop, MA 02152

    • 5 Beds
    • 2.5 Baths
    • 1,923 Sq Ft
    • Built 1926

    Last Sold Summary

    • $406/SF
    • 75 Days On Market

    Current Estimated Value $813,630

    Last Listing Agent Mary Ann Cash Charlesgate Realty Group, llc

    62 Lowell Rd, Winthrop, MA 02152
    • /37

      Est $721,880

      Not Listed For Sale

      105 Almont St, Winthrop, MA 02152

      • 3 Beds
      • 1.5 Baths
      • 1,564 Sq Ft
      • Built 1915
      105 Almont St, Winthrop, MA 02152

      Last Sold Summary

      • 12 Days On Market

      Last Listing Agent Nicole Bettano Real Broker MA, LLC

  • /40

    $549,999

    $28K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,205 Sq Ft

    1 Seal Harbor Rd Unit 413, Winthrop, MA 02152

    Welcome to coastal living at its finest at the highly desirable Seal Harbor One. Perched on the fourth floor, this spacious and thoughtfully designed 2-bedroom, 2-bath residence offers an ideal layout with private bedroom suites, each featuring its own full bathroom and generous walk-in closet. Set on a stunning peninsula surrounded by the Atlantic Ocean, Seal Harbor offers a truly unique

    Tammy Merk Lantern Residential

    1 Seal Harbor Rd Unit 413, Winthrop, MA 02152
  • /38

    $747,000

    Sold Jul 17, 2026

    4 Woodside Park, Winthrop, MA 02152

    • 4 Beds
    • 1.5 Baths
    • 2,167 Sq Ft
    • Built 1900

    Last Sold Summary

    • 2% Below List Price
    • $345/SF
    • 7 Days On Market

    Current Estimated Value $777,004

    Last Listing Agent Elizabeth Ferrara Cottage Hill Real Estate

    4 Woodside Park, Winthrop, MA 02152
    • /30

      Est $602,357

      Not Listed For Sale

      58 Almont St, Winthrop, MA 02152

      • 3 Beds
      • 2 Baths
      • 1,072 Sq Ft
      • Built 1951
      58 Almont St, Winthrop, MA 02152

      Last Sold Summary

      • 3 Days On Market

      Last Listing Agent Elizabeth Ferrara Cottage Hill Real Estate

  • /21

    $600,000

    • 2 Beds
    • 2 Baths
    • 912 Sq Ft

    194 Washington Ave Unit 2, Winthrop, MA 02152

    Welcome to coastal living at its best — where ocean views meet beautiful golf course views, and the beach is just a five-minute walk from your front door.Fully rebuilt in 2025, this exceptional first-floor 2-bedroom, 2-bath residence offers the rare combination of brand-new luxury, thoughtful design, and an incredible Winthrop-by-the-Sea location. Every detail was carefully considered, creating a

    Ella Goren Sunrise Realty & Investment LLC

    194 Washington Ave Unit 2, Winthrop, MA 02152

Showing Results 201 - 240, Page 6 of 18

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