3,381

Downtown Winthrop Homes

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    • /28

      Est $1,003,470 Not Listed For Sale

      • 6 Beds
      • 3 Baths
      • 3,541 Sq Ft

      70 Shirley St, Winthrop, MA 02152

      70 Shirley St, Winthrop, MA 02152
  • /32

    $594,900 Pending

    • 2 Beds
    • 2 Baths
    • 985 Sq Ft

    10 Somerset Ave Unit 206, Winthrop, MA 02152

    Welcome to The Somerset—Winthrop’s newest boutique condo development, where coastal charm meets modern luxury. This spacious 2-bedroom, 2-bath home is designed for effortless living, featuring a sun-drenched open layout, private balcony, and oversized walk-in wardrobes in both bedrooms. Enjoy a sleek kitchen with stainless steel appliances, quartz countertops, and soft-close cabinetry, flowing

    Charlesgate New Development Team Charlesgate Realty Group, llc

    10 Somerset Ave Unit 206, Winthrop, MA 02152
  • /15

    $688,000 Sold May 06, 2025

    • 1,700 Sq Ft
    • $405/SF
    • 153 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1928

    29 Buckthorn Terrace, Winthrop, MA 02152

    JUST REDUCED for the Spring market. Tucked away on a quiet side street you'll find 29 Buckthorn Terrace, a pretty yellow house. This three bedroom home is filled with charm and is extremely well built. If you like the character of hardwood floors, crown molding, natural woodwork and desire a heated garage, this might be the right home for you. Along with the living room, dining room and

    Mary Ann Cash Charlesgate Realty Group, llc

    29 Buckthorn Terrace, Winthrop, MA 02152
    • /40

      Est $1,327,600 Not Listed For Sale

      • 7 Beds
      • 4.5 Baths
      • 3,648 Sq Ft

      76 Atlantic St, Winthrop, MA 02152

      76 Atlantic St, Winthrop, MA 02152
  • /23

    $555,000 Pending

    • 1 Bed
    • 1 Bath
    • 684 Sq Ft

    10 Somerset Ave Unit 401, Winthrop, MA 02152

    The Somerset – Winthrop Center’s Premier Boutique Condo Living by the Sea! This thoughtfully curated collection of 29 modern residences includes studio, 1BR, 1+, and 2BR layouts ,each designed with a clean, coastal aesthetic and high-quality finishes. Inside, open-concept floor plans, quartz countertops, stainless steel appliances, central A/C, and sleek modern design. Most homes include garage

    Charlesgate New Development Team Charlesgate Realty Group, llc

    10 Somerset Ave Unit 401, Winthrop, MA 02152
  • /30

    $559,000 Sold May 02, 2025

    • 1,072 Sq Ft
    • $521/SF
    • 3 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1951

    58 Almont St, Winthrop, MA 02152

    Charming Single-Level Home Just Blocks from the Beach! Rarely available single-level living in a prime Winthrop location! Nestled on a one-way street, this home is just a few blocks from the beach and close to all the local amenities you need. Featuring hardwood floors throughout, this home offers two bedrooms, two full baths, plus an office and a dedicated laundry space. The primary bedroom

    Elizabeth Ferrara Cottage Hill Real Estate

    58 Almont St, Winthrop, MA 02152
    • /34

      Est $627,389 Not Listed For Sale

      • 4 Beds
      • 1 Bath
      • 1,135 Sq Ft

      396 Winthrop St, Winthrop, MA 02152

      396 Winthrop St, Winthrop, MA 02152
  • /20

    $383,000 Pending

    • 1 Bed
    • 1 Bath
    • 475 Sq Ft

    10 Somerset Ave Unit 403, Winthrop, MA 02152

    The Somerset – Winthrop Center’s Premier Boutique Condo Living by the Sea! This thoughtfully curated collection of 29 modern residences includes studio, 1BR, 1+, and 2BR layouts ,each designed with a clean, coastal aesthetic and high-quality finishes. Inside, open-concept floor plans, quartz countertops, stainless steel appliances, central A/C, and sleek modern design. Most homes include garage

    Charlesgate New Development Team Charlesgate Realty Group, llc

    10 Somerset Ave Unit 403, Winthrop, MA 02152
  • /30

    $825,000 Sold May 02, 2025

    • 1,972 Sq Ft
    • $418/SF
    • 15 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 2006

    550 Pleasant St Unit 405, Winthrop, MA 02152

    Coming Soon! Experience waterfront luxury living within this stunning residence offering stunning south facing views of the waterfront, marina and Boston skyline! Unit 405 is perfectly located within the building and spans 1972 square feet providing an abundance of space for comfortable living and entertaining. Offering two bedrooms and two bathrooms, features include a gas fireplace, master

    The GBRI Team Northeastern Realty Group

    550 Pleasant St Unit 405, Winthrop, MA 02152
    • /6

      Est $321,827 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 772 Sq Ft

      800 Governors Dr Unit 6, Winthrop, MA 02152

      800 Governors Dr Unit 6, Winthrop, MA 02152
  • /31

    $499,900 Pending

    • 3 Beds
    • 2 Baths
    • 1,595 Sq Ft

    110 Summit Ave Unit 1, Winthrop, MA 02152

    Coastal charm meets timeless elegance in this spacious 3-bedroom, 2-bath first-floor condo just moments from Winthrop’s stunning shoreline. Nestled within a beautifully maintained Victorian, this one-of-a-kind home blends historic character with everyday convenience. From the moment you enter, you’ll appreciate the soaring ceilings, intricate dental crown molding, sunlit bay windows, and

    Alison ludwig Keller Williams Realty-Merrimack

    110 Summit Ave Unit 1, Winthrop, MA 02152
  • /25

    $657,500 Sold May 01, 2025

    • 1,563 Sq Ft
    • $421/SF
    • 3 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1955

    81 Putnam St, Winthrop, MA 02152

    Nestled in the heart of Winthrop Center, this inviting 3 bedroom single family ranch offers the perfect blend of comfort, character and functionality. The ultimate entertainment hub, this home showcases a recently renovated kitchen featuring stainless appliances, quartz countertops and a seamless flow into the living and dining areas. Enjoy outdoor dinners on a spacious deck before heading for a

    Erica Gore Century 21 Seaport

    81 Putnam St, Winthrop, MA 02152
    • /27

      Est $334,735 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 772 Sq Ft

      700 Governors Dr Unit 5, Winthrop, MA 02152

      700 Governors Dr Unit 5, Winthrop, MA 02152
  • /17

    $349,900 Pending

    • 2 Beds
    • 1 Bath
    • 723 Sq Ft

    300 Governors Dr Unit 9, Winthrop, MA 02152

    Welcome to this lovely Condo, located in an exceptionally affordable complex! This corner unit is a one of a kind in mint move in condition. Ceramic title bath, large closets bedrooms. Many extras. Come take a look!!!! Additionally, this unit comes with the convenience of off-street parking, ensuring your vehicle is always secure. Its prime location offers easy access to public transportation,

    Cleide Paula Dasilva LPT Realty, LLC

    300 Governors Dr Unit 9, Winthrop, MA 02152
  • /25

    $725,000 Sold Apr 15, 2025

    • 1,428 Sq Ft
    • $508/SF
    • 5 Days On Market
    • 2 Beds
    • 1.5 Baths
    • Built 1900

    206 Washington Ave, Winthrop, MA 02152

    Sellers will review offers Monday 3/33 @ 5pm.Nestled in a prime Winthrop location, this charming home blends gorgeous original details with thoughtful modern updates. Enjoy breathtaking harbor and lake views from almost every room, plus a sundrenched enclosed porch for year-round enjoyment. Step inside to a warm and inviting living room with original wood details, fireplace, and beamed ceilings.

    George Sarkis Douglas Elliman Real Estate - The Sarkis Team

    206 Washington Ave, Winthrop, MA 02152
    • /18

      Est $338,399 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 782 Sq Ft

      600 Governors Dr Unit 20, Winthrop, MA 02152

      600 Governors Dr Unit 20, Winthrop, MA 02152
  • /38

    $949,000 Pending

    • 4 Beds
    • 3 Baths
    • 4,101 Sq Ft

    175 Pleasant St, Winthrop, MA 02152

    Step into timeless charm with this stately 1896 Colonial Revival nestled on a corner lot. Brimming with original detail, this non-conforming two-family offers a flexible layout across 8+ elegant rooms. The grand staircase, French doors, high ceilings, and two fireplaces bring character and warmth throughout. Enjoy four spacious second-floor bedrooms, a sun-soaked landing with a large picture

    Leighann Eruzione Lantern Residential

    175 Pleasant St, Winthrop, MA 02152
  • /15

    $383,000 Sold Apr 08, 2025

    • 782 Sq Ft
    • $490/SF
    • 23 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1971

    800 Governors Park Unit 25, Winthrop, MA 02152

    Newly renovated 2- bedroom, 1 bath Condo. This unit has gleaming hardwood floors throughout. Enjoy your morning coffee on your private balcony. The bathroom features new bathtub and shower doors, and beautiful pedestal sink. Governor's Park offers a gym and inground pool, for your summer enjoyment. There is public transportation at the corner of the Condo complex to Orient Height train station

    James Polino Compass

    800 Governors Park Unit 25, Winthrop, MA 02152
    • /15

      Est $316,368 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 761 Sq Ft

      600 Governors Dr Unit 3, Winthrop, MA 02152

      600 Governors Dr Unit 3, Winthrop, MA 02152
  • /38

    $1,099,000 Pending

    • 6 Beds
    • 2.5 Baths
    • 2,692 Sq Ft

    86 Chester Ave, Winthrop, MA 02152

    Experience a complete transformation in this meticulously renovated 2-family home. Perched on a prized corner lot, this residence has undergone extensive updates, including new flooring, walls, electrical, kitchen, plumbing, and a newer roof. The result is a modern, move-in-ready space. Enjoy breathtaking, unobstructed views of Winthrop's verdant Golf Course from all three levels. This oversized

    Kyle MacNichol Redfin Corp.

    86 Chester Ave, Winthrop, MA 02152
  • /22

    $1,278,000 Sold Apr 07, 2025

    • 2,717 Sq Ft
    • $470/SF
    • 120 Days On Market
    • 5 Beds
    • 4 Baths
    • Built 1936

    242 Main St, Winthrop, MA 02152

    Welcome to this beautifully gut-renovated multi-family home, offering two spacious units, each with two levels of living space. Unit 1 features 2 bedrooms and 2 bathrooms, while Unit 2 boasts 3 bedrooms and 2 bathrooms, providing plenty of room for comfortable living.Both units are move-in ready, with modern updates throughout, including sleek finishes, new flooring, and updated kitchens and

    Nicole Bettano Lantern Residential

    242 Main St, Winthrop, MA 02152
    • /16

      Est $382,693 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 989 Sq Ft

      400 Governors Dr Unit 28, Winthrop, MA 02152

      400 Governors Dr Unit 28, Winthrop, MA 02152
  • /14

    $381,000 Pending

    • 1 Bed
    • 1 Bath
    • 500 Sq Ft

    10 Somerset Ave Unit 303, Winthrop, MA 02152

    Welcome to The Somerset—Winthrop’s newest boutique condo development! This collection of 29 thoughtfully designed homes offers studios, 1-bed, 1+ bed, and 2-bedroom layouts with quality finishes and a coastal vibe. Enjoy open-concept living, stainless steel appliances, quartz countertops, central A/C, and stylish modern touches. Most units include garage parking, and select homes feature private

    Charlesgate New Development Team Charlesgate Realty Group, llc

    10 Somerset Ave Unit 303, Winthrop, MA 02152
  • /36

    $705,000 Sold Apr 01, 2025

    • 1,679 Sq Ft
    • $420/SF
    • 5 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1919

    4 Palmyra St Unit 2, Winthrop, MA 02152

    Fall in love with this stunning 3-bed, 2-bath multi-level condo! The main level boasts an open-concept living space with a bright and sunny living room with water views. The modern kitchen is equipped with Quartz countertops, stainless steel appliances, a gas range, and a breakfast bar, seamlessly flowing into the dining area—ideal for entertaining. Two well-appointed bedrooms, each with ample

    Kevin McMath Lamacchia Realty, Inc.

    4 Palmyra St Unit 2, Winthrop, MA 02152
    • /25

      Est $371,146 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 977 Sq Ft

      400 Governors Dr Unit 4, Winthrop, MA 02152

      400 Governors Dr Unit 4, 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
    • /20

      Est $338,467 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 723 Sq Ft

      300 Governors Dr Unit 16, Winthrop, MA 02152

      300 Governors Dr Unit 16, 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
    • /19

      Est $350,462 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 723 Sq Ft

      300 Governors Dr Unit 12, Winthrop, MA 02152

      300 Governors Dr Unit 12, 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
    • /26

      Est $327,022 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 714 Sq Ft

      300 Governors Dr Unit 5, Winthrop, MA 02152

      300 Governors Dr Unit 5, 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
    • /11

      Est $320,562 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 714 Sq Ft

      300 Governors Dr Unit 4, Winthrop, MA 02152

      300 Governors Dr Unit 4, 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
    • /19

      Est $370,941 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 780 Sq Ft

      100 Governors Dr Unit 16, Winthrop, MA 02152

      100 Governors Dr Unit 16, 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
    • /24

      Est $351,458 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 780 Sq Ft

      100 Governors Dr Unit 15, Winthrop, MA 02152

      100 Governors Dr Unit 15, 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
    • /19

      Est $346,545 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 782 Sq Ft

      1100 Governors Dr Unit 19, Winthrop, MA 02152

      1100 Governors Dr Unit 19, 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

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