3,427

Downtown Winthrop Homes

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  • /19

    $665,000 Pending

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

    34 Fremont St, Winthrop, MA 02152

    34 Fremont gives you something most homes in town can’t: space to grow into on a bigger-than-normal lot near Winthrop Center. The main level flows the way a home should: kitchen with pantry, dining and living rooms connected, and an office when you need a door closed. Upstairs you’ll find three comfortable bedrooms plus two additional rooms that are perfect for kids’ bedrooms, a second office,

    The Reference Group Reference Real Estate

    34 Fremont St, Winthrop, MA 02152
  • /51

    $3,000 - $4,000 total monthly price

    • 1 - 3 Beds
    • 2 Baths
    • 836 Sq Ft
    • Condo for Rent

    80 Shirley St, Winthrop, MA 02152

    Gorgeous farmhouse revival!! Coastal vibes flow throughout this stunning brand new renovation. Best of both worlds with proximity to the beach and the city. Less than a 5 minute walk to the nicest beach close to Boston. An easy 15 minute drive and you're in the middle of the city. The unit boasts a modern open floor plan. Actual high end finishes throughout for an obvious upscale vibe. Huge

    80 Shirley St, Winthrop, MA 02152
  • /32

    $462,000 Sold Sep 03, 2025

    • 1,165 Sq Ft
    • $397/SF
    • 7 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1900

    94 Lincoln St Unit 2, Winthrop, MA 02152

    This charming, move-in-ready 2-bed, 1-bath condo in a gorgeous brownstone building offers historic character and modern convenience just minutes from downtown Boston! Beautiful original hardwood floors and bay window add warmth and timeless appeal. Both bedrooms are generously sized and filled with natural light. The second bedroom has a walk-in closet. The spacious, eat-in kitchen features tile

    David Ladner RE/MAX Harmony

    94 Lincoln St Unit 2, Winthrop, MA 02152
    • /37

      Est $722,863 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 1,564 Sq Ft

      105 Almont St, Winthrop, MA 02152

      105 Almont St, Winthrop, MA 02152
  • /22

    $550,000 Pending

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

    87 Hermon St, Winthrop, MA 02152

    This charming 3 bedroom and 1 bathroom home has been family owned for over 63 years and is ready for a new owner to usher it into its next stage of life! The bones are there and it's ready for a beautiful transformation. It is very centrally located in town...just minutes from the Center Business District, parks and the beach. You can experience small-town living while being a very short commute

    James Polino Compass

    87 Hermon St, Winthrop, MA 02152
  • /11

    $3,150 total monthly price

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

    35 Lincoln St Unit 1, Winthrop, MA 02152

    Fully renovated unit with all the amenities, and terrific outdoor spaces. Unit 1 of this 3 unit building has 2 bedrooms and 1 bath, and a mix modern conveniences with classic details. Single floor of living, all on the first floor. Open-concept living/kitchen, generous bedrooms with glass enclosed walk in shower and organized closets, enhanced by high ceilings, and large windows throughout. Great

    Daniel Vannoni Housequarters

    35 Lincoln St Unit 1, Winthrop, MA 02152
  • /41

    $830,000 Sold Aug 30, 2025

    • 2,958 Sq Ft
    • $281/SF
    • 48 Days On Market
    • 5 Beds
    • 2 Baths
    • Built 1920

    37-39 Hutchinson St, Winthrop, MA 02152

    Endless Potential in Prime Seaside Location – 02152 Welcome to this oversized two-family home located in the highly desirable seaside community of Winthrop, 02152. Perfectly situated on a generous lot, this property offers a rare opportunity for investors, multi-generational living, or owner-occupants looking to customize and create value.Each unit features spacious layouts with room to grow, and

    Nicole Bettano Lantern Residential

    37-39 Hutchinson St, Winthrop, MA 02152
    • /38

      Est $782,957 Not Listed For Sale

      • 3 Beds
      • 3.5 Baths
      • 2,049 Sq Ft

      25 Almont St Unit B, Winthrop, MA 02152

      25 Almont St Unit B, Winthrop, MA 02152
  • /10

    $319,000 Pending

    • 2 Beds
    • 1 Bath
    • 772 Sq Ft

    1100 Governors Dr Unit 6, Winthrop, MA 02152

    Coastal Convenience Meets City Access-Welcome home to this beautifully maintained 4-room, 2-bedroom, 1-bath condo offering comfort, convenience all just minutes away from Logan Airport, Boston and Beaches. Located in a professionally managed complex, this unit features two parking spots, in-ground pool, tennis courts and on site laundry facility. Whether you’re a first time buyer, downsizing or a

    Colleen Eddy Return Realty Group, Inc.

    1100 Governors Dr Unit 6, Winthrop, MA 02152
  • /17

    $350,000 Sold Aug 19, 2025

    • 723 Sq Ft
    • $484/SF
    • 7 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1971

    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
    • /28

      Est $896,623 Not Listed For Sale

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

      70 Shirley St, Winthrop, MA 02152

      70 Shirley St, Winthrop, MA 02152
  • /36

    $722,000 Pending

    • 3 Beds
    • 1.5 Baths
    • 1,325 Sq Ft

    19 Pleasant Park Rd, Winthrop, MA 02152

    Welcome to 19 Pleasant Park Road - a beautifully updated coastal retreat that blends timeless character with modern comfort. Step inside to discover warm hardwood floors, sun-filled rooms, and a layout designed for easy everyday living. The inviting dining room flows seamlessly into the living space, while the updated kitchen features stainless steel appliances and classic white cabinetry. Both

    Laura Cohron Fiv Realty Co.

    19 Pleasant Park Rd, Winthrop, MA 02152
  • /38

    $1,060,000 Sold Aug 15, 2025

    • 2,692 Sq Ft
    • $394/SF
    • 36 Days On Market
    • 6 Beds
    • 2.5 Baths
    • Built 1900

    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
    • /40

      Est $1,278,361 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
  • /37

    $899,900 Pending

    • 4 Beds
    • 2 Baths
    • 2,366 Sq Ft

    80 Shirley St, Winthrop, MA 02152

    Gorgeous farmhouse revival!!! Coastal vibes flow through this stunning brand new renovation. Best of both worlds with proximity to the beach and the city. Less than a 5 minute walk to the nicest beach close to Boston. An easy 15 minute drive and you're in the middle of the city. Both units boast modern open floor plans. Actual high end finishes throughout for an obvious upscale vibe. Huge

    Nick Burnes Red Tree Real Estate

    80 Shirley St, Winthrop, MA 02152
  • /31

    $492,500 Sold Aug 14, 2025

    • 1,595 Sq Ft
    • $309/SF
    • 10 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1916

    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
    • /27

      Est $341,994 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
  • /34

    $735,000 Pending

    • 5 Beds
    • 3.5 Baths
    • 2,475 Sq Ft

    9 Marshall St, Winthrop, MA 02152

    Discover the best of coastal living in this Winthrop waterfront community, where local dining, seaside charm, and effortless access to public transit create a lifestyle of ease and enjoyment. Spanning approximately 2,475 square feet, this expansive 5-bedroom, 3.5-bath home offers three levels of versatile living space along with a private outdoor deck and yard. Ideally situated within walking

    Ricardo Rodriguez Coldwell Banker Realty - Boston

    9 Marshall St, Winthrop, MA 02152
  • /38

    $935,000 Sold Aug 01, 2025

    • 4,101 Sq Ft
    • $228/SF
    • 22 Days On Market
    • 4 Beds
    • 3 Baths
    • Built 1896

    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
    • /18

      Est $345,320 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
  • /34

    $899,000 Pending

    • 4 Beds
    • 2 Baths
    • 2,386 Sq Ft

    41 Summit Ave, Winthrop, MA 02152

    Lovely custom built ranch offering endless possibilities! Perfect for multi-generational living or added income with a fully equipped lower level apartment. The main floor features a cherry wood kitchen with granite countertops, a spacious fireplace living room, tiled bath with separate shower and tub, generous bedrooms, den, and a bright sunroom with ocean views. Enjoy central air and an

    Elizabeth Ferrara Cottage Hill Real Estate

    41 Summit Ave, Winthrop, MA 02152
  • /41

    $867,000 Sold Jul 31, 2025

    • 2,494 Sq Ft
    • $348/SF
    • 24 Days On Market
    • 5 Beds
    • 2 Baths
    • Built 1920

    26 Enfield Rd, Winthrop, MA 02152

    Charming two-family in desirable area of Winthrop. Steps away from Ingleside Park's playground, roller hockey court and baseball field. The restaurants of Winthrop's center are close proximity as well. Great opportunity on one of the nicest streets in Winthrop.

    Nicholas Martino Noddle Island Real Estate

    26 Enfield Rd, Winthrop, MA 02152
    • /15

      Est $326,825 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
  • /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
  • /41

    $1,100,000 Sold Jul 24, 2025

    • 4,223 Sq Ft
    • $260/SF
    • 38 Days On Market
    • 5 Beds
    • 3 Baths
    • Built 1900

    52 Washington Ave, Winthrop, MA 02152

    Fantastic Owner-Occupied Multifamily Opportunity in Winthrop! This centrally located home is perfect for both investors and owner-occupants. The owner's unit spans two levels and showcases beautiful hardwood floors, original woodwork, and two full bathrooms offering both charm and functionality. The first-floor unit features a spacious kitchen, hardwood floors, and two generously sized bedrooms.

    Elizabeth Ferrara Cottage Hill Real Estate

    52 Washington Ave, Winthrop, MA 02152
    • /20

      Est $368,147 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 977 Sq Ft

      500 Governors Dr Unit 8, Winthrop, MA 02152

      500 Governors Dr Unit 8, Winthrop, MA 02152
  • /31

    $749,900 Pending

    • 5 Beds
    • 2.5 Baths
    • 2,394 Sq Ft

    426 Winthrop St, Winthrop, MA 02152

    Welcome home to this open concept colonial home in sought after Winthrop! The home offers gleaming hardwood floors with a sunken living room equipped with a surround sound system throughout. The personally crafted kitchen/dining area has beautiful maple cabinets & granite countertops. Entertain family and friends through elegant French doors leading to a to a large patio and with fenced yard

    Jim Fitzgerald RE/MAX Realty Plus

    426 Winthrop St, Winthrop, MA 02152
  • /19

    $830,000 Sold Jul 21, 2025

    • 2,000 Sq Ft
    • $415/SF
    • 32 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1930

    509 Pleasant St, Winthrop, MA 02152

    Welcome to 509 Pleasant, where coastal charm meets modern chic. This 3 bed/2 bath cottage style home is located in the ideal spot for both beach and city lovers. It features a smart system including Nest thermostat and Ring doorbell, a newer roof, recessed lighting, two fireplaces, a walk-in closet, in-built cabinets, a fully finished basement, a bonus room ideal for a playroom or gym, and an

    Hayley Buonopane Conway - Swampscott

    509 Pleasant St, Winthrop, MA 02152
    • /32

      Est $380,627 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 826 Sq Ft

      400 Governors Dr Unit 37, Winthrop, MA 02152

      400 Governors Dr Unit 37, Winthrop, MA 02152
  • /28

    $678,000 Sold Jul 14, 2025

    • 1,372 Sq Ft
    • $494/SF
    • 12 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1949

    183 Pauline St, Winthrop, MA 02152

    Welcome to 183 Pauline St. in the desirable town of Winthrop. Owned by the same family for generations, this 3 bed, 2 bath cape cod style home is in need of some updating but has much to offer. Mostly hardwood flooring throughout with picture windows in living/dining room, kitchen that leads to the deck overlooking level backyard, primary bedroom & full bath complete the first level. Second level

    Jared Freni RE/MAX Andrew Realty Services

    183 Pauline St, Winthrop, MA 02152
    • /21

      Est $369,232 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 821 Sq Ft

      400 Governors Dr Unit 32, Winthrop, MA 02152

      400 Governors Dr Unit 32, Winthrop, MA 02152
  • /40

    $935,000 Sold Jul 10, 2025

    • 2,124 Sq Ft
    • $440/SF
    • 4 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 1920

    96-98 Woodside Ave, Winthrop, MA 02152

    Excellent investment or owner-occupant opportunity in the heart of Winthrop! This two-family home features over 2,100 sq. ft. of living space, including a first-floor unit with 6 rooms, 2 bedrooms, and 1 bath, and a second-floor unit with 7 rooms, 2 bedrooms, and 1 bath—providing a total of 13 rooms across both units. The 3rd floor, unfinished walk-up attic is already plumbed and ready for future

    John Young Ledge & Young Real Estate

    96-98 Woodside Ave, Winthrop, MA 02152
    • /25

      Est $368,200 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
  • /39

    $885,000 Sold Jun 26, 2025

    • 2,454 Sq Ft
    • $361/SF
    • 5 Days On Market
    • 6 Beds
    • 2 Baths
    • Built 1910

    437 Winthrop St, Winthrop, MA 02152

    Detached Two Family that is conveniently located right next to Winthrop Center. This two-family Has a ton of updates that includes, Newer Roof, Newer windows, Newer electric service, wiring and electric panels, forced air by gas(can easily add Central A/C) Newer kitchen upstairs and more. There is a level fenced-in yard with two large balconies, There are two separate storage rooms in the

    Jeffrey Bowen eRealty Advisors, Inc.

    437 Winthrop St, Winthrop, MA 02152
    • /20

      Est $346,104 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
  • /28

    $665,000 Sold Jun 18, 2025

    • 1,600 Sq Ft
    • $416/SF
    • 6 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 1966

    128 Lincoln St, Winthrop, MA 02152

    Opportunity meets potential in this bright and spacious 4BR, 2BA, custom designed split entry with 2 levels of living, available for the first time in over 50 years. Owned and cared for by one family since it was built in 1966. Now ready for the next owner. Needs some TLC. Sitting on a 6,000+ sf level corner lot, centrally located and across from Ingleside Park. Features include a two-zone gas

    Carol Henriquez Coldwell Banker Realty - Cambridge

    128 Lincoln St, Winthrop, MA 02152
    • /19

      Est $357,934 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
  • /31

    $545,000 Sold Jun 04, 2025

    • 999 Sq Ft
    • $546/SF
    • 3 Days On Market
    • 1 Bed
    • 1 Bath
    • Built 2006

    550 Pleasant St Unit 209, Winthrop, MA 02152

    Experience waterfront living at the Residences at Atlantis Marina in this beautifully upgraded 1-bedroom, 1-bathroom unit. Enjoy breathtaking Marina views from your private balcony, perfect for relaxing and unwinding. The thoughtfully designed interior features stainless steel appliances, upgraded countertops, and ample storage space. Convenience is key with in-unit laundry and two dedicated

    The Reference Group Reference Real Estate

    550 Pleasant St Unit 209, Winthrop, MA 02152
    • /26

      Est $334,675 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
  • /41

    $1,400,000 Sold May 29, 2025

    • 3,000 Sq Ft
    • $467/SF
    • 6 Days On Market
    • 6 Beds
    • 5 Baths
    • Built 1890

    89-91 Hermon St, Winthrop, MA 02152

    Welcome to 89-91 Hermon St, a beautifully renovated split-level Victorian home, completely transformed in 2023 with no expense spared. Featuring 6 bedrooms, 5 bathrooms, a fully finished basement, and plenty of parking. This home is packed with upgrades like a GAF roofing system, Anderson windows, spray foam insulation, Goodman central heat and AC, all-new electrical, and custom kitchen cabinets.

    Juan Cano Broad Sound Real Estate, LLC

    89-91 Hermon St, Winthrop, MA 02152

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