Winthrop, MA Homes

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  /26

  $525,000

  • 2 Beds
  • 2 Baths
  • 865 Sq Ft

  600 Shirley St Unit 16, Winthrop, MA 02152

  Always wanted to live across from the beach? This might be the place for you! Enjoy breathtaking water and Boston skyline views from this beautifully renovated 2-bed, 2-bath condo at the former Historic Crystal Cove Hotel. Offering first-floor convenience with a private entrance and two deeded parking spaces right outside your door, this home lives like a private residence. The open layout

  Elizabeth Crowley William Raveis R.E. & Home Services

  600 Shirley St Unit 16, Winthrop, MA 02152
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  /29

  $1,375 per month

  • 5 Beds
  • 2 Baths
  • 1,271 Sq Ft
  • Condo for Rent

  42 Irwin St, Winthrop, MA 02152

  42 Irwin St, Winthrop, MA 02152
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  /24

  $295,000 Sold May 13, 2025

  • 764 Sq Ft
  • $386/SF
  • 27 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 1900

  203 Winthrop Shore Dr Unit 8, Winthrop, MA 02152

  INCREDIBLE VALUE!!! This Open Penthouse Condo with vaulted ceilings and exposed beams has 1 Bedroom and 1 Bath and spans 764 square feet and is priced to sell. Classic building with wraparound porches across from Winthrop Beach. Come and experience oceanfront living just minutes from Boston. Price includes a full off-street parking. a ceiling fan. The kitchen boasts white cabinetry, granite

  Charles Roderick eXp Realty

  203 Winthrop Shore Dr Unit 8, Winthrop, MA 02152
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  /22

  Est $458,920 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 905 Sq Ft

  1 Seal Harbor Rd Unit 101, Winthrop, MA 02152

  1 Seal Harbor Rd Unit 101, Winthrop, MA 02152
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  /21

  $779,000

  • 3 Beds
  • 1.5 Baths
  • 1,792 Sq Ft

  138 Grand View Ave, Winthrop, MA 02152

  Experience the thrill and excitement of oceanfront living in this move-in ready seaside single with 3 bedrooms and 1.5 bathrooms. Enjoy stunning, dramatic views of the ocean and Boston skyline. The home features a newly refreshed kitchen and a spacious open floor plan with a fireplace, inviting both ocean views and abundant natural light. Beautiful oak hardwood floors enhance the interior, while

  James Polino Compass

  138 Grand View Ave, Winthrop, MA 02152
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  /17

  $3,200 per month

  • 3 Beds
  • 1.5 Baths
  • 1,574 Sq Ft
  • Apartment for Rent

  15 George St Unit 2, Winthrop, MA 02152

  Available 8/1 - this HUGE 3 bedroom, 1.5 bath apartment is located on a quiet street, just blocks from Winthrop Center and minutes from Boston. This home has two floors of living space, with a front porch, living room, dining room, newly-renovated kitchen (42' cabinets, granite, stainless), and bath located on the first floor and three large bedrooms and a full bathroom located on the second

  Matthew Morano Dorado Properties

  15 George St Unit 2, Winthrop, MA 02152
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  /27

  $635,000 Sold May 09, 2025

  • 1,200 Sq Ft
  • $529/SF
  • 4 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1910

  67 Bay View Ave Unit 1L, Winthrop, MA 02152

  Experience coastal living at its finest in this beautifully renovated 2-bed, 2-bath condo, offering breathtaking views of the bay and the iconic Winthrop water tower. Step inside to discover elegant new flooring, sleek modern appliances, and the convenience of central air and heating. Flooded with natural light, the open-concept living space seamlessly connects to expansive outdoor areas—ideal

  The Reference Group Reference Real Estate

  67 Bay View Ave Unit 1L, Winthrop, MA 02152
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  /29

  Est $663,360 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,306 Sq Ft

  3 Seal Harbor Rd Unit 835, Winthrop, MA 02152

  3 Seal Harbor Rd Unit 835, Winthrop, MA 02152
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  /30

  $825,000

  • 3 Beds
  • 2.5 Baths
  • 2,112 Sq Ft

  75 Sewall Ave, Winthrop, MA 02152

  Discover this vintage 1970s-style gem just a block from the ocean, perfectly situated in one of Winthrop's most sought-after neighborhoods. This inviting single-family home features three spacious bedrooms and two and a half baths, ideal for comfortable living. Step inside to find a blend of retro charm and modern convenience. The spacious mezzanine living room has soaring ceilings and is open to

  Harry Silverstein Keller Williams Realty Boston Northwest

  75 Sewall Ave, Winthrop, MA 02152
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  /29

  $900 per month

  • 5 Beds
  • 2 Baths
  • 1,271 Sq Ft
  • Condo for Rent

  42 Irwin St, Winthrop, MA 02152

  42 Irwin St, Winthrop, MA 02152
• 

  

  /29

  $900,000 Sold May 09, 2025

  • 2,988 Sq Ft
  • $301/SF
  • 7 Days On Market

  • 8 Beds
  • 3 Baths
  • Built 1957

  84 Banks St, Winthrop, MA 02152

  Rare opportunity to own a double lot two-family home with expansion possibilities for a third unit. This well-maintained property offers stunning views of Belle Isle marsh and direct gated access to scenic walking trails and tranquil vistas. The fenced-in backyard is ready to enjoy with mature fruit trees, flowering shrubs, a deck and koi pond that await your fish. The main unit showcases a

  Erica Gore Century 21 Seaport

  84 Banks St, Winthrop, MA 02152
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  /27

  Est $903,390 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,674 Sq Ft

  3 Seal Harbor Rd Unit 636, Winthrop, MA 02152

  3 Seal Harbor Rd Unit 636, Winthrop, MA 02152
• 

  

  /27

  $814,500 Pending

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

  77 Otis St, Winthrop, MA 02152

  Welcome to coastal living on Point Shirley. This beautifully renovated 4BD, 2BA home invites you to slow down and enjoy life by the beach. Start your day watching the sun rise from your yoga/sunroom, or with a cup of coffee on your front porch. With tall ceilings and an open-concept layout you'll have sight lines from the living room to the dining room to the modern kitchen with quartz counters,

  Molly Walker Coldwell Banker Realty - Scituate

  77 Otis St, Winthrop, MA 02152
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  /21

  $3,400 per month

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

  58 Beacon St, Winthrop, MA 02152

  Single family opportunity in highly sought after Winthrop location! Newly renovated, this residence boasts charm with cedar shingles and a private porch just steps away from Winthrop beach. Enter into the open living/dinning space with chef inspired kitchen, hardwood floors throughout, recessed lighting and ample storage space. The second floor features a perfect flex space for an office, 2

  Alexandria Cornelio JD Advisors, Inc

  58 Beacon St, Winthrop, MA 02152
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  /29

  $635,000 Sold May 09, 2025

  • 968 Sq Ft
  • $656/SF
  • 6 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1880

  31 River Rd, Winthrop, MA 02152

  Charming 2-bedroom, 1-bath home in the sought-after Cottage Park area of Winthrop! Cozy new front porch leads you into an inviting living room w/ gleaming HW floors & plenty of natural light. The dining room, featuring a custom built-in china cabinet w/ 3 drawers for add'l storage, flows seamlessly into the kitchen w/ ample cabinet space, tile flooring & a breakfast bar. Enjoy new SS smart

  Paul Cervone Lamacchia Realty, Inc.

  31 River Rd, Winthrop, MA 02152
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  /21

  Est $512,937 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 840 Sq Ft

  3 Seal Harbor Rd Unit 634, Winthrop, MA 02152

  3 Seal Harbor Rd Unit 634, Winthrop, MA 02152
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  /28

  $524,900 Pending

  • 2 Beds
  • 2 Baths
  • 1,219 Sq Ft

  30 Crystal Cove Ave Unit 2, Winthrop, MA 02152

  Nestled in Winthrop’s sought-after Crystal Cove neighborhood, this beautifully maintained two-level condo perfectly combines timeless character with stylish comfort. A grand staircase serves as the home’s architectural showpiece, adding elegance and a sense of grandeur. The sun-filled unit features an updated kitchen, two bedrooms and renovated bathrooms offering modern finishes and

  Erica Gore Century 21 Seaport

  30 Crystal Cove Ave Unit 2, Winthrop, MA 02152
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  /10

  $4,295 per month

  • 4 Beds
  • 2 Baths
  • 1,800 Sq Ft
  • Condo for Rent

  25 Pratt St Unit 2, Boston, MA 02134

  25 Pratt St Unit 2, Boston, MA 02134
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  /12

  $450,000 Sold May 09, 2025

  • 700 Sq Ft
  • $643/SF
  • 216 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 1920

  158 Shirley St Unit 1, Winthrop, MA 02152

  Welcome to your dream retreat by the beach! This fully renovated one-bedroom condo offers a perfect blend of modern luxury and coastal charm. From the sleek stainless steel appliances to the elegant granite countertops and upgraded cabinets, every detail in the kitchen exudes sophistication. The addition of a kitchen island creates a central hub for gatherings, while in-unit laundry adds

  Leighann Eruzione Lantern Residential

  158 Shirley St Unit 1, Winthrop, MA 02152
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  /32

  Est $663,128 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,286 Sq Ft

  3 Seal Harbor Rd Unit 633, Winthrop, MA 02152

  3 Seal Harbor Rd Unit 633, Winthrop, MA 02152
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  /7

  $500,000 Pending

  • 1 Bed
  • 1 Bath
  • 633 Sq Ft

  10 Somerset Ave Unit 211, 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 211, Winthrop, MA 02152
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  /35

  $3,500 per month

  • 3 Beds
  • 1 Bath
  • 1,200 Sq Ft
  • Apartment for Rent

  144 Circuit Rd Unit 1, Winthrop, MA 02152

  Stunning 3-Bedroom in Winthrop’s Desirable Maze AreaWelcome to this beautifully maintained 3-bedroom, 1-bath apartment in a charming two-family home, ideally located in Winthrop’s sought-after Maze neighborhood. Spanning two levels, this spacious first-floor unit features a modern kitchen, a large living room, and a formal dining room—perfect for everyday living and entertaining.Enjoy the

  Karen Urbino Century 21 Cityside

  144 Circuit Rd Unit 1, Winthrop, MA 02152
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  /25

  $490,000 Sold May 07, 2025

  • 1,270 Sq Ft
  • $386/SF
  • 74 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1925

  111 Locust St Unit 2, Winthrop, MA 02152

  Back on market due to buyer financing. Charming light filled 3 bedroom condo steps to Winthrop Beach offers coastal living at its finest. Well thought-out layout maximizes comfort and functionality. The open living/dining rooms are bright and inviting with ample space for relaxing or entertaining. Each of the 3 bedrooms are generously sized perfect for family, guests or a home office. Large

  Christine D'Ambrosio Lantern Residential

  111 Locust St Unit 2, Winthrop, MA 02152
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  /38

  Est $532,578 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 871 Sq Ft

  3 Seal Harbor Rd Unit 541, Winthrop, MA 02152

  3 Seal Harbor Rd Unit 541, Winthrop, MA 02152
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  /28

  $500,000 Pending

  • 3 Beds
  • 1 Bath
  • 1,120 Sq Ft

  66 Plummer Ave Unit 2, Winthrop, MA 02152

  Welcome to 66 Plummer Ave, a well-appointed 3-bedroom, 1-bath condo that offers the perfect blend of comfort, space, and convenience. This sun-filled home features beautiful hardwood floors and a spacious layout with a separate living room, dining room, and kitchen—ideal for both daily living and entertaining. Enjoy your morning coffee or unwind in the evening on either of the two private decks.

  The Reference Group Reference Real Estate

  66 Plummer Ave Unit 2, Winthrop, MA 02152
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  /18

  $2,750 per month

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

  90 Winthrop Shore Dr Unit uni2 2-bed, Winthrop, MA 02152

  This cozy studio apartment is an ideal space for any beach lover with Winthrop Beach just across the road. The unit is ideally situated right on Winthrop Shore Drive and is flooded with natural light!This spacious studio apartment is an ideal space for any beach lover with Winthrop Beach just across the road! Features include an updated eat-in kitchen, hardwood floors, a tiled bathroom,

  90 Winthrop Shore Dr Unit uni2 2-bed, Winthrop, MA 02152
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  /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
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  /32

  Est $520,948 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 840 Sq Ft

  3 Seal Harbor Rd Unit 434, Winthrop, MA 02152

  3 Seal Harbor Rd Unit 434, Winthrop, MA 02152
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  /12

  $799,900

  • 4 Beds
  • 2 Baths
  • 2,103 Sq Ft

  56 Main St, Winthrop, MA 02152

  OPPORTUNITY KNOCKS.......Two family with large yard located right on the bus line with a very short ride to the T to Boston. There are 6 off street parking spaces! The home was gutted in 2001. The owner's unit is on the second and third floors with an open floor plan and loads of natural lighting. It contains a living room, dining area, kitchen, bath and bedroom on the second floor and a

  Sharon Tallent Compass

  56 Main St, Winthrop, MA 02152
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  /16

  $3,600 per month

  • 3 Beds
  • 2 Baths
  • 1,629 Sq Ft
  • Apartment for Rent

  338 Pleasant St Unit 1, Winthrop, MA 02152

  JUST IN TIME FOR A BEACH SEASON! Welcome to the highly desired Maze location of town! This beautifully renovated pet friendly apartment checks all the boxes! With two levels of living space, the primary floor offers a bright open concept Living & Dining space with high ceilings, recessed lighting & crown moulding. The kitchen is fully equipped with SS appliances, warm shaker style custom

  Atiyeh Cassidy Blue Sky Realty

  338 Pleasant St Unit 1, Winthrop, MA 02152
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  /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
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  /40

  Est $613,489 Not Listed For Sale

  • 1 Bed
  • 2 Baths
  • 1,263 Sq Ft

  3 Seal Harbor Rd Unit 332, Winthrop, MA 02152

  3 Seal Harbor Rd Unit 332, Winthrop, MA 02152
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  /35

  $925,000

  • 4 Beds
  • 2 Baths
  • 2,532 Sq Ft

  200 Woodside Ave, Winthrop, MA 02152

  Incredible opportunity to own a well-maintained 2-family home perfectly suited for investors or owner-occupants in seaside Winthrop! Conveniently located within steps to the water as well as the Center Business District, this property combines location, functionality, & value. With over 2,500 sq ft of living space & many updates made since 2016, this multi-family also ensures comfort & peace of

  Atiyeh Cassidy Blue Sky Realty

  200 Woodside Ave, Winthrop, MA 02152
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  /20

  $2,850 per month

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

  87 Winthrop Shore Dr Unit uni5 2-bed 1-bath, Winthrop, MA 02152

  Calling all beach lovers! This newly renovated 2 bedroom apartment features hardwood floors, granite counters, stainless steel appliances, a tiled bathroom, a porch with ocean views, and laundry on-site! This space is flooded with natural sunlight and provides gorgeous views of Winthrop Beach.Our building is only a 20 minute ride to Downtown Boston, 15 minutes to Logan Airport, 20 minutes to

  87 Winthrop Shore Dr Unit uni5 2-bed 1-bath, Winthrop, MA 02152
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  /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
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  /16

  Est $528,730 Not Listed For Sale

  • 1 Bed
  • 1.5 Baths
  • 1,033 Sq Ft

  3 Seal Harbor Rd Unit 331, Winthrop, MA 02152

  3 Seal Harbor Rd Unit 331, Winthrop, MA 02152
• 

  

  /42

  $749,000

  • 4 Beds
  • 2 Baths
  • 2,130 Sq Ft

  54 Otis St, Winthrop, MA 02152

  Rare opportunity to own two 4,000 Sq ft lots side by side in the beautiful Point Shirley neighborhood. 54 Otis Street and O Otis Street to be sold together in this sale.54 Otis Street in Winthrop, Massachusetts. This charming single-family home built in 1900, offering 2,130 sq ft of living space on a 4,000 sq ft lot. This residence features 8 rooms, providing ample space for comfortable living.

  Stephen Visco East Coast Realty, Inc.

  54 Otis St, Winthrop, MA 02152
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  /22

  $2,900 per month

  • 3 Beds
  • 1 Bath
  • 1,500 Sq Ft
  • Apartment for Rent

  21 Sunnyside Ave Unit 2, Winthrop, MA 02152

  OCEANSIDE SEVEN ROOM APARTMENT OVERLOOKING SALT WATER MARSH, PRIVATE BEACH ONE BLOCK AWAY, THREE BEDROOMS WITH AN ADDITIONAL ROOM FOR AN OFFICE , FULL DINING AND LIVING ROOM OPEN FLOOR PLAN, ALL NEW WINDOWS SHARED DRIVEWAY AND BACKYARD, STORAGE IN BASEMENT, EAT IN KITCHEN, PLENTY OF CLOSET SPACE. CLOSE TO BEACHES, BUS STOP AND BLUE LINE TRAIN STATION 10 min to airport 15 min to Boston Tenants pay

  Stephanie Macisaac East Coast Realty

  21 Sunnyside Ave Unit 2, Winthrop, MA 02152
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  /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
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  /28

  Est $534,287 Not Listed For Sale

  • 1 Bed
  • 1.5 Baths
  • 1,033 Sq Ft

  3 Seal Harbor Rd Unit 231, Winthrop, MA 02152

  3 Seal Harbor Rd Unit 231, Winthrop, MA 02152

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