Winthrop, MA Homes

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  /25

  $469,000 Pending

  • 2 Beds
  • 1 Bath
  • 1,100 Sq Ft

  95 Shirley St Unit 3, Winthrop, MA 02152

  Top floor unit with exposed brick and a private garage, offering the perfect blend of character and modern updates! This sun filled home features a spacious open floor plan with white kitchen cabinetry, quartz countertops, and wood floors throughout. Generous bedrooms include a primary with a large closet and a second bedroom with a brand new custom closet system and washer and dryer for

  Elizabeth Ferrara Cottage Hill Real Estate

  95 Shirley St Unit 3, Winthrop, MA 02152
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  /10

  $2,400 Per Month

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

  97 Winthrop Shore Dr Unit 1, Winthrop, MA 02152

  Utilities included!! Updated 1-bedroom, 1-bath residence ideally situated along Winthrop Shore Drive. This well-appointed unit offers a refreshed interior, open kitchen/living area, eat in kitchen, in-unit laundry, and one dedicated parking space. directly across from Winthrop Beach, the home offers effortless access to the shoreline just steps from your door. Enjoy morning walks along the water,

  Acone & Company Team Darwin Associates

  97 Winthrop Shore Dr Unit 1, Winthrop, MA 02152
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  /32

  $850,000 Sold Jul 17, 2025

  81 Lowell Rd, Winthrop, MA 02152

  • 3 Beds
  • 2 Baths
  • 1,998 Sq Ft
  • Built 1900

  Last Sold Summary

  • 3% Below List Price
  • $425/SF
  • 12 Days On Market

  Current Estimated Value $816,096

  Last Listing Agent Randall Horn Entourage Realty LLC

  81 Lowell Rd, Winthrop, MA 02152
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  /42

  Est $697,239 Not Listed For Sale

  1 Seal Harbor Rd Unit PH16, Winthrop, MA 02152

  • 2 Beds
  • 2 Baths
  • 1,417 Sq Ft
  • Built 1983

  1 Seal Harbor Rd Unit PH16, Winthrop, MA 02152

  Last Sold Summary

  • 16% Above List Price
  • $423/SF
  • 6 Days On Market

  • Last Sold Price $599,900
  • May 09, 2023

  Last Listing Agent Ed Deveau Century 21 Mario Real Estate
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  /42

  $799,999

  • 2 Beds
  • 2 Baths
  • 1,417 Sq Ft

  1 Seal Harbor Rd Unit PH16, Winthrop, MA 02152

  Rarely available PENTHOUSE unit w/ sweeping, unobstructed Atlantic Ocean views from private top-flr balcony. 2BR/2BA residence renovated in 2024 featuring oversized windows w/ abundant natural light in living area, built in window seat, white oak HW floors throughout w/ inlay foyer detail under skylight/ recessed lighting. Updated kitchen w/ honed granite counters, SS appliances & blue glass

  Meg Grady Lantern Residential

  1 Seal Harbor Rd Unit PH16, Winthrop, MA 02152
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  /28

  $2,400

  Total Monthly Price

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

  25 Pratt St Unit 1, Boston, MA 02134

  Rent:$2,400 / mo.Beds:1 BedBaths:1 BathLaundry:Laundry on SiteUnit Level:1Parking:For Rent, Outdoor, $200 / Month

  25 Pratt St Unit 1, Boston, MA 02134
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  /24

  $1,260,000 Sold Mar 31, 2026

  37 Trident Ave, Winthrop, MA 02152

  • 8 Beds
  • 3 Baths
  • 3,708 Sq Ft
  • Built 1900

  Last Sold Summary

  • 3% Below List Price
  • $340/SF
  • 86 Days On Market

  Current Estimated Value $1,256,285

  Last Listing Agent David Parish Connor Real Estate

  37 Trident Ave, Winthrop, MA 02152
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  /20

  Est $608,887 Not Listed For Sale

  1 Seal Harbor Rd Unit 513, Winthrop, MA 02152

  • 2 Beds
  • 2 Baths
  • 1,205 Sq Ft
  • Built 1983

  1 Seal Harbor Rd Unit 513, Winthrop, MA 02152

  Last Sold Summary

  • 2% Below List Price
  • $517/SF
  • 46 Days On Market

  • Last Sold Price $623,500
  • Aug 31, 2024

  Last Listing Agent Jessica Pumphret Blue Sky Realty
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  /35

  $650,000

  • 3 Beds
  • 1.5 Baths
  • 1,728 Sq Ft

  47 Highland Ave, Winthrop, MA 02152

  Wonderful opportunity to own a coastal Winthrop home with tremendous potential. A welcoming mudroom opens to a spacious foyer and a large living and dining area with great flow for everyday living. A bonus front room offers flexible space for a home office, playroom, or an expanded open-concept layout. The kitchen leads directly to the back deck for warm-weather entertaining. Upstairs features

  Elizabeth Ferrara Cottage Hill Real Estate

  47 Highland Ave, Winthrop, MA 02152
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  /4

  $2,500 Per Month

  • 2 Beds
  • 1 Bath
  • 1,050 Sq Ft
  • Apartment for Rent

  31 Pleasant St Unit 2, Winthrop, MA 02152

  Recently updated two bedroom, one bathroom apartment located in professionally managed three family. This unit has hardwood floors, updated kitchen and more. The property is in close proximity to the public transportation, shopping, schools and more. Also, has easy access to Boston and many beaches.

  Timothy Shanahan Merrimack Realty Group, Chelmsford

  31 Pleasant St Unit 2, Winthrop, MA 02152
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  /42

  $785,000 Sold May 16, 2025

  95 Summit Ave Unit 4, Winthrop, MA 02152

  • 4 Beds
  • 2 Baths
  • 1,680 Sq Ft
  • Built 1890

  Last Sold Summary

  • 7% Above List Price
  • $467/SF
  • 6 Days On Market

  Current Estimated Value $768,564

  Last Listing Agent Joseph Schutt Unit Realty Group, LLC

  95 Summit Ave Unit 4, Winthrop, MA 02152
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  /42

  Est $633,494 Not Listed For Sale

  1 Seal Harbor Rd Unit 414, Winthrop, MA 02152

  • 2 Beds
  • 2 Baths
  • 1,327 Sq Ft
  • Built 1983

  1 Seal Harbor Rd Unit 414, Winthrop, MA 02152

  Last Sold Summary

  • 11% Above List Price
  • $430/SF
  • 17 Days On Market

  • Last Sold Price $570,000
  • May 15, 2024

  Last Listing Agent Jeffrey Carter Keller Williams Realty Evolution
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  /20

  $475,000 Open Sun 12PM - 1PM

  • 1 Bed
  • 1 Bath
  • 623 Sq Ft

  140 Shirley St Unit 230, 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 one-bedroom 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 lighting,

  Kovacs Savage Team Byrnes Real Estate Group LLC

  140 Shirley St Unit 230, Winthrop, MA 02152
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  /19

  $2,300 - $2,400

  Total Monthly Price

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

  220 Winthrop St, Winthrop, MA 02152

  Live in one of Winthrop’s most iconic landmark buildings at 220 Winthrop Street, known locally as The Wadsworth Building. Originally a cornerstone of Winthrop Center’s commercial life, this historic structure has been thoughtfully updated to offer distinctive residential apartments above neighborhood retail, blending classic New England character with modern interior finishes.The building

  220 Winthrop St, Winthrop, MA 02152
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  /42

  $1,325,000 Sold Aug 15, 2025

  45 Highland Ave, Winthrop, MA 02152

  • 10 Beds
  • 4 Baths
  • 4,671 Sq Ft
  • Built 1900

  Last Sold Summary

  • 5% Below List Price
  • $284/SF
  • 35 Days On Market

  Current Estimated Value $1,329,750

  Last Listing Agent Jonathan Mathews Legacy Realty Advisors LLC

  45 Highland Ave, Winthrop, MA 02152
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  /19

  Est $594,699 Not Listed For Sale

  1 Seal Harbor Rd Unit 104, Winthrop, MA 02152

  • 2 Beds
  • 2 Baths
  • 1,230 Sq Ft
  • Built 1983

  1 Seal Harbor Rd Unit 104, Winthrop, MA 02152

  Last Sold Summary

  • 9% Above List Price
  • $443/SF
  • 4 Days On Market

  • Last Sold Price $545,000
  • Jun 13, 2024

  Last Listing Agent Peggie Gilbert Coldwell Banker Peggy Carter Team
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  /8

  $549,000

  • Land
  • 8,276 Sq Ft
  • $2,889,474 per Acre

  54 Wilshire St, Winthrop, MA 02152

  Rare Winthrop duplex development opportunity offering the chance to build ground-up new construction in a highly desirable coastal community. The project allows for two spacious 2,500+ sqft units, ideal for resale as luxury condos or as long-term income-producing properties. Each unit includes two off-street parking spaces, a valuable amenity in this sought-after location. With strong buyer

  Lou Markakis Lynnway Associates

  54 Wilshire St, Winthrop, MA 02152
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  /16

  $2,975 Per Month

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

  235 Washington Ave Unit 2, Winthrop, MA 02152

  Waterfront living at its finest! Enjoy stunning harbor views overlooking three marinas from this beautiful 2-bedroom, 1-bath condominium. Heat and hot water are included! Every room offers gorgeous water views, with picture windows flooding the space in natural light. The open floor plan features a kitchen with a large island, a spacious master bedroom and exposed brick. Relax on the shared patio

  Caroline Ligotti Coldwell Banker Realty - Boston

  235 Washington Ave Unit 2, Winthrop, MA 02152
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  /42

  $777,000 Sold Nov 26, 2025

  32 Hale Ave, Winthrop, MA 02152

  • 3 Beds
  • 2 Baths
  • 1,418 Sq Ft
  • Built 1920

  Last Sold Summary

  • 11% Below List Price
  • $548/SF
  • 144 Days On Market

  Current Estimated Value $747,178

  Last Listing Agent Sharon Tallent Compass

  32 Hale Ave, Winthrop, MA 02152
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  /41

  Est $551,907 Not Listed For Sale

  3 Seal Harbor Rd Unit 846, Winthrop, MA 02152

  • 1 Bed
  • 1.5 Baths
  • 1,106 Sq Ft
  • Built 1987

  3 Seal Harbor Rd Unit 846, Winthrop, MA 02152

  Last Sold Summary

  • $497/SF
  • 20 Days On Market

  • Last Sold Price $550,000
  • Mar 10, 2025

  Last Listing Agent Cathie Curran Charlesgate Realty Group, llc
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  /36

  $700,000

  • 3 Beds
  • 1 Bath
  • 1,250 Sq Ft

  51 Undine Ave, Winthrop, MA 02152

  Experience coastal living in a vibrant beachside community featuring a park with tennis and basketball courts, a dog park, and a scenic shoreline overlooking the Boston skyline. This thoughtfully updated home offers peace of mind with a recently painted exterior, a roof approximately 5 years old, and upgraded electrical and plumbing systems. Inside, you’ll find newer flooring, fresh interior

  The Caceda Team Coldwell Banker Realty - Lynnfield

  51 Undine Ave, Winthrop, MA 02152
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  /37

  $2,750

  Total Monthly Price

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

  92 Winthrop Shore Dr Unit 2, Winthrop, MA 02152

  92 Winthrop Shore Dr Unit 2, Winthrop, MA 02152
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  /22

  $719,000 Sold Dec 30, 2025

  92 Plummer Ave, Winthrop, MA 02152

  • 3 Beds
  • 1.5 Baths
  • 1,449 Sq Ft
  • Built 1937

  Last Sold Summary

  • $496/SF
  • 5 Days On Market

  Current Estimated Value $711,752

  Last Listing Agent Susan DeFelice Keller Williams Realty Boston-Metro | Back Bay

  92 Plummer Ave, Winthrop, MA 02152
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  /29

  Est $677,308 Not Listed For Sale

  3 Seal Harbor Rd Unit 835, Winthrop, MA 02152

  • 2 Beds
  • 2 Baths
  • 1,306 Sq Ft
  • Built 1987

  3 Seal Harbor Rd Unit 835, Winthrop, MA 02152

  Last Sold Summary

  • 7% Above List Price
  • $485/SF
  • 25 Days On Market

  • Last Sold Price $633,000
  • May 02, 2024

  Last Listing Agent Mark Carangelo Mark Carangelo
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  /6

  $2,460,000

  • Land
  • 11,325 Sq Ft
  • $9,461,538 per Acre

  63-69 Putnam St, Winthrop, MA 02152

  ++The Breakwater++A rare coastal investment and development opportunity in the heart of Winthrop, Massachusetts. The mixed use property currently consists of a cash-flowing four-unit mixed-use building with stable in-place NOI of 71,300, combined with a Board of Appeals–approved plan to construct a new 12-unit building with podium parking beneath — all on one site steps from the harbor and in the

  The Bill Butler Group Leading Edge Real Estate

  63-69 Putnam St, Winthrop, MA 02152
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  /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

  Leighann Eruzione Lantern Residential

  180 Shirley St Unit 3, Winthrop, MA 02152
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  /23

  $369,000 Sold Jul 18, 2025

  203 Winthrop Shore Dr Unit 6, Winthrop, MA 02152

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

  Last Sold Summary

  • 6% Above List Price
  • $509/SF
  • 21 Days On Market

  Current Estimated Value $348,608

  Last Listing Agent Charles Roderick eXp Realty

  203 Winthrop Shore Dr Unit 6, Winthrop, MA 02152
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  /42

  Est $688,206 Not Listed For Sale

  3 Seal Harbor Rd Unit 733, Winthrop, MA 02152

  • 2 Beds
  • 2 Baths
  • 1,286 Sq Ft
  • Built 1987

  3 Seal Harbor Rd Unit 733, Winthrop, MA 02152

  Last Sold Summary

  • 2% Above List Price
  • $525/SF
  • 16 Days On Market

  • Last Sold Price $675,000
  • Feb 04, 2025

  Last Listing Agent Cathie Curran Charlesgate Realty Group, llc
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  $849,900 Open Sun 12PM - 1:30PM

  • 5 Beds
  • 3 Baths
  • 2,843 Sq Ft

  7 Willis Ave, Winthrop, MA 02152

  Corner Lot Modern 2 family close to the bay next to Mary Kelly Pavilion.1st floor has 4 large rooms & 2 bed.Kitchen has Induction Stove Top Granite Island & Counter Tops.Stainless Steel Induction Wall Microwave & Wall Oven.Top of the line Stainless Steel Refrigerator & Dishwasher.Granite tile floor. Plenty of Cabinet Space. Beautiful Tiger Hardwood Floors & Natural Woodwork Throughout. Crown

  Philip Consolo Century 21 North East

  7 Willis Ave, Winthrop, MA 02152
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  /25

  $3,300

  Total Monthly Price

  • 3 Beds
  • 2 Baths
  • 1,900 Sq Ft
  • Condo for Rent

  66 Sagamore Ave Unit 2, Winthrop, MA 02152

  3 Bedrooms2 BathroomsUtilities: Tenant pays gas, Electric and Oil heat.Laundry: In unit.Parking: 1 off-street included.Pets: No pets.Level: 2nd and 3rd FloorsAvailability: April or MayMove in Costs: Security Deposit and First Month's rent.

  66 Sagamore Ave Unit 2, Winthrop, MA 02152
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  $775,000 Sold Jan 30, 2026

  100 Cottage Ave, Winthrop, MA 02152

  • 3 Beds
  • 2.5 Baths
  • 2,293 Sq Ft
  • Built 1915

  Last Sold Summary

  • 12% Below List Price
  • $338/SF
  • 100 Days On Market

  Current Estimated Value $776,094

  Last Listing Agent Reserve Team Reference Real Estate

  100 Cottage Ave, Winthrop, MA 02152
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  /31

  Est $704,685 Not Listed For Sale

  3 Seal Harbor Rd Unit 644, Winthrop, MA 02152

  • 2 Beds
  • 2 Baths
  • 1,302 Sq Ft
  • Built 1987

  3 Seal Harbor Rd Unit 644, Winthrop, MA 02152

  Last Sold Summary

  • 1% Below List Price
  • $546/SF
  • 11 Days On Market

  • Last Sold Price $711,000
  • Dec 19, 2024

  Last Listing Agent Mark Carangelo Mark Carangelo
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  /13

  $360,000

  • 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
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  /36

  $4,500 Per Month

  • 4 Beds
  • 2.5 Baths
  • 2,600 Sq Ft
  • Apartment for Rent

  33 Court Rd Unit 2, Winthrop, MA 02152

  Located in Winthrop’s coveted Maze neighborhood, this waterfront upper-level residence spans the top two floors of a beautifully maintained two-family home. Offering an open and airy layout, the home features an oversized living room with bay windows, an updated kitchen with granite countertops, white cabinetry, stainless steel appliances, and a large breakfast bar perfect for entertaining. A

  Zechariah Cook Douglas Elliman Real Estate - Park Plaza

  33 Court Rd Unit 2, Winthrop, MA 02152
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  /30

  $950,000 Sold Nov 21, 2025

  40 Cottage Park Rd, Winthrop, MA 02152

  • 5 Beds
  • 3 Baths
  • 2,550 Sq Ft
  • Built 1900

  Last Sold Summary

  • $373/SF
  • 8 Days On Market

  Current Estimated Value $937,878

  Last Listing Agent The Reference Group Reference Real Estate

  40 Cottage Park Rd, Winthrop, MA 02152
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  /42

  Est $661,393 Not Listed For Sale

  3 Seal Harbor Rd Unit 635, Winthrop, MA 02152

  • 2 Beds
  • 2 Baths
  • 1,306 Sq Ft
  • Built 1987

  3 Seal Harbor Rd Unit 635, Winthrop, MA 02152

  Last Sold Summary

  • 12% Above List Price
  • $452/SF
  • 7 Days On Market

  • Last Sold Price $590,000
  • Feb 19, 2025

  Last Listing Agent Cathie Curran Charlesgate Realty Group, llc
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  /20

  $325,000 Open Sun 11:30AM - 1PM

  • 2 Beds
  • 1 Bath
  • 698 Sq Ft

  173 Shirley St Unit 2, Winthrop, MA 02152

  Opportunity in Winthrop just moments from the beach. This 2-bedroom, 1-bath first-floor condo offers 698 sq ft of single-level living with easy access, hardwood flooring, tile bath, gas heat, and one assigned off-street parking space. The monthly association fee includes heat, hot water, water, sewer, laundry facilities, exterior maintenance, landscaping, snow removal, and refuse removal, helping

  The TrustPoint Group eXp Realty

  173 Shirley St Unit 2, Winthrop, MA 02152
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  /14

  $2,700

  Total Monthly Price

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

  26 Forrest St Unit 2, Winthrop, MA 02152

  Steps from Winthrop Beach, this spacious 2-bedroom condo is the perfect location with easy access to Boston.Suitable for two people, you will love living here.Includes a tandem parking spot, in-unit washer and dryer, and basement storage space.Lease term is flexible - anywhere between 6-12 months. Please message me any questions!The blue line is a 10 min drive away,

  26 Forrest St Unit 2, Winthrop, MA 02152
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  /39

  $538,000 Sold Oct 17, 2025

  12 Sewall Ave Unit 2, Winthrop, MA 02152

  • 2 Beds
  • 2 Baths
  • 874 Sq Ft
  • Built 1925

  Last Sold Summary

  • $616/SF
  • 26 Days On Market

  Last Listing Agent Alex Walsh Access

  12 Sewall Ave Unit 2, Winthrop, MA 02152
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  /32

  Est $681,433 Not Listed For Sale

  3 Seal Harbor Rd Unit 633, Winthrop, MA 02152

  • 2 Beds
  • 2 Baths
  • 1,286 Sq Ft
  • Built 1987

  3 Seal Harbor Rd Unit 633, Winthrop, MA 02152

  Last Sold Summary

  • 17% Above List Price
  • $453/SF
  • 20 Days On Market

  • Last Sold Price $583,000
  • May 12, 2023

  Last Listing Agent Mark Carangelo Mark Carangelo

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