Winthrop, MA Homes

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  /28

  $764,000

  $15K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,800 Sq Ft

  189 Shirley St Unit 1, Winthrop, MA 02152

  Welcome to coastal living at its finest in this truly unique and beautifully appointed townhome residence. Spanning three expansive levels, this exceptional three-bedroom, two-and-a-half-bath home seamlessly blends comfort, style, and privacy in the one and only seaside community of Winthrop 02152 Privately situated with its own separate entrance, this rare offering lives like a single-family

  

  Nicole Bettano

  Lantern Residential

  189 Shirley St Unit 1, Winthrop, MA 02152
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  /16

  Starting at $1,795

  Total Monthly Price

  • Studio - 2 Beds

  91 Veterans Rd, Winthrop, MA 02152

  Welcome to The Abby at 91 Veterans Road in Winthrop, MA, where city-access meets coastal charm. Nestled just steps from the beach and the Winthrop Golf Club, this professionally managed community offers modern, pet-friendly apartments with reserved parking, in-unit laundry, and easy highway and public-transit access to Boston.Walkable town, breeze-filled viewsResidents love Winthrop’s

  The Abby

  

  91 Veterans Rd, Winthrop, MA 02152
• 

  

  

  /26

  $949,000

  Sold Oct 03, 2025

  26 Sargent St, Winthrop, MA 02152

  • 5 Beds
  • 2.5 Baths
  • 2,237 Sq Ft
  • Built 1887

  Last Sold Summary

  • 14% Below List Price
  • $424/SF
  • 27 Days On Market

  Current Estimated Value $933,003

  Last Listing Agent Mike Wetherbee Cameron Real Estate Group

  26 Sargent St, Winthrop, MA 02152
• 

  

  

  /30

  Est $741,943

  Not Listed For Sale

  3 Seal Harbor Rd Unit 744, Winthrop, MA 02152

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

  3 Seal Harbor Rd Unit 744, Winthrop, MA 02152

  Last Sold Summary

  • 60 Days On Market

  Last Listing Agent Charles Roderick eXp Realty LLC - Corporate Office
• 

  

  

  /42

  $875,000

  Pending

  • 4 Beds
  • 3 Baths
  • 2,016 Sq Ft

  126 Brookfield Rd, Winthrop, MA 02152

  Two-family home in a prime Winthrop location, directly across from Ingleside Park and minutes from Winthrop Center. Each unit offers 2 bedrooms, 1 full bath, a bright living room, eat-in kitchen, and private porch. Set on a 0.14-acre lot, the property features a partially fenced backyard—ideal for entertaining, gardening, grilling, or relaxing. The lower level, accessible via a private rear

  

  Marissa Amin

  Amo Realty - Boston City Properties

  126 Brookfield Rd, Winthrop, MA 02152
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  /39

  $2,350

  Total Monthly Price

  • Studio
  • 1 Bath
  • 400 Sq Ft
  • Condo for Rent

  600 Shirley St Unit 9, Winthrop, MA 02152

  2nd floor walk-up, this studio condominium is for lease starting Sept. 2026. A former waterfront hotel in Winthrop, MA, The Cove, is renovated and modernized. Here is the opportunity to live across the Bay from Boston; Logan Airport is accessible by public transportation. Excellent commuter location or landing-pad! Unit 9 is available either Unfurnished, or Furnished, with a queen-sized bed

  600 Shirley St Unit 9, Winthrop, MA 02152
• 

  

  /40

  $560,000

  Sold Oct 30, 2025

  41 Sargent St, Winthrop, MA 02152

  • 3 Beds
  • 2 Baths
  • 1,724 Sq Ft
  • Built 1925

  Last Sold Summary

  • $325/SF
  • 2 Days On Market

  Current Estimated Value $638,504

  Last Listing Agent Erin Dinsmoor Keller Williams Realty Metropolitan

  41 Sargent St, Winthrop, MA 02152
• 

  

  /26

  Est $373,899

  Not Listed For Sale

  235 Washington Ave Unit 6, Winthrop, MA 02152

  • 2 Beds
  • 1 Bath
  • 860 Sq Ft
  • Built 1900

  235 Washington Ave Unit 6, Winthrop, MA 02152

  Last Sold Summary

  • 14 Days On Market

  Last Listing Agent Cathie Curran Charlesgate Realty Group, llc
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  /33

  $1,399,000

  Open Sun 12PM - 1PM $126K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 2,475 Sq Ft

  89R Upland Rd, Winthrop, MA 02152

  Perched above the shoreline with sweeping, unobstructed water views toward Broad Sound and Revere Beach, this extensively reconstructed and thoughtfully expanded coastal home offers an exceptional combination of natural light, modern design, and quality craftsmanship. Recently completed following an extensive reconstruction and thoughtful expansion, the home features 4 bedrooms, 2.5 baths,

  

  David Cody

  Orchard Park Realty

  89R Upland Rd, Winthrop, MA 02152
• 

  

  /20

  $2,100 Plus Fees

  • 1 Bed
  • 1 Bath
  • Condo for Rent

  87 Winthrop Shore Dr Unit 1, Winthrop, MA 02152

  Awesome this nice 1 Bed 1 Bath place in the WINTHROP area is available for Sep 1, 2019. Included Features are: Gas Heat, and Gas Hot Water.Boston Pads is not responsible for any errors, omissions and change in price, prior sale, rent and withdrawal without notice. All information from sources reliable but not guaranteed. Photographs, videos, description and information about the

  87 Winthrop Shore Dr Unit 1, Winthrop, MA 02152
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  /35

  $605,000

  Sold Dec 19, 2025

  88 Grand View Ave, Winthrop, MA 02152

  • 2 Beds
  • 1 Bath
  • 1,262 Sq Ft
  • Built 1945

  Last Sold Summary

  • 9% Below List Price
  • $479/SF
  • 153 Days On Market

  Current Estimated Value $638,170

  Last Listing Agent Elizabeth Ferrara Cottage Hill Real Estate

  88 Grand View Ave, Winthrop, MA 02152
• 

  

  /38

  Est $949,882

  Not Listed For Sale

  175 Pleasant St, Winthrop, MA 02152

  • 4 Beds
  • 3 Baths
  • 4,101 Sq Ft
  • Built 1896

  175 Pleasant St, Winthrop, MA 02152

  Last Sold Summary

  • 22 Days On Market

  Last Listing Agent Leighann Eruzione Bowdoin Real Estate Partners
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  /25

  $350,000

  $29K PRICE DROP Pending

  • 2 Beds
  • 1 Bath
  • 977 Sq Ft

  1000 Governors Dr Unit 4, Winthrop, MA 02152

  Get ready to discover your next dream home! A fantastic condo for sale in the vibrant town of Winthrop, MA. This inviting residence features two generously sized bedrooms and a modern bathroom, complemented by an open concept living room and kitchen area.Situated in a large, welcoming complex, you'll enjoy excellent amenities including a tennis court and convenient laundry facilities in the

  

  Jose Rojas

  William Raveis R.E. & Home Services

  1000 Governors Dr Unit 4, Winthrop, MA 02152
• 

  

  /16

  $2,950 Plus Fees

  • 2 Beds
  • 1 Bath
  • Condo for Rent

  70 Cottage Park Rd Unit 1, Winthrop, MA 02152

  Photos coming soon!Central AC & HeatPrivate laundry in basementModern Kitchen w/ all new stainless steel appliancesDishwasher & DisposalLarge open living room & dining room w/ wall mounted 70' smart TVSun room/ office nookPets are negotiableOff Street parking is negotiableBoston Pads is not responsible for any errors, omissions and change in price,

  70 Cottage Park Rd Unit 1, Winthrop, MA 02152
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  /34

  $722,000

  Sold Sep 25, 2025

  41 Centre St, Winthrop, MA 02152

  • 5 Beds
  • 1.5 Baths
  • 1,776 Sq Ft
  • Built 1910

  Last Sold Summary

  • 2% Below List Price
  • $407/SF
  • 12 Days On Market

  Current Estimated Value $740,370

  Last Listing Agent Leighann Eruzione Bowdoin Real Estate Partners

  41 Centre St, Winthrop, MA 02152
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  /42

  Est $722,516

  Not Listed For Sale

  831 Shirley St, Winthrop, MA 02152

  • 2 Beds
  • 2 Baths
  • 1,738 Sq Ft
  • Built 1910

  831 Shirley St, Winthrop, MA 02152

  Last Sold Summary

  • 11 Days On Market

  Last Listing Agent Elaine Akerberg Elite Realty Experts, LLC
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  /42

  $1,199,900

  $100K PRICE DROP

  • 5 Beds
  • 4 Baths
  • 2,799 Sq Ft

  193 Winthrop St, Winthrop, MA 02152

  $2,500 bonus to buyer or buyer broker* Exceptional opportunity to live where you work. Corner lot with off-street parking, this unique property offers endless possibilities for investors, developers, or owner-occupants.The ground level features professional office space complete with a reception area, conference room, workspace, and 1/2 bath. Also included is a vacant 2-level, 2-bedroom, 1.5-bath

  

  Lisa Licata-Schepici

  L.L.S. Realty LLC

  193 Winthrop St, Winthrop, MA 02152
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  /20

  $3,300

  Total Monthly Price

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

  87 Washington Ave Unit 1BR Waterfront Oasis, Winthrop, MA 02152

  An oceanfront oasis just minutes from Boston. This fully renovated 800 sq. ft. private furnished walk-out apartment on the ground level of a 2 family owner occupied home in Winthrop, MA offers a rare combination of comfort, convenience, outdoor living, and true coastal lifestyle.The apartment is fully furnished and move-in ready with a full kitchen, seating for 4, full-size refrigerator,

  87 Washington Ave Unit 1BR Waterfront Oasis, Winthrop, MA 02152
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  /41

  $1,175,000

  Sold Sep 17, 2025

  72 Sewall Ave, Winthrop, MA 02152

  • 4 Beds
  • 3.5 Baths
  • 2,214 Sq Ft
  • Built 2009

  Last Sold Summary

  • 7% Below List Price
  • $531/SF
  • 15 Days On Market

  Current Estimated Value $1,172,407

  Last Listing Agent Elizabeth Ferrara Cottage Hill Real Estate

  72 Sewall Ave, Winthrop, MA 02152
• 

  

  /25

  Est $484,480

  Not Listed For Sale

  111 Locust St Unit 2, Winthrop, MA 02152

  • 3 Beds
  • 1 Bath
  • 1,270 Sq Ft
  • Built 1925

  111 Locust St Unit 2, Winthrop, MA 02152

  Last Sold Summary

  • 74 Days On Market

  Last Listing Agent Christine D'Ambrosio Bowdoin Real Estate Partners
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  /37

  $849,900

  Open Sun 11AM - 1PM

  • 5 Beds
  • 2.5 Baths
  • 2,437 Sq Ft

  43 Dolphin Ave, Winthrop, MA 02152

  Welcome to 43 Dolphin Ave, a charming, move-in-ready Colonial offering ocean views in a desirable Winthrop location just moments from the newly renovated Winthrop Beach. The inviting main level features a sun-filled living room with a gas fireplace and classic arched doorways, a spacious kitchen overlooking the covered deck and fenced backyard, a formal dining room, a half bath, and a versatile

  Patricia Nunez Redfin Corp.

  43 Dolphin Ave, Winthrop, MA 02152
• 

  

  /31

  $2,550

  Total Monthly Price

  • 1 Bed
  • 1 Bath
  • 9,999 Sq Ft
  • Condo for Rent

  12 Sewall Ave Unit 3, Winthrop, MA 02152

  12 Sewall Ave Unit 3, Winthrop, MA 02152
• 

  

  /22

  $380,000

  Sold Oct 15, 2025

  200 Governors Dr Unit 39, Winthrop, MA 02152

  • 2 Beds
  • 1 Bath
  • 782 Sq Ft
  • Built 1971

  Last Sold Summary

  • $486/SF
  • 7 Days On Market

  Current Estimated Value $382,667

  Last Listing Agent The Movement Group Compass

  200 Governors Dr Unit 39, Winthrop, MA 02152
• 

  

  /16

  Est $498,231

  Not Listed For Sale

  62 Park Ave Unit 1, Winthrop, MA 02152

  • 3 Beds
  • 1 Bath
  • 1,050 Sq Ft
  • Built 1884

  62 Park Ave Unit 1, Winthrop, MA 02152

  Last Sold Summary

  • 34 Days On Market

  Last Listing Agent Jaime Venezia Real Estate Pros Inc.
• 

  

  /35

  $649,000

  Open Wed 11:30AM - 1:30PM

  • 2 Beds
  • 2 Baths
  • 1,024 Sq Ft

  10 Somerset Ave Unit 402, Winthrop, MA 02152

  Start your homeownership journey at Unit 402 at The Somerset, a bright and spacious top-floor 2-bedroom, 2-bath condo in the heart of Winthrop. Designed for modern living, this move-in-ready home features an open-concept layout, two private balconies, quartz countertops, stainless steel appliances, central A/C, and generous closet space. Garage parking is included, along with access to an

  Charlesgate New Development Team Charlesgate Realty Group, llc

  10 Somerset Ave Unit 402, Winthrop, MA 02152
• 

  

  /10

  $3,400

  Total Monthly Price

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

  411 Shirley St Unit 2, Winthrop, MA 02152

  This property at 411 Shirley St offers a lovely 1300 square foot apartment to call home. It includes essential amenities such as air conditioning, a dishwasher, and laundry hook ups. The living room provides ample space for relaxation and entertainment, while the bedrooms are designed to accommodate various layouts. The bathroom is equipped with standard fixtures for convenience. The property

  411 Shirley St Unit 2, Winthrop, MA 02152
• 

  

  /42

  $1,650,000

  Sold May 29, 2026

  201 Cliff Ave, Winthrop, MA 02152

  • 8 Beds
  • 6.5 Baths
  • 5,362 Sq Ft
  • Built 1978

  Last Sold Summary

  • 8% Below List Price
  • $308/SF
  • 100 Days On Market

  Current Estimated Value $1,595,960

  Last Listing Agent Connie Doto Connie Doto Realty Group

  201 Cliff Ave, Winthrop, MA 02152
• 

  

  /20

  Est $435,061

  Not Listed For Sale

  148 Winthrop Shore Dr Unit 2, Winthrop, MA 02152

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

  148 Winthrop Shore Dr Unit 2, Winthrop, MA 02152

  Last Sold Summary

  • 53 Days On Market

  Last Listing Agent Robert Bennett Dream Seekers Realty, LLC
• 

  

  /41

  $799,986

  $30K PRICE DROP

  • 6 Beds
  • 2 Baths
  • 2,560 Sq Ft

  50 Main St, Winthrop, MA 02152

  Excellent opportunity to own a well-maintained 2-family property in the highly desirable seaside community of Winthrop! Perfect for investors, owner-occupants or multi-generational living, this spacious property offers two large units featuring 3 bedrooms,1 full bathroom, hardwood floors, generous living areas and a bonus office room! Separate utilities and washer/dryer hookups add convenience

  Matt Tasgin United Brokers

  50 Main St, Winthrop, MA 02152
• 

  

  /18

  $2,650

  Total Monthly Price

  • 1 Bed
  • 1.5 Baths
  • 878 Sq Ft
  • Condo for Rent

  56 Winthrop Shore Dr Unit 1F, Winthrop, MA 02152

  56 Winthrop Shore Dr Unit 1F, Winthrop, MA 02152
• 

  

  /4

  $450,000

  Sold Apr 23, 2026

  86 Undine Ave, Winthrop, MA 02152

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

  Last Sold Summary

  • 10% Below List Price
  • $726/SF
  • 97 Days On Market

  Current Estimated Value $455,079

  Last Listing Agent Reserve Team Reference Real Estate

  86 Undine Ave, Winthrop, MA 02152
• 

  

  /37

  Est $568,717

  Not Listed For Sale

  46 Jefferson St Unit 1, Winthrop, MA 02152

  • 3 Beds
  • 2 Baths
  • 1,320 Sq Ft
  • Built 1900

  46 Jefferson St Unit 1, Winthrop, MA 02152

  Last Sold Summary

  • 35 Days On Market

  Last Listing Agent Nicole Bettano Lantern Residential
• 

  

  /42

  $639,000

  $40K PRICE DROP

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

  3 Seal Harbor Rd Unit 342, Winthrop, MA 02152

  Seal Harbor in Winthrop offers an elevated coastal living experience that is unparalleled. Timeless detail inside & out of this building is complemented by white-glove concierge service. Unit 342 is a luxury residence with ocean & pool views from every window. It is conveniently located a few steps from the new elevators & welcomes you into an open floor plan with striking natural sunlight;

  Nancy McLaughlin Redfin Corp.

  3 Seal Harbor Rd Unit 342, Winthrop, MA 02152
• 

  

  /8

  $2,400

  Total Monthly Price

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

  25 Pratt St Unit 1, Boston, MA 02134

  Spacious 1-bedroom, 1-bath apartment in Allston with a modern eat-in kitchen, dishwasher, and disposal. Features ceramic tile flooring, a private porch, and plenty of natural light. Laundry on-site. Outdoor parking is available for $200/month. Conveniently located near the Green Line, Allston Village, and Boston University.

  25 Pratt St Unit 1, Boston, MA 02134
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  /36

  $715,000

  Sold Dec 30, 2025

  19 Pleasant Park Rd, Winthrop, MA 02152

  • 3 Beds
  • 1.5 Baths
  • 1,325 Sq Ft
  • Built 1920

  Last Sold Summary

  • 2% Below List Price
  • $540/SF
  • 35 Days On Market

  Current Estimated Value $720,161

  Last Listing Agent Laura Cohron Fiv Realty Co.

  19 Pleasant Park Rd, Winthrop, MA 02152
• 

  

  /42

  Est $926,077

  Not Listed For Sale

  211 Cliff Ave Unit 2, Winthrop, MA 02152

  • 3 Beds
  • 2 Baths
  • 2,600 Sq Ft
  • Built 1910

  211 Cliff Ave Unit 2, Winthrop, MA 02152

  Last Sold Summary

  • 7 Days On Market

  Last Listing Agent Mike Hayes Century 21 North East
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  /42

  $1,499,000

  $101K PRICE DROP

  • 5 Beds
  • 3 Baths
  • 2,889 Sq Ft

  516 Pleasant St, Winthrop, MA 02152

  Every evening, the harbor turns amber from the west, 516 Pleasant Street has a front-row seat. A one-of-a-kind home set along Winthrop's harbor front with direct water access, a concrete seawall, and a private boat launch, (all outside the flood-zone by the way!!) this residence offers a lifestyle that cannot be assembled from scratch in today's coastal market. The rights to rebuild a pier remain

  Amanda George Lamacchia Realty, Inc.

  516 Pleasant St, Winthrop, MA 02152
• 

  

  /17

  $3,700

  Total Monthly Price

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

  953 Shirley St Unit 2, Winthrop, MA 02152

  Stylish 3-Bedroom Apartment by the shores of Winthrop!!Welcome to your new home in Boston’s vibrant Winthrop neighborhood! This spacious and updated 3-bedroom, 1-bathroom apartment offers comfort and convenience in a prime location. Each bedroom is generously sized, perfect for creating your own personal retreat. The open living area boasts ample natural light, creating a warm and

  953 Shirley St Unit 2, Winthrop, MA 02152
• 

  

  /26

  $715,000

  Sold Jan 27, 2026

  174 Winthrop St Unit 2, Winthrop, MA 02152

  • 3 Beds
  • 2.5 Baths
  • 1,973 Sq Ft
  • Built 1880

  Last Sold Summary

  • 3% Below List Price
  • $362/SF
  • 107 Days On Market

  Last Listing Agent Leighann Eruzione Bowdoin Real Estate Partners

  174 Winthrop St Unit 2, Winthrop, MA 02152
• 

  

  /14

  Est $393,220

  Not Listed For Sale

  308 Shirley St Unit 2, Winthrop, MA 02152

  • 2 Beds
  • 1 Bath
  • 890 Sq Ft
  • Built 1900

  308 Shirley St Unit 2, Winthrop, MA 02152

  Last Sold Summary

  • 3 Days On Market

  Last Listing Agent Maria Mainini JDS Realty Group

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