Winthrop, MA Homes

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  /33

  $1,525,000

  Open Fri 6PM - 7PM

  • 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 reimagined coastal home has been recently completed. The home features 4 bedrooms, 2.5 baths, central air, natural gas heat, a new HVAC system, new water heater, new kitchen, new baths, new flooring, new windows, new siding, new roof, and extensive

  

  David Cody

  Orchard Park Realty

  89R Upland Rd, Winthrop, MA 02152
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  /9

  $2,695 Per Month

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

  87 Dr Unit 2, Winthrop, MA 02152

  Oceanfront updated two-bedroom, one bath, eat-in kitchen with Quartz countertops, stainless steel appliances, an updated bath, and a private deck overlooking Winthrop Beach! Additional features include central heat and AC, hardwoods, and a building laundry. The rent includes hot water. The unit is ready for occupancy on June 1, 2026.

  

  Saul Perlera

  Perlera Real Estate

  87 Dr Unit 2, Winthrop, MA 02152
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  /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 $901,621

  Last Listing Agent Mike Wetherbee Cameron Real Estate Group

  26 Sargent St, Winthrop, MA 02152
• 

  

  

  /25

  Est $489,000

  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
• 

  

  

  /42

  $1,300,000

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

  193 Winthrop St, Winthrop, MA 02152

  Exceptional opportunity to live where you work. Situated on a 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 unit that has been

  

  Lisa Licata-Schepici

  L.L.S. Realty LLC

  193 Winthrop St, 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
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  /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 $674,474

  Last Listing Agent Erin Dinsmoor Keller Williams Realty Metropolitan

  41 Sargent St, Winthrop, MA 02152
• 

  

  /16

  Est $488,267

  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
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  /28

  $779,000

  Open Sun 12PM - 2PM

  • 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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  /12

  $3,000 Per Month

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

  38 Hawthorn Ave Unit 1, Winthrop, MA 02152

  First floor apartment with its own entrance door for rent steps aways from Winthrop Beach! The unit features large 3 bedrooms, new bathroom, eat-in kitchen with a pantry, living room and formal dining room. The unit offers hardwood floors, high ceiling, recessed lighting, and front & back porches. Steps to Winthrop beach and transportation and quick access to major highways. The apartment is

  

  Saul Perlera

  Perlera Real Estate

  38 Hawthorn Ave 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 $608,403

  Last Listing Agent Elizabeth Ferrara Cottage Hill Real Estate

  88 Grand View Ave, Winthrop, MA 02152
• 

  

  /20

  Est $463,582

  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
• 

  

  /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
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  /30

  $3,100 Plus Fees

  • 2 Beds
  • 1 Bath
  • Condo for Rent

  370 Main St Unit 2, Winthrop, MA 02152

  This nice Furnished 2 Bedrooms 1 Bath place in the Winthrop area is available for Now.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 properties reflect conditions at the time the information was

  370 Main St Unit 2, 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 $708,876

  Last Listing Agent Leighann Eruzione LeighAnn Eruzione-Callinan

  41 Centre St, Winthrop, MA 02152
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  /30

  Est $642,945

  Not Listed For Sale

  142 Pleasant St Unit 6, Winthrop, MA 02152

  • 2 Beds
  • 2.5 Baths
  • 1,404 Sq Ft
  • Built 1968

  142 Pleasant St Unit 6, Winthrop, MA 02152

  Last Sold Summary

  • 36 Days On Market
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  /40

  $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
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  /20

  $1,750 Plus Fees

  • Studio
  • 1 Bath
  • Condo for Rent

  312 Shirley St Unit 208, Winthrop, MA 02152

  This nice Studio 1 Bath place in the Winthrop area is available for Now. Included Features are: Laundry in Common Area.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 properties reflect

  312 Shirley St Unit 208, 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 $1,106,947

  Last Listing Agent Elizabeth Ferrara Cottage Hill Real Estate

  72 Sewall Ave, Winthrop, MA 02152
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  /37

  Est $590,725

  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
• 

  

  /42

  $829,000

  • 4 Beds
  • 2.5 Baths
  • 2,700 Sq Ft

  546 Shirley St, Winthrop, MA 02152

  Steps from the shore, this corner lot offers coastal living w a wide, expansive front porch perfect for catching the harbor breeze or entertaining. This move-in ready home features 2,700 sq.ft. of spacious living and an unbeatable beachside location. The interior boasts hardwood floors throughout most of the home, featuring four bedrooms and 2.5 bathrooms. Additionally, a finished third floor

  Melissa Flamburis Redfin Corp.

  546 Shirley St, Winthrop, MA 02152
• 

  

  /5

  $2,000 Plus Fees

  • 1 Bed
  • 1 Bath
  • Condo for Rent

  312 Shirley St Unit 203, Winthrop, MA 02152

  This nice Furnished 1 Bedroom 1 Bath place in the Winthrop area is available for Now. Included Features are: Laundry in Unit.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 properties reflect

  312 Shirley St Unit 203, Winthrop, MA 02152
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  /42

  $940,000

  Sold Jul 30, 2025

  19 Orlando Ave, Winthrop, MA 02152

  • 4 Beds
  • 2.5 Baths
  • 2,470 Sq Ft
  • Built 1900

  Last Sold Summary

  • 1% Below List Price
  • $381/SF
  • 15 Days On Market

  Current Estimated Value $915,019

  Last Listing Agent Cathie Curran Charlesgate Realty Group, llc

  19 Orlando Ave, Winthrop, MA 02152
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  /42

  Est $938,940

  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
• 

  

  /42

  $649,000

  $30K 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
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  /13

  $2,700 Plus Fees

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

  400 Governors Dr Unit 5, Winthrop, MA 02152

  Winthrop, MA - Nice Two Bedrooms Ground Level Condo For Rent With Heat And Hot Water Included In The Rent. Available July 1, 2026. FEATURES: Kitchen With Stainless Steel Appliances (Stove, Refrigerator, Dishwasher), Quartz Countertop; Ceramic Title And Pergo Hardwood Floors; Wall Air Conditioning; Coin-Op Laundry Facilities In The Building; Off-Street Parking For two Cars. This Condo

  400 Governors Dr Unit 5, Winthrop, MA 02152
• 

  

  /40

  $935,000

  Sold Jul 10, 2025

  96-98 Woodside Ave, Winthrop, MA 02152

  • 4 Beds
  • 2 Baths
  • 2,124 Sq Ft
  • Built 1920

  Last Sold Summary

  • 4% Above List Price
  • $440/SF
  • 4 Days On Market

  Last Listing Agent John Young Ledge & Young Real Estate

  96-98 Woodside Ave, Winthrop, MA 02152
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  /14

  Est $389,101

  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
• 

  

  /10

  $399,000

  Open Sat 12PM - 2PM

  • 1 Bed
  • 1 Bath
  • 546 Sq Ft

  10 Somerset Ave Unit 304, Winthrop, MA 02152

  LAST STUDIO AVAILABLE! Discover effortless coastal living at Unit 304 at The Somerset, a boutique condominium community ideally located in the heart of Winthrop. This well-appointed studio offers a bright and airy open layout designed for both comfort and functionality, featuring a flexible bonus room with a sliding barn door ideal for a home office, guest room, or additional living space. The

  Charlesgate New Development Team Charlesgate Realty Group, llc

  10 Somerset Ave Unit 304, Winthrop, MA 02152
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  /9

  $1,995 Plus Fees

  • 1 Bed
  • 1 Bath
  • Condo for Rent

  435 Shirley St Unit 36, Winthrop, MA 02152

  1 Bedroom1 BathroomPet Policy: Cat/Dog Negotiable.Utilities: Tenant Pays Electric. Heat and Hot Water included.Laundry: In Building.Parking: 1-car Included. Parking Lot.Level: Top Floor.Availability: July 1Move-In Costs Fees:Last Month Rent: $1,995First Month Rent: $1,995Security Deposit: $1,995

  435 Shirley St Unit 36, Winthrop, MA 02152
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  /29

  $650,000

  Sold Jul 23, 2025

  167 Winthrop Shore Dr Unit 2, Winthrop, MA 02152

  • 4 Beds
  • 1.5 Baths
  • 1,836 Sq Ft
  • Built 1903

  Last Sold Summary

  • 7% Below List Price
  • $354/SF
  • 91 Days On Market

  Last Listing Agent Mark Mulkerrin Coldwell Banker Realty - Sharon

  167 Winthrop Shore Dr Unit 2, Winthrop, MA 02152
• 

  

  /35

  Est $627,034

  Not Listed For Sale

  30 Underhill St Unit 1, Winthrop, MA 02152

  • 3 Beds
  • 2 Baths
  • 1,200 Sq Ft
  • Built 1900

  30 Underhill St Unit 1, Winthrop, MA 02152

  Last Sold Summary

  • 37 Days On Market
• 

  

  /42

  $1,600,000

  • 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, this residence offers a lifestyle that cannot be assembled from scratch in today's coastal market. The rights to rebuild a pier remain intact, a dormant asset in a harbor where

  Amanda George Lamacchia Realty, Inc.

  516 Pleasant St, Winthrop, MA 02152
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  /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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  /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 $373,096

  Last Listing Agent The Movement Group Compass

  200 Governors Dr Unit 39, Winthrop, MA 02152
• 

  

  /26

  Est $752,953

  Not Listed For Sale

  55 Nahant Ave, Winthrop, MA 02152

  • 2 Beds
  • 1.5 Baths
  • 1,740 Sq Ft
  • Built 1900

  55 Nahant Ave, Winthrop, MA 02152

  Last Sold Summary

  • 1 Day On Market
• 

  

  /42

  $850,000

  • 5 Beds
  • 3 Baths
  • 3,035 Sq Ft

  18-20 Fairview St, Winthrop, MA 02152

  Rare opportunity to own a legal 2 family with an inlaw apartment in one of Winthrop's most desirable locations! Completely vacant and ready for its next owner, this brick-front property offers tremendous potential for investors, owner-occupants, or multigenerational living. No flood insurance required. The spacious owner's unit lives like a single-family home, featuring 7 rooms, 3 bedrooms, a

  Laura Baliestiero Coldwell Banker Realty - Concord

  18-20 Fairview St, Winthrop, MA 02152
• 

  

  /20

  $2,495 Plus Fees

  • 2 Beds
  • 1 Bath
  • Condo for Rent

  90 Winthrop Shore Dr Unit B, Winthrop, MA 02152

  This nice 2 Bedrooms 1 Bath place in the Winthrop area is available for Now. Included Features are: Laundry in Coin-Op.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 properties reflect

  90 Winthrop Shore Dr Unit B, Winthrop, MA 02152
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  /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 $1,774,187

  Last Listing Agent Connie Doto Connie Doto Realty Group

  201 Cliff Ave, Winthrop, MA 02152
• 

  

  /20

  Est $610,670

  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

  • 46 Days On Market

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