Winthrop, MA Homes

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  /25

  $529,000

  • 2 Beds
  • 1 Bath
  • 769 Sq Ft

  43 Sagamore Ave Unit 1, Winthrop, MA 02152

  Welcome home to this pristine and exceptionally well-kept two-bedroom, one-bath condominium in the heart of Winthrop’s vibrant 02152 community. This inviting home offers comfortable living along with private outdoor space—perfect for relaxing, entertaining, or enjoying coastal breezes. Conveniently located with easy access to Orient Heights, major highways, Logan Airport, and downtown Boston,

  

  Nicole Bettano

  Lantern Residential

  (857) 420-5091

  43 Sagamore Ave Unit 1, Winthrop, MA 02152
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  /16

  $2,895 total monthly price

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

  181 Winthrop Shore Dr Unit 2, Winthrop, MA 02152

  **AVAILABLE MAY 1ST**Amazing 2 bedroom 1 bathroom** 2ND FLOOR WITH OCEAN VIEWS- off the living room you are going to love how this apartment makes you feel. This spacious unit is drenched in sunlight and features gleaming hardwood floors, ceramic tile, high ceilings, laundry in unit, large eat in kitchen, shared back yard, and a shed for extra storage. Pets Negotiable. Get ready to enjoy life by

  

  Kyle Cabral

  Southpaw Residential

  (617) 657-2486

  181 Winthrop Shore Dr Unit 2, Winthrop, MA 02152
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  /31

  $680,000 Sold Apr 23, 2025

  620 Shirley St Unit 3, Winthrop, MA 02152

  • 3 Beds
  • 2 Baths
  • 1,355 Sq Ft
  • Built 2023

  Last Sold Summary

  • 1% Below List Price
  • $502/SF
  • 38 Days On Market

  Last Listing Agent Patrick Fahey Access

  620 Shirley St Unit 3, Winthrop, MA 02152
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  /16

  Est $483,639 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

  • 3% Above List Price
  • $448/SF
  • 34 Days On Market

  Last Sold Price $470,000

  Last Listing Agent Jaime Venezia Real Estate Pros Inc.
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  /42

  $829,974

  • 5 Beds
  • 2.5 Baths
  • 2,212 Sq Ft

  19 Moore St, Winthrop, MA 02152

  Rare opportunity just one street from the beach, offering strong rental income potential ideal for investors and owner-occupants alike. This well-maintained two-family offers a flexible layout with a 2-bedroom 1st floor unit and a spacious second unit with 3 bedrooms & 1.5 baths across two levels. The second unit is currently rented for $3,650/month, providing immediate income, while the 1st

  Mission Impossible Team United Brokers

  19 Moore St, Winthrop, MA 02152
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  /14

  $2,750 per month plus fees

  • 2 Beds
  • 1 Bath
  • Condo for Rent

  90 Winthrop Shore Dr Unit 2, Winthrop, MA 02152

  This nice 2 Bedrooms 1 Bath place in the Winthrop area is available for 06-01-2026. Included Features are: Front Porch, and 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

  90 Winthrop Shore 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 $928,558

  Last Listing Agent Mike Wetherbee Cameron Real Estate Group

  26 Sargent St, Winthrop, MA 02152
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  /20

  Est $462,944 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

  • 4% Below List Price
  • $650/SF
  • 53 Days On Market

  Last Sold Price $480,000

  Last Listing Agent Robert Bennett Dream Seekers Realty, LLC
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  /17

  $499,000 Open Sat 10:30AM - 12PM

  • 2 Beds
  • 2 Baths
  • 1,116 Sq Ft

  247 Washington Ave Unit 9, Winthrop, MA 02152

  Corner-positioned harborfront residence at Nautilus Condominiums with unobstructed Boston skyline and water views from every room. This 2-bedroom, 2-bath home spans 1,100+ sq ft and benefits from a south-to-west exposure, delivering consistent natural light throughout the day. A private balcony is set directly over the harbor, extending the living space outward. The layout balances openness and

  Federico Creatini eXp Realty

  247 Washington Ave Unit 9, Winthrop, MA 02152
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  /6

  $1,950 total monthly price

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

  6 Jefferson St Unit 20, Winthrop, MA 02152

  HEAT & HOT WATER INCLUDED!! Bright and sunny 1 bedroom apartment located within walking distance to Winthrop Center. Available for 4.1.26. Common coin-op laundry in the building and 1 parking spot! Close to the bus, MBTA, Airport & Boston.

  Atiyeh Cassidy Blue Sky Realty

  6 Jefferson St Unit 20, 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 $576,416

  Last Listing Agent Erin Dinsmoor Keller Williams Realty Metropolitan

  41 Sargent St, Winthrop, MA 02152
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  /28

  Est $669,127 Not Listed For Sale

  88 Winthrop St, Winthrop, MA 02152

  • 3 Beds
  • 1 Bath
  • 1,668 Sq Ft
  • Built 1850

  88 Winthrop St, Winthrop, MA 02152

  Last Sold Summary

  • 33% Above List Price
  • $301/SF
  • 3 Days On Market

  Last Sold Price $502,000

  Last Listing Agent Luca Amara LA Realty and Property Consulting, LLC
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  /30

  $659,000 Open Sun 12PM - 1:30PM

  • 2 Beds
  • 1 Bath
  • 1,220 Sq Ft

  51 Harbor View Ave Unit 2, Winthrop, MA 02152

  Street-Level Coastal Condo with Sweeping Views! Welcome to The Condos at 51 Harborview. This street-level condo offers easy access with sweeping harbor and city skyline views. The home features two bedrooms, one bath, and a modern kitchen and bath with quartz countertops, tile backsplash, stainless steel appliances, and luxury vinyl flooring.Relax or entertain on the front porch, deck off the

  Susan Doig Donnelly + Co.

  51 Harbor View Ave Unit 2, Winthrop, MA 02152
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  /14

  $2,000 per month plus fees

  • Studio
  • 1 Bath
  • Condo for Rent

  312 Shirley St Unit 210, Winthrop, MA 02152

  This nice Studio 1 Bath place in the Winthrop area is available for Now. Included Features are: Electric Heat, and Laundry in Basement.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

  312 Shirley St Unit 210, 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 $615,485

  Last Listing Agent Elizabeth Ferrara Cottage Hill Real Estate

  88 Grand View Ave, Winthrop, MA 02152
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  /30

  Est $648,344 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

  • 2% Above List Price
  • $452/SF
  • 36 Days On Market

  Last Sold Price $635,000

  Last Listing Agent The Reference Group Reference Real Estate
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  /23

  $624,900

  • 2 Beds
  • 1 Bath
  • 874 Sq Ft

  140 Shirley St Unit 201, Winthrop, MA 02152

  Special Financing Available (30yr Fixed @ 4.25%) on this project for some buyers. 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 two-bedroom, one-bath home in a 10-unit building captures the essence of coastal living with its fresh, nautical-inspired style

  Kovacs Savage Team Byrnes Real Estate Group LLC

  140 Shirley St Unit 201, Winthrop, MA 02152
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  /18

  $3,200 total monthly price

  • 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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  /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 $735,044

  Last Listing Agent Leighann Eruzione Lantern Residential

  41 Centre St, Winthrop, MA 02152
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  /37

  Est $571,490 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

  • 4% Above List Price
  • $417/SF
  • 35 Days On Market

  Last Sold Price $550,000

  Last Listing Agent Nicole Bettano Lantern Residential
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  /22

  $499,999 Pending

  • 3 Beds
  • 1 Bath
  • 1,374 Sq Ft

  23 Trident Ave Unit 1, Winthrop, MA 02152

  A Spacious 3-Bedroom Coastal Condo, Just Moments from the Beach, and shy of 1400 sqft living space with Deeded Parking in the Heart of Winthrop. This beautifully maintained first-floor home offers the perfect blend of coastal charm, comfort, and convenience. The sun-filled layout features three generously sized bedrooms, an ambient bathroom, and a versatile bonus space ideal for a home

  The Boston ONE Team Serhant

  23 Trident Ave Unit 1, Winthrop, MA 02152
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  /7

  $2,950 per month plus fees

  • 2 Beds
  • 1 Bath
  • Condo for Rent

  76 Fremont St Unit 3, Winthrop, MA 02152

  Fee Disclosure:Last Month Rent: $2,950First Month Rent: $2,950Security Deposit: $2,950Lock Key Fee: $100Disclaimer: Note: Unit designations or address may vary depending on a particular listing platform. Benjamin Apartments LLC makes a good faith effort to post accurate photographs and descriptions of the apartments listed for rent, but because the information is supplied

  76 Fremont St Unit 3, 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 $1,169,162

  Last Listing Agent Elizabeth Ferrara Cottage Hill Real Estate

  72 Sewall Ave, Winthrop, MA 02152
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  /42

  Est $965,247 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

  • 5% Above List Price
  • $352/SF
  • 7 Days On Market

  Last Sold Price $915,000

  Last Listing Agent Mike Hayes Century 21 North East
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  /9

  $569,000 Open Sat 10:30AM - 12:30PM

  • 2 Beds
  • 1 Bath
  • 898 Sq Ft

  10 Somerset Ave Unit 207, Winthrop, MA 02152

  Welcome to Unit 207 at The Somerset—Winthrop’s boutique condo community, where coastal living meets modern design. This spacious 2-bedroom, 1-bath home features an open-concept living and dining area, a well-appointed kitchen with quartz countertops and stainless steel appliances, central A/C, and modern finishes throughout, plus access to a fitness room, elevator, and resident lounge for added

  Charlesgate New Development Team Charlesgate Realty Group, llc

  10 Somerset Ave Unit 207, Winthrop, MA 02152
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  /13

  $2,900 total monthly price

  • 3 Beds
  • 1 Bath
  • 1,000 Sq Ft
  • Apartment for Rent

  49r Siren St Unit 1, Winthrop, MA 02152

  First Floor Unit within close proximity to Beach and Park Areas. The Unit features: 3 bedrooms, 1 bath, Living Room, and a kitchen. Features include, Hardwood Flooring in main areas, an updated kitchen with stainless steel appliances. Recently painted and hardwood flooring resurfaced. Off-Street parking for 1 Car.

  The Caceda Team Coldwell Banker Realty - Lynnfield

  49r Siren St Unit 1, Winthrop, MA 02152
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  /26

  $640,000 Sold May 23, 2025

  83 Chester Ave, Winthrop, MA 02152

  • 3 Beds
  • 1.5 Baths
  • 1,050 Sq Ft
  • Built 1900

  Last Sold Summary

  • 11% Above List Price
  • $610/SF
  • 5 Days On Market

  Current Estimated Value $646,982

  Last Listing Agent Mary Ann Cash Charlesgate Realty Group, llc

  83 Chester Ave, Winthrop, MA 02152
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  /14

  Est $390,195 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

  • 16% Above List Price
  • $378/SF
  • 3 Days On Market

  Last Sold Price $336,000

  Last Listing Agent Maria Mainini JDS Realty Group
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  /32

  $515,000 Open Sat 11AM - 1PM

  • 2 Beds
  • 1 Bath
  • 1,325 Sq Ft

  26 Forrest St Unit 1, Winthrop, MA 02152

  Half a block from Winthrop Beach, this spacious 2-bedroom first-floor condo offers over 1,300 square feet of character-filled coastal living in a classic 1890 three-family home. From the moment you enter, you’ll appreciate the welcoming foyer and period details, including Chelsea-tiled fireplaces, high ceilings, and hardwood floors throughout the main living areas. A formal living room and a

  Clara Arroyave eXp Realty

  26 Forrest St Unit 1, Winthrop, MA 02152
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  /5

  $1,850 per month plus fees

  • Studio
  • 1 Bath
  • Condo for Rent

  90 Winthrop Shore Dr Unit 9, Winthrop, MA 02152

  This nice Studio 1 Bath place in the Winthrop area is available for 05-01-2026. Included Features are: Electric Heat, and Laundry in Common Area. 1.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

  90 Winthrop Shore Dr Unit 9, 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 $929,087

  Last Listing Agent Cathie Curran Charlesgate Realty Group, llc

  19 Orlando Ave, Winthrop, MA 02152
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  /35

  Est $608,917 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

  • 6% Below List Price
  • $538/SF
  • 37 Days On Market

  Last Sold Price $645,000

  Last Listing Agent Elizabeth Ferrara Cottage Hill Real Estate
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  /27

  $539,900 Pending

  • 1 Bed
  • 1 Bath
  • 767 Sq Ft

  10 Somerset Ave Unit 408, Winthrop, MA 02152

  Welcome to Unit 408 – a spacious 1-bedroom + den home at The Somerset, Winthrop’s newest boutique condo community blending coastal charm with modern comfort. This thoughtfully designed layout offers an open-concept living space, a versatile den ideal for a home office or guest room, and a walk-in closet in the bedroom. Enjoy upscale finishes throughout—quartz countertops, stainless steel

  Charlesgate New Development Team Charlesgate Realty Group, llc

  10 Somerset Ave Unit 408, Winthrop, MA 02152
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  /14

  $2,050 total monthly price

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

  20 Coral Ave Unit 7, Winthrop, MA 02152

  Looking for a space that fits your fast-paced work life and your need to unplug by the ocean? This updated one-bedroom unit in Winthrop strikes that perfect balance. Tucked just one block from Winthrop Shore Drive beach, this apartment offers more than just a place to live—it gives you a lifestyle. Wake up, grab your morning coffee, take a yoga/fitness class and hop on public bus transportation

  Joanne Vanbuskirk Charlesgate Realty Group, llc

  20 Coral Ave Unit 7, Winthrop, MA 02152
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  /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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  /42

  Est $1,061,218 Not Listed For Sale

  172 Cliff Ave, Winthrop, MA 02152

  • 3 Beds
  • 3.5 Baths
  • 3,200 Sq Ft
  • Built 2008

  172 Cliff Ave, Winthrop, MA 02152

  Last Sold Summary

  • 8% Above List Price
  • $306/SF
  • 6 Days On Market

  Last Sold Price $980,000

  Last Listing Agent Stephen Hines Lantern Residential
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  /29

  $649,000

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

  3 Seal Harbor Rd Unit 344, Winthrop, MA 02152

  Situated at the ocean's edge in Winthrop, Seal Harbor is located just fifteen minutes from Boston's financial district. Building is amenity-rich- 24/7 concierge, on-site management, secure underground deeded garage parking, heated outdoor pool with shower, bathrooms, full poolhouse kitchen, outdoor Jacuzzi & 2 gas grills, year-round access to an indoor pool on the 9th floor, complete with

  Mark Carangelo Mark Carangelo

  3 Seal Harbor Rd Unit 344, Winthrop, MA 02152
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  /20

  $3,100 per month 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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  /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
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  /42

  Est $706,676 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

  • 18% Above List Price
  • $423/SF
  • 6 Days On Market

  Last Sold Price $599,900

  Last Listing Agent Ed Deveau Century 21 Mario Real Estate

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