Winthrop, MA Homes

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  /27

  $399,900

  • 2 Beds
  • 1 Bath
  • 782 Sq Ft

  1000 Governors Dr Unit 25, Winthrop, MA 02152

  Welcome to Governor’s Park Condominiums in Winthrop! This well-maintained third-floor, two-bedroom, one-bath unit offers the perfect balance of city convenience and coastal charm. Featuring an open-concept layout with a spacious living room and kitchen/dining area, this home also includes hardwood floors, granite countertops, SS appliances, a private balcony, and two deeded off-street parking

  Lindita Murrizi Return Realty Group, Inc.

  1000 Governors Dr Unit 25, Winthrop, MA 02152
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  /23

  $4,800 total monthly price

  • 5 Beds
  • 2.5 Baths
  • 2,500 Sq Ft
  • House for Rent

  138 Loring Rd, Winthrop, MA 02152

  Welcome to 138 Loring Road , the MOST DESIRABLE NEIGHBORHOOD IN WINTHROP. Available Jan 1 , This 5 bedroom single family home offers the perfect blend of Charm with Modern Upgrades, Space, and Comfort. Sun filled home, gleaming hardwood floors throughout, updated kitchen , new modern stainless steel appliances, new washer and dryer, spacious living and dining room, generous sized bedrooms,

  Kevin Ferrara Cottage Hill Real Estate

  138 Loring Rd, Winthrop, MA 02152
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  /37

  $960,000 Sold Sep 11, 2025

  • 3,272 Sq Ft
  • $293/SF
  • 84 Days On Market

  • 5 Beds
  • 3 Baths
  • Built 1967

  115 Almont St, Winthrop, MA 02152

  115 Almont, where coastal vibes meet versatile living areas to offer something for everyone. Don't miss your chance to see this expansive 5 bedroom 3 bathroom colonial just minutes to Winthrop Beach, fantastic restaurants, schools & more. Upon entry, you are greeted with a beautiful living room with working fireplace, updated eat-in kitchen, full bathroom and first floor bedroom. This setup would

  Christine Goldstein Lyv Realty

  115 Almont St, Winthrop, MA 02152
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  /36

  Est $764,960 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 1,563 Sq Ft

  404 Revere St, Winthrop, MA 02152

  404 Revere St, Winthrop, MA 02152
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  /27

  $1,055,000

  • 4 Beds
  • 3 Baths
  • 2,028 Sq Ft

  41 Harbor View Ave, Winthrop, MA 02152

  The street name; 'Harbor View Ave" says it all! Sweeping unobstructed views of the open ocean, Boston Harbor, & city skyline! Nestled atop one of Winthrop’s highest elevations, delivering a rare combination of breathtaking coastal scenery & beach access. This sun-drenched 3 unit home offers 4 bedrooms, 3 full baths, garage parking, making it ideal for homeowners, developers, or investors. From

  Brian Perrin Brian J. Perrin Real Estate

  41 Harbor View 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
• 

  

  /31

  $390,000 Sold Sep 10, 2025

  • 679 Sq Ft
  • $574/SF
  • 5 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1902

  23 Winthrop Shore Dr Unit 2, Winthrop, MA 02152

  Beautifully Renovated Condo with Water Views in Winthrop! This thoughtfully updated condo offers modern living on coveted Winthrop Shore Drive, directly facing Winthrop Beach. Featuring a stylish kitchen and open-concept layout, this bright and inviting unit is perfect as a first home, second home, or investment property. Enjoy peaceful water views from the living room or sip your morning

  Mariel Yovino Compass

  23 Winthrop Shore Dr Unit 2, Winthrop, MA 02152
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  /21

  Est $904,282 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,306 Sq Ft

  116 Grovers Ave, Winthrop, MA 02152

  116 Grovers Ave, Winthrop, MA 02152
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  /30

  $89,000

  • 2 Beds
  • 2 Baths
  • 600 Sq Ft

  550 Pleasant St Unit 11D, Winthrop, MA 02152

  Waterfront living at its finest with this live-aboard houseboat, offering all the comforts of a traditional condo. Built in 1989 by Hatteras Boats, one of the most respected names in the industry, this flagship model combines quality craftsmanship and functional charm. Step inside to an inviting open-concept living room and kitchen, filled with natural light, enhanced by high ceilings. The

  Drew Boujoulian Coldwell Banker Realty - Boston

  550 Pleasant St Unit 11D, Winthrop, MA 02152
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  /14

  $3,200 total monthly price

  • 3 Beds
  • 1 Bath
  • 1,350 Sq Ft
  • Apartment for Rent

  145 Bartlett Rd Unit 1, Winthrop, MA 02152

  RENOVATED , ALL NEW ,SPACIOUS, 3 BEDROOM , IN THE MOST DESIRABLE NEIGHBORHOOD IN WINTHROP ! Sunfilled , 3 bed, gleaming hardwood floors throughout, brand new kitchen and tiled bathroom new washer and dryer laundry in unit. Plenty of storage, extra storage in basement. All NEW energy saving utilities , CENTRAL A/C, Exclusive private front porch. Walking distance to downtown Winthrop Center,

  Kevin Ferrara Cottage Hill Real Estate

  145 Bartlett Rd Unit 1, Winthrop, MA 02152
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  /14

  $625,000 Sold Sep 09, 2025

  • 1,878 Sq Ft
  • $333/SF
  • 71 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1900

  136 Locust Way, Winthrop, MA 02152

  Well maintained 3 bedroom Colonial just moments from the beach. Large open rooms with lots of natural light. Lots of cabinet space in the super functional kitchen. 1st floor laundry hookups for convenience. 3 full sized bedrooms. Great yard. Nice wrap around porch to enjoy the summer nights. Seller willing to buy down the mortgage rate on this home. PLEASE BOOK SHOWINGS THROUGH SHOWINGTIME.

  Tyler Scaglione Cameron Real Estate Group

  136 Locust Way, Winthrop, MA 02152
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  /42

  Est $981,448 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,138 Sq Ft

  45 Grovers Ave Unit 3, Winthrop, MA 02152

  45 Grovers Ave Unit 3, Winthrop, MA 02152
• 

  

  /25

  $1,200,000

  • 2 Beds
  • 2.5 Baths
  • 1,868 Sq Ft

  1001 Shirley St Unit 1, Winthrop, MA 02152

  As the flagship residence at The Pearl, Unit 1 showcases one of the most spacious layouts in the collection, blending ocean views with striking modern details. Steps from the shoreline in Winthrop’s Point Shirley, it spans two levels with hardwood floors, soaring cathedral beamed ceilings, and a fireplace that anchors the living room while a second warms the primary suite. The chef’s kitchen is

  The Reference Group Reference Real Estate

  1001 Shirley St Unit 1, Winthrop, MA 02152
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  /12

  $1,875 total monthly price

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

  36 Trident Ave Unit 1, Winthrop, MA 02152

  36 Trident Ave Unit 1, Winthrop, MA 02152
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  /17

  $925,000 Sold Sep 08, 2025

  • 2,341 Sq Ft
  • $395/SF
  • 8 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1920

  31 Lincoln St, Winthrop, MA 02152

  Historic charm and modern comfort unite in this warm, inviting 3-bedroom, 2.5-bath home in the Ingleside Park neighborhood. Step inside to find stunning original woodwork, a cozy pellet stove perfect for cool summer nights, fresh paint throughout and the High-velocity AC will keep you cool all summer. 31 Lincoln has tons of upgrades...Brand new copper water line, new PVC drain to the street, new

  The Reference Group Reference Real Estate

  31 Lincoln St, Winthrop, MA 02152
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  /29

  Est $920,429 Not Listed For Sale

  • 5 Beds
  • 1.5 Baths
  • 2,608 Sq Ft

  100 Sagamore Ave, Winthrop, MA 02152

  100 Sagamore Ave, Winthrop, MA 02152
• 

  

  /21

  $979,000

  • 2 Beds
  • 2.5 Baths
  • 1,561 Sq Ft

  1001 Shirley St Unit 3, Winthrop, MA 02152

  Once a cornerstone of the Point Shirley community, this former church has been completely reimagined into five striking townhomes that blend architectural soul with modern precision. The Pearl is a bold statement... Thoughtful design, coastal light, and space that actually feels like home. Unit 3 offers over 1,500 square feet across two levels with an open main floor that feels expansive but

  The Reference Group Reference Real Estate

  1001 Shirley St Unit 3, Winthrop, MA 02152
• 

  

  /22

  $2,900 total monthly price

  • 2 Beds
  • 1 Bath
  • 1,160 Sq Ft
  • Condo for Rent

  38 Trident Ave Unit 1, Winthrop, MA 02152

  ENJOY LUXURY LIVING IN WINTHROP by the sea! Stunning 2 bedroom spacious condo with private entrance, offstreet parking space, close to beach, restaurants, busline and all Winthrop has to offer. This first floor unit offers a charming open floor plan concept, sunfilled rooms, rececessed lights, many details, ceiling fan and beautiful cherry wood floors throughout. There are two bedrooms with

  Linda Forristall Century 21 Seaport

  38 Trident Ave Unit 1, Winthrop, MA 02152
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  /8

  $500,000 Sold Sep 08, 2025

  • 852 Sq Ft
  • $587/SF
  • 4 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 1935

  39 Bay View Ave, Winthrop, MA 02152

  Welcome to this beautiful home with updates throughout, located in a relaxing area just 0.2 miles from the water and directly across from Coughlin park. Recent improvements include a new roof, updated flooring, refreshed countertops and cabinets, and a new water heater. The enclosed front porch with heat is currently used as an office, and there's also a small bonus room used as a nursery—perfect

  Devin Brown Byrnes Real Estate Group LLC

  39 Bay View Ave, Winthrop, MA 02152
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  /31

  Est $618,508 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,350 Sq Ft

  110 Summit Ave Unit 3, Winthrop, MA 02152

  110 Summit Ave Unit 3, Winthrop, MA 02152
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  /42

  $1,067,000

  • 7 Beds
  • 3 Baths
  • 3,628 Sq Ft

  308 Bowdoin St, Winthrop, MA 02152

  This spacious multi-family offers 7 bedrooms and 3 full baths across 3,628 sq. ft., with high ceilings on a 6,429 sq. ft. lot. Rarely available in Winthrop, it offers exceptional size, flexibility, and strong rental potential. A cabin/garage plus driveway for 4 cars adds rare value, while the lot provides outdoor living space. Interiors are well maintained and move-in ready.The first-floor unit

  James Polino Compass

  308 Bowdoin St, Winthrop, MA 02152
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  /18

  $2,200 total monthly price

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

  90 Winthrop Shore Dr Unit 1-b 1-b U10, Winthrop, MA 02152

  This property at 90 Winthrop Shore Dr features 1 bedrooms and 1 bathroom within a total of 7250 square feet. The living room offers a comfortable space with hardwood floors, while the eat-in kitchen is equipped for dining and meal preparation. The bathroom includes essential fixtures and provides convenient access from the main living areas. Each bedroom is adequately sized for various furniture

  90 Winthrop Shore Dr Unit 1-b 1-b U10, Winthrop, MA 02152
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  /40

  $735,000 Sold Sep 05, 2025

  • 2,327 Sq Ft
  • $316/SF
  • 10 Days On Market

  • 4 Beds
  • 1 Bath
  • Built 1920

  4 Circuit Rd, Winthrop, MA 02152

  Prime corner lot in one of Winthrop’s most desirable neighborhoods! This home has great bones and is ready for new owners to make it their own. With an ideal layout, the second floor offers the perfect space for a primary suite with walk-in closet and full bath. The first floor features a spacious living room, with the opportunity to open up the kitchen and dining area for a large island and

  Elizabeth Ferrara Cottage Hill Real Estate

  4 Circuit Rd, Winthrop, MA 02152
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  /21

  Est $454,969 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 806 Sq Ft

  103 Summit Ave Unit 3, Winthrop, MA 02152

  103 Summit Ave Unit 3, Winthrop, MA 02152
• 

  

  /22

  $1,199,000

  • 4 Beds
  • 3 Baths
  • 2,654 Sq Ft

  70 Edgehill Rd, Winthrop, MA 02152

  Nestled on a peaceful street, this charming single family home presents an incredible opportunity for generational living. Sandwiched between Donavan's Beach and Ingleside Park you can walk and enjoy the coastal living, with space to play. Recently renovated from rooftop to lower level, this is a turn key home. Multiple levels for gathers, private workspace with loads of natural light. Incredible

  Kelvin Peters MIG

  70 Edgehill Rd, Winthrop, MA 02152
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  /24

  $3,400 total monthly price

  • 4 Beds
  • 1.5 Baths
  • 1,750 Sq Ft
  • Apartment for Rent

  293 Main St Unit 2, Winthrop, MA 02152

  Available now! This spacious 4-bedroom, 1.5-bath rental offers the comfort and flow of a single-family home with the convenience of shared amenities. Spread over two levels of living, you’re welcomed by an inviting first floor with roomy living area, perfect for gathering, relaxing, or working from home, along with a well-laid-out kitchen and half bath for everyday ease. Upstairs, you’ll find

  Leighann Eruzione Lantern Residential

  293 Main St Unit 2, Winthrop, MA 02152
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  /42

  $625,000 Sold Sep 04, 2025

  • 2,130 Sq Ft
  • $293/SF
  • 28 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1900

  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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  /19

  Est $457,371 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 965 Sq Ft

  103 Summit Ave Unit 2, Winthrop, MA 02152

  103 Summit Ave Unit 2, Winthrop, MA 02152
• 

  

  /28

  $685,000 Open Sat 11AM - 1PM

  • 2 Beds
  • 2 Baths
  • 1,283 Sq Ft

  51 Cutler St Unit 3, Winthrop, MA 02152

  Enjoy turn-key living just steps from Winthrop Beach! This stunning condo blends seaside tranquility with modern comfort. A dramatic picture window in the living room frames sweeping ocean views, filling the home with natural light and salt air breezes. Sun-filled open spaces feature hardwood floors and a coastal-modern design. The chef's kitchen offers sleek cabinetry, high-end appliances, and a

  Sobel Group Compass

  51 Cutler St Unit 3, Winthrop, MA 02152
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  /12

  $2,275 total monthly price

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

  1 Pond St Unit 3B, Winthrop, MA 02152

  **AVAILABLE NOW** This is a spacious 1 bedroom/ 1 bath apartment overlooking the beautifully kept grounds of Fort Heath! It is recently remodeled with new laminate flooring throughout as well as new countertops in the kitchen. The unit includes a gas stove, dishwasher and refrigerator. It boasts new kitchen cabinets and a new vanity in bathroom as well as a walk-in closet in the bedroom. There is

  James Polino Compass

  1 Pond St Unit 3B, Winthrop, MA 02152
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  /32

  $462,000 Sold Sep 03, 2025

  • 1,165 Sq Ft
  • $397/SF
  • 7 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1900

  94 Lincoln St Unit 2, Winthrop, MA 02152

  This charming, move-in-ready 2-bed, 1-bath condo in a gorgeous brownstone building offers historic character and modern convenience just minutes from downtown Boston! Beautiful original hardwood floors and bay window add warmth and timeless appeal. Both bedrooms are generously sized and filled with natural light. The second bedroom has a walk-in closet. The spacious, eat-in kitchen features tile

  David Ladner RE/MAX Harmony

  94 Lincoln St Unit 2, Winthrop, MA 02152
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  /30

  Est $362,033 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 894 Sq Ft

  103 Summit Ave Unit 1, Winthrop, MA 02152

  103 Summit Ave Unit 1, Winthrop, MA 02152
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  /38

  $1,125,000 Open Sun 12PM - 1PM

  • 4 Beds
  • 3.5 Baths
  • 2,575 Sq Ft

  191 Court Rd Unit 3, Winthrop, MA 02152

  Coastal luxury meets modern elegance in this completely renovated 4-bed, 3.5-bath waterfront condo with breathtaking ocean and Boston skyline views. Unit 3 at 191 Court features two private owner’s suites on separate levels, sleek modern bathrooms, and an open-concept living/dining area filled with natural light and ocean breezes. The chef’s kitchen boasts premium Samsung stainless steel

  Kristen Karshis Keller Williams Realty Evolution

  191 Court Rd Unit 3, Winthrop, MA 02152
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  /5

  $1,850 total monthly price

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

  2 Jefferson St Unit 13, Winthrop, MA 02152

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

  Atiyeh Cassidy Blue Sky Realty

  2 Jefferson St Unit 13, Winthrop, MA 02152
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  /29

  $735,000 Sold Sep 02, 2025

  • 1,165 Sq Ft
  • $631/SF
  • 15 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1900

  148 Winthrop Shore Dr Unit 4, Winthrop, MA 02152

  Experience the ultimate home getaway in this beautifully renovated 2 bed, 2 bath condo with stunning, unobstructed ocean views and deeded parking in Winthrop's growing community! Enjoy sunsets and sea breezes from your private balcony. Inside, 10+ ft ceilings, white oak floors, central AC, custom blinds, and smart home features offer lots of comfort and style. The chef’s kitchen boasts a

  George Sarkis Douglas Elliman Real Estate - The Sarkis Team

  148 Winthrop Shore Dr Unit 4, Winthrop, MA 02152
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  /21

  Est $765,113 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,668 Sq Ft

  100 Locust St, Winthrop, MA 02152

  100 Locust St, Winthrop, MA 02152
• 

  

  /13

  $290,000

  • 1 Bed
  • 1 Bath
  • 550 Sq Ft

  483 Shirley St Unit 4, Winthrop, MA 02152

  LOWEST PRICED CONDO IN WINTHROP. If you’ve been looking for a 1 bed 1 bath condo in the heart of Winthrop Shore, look no further. Conveniently located next to some of the best restaurants & shops in town, and only a street away from Winthrop Beach. HOA fee includes heat, hot water, and much more. Come make this hidden gem your own - and yes your pets are welcome! Just minutes from Boston, a

  Team Lillian Montalto Lillian Montalto Signature Properties

  483 Shirley St Unit 4, Winthrop, MA 02152
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  /18

  $2,600 total monthly price

  • 2 Beds
  • 1 Bath
  • 1,100 Sq Ft
  • Apartment for Rent

  20 Beacon St Unit 2, Winthrop, MA 02152

  VERY NICE 2 BEDROOM RENTAL, STEPS TO THE BEACH! This location has the harbor at one end of the street and the ocean at the other! Hardwood floors, Lots of windows for natural light and some recessed lighting too. Fully applianced, updated eat-in kitchen includes LAUNDRY in UNIT, stackable washer and dryer, gas stove and pantry area. The updated tile bath has a jacuzzi tub and the apartment has

  Sharon Tallent Compass

  20 Beacon St Unit 2, Winthrop, MA 02152
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  /21

  $711,000 Sold Sep 02, 2025

  • 1,792 Sq Ft
  • $397/SF
  • 102 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1991

  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
• 

  

  /21

  Est $881,444 Not Listed For Sale

  • 5 Beds
  • 2.5 Baths
  • 2,840 Sq Ft

  3 Almont St, Winthrop, MA 02152

  3 Almont St, Winthrop, MA 02152

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