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Winthrop, MA Homes for Sale

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  • /42

    $900,000

    • 5 Beds
    • 2.5 Baths
    • 3,776 Sq Ft

    339 Winthrop St, Winthrop, MA 02152

    This beautifully maintained two-family home offers the perfect blend of meticulous care, charm and city convenience. Just minutes from downtown Boston and Logan Airport, enjoy easy commuting paired with the tranquility of a vibrant beachside community. Nearly 4,000 sq. ft. of living space features hardwood floors, a custom kitchen with island, gas fireplace, and a flexible floor plan with home

    Danielle McCarthy Berkshire Hathaway HomeServices Commonwealth Real Estate

    339 Winthrop St, Winthrop, MA 02152
  • /30

    $849,900

    • 5 Beds
    • 2.5 Baths
    • 2,065 Sq Ft

    105 Circuit Rd, Winthrop, MA 02152

    This is your PERFECT OPPORTUNITY to purchase a traditional Whittemore style home in Winthrop's highly sought-after Maze neighborhood to make your own. This charming, OVERSIZED single family home offers plenty of room for everyone with FIVE (5) bedrooms (including top floor primary that could be turned into a suite) 2.5 baths and a fully finished basement with separate walkout. Available for the

    Ed Deveau Century 21 Mario Real Estate

    105 Circuit Rd, Winthrop, MA 02152
  • /24

    $787,000

    • 2 Beds
    • 2 Baths
    • 1,233 Sq Ft

    10 Somerset Ave Unit 307, Winthrop, MA 02152

    Welcome to Unit 307—the largest residence at The Somerset, a boutique condo community in the heart of Winthrop. This 2-bedroom, 2-bath home features a spacious, open-concept kitchen and living area with quartz countertops, stainless steel appliances, central air conditioning, and modern finishes throughout. The Somerset offers amenities including a fitness room, elevator, and resident lounge,

    Charlesgate New Development Team Charlesgate Realty Group, llc

    10 Somerset Ave Unit 307, Winthrop, MA 02152
  • /35

    $695,000

    • 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
  • /40

    $599,900

    • 3 Beds
    • 2 Baths
    • 1,314 Sq Ft

    95 Summit Ave Unit 1, Winthrop, MA 02152

    Just steps from Winthrop Beach, this stunning condominium blends seaside tranquility with modern comfort. Gut renovated and completed in 2021, windows at every turn fill 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 is appointed with sleek white cabinetry, stainless steel appliances, and a spacious

    Ann DiMascio Lamacchia Realty, Inc.

    95 Summit Ave Unit 1, Winthrop, MA 02152
  • /27

    $700,000

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

    51 Cutler St Unit 3, Winthrop, MA 02152

    Just steps from Winthrop Beach, this stunning condominium 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 spacious layout

    Sobel Group Compass

    51 Cutler St Unit 3, Winthrop, MA 02152
  • /24

    $950,000

    • 3 Beds
    • 2 Baths
    • 2,200 Sq Ft

    5 Quincy Ave, Winthrop, MA 02152

    A bungalow with traditional Craftsman touches—wide overhanging eaves, tapered porch posts, pitched roof Inside, the home retains much of its original woodwork: rich oak with built-in cabinetry, window and door casings with decorative moulding, wainscoting and a fireplace mantel in living room. classic details are complemented by contemporary updates—recessed lighting, updated fixtures, clean

    Jason Saphire www.HomeZu.com

    5 Quincy Ave, Winthrop, MA 02152
  • /38

    $1,175,000

    • 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
  • /42

    $895,000

    • 4 Beds
    • 2.5 Baths
    • 2,397 Sq Ft

    2 Deane Ave, Winthrop, MA 02152

    Exciting opportunity to own a home w/approved inlaw-ADU/au-pair within walking distance to the ocean! Or enjoy views of the Boston skyline from patio.Collect rent! Perfect for multi-generation living. Located in Winthrop Highlands this home has been renovated on 4 levels. Natural light pours into every room. The front hall embraces details from its period. First floor features a custom kitchen

    Marina Tramontozzi True North Realty

    2 Deane Ave, Winthrop, MA 02152
  • /26

    $739,900

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

    174 Winthrop St Unit 2, Winthrop, MA 02152

    Step inside this beautifully reimagined residence where timeless charm meets modern comfort. This 3 bedroom, 2.5 bath home has been fully renovated with thoughtful design choices that highlight the building’s historic character while adding the conveniences of today. Original hardwood floors anchor the sun-filled interior, where a welcoming living area flows into a stylish kitchen, complemented

    Leighann Eruzione Lantern Residential

    174 Winthrop St Unit 2, Winthrop, MA 02152
  • /41

    $750,000

    • 4 Beds
    • 2 Baths
    • 1,870 Sq Ft

    3 Buckthorn Terrace Unit 2, Winthrop, MA 02152

    Back to Market due to buyer financing.....Tucked away on a quiet street, this home boasts stately features and has been meticulously renovated. From the elegant newel post to the timeless kitchen details, nothing was overlooked. During the condo conversion, preserving the home's original integrity was a priority. The first floor offers 2 bedrooms, laundry, and a full bath with marble tile floors.

    Elizabeth Ferrara Cottage Hill Real Estate

    3 Buckthorn Terrace Unit 2, Winthrop, MA 02152
  • /32

    $839,900

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

    100 Cottage Ave, Winthrop, MA 02152

    Ideally located just steps from the Winthrop Yacht Club, The Landing, local restaurants, and both Winthrop and Yirrell Beach, this spacious single-family home offers stunning water views and a clear line to Boston’s skyline. The first level features a unique and expansive layout with a formal living and dining room anchored by a double-sided fireplace wrapped in lava-rock, plus two additional

    The Reference Group Reference Real Estate

    100 Cottage Ave, Winthrop, MA 02152
  • /42

    $870,000

    • 4 Beds
    • 3.5 Baths
    • 2,350 Sq Ft

    136 Pauline St, Winthrop, MA 02152

    Beautifully renovated 4-bedroom, 3.5-bath single-family home, fully gutted and updated in 2020. This turnkey property features an open floor plan with seamless flow between the spacious living room, dining area, and modern kitchen—perfect for today’s lifestyle and entertaining. The primary suite includes a walk-in closet and private en-suite bath. A finished basement (2021) provides flexible

    Anthony Carestia William Raveis R.E. & Home Services

    136 Pauline St, Winthrop, MA 02152
  • /21

    $669,009

    • 2 Beds
    • 2 Baths
    • 971 Sq Ft

    148 Winthrop Shore Dr Unit 5, Winthrop, MA 02152

    Welcome to your slice of coastal paradise just outside of Boston. Nestled in the quaint seaside town of Winthrop, this stunning condo offers an unparalleled living experience with exceptional water views.Step inside to discover a meticulously designed space, with an open-concept layout that seamlessly blends the living, dining, and kitchen areas, creating an inviting atmosphere flooded with

    Nicole Bettano Lantern Residential

    148 Winthrop Shore Dr Unit 5, Winthrop, MA 02152
  • /40

    $829,999

    • 4 Beds
    • 2 Baths
    • 2,000 Sq Ft

    876 Shirley St Unit 1, Winthrop, MA 02152

    Direct Beach Front Living. Feel like you're on vacation every day! This spacious 2 level, 7 room, 4 bed, 2 bath condo is located Directly on Yirrell Beach. The sand in your own back yard. Ocean breeze and sounds of the waves crashing onto the shore, are sure to relax you after a long day. Every day the view is different. Featuring beautiful cherry hard wood floors, Family room, Formal dining

    Jim Iannuzzi Amo Realty - Boston City Properties

    876 Shirley St Unit 1, Winthrop, MA 02152
  • /39

    $875,000

    • 4 Beds
    • 2 Baths
    • 2,972 Sq Ft

    123 Hermon St, Winthrop, MA 02152

    Well maintained spacious two family in a prime location. Both apartments are 1,486 sf and have open floor plans, wood flooring and high ceilings. Unit 1 has a great eat in kitchen with washer and dryer area in the hallway. Bedrooms are good size with double closets. There is a seamless flow from the front door to the open living / dining room. This unit offers easy access to the yard and the

    Valerie Lane Brad Hutchinson Real Estate

    123 Hermon St, Winthrop, MA 02152
  • /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
  • /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
  • /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
  • /30

    $949,900

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

    40 Cottage Park Rd, Winthrop, MA 02152

    Nestled in the sought-after Cottage Park neighborhood, this beautifully maintained two-family home offers over 2,400 sq ft of living space, a garage plus 3 off-street parking spaces, and is being delivered vacant—perfect for owner-occupants or investors. Unit 1 features 2 bedrooms, a sunroom, and classic wood floors. Unit 2 spans two levels with 3 bedrooms, 2 full baths, central air, and a family

    The Reference Group Reference Real Estate

    40 Cottage Park Rd, Winthrop, MA 02152
  • /34

    $719,000

    • 3 Beds
    • 2 Baths
    • 1,365 Sq Ft

    32 Pearl Ave, Winthrop, MA 02152

    Wake up to ocean breezes and the sunrise just at the end of the street. The kitchen blends charm and function with granite counters, hardwood cabinetry, farmhouse sink. 10’ ceilings throughout and abundant natural light create an open, airy feel. Step onto the 2nd floor balcony for morning coffee or evening sunsets. Ideal for entertaining, the fenced yard, ample parking, andOcean views from porch

    Elizabeth Ferrara Cottage Hill Real Estate

    32 Pearl Ave, Winthrop, MA 02152
  • /34

    $735,000

    • 5 Beds
    • 3.5 Baths
    • 2,475 Sq Ft

    9 Marshall St, Winthrop, MA 02152

    Discover the best of coastal living in this Winthrop waterfront community, where local dining, seaside charm, and effortless access to public transit create a lifestyle of ease and enjoyment. Spanning approximately 2,475 square feet, this expansive 5-bedroom, 3.5-bath home offers three levels of versatile living space along with a private outdoor deck and yard. Ideally situated within walking

    Ricardo Rodriguez Coldwell Banker Realty - Boston

    9 Marshall St, Winthrop, MA 02152
  • /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
  • /26

    $999,000

    • 5 Beds
    • 2 Baths
    • 1,920 Sq Ft

    95 Banks St, Winthrop, MA 02152

    Beautifully maintained 2-family with extensive updates, ideal for an owner-occupier or investor seeking strong market rents. Major improvements include a newer roof, updated heating system, central air on the second floor, and fresh paint. Exterior features showcase a large yard, fenced space, resurfaced driveway and parking for 3, concrete patio, composite railings, irrigation system, and

    Kristen Karshis Keller Williams Realty Evolution

    95 Banks St, Winthrop, MA 02152
  • /40

    $799,000

    • 3 Beds
    • 2 Baths
    • 1,980 Sq Ft

    380 Pleasant St, Winthrop, MA 02152

    Spacious Home with Water Views located at the entrance of the Desirable “Maze Area”. Welcome to this large & inviting home located steps from Donovan Beach & Ingleside Park. With beautiful water views and an abundance of living space, this property offers the perfect blend of comfort, convenience and coastal charm. Step inside the welcoming foyer, which flows into a sun-filled open living room

    Colleen Eddy Return Realty Group, Inc.

    380 Pleasant St, 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
  • /10

    $1,499,000

    • 5 Beds
    • 3 Baths
    • 3,200 Sq Ft

    73 Grovers Ave, Winthrop, MA 02152

    (ENTRY ONLY) 73 Grovers Ave, Winthrop multi-family residence presents a unique opportunity to own a substantial property with considerable potential. The residence offers a canvas for realizing your vision. The residence includes a total of five bedrooms throughout its 3 stories, providing ample private space for occupants. Each of the 3 full bathrooms are equipped to serve the needs of a busy

    Joseph Germano Cape Real Estate

    73 Grovers Ave, Winthrop, MA 02152
  • /31

    $529,900

    • 2 Beds
    • 2 Baths
    • 800 Sq Ft

    35 Somerset Ave Unit 6, Winthrop, MA 02152

    UPSCALE 2 BEDROOM, 2 BATH TOP FLOOR UNIT WITH ROOFTOP EXCLUSIVE OUTDOOR DECK......A two year old renovation and a must see! Bright sun-filled condo with a spacious kitchen/living room combo with plenty of cabinets and huge center island with pretty pendant lighting......perfect for entertaining and personal enjoyment. Two large bedrooms, one a main suite with it's own full bath and the other

    Sharon Tallent Compass

    35 Somerset Ave Unit 6, Winthrop, MA 02152
  • /31

    $449,900

    • 2 Beds
    • 2 Baths
    • 1,460 Sq Ft

    15 Ocean Dr Unit 105, Winthrop, MA 02152

    15 Ocean Dr #105 delivers flexible two-level living with dramatic ceiling height and oversized windows just minutes to the beach. Newly renovated with 2 luxurious full baths, in-unit laundry, central A/C, one deeded parking, and access to a common roof deck. Smart layout features a main kitchen on the upper level and a lower-level kitchenette with a separate entrance-ideal for guests,

    Sarah Strangie Keller Williams Realty Boston-Metro | Back Bay

    15 Ocean Dr Unit 105, Winthrop, MA 02152
  • /23

    $780,000

    • 5 Beds
    • 2.5 Baths
    • 1,923 Sq Ft

    62 Lowell Rd, Winthrop, MA 02152

    Welcome to the "Maze!" This Whittemore designed home is solidly built and filled with character and charm. With great bones and endless potential, this 4+ bedroom, 2.5 bath single is the perfect canvas to create space you've been dreaming of, all in one of Winthrop's most sought after locations. Some of the wonderful features include a wood-burning fireplace, bright eat in kitchen with

    Mary Ann Cash Charlesgate Realty Group, llc

    62 Lowell Rd, Winthrop, MA 02152
  • /33

    $1,800,000

    • 5 Beds
    • 4 Baths
    • 3,866 Sq Ft

    144 Quincy Ave, Winthrop, MA 02152

    Welcome to the Highlands, Winthrop’s most coveted neighborhood- where modern design meets sweeping Boston views. This newly built two-family sits high on the hill with sunlit interiors, wide white oak floors, and timeless details throughout. The main unit offers an open layout with living room and fireplace, Thermador-Pro kitchen with island, beverage bar, and pantry, plus a dining area opening

    Leighann Eruzione Lantern Residential

    144 Quincy Ave, Winthrop, MA 02152
  • /37

    $1,175,000

    • 5 Beds
    • 2.5 Baths
    • 3,458 Sq Ft

    66 Lowell Rd, Winthrop, MA 02152

    10 room + pristine home exuding warmth & quintessential New England charm in the sought after Maze neighborhood Timeless Whittemore style. Inviting enclosed porch with rich woodwork. Dramatic oversized windows and graceful flow throughout. Exquisite living room featuring statement fireplace wall. Talented master woodworker and renowned architect custom designed and blended functionality with

    Stacey Steck Gibson Sotheby's International Realty

    66 Lowell Rd, Winthrop, MA 02152
  • /42

    $1,799,000

    • 6 Beds
    • 3.5 Baths
    • 4,455 Sq Ft

    191 Cottage Park Rd, Winthrop, MA 02152

    Queen Anne Victorian in the Cottage Park neighborhood, 2 blocks from the Cottage Park Yacht Club. Over 4,400 square feet of living space with 6 bedrooms, 3.5 fully renovated baths, 2nd floor laundry room and 2 finished basement rooms. Stunning details include high ceilings, hand carved newel posts and mantels, 3 Chelsea tile fireplaces, oak flooring and woodworking, wainscoted staircases, window

    Anthony Giacalone Tony's Realty

    191 Cottage Park Rd, Winthrop, MA 02152
  • /40

    $1,200,000

    • 3 Beds
    • 2.5 Baths
    • 1,700 Sq Ft

    916 Shirley St Unit 1, Winthrop, MA 02152

    At 916 Shirley, we redefine coastal luxury living with our exceptional collection of waterfront condos. Immerse yourself in the essence of waterfront living-breathe in the salty ocean air, bask in the warmth of the sun, & let every wave carry you closer to serenity. Here you will find 3 bedrooms, 2.5 bathrooms, 3 private outdoor decks, 3 levels of finished living space, 2 parking spaces, EV

    Mark Sciaraffa Sciaraffa Real Estate, LLC

    916 Shirley St Unit 1, Winthrop, MA 02152
  • /14

    $1,200,000

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

    50-52 Wilshire St, Winthrop, MA 02152

    Just Renovated – Perfect for Owner-Occupants or Investors!Welcome to 50-52 Wilshire Street, a fully updated two-family home located in the picturesque seaside community of Winthrop, Massachusetts. This property has 5 bedrooms and 2 bathrooms. Fresh from a complete renovation, this property blends modern finishes with timeless New England charm, offering unmatched flexibility for both comfortable

    Bin Yan Ark Real Estate Inc.

    50-52 Wilshire St, Winthrop, MA 02152
  • /42

    $639,000

    • 4 Beds
    • 2 Baths
    • 1,483 Sq Ft

    54 Townsend St, Winthrop, MA 02152

    Welcome to this delightful charming home located in the highly sought-after Point Shirley section of Winthrop.With 7+ rooms, 3+ bdrms, and 13⁄4 baths, this lovingly maintained home offers timeless character and stunning views. Begin your day on the charming front porch perfect for morning coffee, a good book, or an evening beverage while soaking in the coastal scenery. Inside, the living room

    Cathie Curran Charlesgate Realty Group, llc

    54 Townsend St, Winthrop, MA 02152
  • /42

    $1,170,000

    • 5 Beds
    • 2 Baths
    • 2,151 Sq Ft

    328-330 Revere St, Winthrop, MA 02152

    This property is what the competition see as a "Triple Threat" *TURN KEY *LOCATION & *BIG LOT OF LAND! The first floor's Craftsman style details have had restoration, preserving the stain glass windows, hardwood floors, working wood fireplace, beamed ceilings & built-ins to really embody the character of days gone by. A gas stove with hood vent, & sliders to a deck off the kitchen, makes this

    Debra Messana LAER Realty Partners

    328-330 Revere St, Winthrop, MA 02152
  • /42

    $725,000

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

    32 Hale Ave, Winthrop, MA 02152

    A spectacular hilltop home with unmatched 360 views. A once-in-a-lifetime opportunity to own this exceptional hilltop property offering panoramic views of the Atlantic Ocean, Boston Harbor, Winthrop Harbor, and the Boston skyline. Ocean views from every room and all three decks make this home truly one of a kind. Steeped in history, this site was purposely chosen by Patriot troops during the

    Sharon Tallent Compass

    32 Hale Ave, Winthrop, MA 02152
  • /32

    $549,900

    • 2 Beds
    • 2 Baths
    • 773 Sq Ft

    600 Shirley St Unit 3, Winthrop, MA 02152

    “The Cove at 600” was converted in 2022 and is located on the site of the historic Crystal Cove Hotel with breathtaking views of the Boston Skyline and the Atlantic Ocean. Unit 3, located on the side of the building with a private entrance, exclusive use patio and exclusive use deck at the front of the building offers many ways to take in the view and the sea air. The open concept living room and

    Erika Leigh Pereira Keller Williams Realty Boston Northwest

    600 Shirley St Unit 3, Winthrop, MA 02152
  • /37

    $949,000

    • 4 Beds
    • 2 Baths
    • 2,366 Sq Ft

    80 Shirley St, Winthrop, MA 02152

    Gorgeous farmhouse revival!!! Coastal vibes flow through this stunning brand new renovation. Best of both worlds with proximity to the beach and the city. Less than a 5 minute walk to the nicest beach close to Boston. An easy 15 minute drive and you're in the middle of the city. Both units boast modern open floor plans. Actual high end finishes throughout for an obvious upscale vibe. Huge

    Nick Burnes Red Tree Real Estate

    80 Shirley St, Winthrop, MA 02152

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