Winthrop, MA Homes for Sale

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Discover the charm of Winthrop, Massachusetts, a coastal gem offering a unique blend of seaside tranquility and convenient access to Boston. Explore a diverse real estate market featuring everything from historic homes with character to modern condos boasting ocean views. Life in Winthrop means waking up to the sounds of the waves and enjoying breathtaking sunsets over the Atlantic.

Beyond its beautiful homes, Winthrop provides a vibrant community atmosphere. Stroll along the picturesque beaches, indulge in fresh seafood at local restaurants, and explore charming shops. Enjoy outdoor activities like boating, fishing, and swimming, or take a relaxing walk through scenic parks and nature reserves. Winthrop's friendly neighborhoods and welcoming spirit make it a truly special place to call home.

Winthrop's prime location offers the best of both worlds. Enjoy the peace and quiet of a seaside town while remaining close to the cultural and professional opportunities of Boston. With convenient transportation options, commuting is a breeze. Experience the unique lifestyle that Winthrop offers – a perfect blend of coastal living, community spirit, and easy access to urban amenities.

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Winthrop, MA Homes for Sale

$524,900

2 Beds ⋅ 3 Baths ⋅ 73572947 MLS ⋅ ACTIVE Status

A True Pride of Home Ownership!!! LOW CONDO FEE comes w/This Meticulously Maintained 2 Bed 2.5 Bath Penthouse Condo w/ 2 OFF STREET PARKING SPACES is Nestled in a Quiet Residential Neighborhood Just Steps from 4 Beaches, EZ ACCESS TO Public Transportation, Fine Shops and Dining and is Only a 10 Minute Drive to Downtown Boston/Logan Airport. Natural Light Spills Into This Unit Through the Over Sized Windows and 3 Sky Lights on the 2nd Level. Other Notable Features Include Newly Installed Waterproof Vinyl Plank Flooring , Fresh Paint Throughout, Central Heat /AC, Custom Blinds, Galley Kitchen, In Unit Washer and Dryer, Recessed Lighting, Newer Oversized Windows on 2nd Level, Private Balcony Off Both Bedrooms w/ Ocean Views, Common Roof Deck w/ Ocean Views, Extra DEEDED Storage in Basement and Much Much More!!!

15 Ocean Ave Unit 203, Winthrop

Listing courtesy of Listing Agent: Kenneth Celano from Listing Office: Turn Key Realty.

$549,900

2 Beds ⋅ 2 Baths ⋅ 73571733 MLS ⋅ ACTIVE Status

35 Somerset Unit 3A, Winthrop

Listing courtesy of Listing Agent: Mark Savage from Listing Office: Byrnes Real Estate Group LLC.

$473,900

1 Beds ⋅ 1 Baths ⋅ 73570684 MLS ⋅ ACTIVE Status ⋅ ['Somerset'] BLDG.

Welcome to The Somerset, Winthrop's premier boutique condominium community, where coastal charm meets effortless modern living. This thoughtfully designed 693± sq. ft. one-bedroom, one-bath residence offers an open-concept layout with a spacious living area, oversized bedroom with walk-in closet, quartz countertops, stainless steel appliances, in-unit laundry, and contemporary finishes throughout. Located in the heart of Winthrop, The Somerset has become a sought-after address, transforming a landmark property into a vibrant 29-home condominium community that celebrates the town's rich seaside character while offering today's conveniences. Residents enjoy an elevator, fitness center, coffee station, resident lounge, and secure mailroom. Just moments from beaches, local restaurants, cafés, the ferry, and downtown Boston, this move-in-ready home offers the perfect blend of coastal tranquility and city accessibility.

10 Somerset Unit U.305, Winthrop

Listing courtesy of Listing Agent: Charlesgate New Development Team from Listing Office: Charlesgate Realty Group, llc.

$625,000

3 Beds ⋅ 1 Baths ⋅ 73569960 MLS ⋅ ACTIVE Status

Welcome to 33 Bay View Ave, a charming coastal bungalow offering the perfect blend of comfort, convenience, and seaside living in Winthrop. This 3-bedroom, 1-bath home features hardwood floors, a bright and inviting living space, dedicated dining area, and a functional kitchen with new appliances. Enjoy water views and take advantage of the spacious fenced in yard, ideal for entertaining, gardening, or relaxing outdoors. Additional highlights include an enclosed porch, wood deck, patio, first-floor laundry, and off street parking. Located just moments from the beach, parks, walking and biking trails, public transportation, and all that Winthrop has to offer. A great opportunity to enjoy the coastal lifestyle while remaining just minutes from Boston and Logan Airport.

33 Bay View Ave, Winthrop

Listing courtesy of Listing Agent: Michael Cimmino from Listing Office: Real Broker MA, LLC.

$539,000

1 Beds ⋅ 1 Baths ⋅ 73569128 MLS ⋅ ACTIVE Status

Oversized one bedroom condo in Winthrop's historic Playmakers building, just minutes from Winthrop Center. This bright, modern unit features an open concept living space with cathedral ceilings and hardwood floors throughout. The kitchen offers a large island, stone countertops, stainless steel appliances, a gas stove, and a wine chiller. A spacious bedroom and office sit on the primary floor, with ladders leading up to two additional multi-use loft spaces. Stacked washer and dryer in unit. One off-street parking spot. Steps to public transportation, parks, tennis courts, and less than a half mile to the beach.

60 Hermon St Unit 3, Winthrop

Listing courtesy of Listing Agent: Reserve Team from Listing Office: Reference Real Estate.

$649,000

3 Beds ⋅ 2 Baths ⋅ 73568805 MLS ⋅ ACTIVE Status

A rare opportunity to own a beachside home in this highly desirable coastal neighborhood! This 3 bdrm, 1 3/4 bath Beach Bungalow is the perfect condo alternative! The Main BDRM & FR have been fully renovated offering a Classic timeless design! New doors, recessed lighting, smooth ceilings, custom trim & crown molding, walk in closet, built in seating/cabinet, custom made covers for radiators, fireplace w/wood mantel & shiplap on the walls! Entertain friends, grill, relax on your NEWLY BUILT expansive rear deck w/steps to the beach! Embrace all that living in beach community offers~ Catch a Sunrise, Swimming, Surfing, Sunbathe or Boating! Spacious kitchen w/water views offers New HDWD, New Paint throughout, Natural Gas range, New SS Refrigerator, DW and Dining area! Large unfinished basement has full bath w/shower stall, large cedar closet, Washer & Dryer (2023), Hot water tank 12/2023 with 2 add'l rooms offering endless possibilities! Updates include Roof (2016) with peace of mind having Town water & Town sewer! Point Shirley residents enjoy all the amenities at Coughlin Park and the "Deer Island" walking path ~ both with it's amazing city views of Boston! Bus service to Orient Heights train station, seasonal Ferry Service from Winthrop Landing to Seaport /Aquarium & 5.6 miles to Logan Airport! For the boating enthusiasts, there's multiple Yacht Clubs in this quaint Town of Winthrop! The LIVIN' IS EASY when you've found a home that's updated, in a sought after location and move in ready!!! Seller can offer a quick close!

84 Tafts Ave., Winthrop

Listing courtesy of Listing Agent: Patricia Nemes from Listing Office: Century 21 Tassinari & Assoc..

$710,000

4 Beds ⋅ 2 Baths ⋅ 73568640 MLS ⋅ ACTIVE Status

The perfect blend of comfort, convenience, and affordability! Whether you’re a first-time homebuyer, looking to downsize, or searching for an alternative to condo living, this charming 4-bedroom home offers the space you need with the low-maintenance lifestyle you want all just one block from the beach. The main level features a comfortable bedroom and full bathroom with a convenient walk-in shower, making one-floor living a great option for a variety of needs. You’ll also find main-level laundry, an eat-in kitchen, a convenient mudroom off the entryway to store shoes and umbrellas, and split-unit heating and cooling for year-round comfort. Upstairs are three additional generously sized bedrooms, each offering great closet space, along with a second full bathroom and central air to keep the entire second level comfortable during the warmer months. It’s an ideal low-maintenance alternative to condo living, while still offering the privacy and flexibility of a single-family home within minutes walk to a playground, beaches, restaurants, coffee shops, the public ferry to Boston and yacht clubs. Don't miss out on your opportunity to own in gorgeous Winthrop by the Sea!

542 Shirley St, Winthrop

Listing courtesy of Listing Agent: Christine D'Ambrosio from Listing Office: Bowdoin Real Estate Partners.

$419,900

1 Beds ⋅ 1 Baths ⋅ 73568595 MLS ⋅ ACTIVE Status ⋅ ['Pauline Place'] BLDG.

WINTHROP BY THE SEA IS CALLING! Welcome to Pauline Place at Winthrop Center, a brand-new boutique community perfectly positioned right on the bus line for a quick connection to the T and into Boston. Imagine being the very first person to live in one of these high-end, one-bedroom condos. With five distinct units to choose from, you’ll find gorgeous, color-coordinated kitchens and baths that truly wow. The kitchens are a chef’s dream, featuring sleek LG stainless steel appliances, crisp quartz countertops, stylish shaker cabinets with modern black hardware, and luxury vinyl flooring that ties the whole aesthetic together. The upscale baths, finished with striking tile and glass, feel like a private spa retreat.Every room feels bright and airy thanks to Pella windows that invite the sunlight to pour in. You’ll stay perfectly comfortable year-round with high-efficiency Mitsubishi heating and cooling, and the convenience of in-unit laundry and off-street parking makes daily life a breeze.Step outside and you’re just moments away from local restaurants and shopping. Living here means embracing the best of Winthrop—beaches, boating, marinas, yacht clubs, a golf course, and miles of scenic seaside paths for biking and exploring. ITS A STUNNING PALCE TO CALL HOME AND BEST OF ALL YOU CAN OWN THIS LIFESTYLE FOR LESS THAN THE COST OF RENTING!

22 Pauline St. Unit 5, Winthrop

Listing courtesy of Listing Agent: Highland Group from Listing Office: Compass.

$399,900

1 Beds ⋅ 1 Baths ⋅ 73568569 MLS ⋅ ACTIVE Status ⋅ ['Pauline Place'] BLDG.

22 Pauline St. Unit 3, Winthrop

Listing courtesy of Listing Agent: Highland Group from Listing Office: Compass.

$865,000

2 Beds ⋅ 3 Baths ⋅ 73567772 MLS ⋅ ACTIVE Status ⋅ ['The Pearl'] BLDG.

Historic loft at The Pearl with soaring ceilings, oversized windows, and original wood details. kitchen with premium appliances and stone surfaces. Private deck off the primary suite with radiant heated bath. Two off-street parking spaces, private storage, secure entry. Come and enjoy what Winthrop has to offer, beaches, paths, cafes, a golf course, public pickleball & tennis courts with easy Boston access. Special developer pricing now offered at 865,000.00 Seller reserves the right to accept, reject, or counter any offer and may request highest and best. Pricing and terms subject to change without notice. Buyers are encouraged to submit their strongest offer promptly.

1001 Shirley St Unit 2, Winthrop

Listing courtesy of Listing Agent: Vincenzo Caraglia from Listing Office: Sciaraffa Real Estate, LLC.

$979,900

6 Beds ⋅ 3 Baths ⋅ 73567723 MLS ⋅ PRICE CHANGED Status

Stop by our OPEN HOUSE Sunday 9/13 1:00-2:30 for a viewing. A fantastic value for this home. It’s an opportunity to make it your own, and enjoy the quaint town of Winthrop by the sea. Spacious and beautifully updated, 6-bedroom, 2.5-bath home with the perfect blend of classic character & modern efficiency, all located in the wonderful seaside community of Winthrop by the Sea. Featuring gleaming hardwood floors throughout, newer windows 2 fireplaces giving warmth & charm to the living spaces. Extensive updates include all new mechanical systems including elec. wiring, FWA furnace, cent A/C, on-demand HW, mini-split heat pump/AC units, plumbing lighting, all providing peace of mind for years to come. Generous space, new paint & plaster finishes, & a beautifully finished basement for extra-living space, or entertainment. Kitchen has S.S. appliances and convenient 1st fl stacked washer & dryer. Outside large welcoming porch, groomed backyard, newer asphalt driveway, & an updated 2-car garage w/new overhead doors. Energy conscious buyers can assume the term note solar panels.

217 Pleasant Street, Winthrop

Listing courtesy of Listing Agent: Louis Bonavita from Listing Office: Benton Real Estate Company.

$739,000

3 Beds ⋅ 3 Baths ⋅ 73566786 MLS ⋅ PRICE CHANGED Status

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 home and features direct access to its own secluded backyard retreat — a perfect escape for relaxing, entertaining, or enjoying quiet moments outdoors. Inside, thoughtfully designed living spaces are filled with natural light and offer the ideal balance of elegance and functionality. Just one block from the beach, enjoy the very best of coastal living- and only minutes from downtown Boston, Logan Airport, and public transportation MBTA Orient Heights Blue Line for an effortless daily commute.

189 Shirley St Unit 1, Winthrop

Listing courtesy of Listing Agent: Tammy Merk from Listing Office: Real Broker MA, LLC.

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