Winthrop Real Estate

Welcome to Winthrop, Massachusetts—a charming coastal town nestled in Suffolk County, just a stone's throw away from the bustling city of Boston. Known for its picturesque waterfront views and tight-knit community, Winthrop offers a unique blend of small-town charm and urban convenience, making it a hidden gem in the Greater Boston area.

With its stunning beaches, including the popular Winthrop Beach and Yirrell Beach, residents enjoy a vibrant seaside lifestyle. The town's scenic parks, such as Belle Isle Marsh Reservation, provide ample opportunities for outdoor activities, from leisurely strolls to birdwatching. Winthrop's rich history is reflected in its well-preserved architecture, with quaint homes lining the streets, each telling a story of the town's past.

Culinary enthusiasts will delight in Winthrop's diverse dining scene, which features everything from cozy cafes to waterfront seafood restaurants. Whether you're savoring a fresh lobster roll or enjoying a sunset dinner overlooking the harbor, the local flavors will surely tantalize your taste buds.

Families will appreciate the town’s strong sense of community and excellent school system, which fosters a nurturing environment for children. With easy access to public transportation, commuting to Boston is a breeze, allowing residents to enjoy the best of both worlds—a peaceful suburban lifestyle with the vibrant energy of the city just minutes away.

In Winthrop, you’re not just finding a home; you’re becoming part of a welcoming community that embraces both history and progress. Discover your place in this enchanting town, where every day feels like a vacation by the sea.

Newest Listings in Winthrop

$399,000

1 Beds ⋅ 1 Baths ⋅ 73559020 MLS

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 modern kitchen and living area are complemented by quartz countertops, stainless steel appliances, central A/C, and stylish contemporary finishes throughout. Residents enjoy convenient amenities including a fitness center, elevator access, and a welcoming resident lounge perfect for working remotely or gathering with friends. Just minutes from beaches, waterfront parks, local dining, and cafés, with quick access to downtown Boston via the Blue Line or seasonal ferry. Whether you're looking for a primary residence, investment property, or weekend escape, Unit 304 is home.

10 Somerset Unit U304, Winthrop

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

$975,000

3 Beds ⋅ 3 Baths ⋅ 73557515 MLS

Brand-new construction in the heart of Winthrop, offering a rare opportunity to own a thoughtfully designed new-build townhome in a coastal setting just outside of the city. As construction progresses, buyers may have the opportunity to personalize select interior finishes, making this home uniquely their own. Spanning approximately 2,100 square feet across two levels, the home features an open-concept kitchen, living, and dining area, along with a first-floor bedroom, full bath, and welcoming entry foyer. Upstairs, two spacious bedrooms each offer a private en-suite bath, with conveniently located second-floor laundry. Enjoy a private yard, city views, and one dedicated parking space. Located just minutes from Boston, Logan Airport, Winthrop Center, beaches, local shops, and restaurants, this is one of only two newly constructed townhomes at this address... a truly uncommon opportunity in Winthrop.

200 Main St Unit 1, Winthrop

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

$549,000

2 Beds ⋅ 1 Baths ⋅ 73557185 MLS ⋅ ['Finlayson House On The Point Condominium'] BLDG.

This renovated 2-bedroom, 1-bath condo sits in the heart of Winthrop's Point Shirley, offering single-floor living with vaulted ceilings and skylights that give the space a brightness and openness rarely found at this price point. Natural light pours through every room throughout the day, flowing over hardwood floors that run wall to wall and tie the entire living space together seamlessly. Two private entrances add a level of independence and privacy that sets this home apart from typical condo living. The updated kitchen is well-equipped with gas cooking and stainless steel appliances, and the layout makes everyday living feel easy. In-unit washer/dryer and two off-street parking spots check the boxes that matter most to buyers in this market. Bonus: Private outdoor space add a layer or privacy most condos don't offer. Enjoy the best of coastal living, where the beach is just steps away & commuting to Boston is easy with quick access to the ferry, T stations, Rt. 1A, Logan Airport.

16 Billows Street Unit B, Winthrop

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

$519,000

1 Beds ⋅ 1 Baths ⋅ 73556652 MLS

Waterfront Living at Its Best! Enjoy breathtaking ocean views from this spacious 8th floor condominium offering 974 sq ft of comfortable living space. Relax on your private balcony overlooking the water, or good size bedroom including a large walk-in closet and a separate tub/shower room. This full service building offers outstanding amenities, including concierge service, an oceanside heated pool with BBQ areas, tennis courts, an exercise room, and a scenic walking path along the shoreline. One garage parking space is included. Ideally located walking distance to restaurants. This is coastal living with unmatched convenience. A wonderful place to enjoy waterfront living.

1 Seal Harbor Rd Unit 812, Winthrop

Listing courtesy of Listing Agent: Peggie Gilbert from Listing Office: Coldwell Banker Peggy Carter Team.

$700,000

3 Beds ⋅ 3 Baths ⋅ 73556640 MLS

Luxury living with downtown Boston just a few Train stops away! Escape the hustle and bustle of the city and enjoy the best of coastal living, with the beach right down the street. Step inside to a spacious mudroom that opens to a stunning open-concept kitchen—perfect for entertaining. Gleaming hardwood floors, granite countertops, and sun-drenched windows create a warm and inviting atmosphere throughout. With three beautifully finished levels of living space, there is plenty of room to spread out and make yourself at home. At the very top of the home, the charming widow’s peak offers the perfect opportunity to create your own private reading nook—one that would make any book club jealous! The private, fully fenced yard is ideal for relaxing, entertaining, or gathering around a fire after a day at the beach. Completely renovated in 2019, this beautiful home is ready for its new owner. Come join us for the first showing at the open houses this weekend August 1st and 2nd from 10:30-Noon

189 Shirley Unit 2, Winthrop

Listing courtesy of Listing Agent: Doyle & Waldron Team from Listing Office: Coldwell Banker Realty - Easton.

$849,900

5 Beds ⋅ 3 Baths ⋅ 73556586 MLS

Welcome to 43 Dolphin Ave, a charming, move-in-ready Colonial offering ocean views in a desirable Winthrop location just moments from the newly renovated Winthrop Beach. The inviting main level features a sun-filled living room with a gas fireplace and classic arched doorways, a spacious kitchen overlooking the covered deck and fenced backyard, a formal dining room, a half bath, and a versatile room currently used as a home office. Upstairs, you'll find three spacious bedrooms, a cozy sitting area, and a full bath. A porch roof patio over looking the ocean is a favorite spot to appreciate the views while you sit back and reflect on your day. A perfect ADU or in-law space in the finished lower level with a oversized family room featuring a gas fireplace and bamboo flooring, a three-quarter bath, full kitchen with stainless steel appliances and second refrigerator, with a laundry area, along with a bedroom with a full sized cedar closet. Right out your lower door is an area to have a table or another sitting area under cover. The outdoor shed has doors that open up to the pergola with a bar and tv so you can watch the games during your cookouts. Enjoy the convenience of three off-street parking spaces and easy access to Boston, Logan Airport, scenic waterfront trails, shopping, dining, and more. Don't miss it!

43 Dolphin Ave, Winthrop

Listing courtesy of Listing Agent: Patricia Nunez from Listing Office: Redfin Corp..

$505,000

1 Beds ⋅ 1 Baths ⋅ 73556252 MLS

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 305, Winthrop

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

$410,000

2 Beds ⋅ 1 Baths ⋅ 73555750 MLS

Coastal living at its best! Just steps from the beach, this beautifully maintained 2-bedroom, 1-bath condominium offers the perfect blend of charm, comfort, and convenience. The bright, open-concept living and dining area flows seamlessly into a spacious kitchen featuring rich cabinetry, granite countertops, and large penninsula—ideal for entertaining. A sun-filled enclosed porch provides the perfect spot to enjoy your morning coffee or unwind after a day by the ocean. Additional highlights include low condo fees, ample street parking, generous private dry storage in the basement, and a small four-unit association. Whether you're looking for a year-round home, weekend retreat, or investment opportunity, this move-in ready condo offers an unbeatable location just moments from Winthrop's beaches, restaurants, and Boston.

25 Winthrop Shore Drive Unit 1, Winthrop

Listing courtesy of Listing Agent: Jenny Golic from Listing Office: Bowdoin Real Estate Partners.

$2,250,000

16 Beds ⋅ 6 Baths ⋅ 73554183 MLS

566 Shirley St contains six (6) units, consisting of two (2), 2-Bedroom/1-Bathroom units and four (4), 3-Bedroom/1-Bathroom units with 5,553 square feet of living area in 7,968 square feet of total gross area on a 0.09-acre corner parcel. The Property is across the street from the Crystal Cove Marina and is 1,000 feet from Winthrop Beach and the shores of the Atlantic Ocean. The Property has been well maintained and features all new common area lighting and carpeting, the foundation (interior and exterior) has been repointed. The Property has new blown-in insulation, and the rear deck system has been updated with refinished decks and new railings. The Property also has a new 11-camera security system and credit card operated washers and dryers. Two of the units have been fully renovated and two units have renovated bathrooms. The Property is separately metered for a mix of gas & electric powered heat & hot water, as well as electrictity. The Landlord provides town water & sewer.

566 Shirley St, Winthrop

Listing courtesy of Listing Agent: Stephen Girolamo from Listing Office: Horvath & Tremblay.

$859,900

2 Beds ⋅ 2 Baths ⋅ 73554136 MLS ⋅ ['Seal Harbor Three Condominium'] BLDG.

A rare offering at the prestigious Seal Harbor III, this exceptional corner residence captures breathtaking panoramic water views from an expansive, light filled interior and a private balcony - perfect for enjoying morning coffee, evening sunsets, or simply taking in the every changing waterfront scenery. Completely reimagined with a full gut reno in 2010, the home showcases timeless design, an open concept floor plan, and impeccable craftsmanship throughout. Thoughtfully curated with luxurious finishes and custom details, the residence is designed for both elegant entertaining and effortless everyday living. The spa-inspired primary bath features a steam shower, while the versatile second bedroom-equally suited as a den or private office-is enhanced by a striking custom leather accent wall. Seal Harbor III offers an unmatched lifestyle with exceptional amenities, including 24 hour concierge, deeded garage parking 2 spots tandem(D41T), outdoor/guest parking, heated indoor pool/hot tub, outdoor pool, storage closet, clubhouse, tennis courts and so much more.

3 Seal Harbor Unit 336, Winthrop

Listing courtesy of Listing Agent: Cathie Curran from Listing Office: Charlesgate Realty Group, llc.

$977,700

3 Beds ⋅ 3 Baths ⋅ 73552912 MLS

Location, location, location! Welcome to 211 Grovers Avenue, perfectly situated in the highly sought-after ocean community of Winthrop Highlands. This iconic brick-front Cape Cod sits on a 5,227 sq. ft. lot and radiates timeless character. Inside, you'll find an inviting living room featuring elegant tray ceilings and a warm fireplace. The home offers 3 bedrooms and 2.5 bathrooms, with incredible potential for expansion—the finished basement could easily become a teen suite, family room, or even an income-generating apartment. Outside, enjoy the coastal lifestyle with a great back deck, an attached garage, and a driveway, all just steps from the ocean. PRIVATE SHOWINGS START 8/7 through 8/9 PLEASE TEXT OR EMAIL LISTING AGENT

211 Grovers Ave, Winthrop

Listing courtesy of Listing Agent: Concetta Cicolini from Listing Office: Lamacchia Realty, Inc..

$489,900

3 Beds ⋅ 1 Baths ⋅ 73553580 MLS

Welcome to 16 Underhill Rd. #3, a beautifully updated 3-bedroom, 1-bath condo offering 1,036 sq. ft. of move-in ready living space. This bright and inviting home features modern updates, a functional layout, and private laundry in the basement for added convenience. Enjoy your own private deck, perfect for relaxing or entertaining. The property also includes a private garage plus ample additional parking—a rare find. Ideally located just moments from the beach, you'll love the convenience of coastal living with easy access to local shops, restaurants, and commuter routes. Whether you're looking for a primary residence or a low-maintenance lifestyle near the ocean, this turnkey condo is ready for its next owner.

16 Underhill St Unit 3, Winthrop

Listing courtesy of Listing Agent: Goldpath Real Estate Group from Listing Office: United Brokers.

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