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

$410,000

2 Beds ⋅ 1 Baths ⋅ 73555750 MLS ⋅ NEW Status

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.

$859,900

2 Beds ⋅ 2 Baths ⋅ 73554136 MLS ⋅ ACTIVE Status ⋅ ['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 ⋅ ACTIVE Status

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 ⋅ ACTIVE Status

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.

$749,995

2 Beds ⋅ 2 Baths ⋅ 73553054 MLS ⋅ ACTIVE Status

Step inside and you'll immediately understand why this residence is unlike any other at Seal Harbor. Thoughtfully redesigned with timeless finishes and meticulously maintained, every detail has been curated to create an exceptional coastal retreat. Wake up to panoramic ocean views and unwind each evening with spectacular sunsets from your private covered balcony, where the fresh salt air and endless water views become part of your everyday lifestyle. The stunning open-concept kitchen is the heart of the home, featuring custom cabinetry, premium appliances, an oversized entertaining island with a built-in wine refrigerator, and designer finishes throughout. Retreat to the luxurious primary suite with a custom spa-inspired bath showcasing an oversized steam shower. Beyond your front door, enjoy concierge service, garage parking, a beautifully renovated lobby and elevators, fitness center, game room, and an oceanfront pool that feels like a private resort. Perfectly located just minutes to Boston, Logan Airport, the Winthrop Ferry, beaches, restaurants, and walking paths, this is coastal luxury at its finest.

1 Seal Harbor Unit 700, Winthrop

Listing courtesy of Listing Agent: Candice Pagliarulo Hodgson from Listing Office: Lyv Realty.

$499,900

1 Beds ⋅ 1 Baths ⋅ 73551484 MLS ⋅ ACTIVE Status ⋅ ['Seal Harbor'] BLDG.

Wake up to SPECTACULAR SUNRISES over the Atlantic and fall asleep to the soothing sound of OCEAN WAVES in this affordable OCEANFRONT UNIT at Seal Harbor Condominiums! Offering UNOBSTRUCTED OCEAN VIEWS from EVERY ROOM, this beautifully maintained home delivers the ultimate coastal lifestyle while being a short drive to Boston & Logan Airport! Gleaming HW FLOORS flow throughout the OPEN CONCEPT LIVING & DINING AREAS, where a PRIVATE BALCONY provides the perfect setting to relax w/the ocean as your backdrop. The updated kitchen features SS APPLIANCES, GRANITE counters, w/a FULL HEIGHT BACKSPLASH complementing the stylish cabinetry. A SPACIOUS BEDROOM & UPDATED FULL BATH with a wall of closets complete the space. Experience RESORT STYLE LIVING w/exceptional amenities including an inground pool, fitness center, sauna, steam room, tennis courts, clubhouse, beautifully manicured gardens w/a gazebo, scenic oceanfront walking paths, recreational facilities & the convenience of a 24/7 concierge!

1 Seal Harbor Unit 210, Winthrop

Listing courtesy of Listing Agent: Rita Angelesco from Listing Office: LAER Realty Partners.

$495,000

2 Beds ⋅ 2 Baths ⋅ 73550972 MLS ⋅ ACTIVE Status ⋅ ['34 Underhill Street Condominium'] BLDG.

This like-new 2-bedroom, 2 bath condo at 34 Underhill Street delivers the finish level of new construction at a fraction of the cost. Gut renovated and converted in 2020, every detail was approached with care, from the white shaker kitchen with quartz countertops, blue glass tile backsplash, gold hardware, and stainless steel appliances including gas cooking, to the wide plank hardwood floors that run throughout the entire unit. The primary bedroom features a custom walk-in closet with built-in shelving and drawers, and direct access to a full bath. The open living area is bright and generously sized with recessed lighting and mini-split systems for year-round comfort. Ground-floor entry with private access adds convenience rarely found in condo living. Set steps from the Winthrop coastline with the Boston ferry, Rt. 1A, and Logan Airport all just minutes away, this is a turnkey home in a location that continues to attract buyers who want coastal living without sacrificing quality.

34R Underhill St Unit 3, Winthrop

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

$2,380,000

5 Beds ⋅ 6 Baths ⋅ 73550891 MLS ⋅ ACTIVE Status

One of the most coveted locations in Winthrop, 174 Bartlett Rd is your dream costal retreat where luxury meets seaside living. Completely gut renovated, this exceptional home offers over 6,000 sq ft of beautifully designed living space across four expansive levels. The heart of the home is the stunning chefs kitchen with seamless oversized Brazilian Quartzite island surrounded by premium Sub-Zero, Wolf & Miele appliances, & a fully appointed entertaining bar. Anchored by a striking Valor fireplace, the two thoughtfully designed seating areas & expansive dining room create space for intimate or larger-scale entertaining. The Primary suite is a water view retreat with steam shower & BainUltra therapeutic soaking tub, dual walk-in closets, & private laundry. Welcome guests in the lower level suite, enjoy resort style yard with Gunite in-ground pool, basketball court & grilling island, or end days on the roof top deck with incredible views. This thoughtfully crafted home is unforgettable!

174 Bartlett Road, Winthrop

Listing courtesy of Listing Agent: Atiyeh Cassidy from Listing Office: Blue Sky Realty.

$729,900

4 Beds ⋅ 2 Baths ⋅ 73548082 MLS ⋅ ACTIVE Status

Cape-style home in Point Shirley, steps from the beach and within Winthrop's most walkable stretch of coastline. Built in 1900 and updated with a remodeled kitchen featuring granite counters and recessed lighting, plus a remodeled full bath with a tiled tub and shower. Original hardwood floors run through the main level and all four bedrooms, paired with bay windows that bring in natural light and water views. The main level includes a living room with a fireplace, a formal dining room, and a sunroom that opens to a screened porch. Central air and forced air heat keep the home comfortable year-round. A full basement with sump pump offers storage and utility space, and a paved driveway provides two off-street parking spaces. Ocean views and public beach access nearby. 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.

52 Pebble Ave, Winthrop

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

$615,000

3 Beds ⋅ 2 Baths ⋅ 73547219 MLS ⋅ ACTIVE Status ⋅ ['80-82 Putnam St Condominiums'] BLDG.

Your chance to own a beautiful home in vibrant Winthrop by the Sea! Freshly updated 3-bedroom, 2-bathroom townhome-style condo with an entertainer’s floor plan including a modern kitchen with granite and a peninsula, dining area, large living room, full bath, Central A/C, and private deck. 3 well-sized bedrooms upstairs and a shared Jack and Jill bath with herringbone tile. Convenient in-unit laundry on the main floor, basement storage, and 2-car parking in driveway. Steps to Winthrop Center and an effortless commute with easy MBTA bus connection to the Orient Heights Blue Line.

82 Putnam St Unit 2, Winthrop

Listing courtesy of Listing Agent: Team Ladner from Listing Office: RE/MAX Harmony.

$899,900

3 Beds ⋅ 3 Baths ⋅ 73546996 MLS ⋅ ACTIVE Status

PRIDE OF OWNERSHIP CAN BE YOURS.......METICULOUSLY CARED FOR AND READY FOR THE NEW OWNERS! Located in one of Winthrop's most desirable areas, this Center Entrance Colonial has Harwood oak floors and a bath on every level. A huge fireplaced living room, eat in kitchen with a slider and deck overlooking the enormous (pool size) yard with a garden area and lots of off street parking. The second level has 3 bedrooms and a full bath and laundry. The Main bedroom is King-sized! The Bonus Room in the basement is multi purposed with another full bath, exrta high ceilings, open floor plan and a direct walk out to the yard. Another separate basement area is a handy workshop/storage area. THIS COULD BE THE ONE! In Winthrop by the Sea boasting 2 beaches, new schools, 3 Yacht Clubs, a nine hole golf course and lots of Great Restaurants!

37 Loring Rd., Winthrop

Listing courtesy of Listing Agent: Sharon Tallent from Listing Office: Compass.

$649,000

2 Beds ⋅ 2 Baths ⋅ 73546559 MLS ⋅ ACTIVE Status

Start your homeownership journey at Unit 402 at The Somerset, a bright and spacious top-floor 2-bedroom, 2-bath condo in the heart of Winthrop. Designed for modern living, this move-in-ready home features an open-concept layout, two private balconies, quartz countertops, stainless steel appliances, central A/C, and generous closet space. Garage parking is included, along with access to an elevator, fitness room, and inviting resident lounge. Whether you're purchasing your first home or looking to simplify your lifestyle, this residence offers exceptional value and low-maintenance living. Just minutes from beaches, local restaurants, shops, and convenient transportation to downtown Boston, Unit 402 combines coastal charm with everyday convenience in one of Winthrop's most desirable new communities.

10 Somerset Unit 402, Winthrop

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

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