Winthrop Real Estate

Winthrop Real Estate

Welcome to Winthrop, Massachusetts – a charming coastal gem nestled in Suffolk County, just a stone's throw from the bustling city of Boston. Known for its picturesque waterfront, Winthrop boasts stunning views of the Atlantic Ocean and the Boston skyline, making it a perfect blend of serene living with urban convenience.

With its rich history dating back to the early 17th century, Winthrop has maintained its quaint, small-town charm while offering modern amenities. The town is characterized by its friendly community, beautiful parks, and a vibrant local culture. Residents enjoy a variety of recreational activities, from sunbathing on the sandy shores of Winthrop Beach to exploring the scenic trails of the nearby Belle Isle Marsh Reservation.

Winthrop is also known for its diverse dining scene, with local eateries serving everything from fresh seafood to international cuisine. The town’s annual events, such as the Winthrop Beach Festival and the Winthrop Art Walk, foster a strong sense of community and provide opportunities to celebrate local talent.

Families are drawn to Winthrop for its excellent schools and safe neighborhoods, making it an ideal place to raise children. With easy access to public transportation, commuting to Boston for work or leisure is a breeze, allowing residents to enjoy the best of both worlds.

Whether you’re looking for a cozy seaside home or an investment property, Winthrop offers a unique lifestyle filled with charm, community, and coastal beauty. Discover the magic of Winthrop – where every day feels like a vacation!

Newest Listings in Winthrop

$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 (D41T), outdoor 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.
$749,995
2 Beds ⋅ 2 Baths ⋅ 73553054 MLS
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 ⋅ ['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 ⋅ ['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
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.
$1,260,000
4 Beds ⋅ 6 Baths ⋅ 73550792 MLS
Modern living made easy at 21 Hutchinson St. This unique property has unlimited options of investment opportunities. Come experience modern finishes in this new construction build. Each unit has a layout of 2 bedrooms 2 full bathrooms and 1 half bathroom, in unit laundry and open floor plan. Outside features 2 car garage, 2 electric car charging stations, new fence, and concrete patio area.

21 Hutchinson Street, Winthrop

Listing courtesy of Listing Agent: Matthew Gallego from Listing Office: Gallego Realty.
$950,000
3 Beds ⋅ 3 Baths ⋅ 73550478 MLS
OPEN HOUSE CANCELED! Welcome to the Highlands, where coastal living meets modern comfort. This beautifully maintained single-family offers water views, thoughtfully updated living spaces, and the flexibility today's buyers desire. The sun-filled main level features gleaming hardwood floors throughout, an upgraded kitchen, and an open layout that flows seamlessly to the spacious rear deck overlooking the fenced backyard with a private hot tub—perfect for entertaining or relaxing. Upstairs, the spacious primary suite offers a generous walk-in closet, while two additional bedrooms provide comfortable accommodations. The finished lower level provides versatile bonus living space ideal for a family room, home office, gym, or guest suite. Enjoy the best of indoor-outdoor living with inviting spaces designed for both everyday comfort and effortless entertaining. Just moments from the beach, this move-in-ready home combines modern updates, flexible living space, and an exceptional location.

50 Floyd St, Winthrop

Listing courtesy of Listing Agent: Leighann Eruzione from Listing Office: Bowdoin Real Estate Partners.
$899,900
4 Beds ⋅ 2 Baths ⋅ 73550227 MLS
If you've been waiting for the perfect opportunity to live near the ocean - this is it! Located between Winthrop Harbor and Winthrop Beach, with literal steps to the ocean in either direction, this beautiful, completely renovated single family home offers 4 bedrooms, 2 baths, an updated kitchen, hardwood floors, central air and much more! Great back yard, off-street parking and a beautiful wrap-around front porch with water views that New Englanders dream of. Incredible location - just steps to Winthrop Beach and Winthrop Landing with water ferry access to Downtown Boston. Close to restaurants, parks, shops, multiple yacht clubs, public transportation and much more. Minutes to Boston, Logan Airport and points north. Don't miss this amazing opportunity to find your seaside home this summer.

69 Crystal Cove Avenue, Winthrop

Listing courtesy of Listing Agent: Edward Deveau from Listing Office: Century 21 Mario Real Estate.
$299,900
1 Beds ⋅ 1 Baths ⋅ 73549060 MLS ⋅ ['Winthrop Bay Condominiums'] BLDG.
Super affordable top-floor 1-bedroom condo located less than a block from Winthrop Beach! This surprisingly spacious unit features fresh paint, hardwood floors, high ceilings, partial water views, private parking lot and an HOA fee that includes heat and hot water. An excellent opportunity for first-time buyers or anyone looking to enjoy coastal living at an exceptional value for less than most rents in the area. Winthrop offers the perfect blend of coastal charm and city convenience. With beautiful beaches, scenic waterfront walking trails, award winning local restaurants, marinas, and a welcoming small-town atmosphere, it's an ideal place to call home. Located just minutes from downtown Boston and Logan Airport by car, train or ferry, Winthrop provides a relaxed seaside lifestyle without sacrificing easy access to everything the city has to offer.

267 Washington Ave Unit 6, Winthrop

Listing courtesy of Listing Agent: Richard Harkins from Listing Office: EWK Realty.
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