Winthrop MA Homes for Sale & Real Estate

Home for Sale in Winthrop

Waterfront stunning ocean views from this corner unit with breathtaking sunrises and sunsets. This bright and relaxing 1,005 square foot residence has been lovingly enjoyed by the same owner for 25 years. Spacious living room opened to separate dining room. One bedroom, full bath & generous walk-in closet. Captivating views of the ocean, beach, and boats passing by. Private balcony and underground garage parking, A perfect waterfront retreat you won't want to miss.

Home for Sale in Winthrop

Welcome to Unit 308 at The Somerset?a premier boutique condo community in the heart of Winthrop. This thoughtfully designed 1 + bedroom features an open-concept kitchen and living area, perfect for entertaining or relaxing, along with a versatile bonus room with a sliding barn door for flexible use. Enjoy quartz countertops, stainless steel appliances, central A/C, and stylish finishes throughout. The Somerset offers exceptional amenities, including a fitness room, elevator, and a cozy resident lounge ideal for remote work or casual gatherings. Just moments from sandy beaches, waterfront parks, and local restaurants?with easy access to downtown Boston via the Blue Line or seasonal ferry?this home blends coastal charm with city convenience. Whether you?re seeking your next home or a seaside retreat, Unit 308 delivers style and a lifestyle by the sea. Schedule your tour today!

Home for Sale in Winthrop

Welcome to Unit 207 at The Somerset?Winthrop?s boutique condo community, where coastal living meets modern design. This spacious 2-bedroom, 1-bath home features an open-concept living and dining area, a well-appointed kitchen with quartz countertops and stainless steel appliances, central A/C, and modern finishes throughout, plus access to a fitness room, elevator, and resident lounge for added convenience. Just moments from beaches, waterfront parks, and local restaurants, with easy access to downtown Boston via the Blue Line or seasonal ferry from Winthrop, Unit 207 offers an easy, relaxed lifestyle with the best of the coast and city within reach.

Home for Sale in Winthrop

Built in 2023 and still feeling brand new ? this 3-bedroom stunner puts you steps from the beach and minutes to Downtown Boston. Sunlight pours across hardwood floors, while the sleek kitchen with white shaker cabinets and high-end appliances anchors the open layout. Central air keeps things comfortable year-round, and deeded off-street parking seals the deal. Coastal living without sacrificing city access ? that?s Winthrop done right.

Home for Sale in Winthrop

Special Financing Available (30yr Fixed @ 4.25%) on this project for some buyers. Discover the perfect blend of modern design and seaside charm at 140 Shirley Street, Winthrop?s newest boutique condominium residence?just steps from the shoreline of Winthrop Beach. This two-bedroom, one-bath home in a 10-unit building captures the essence of coastal living with its fresh, nautical-inspired style and high-end finishes. Inside, you?ll find engineered hardwood flooring, recessed lighting, and a bright, open-concept layout ideal for everyday living or entertaining. The contemporary kitchen features double-stacked soft-close shaker cabinets, quartz countertops, and stainless-steel appliances, creating a clean and timeless look. Enjoy the comfort of central heating and cooling, elevator access from the elegant lobby, and garage parking (with the option to purchase a second space). Live moments from the sand, surf, and vibrant coastal community that make Winthrop one of Boston?s best-kept secr

Home for Sale in Winthrop

Special Financing Available (30yr Fixed @ 5.75% No PMI). Discover the perfect blend of modern design and seaside charm at 140 Shirley Street, Winthrop?s newest boutique condominium residence?just steps from the shoreline of Winthrop Beach. This two-bedroom, two-bath home in a 10-unit building captures the essence of coastal living with its fresh, nautical-inspired style and high-end finishes. Inside, you?ll find engineered hardwood flooring, recessed lighting, and a bright, open-concept layout ideal for everyday living or entertaining. The contemporary kitchen features soft-close shaker cabinets, quartz countertops, and stainless-steel appliances, creating a clean and timeless look. Enjoy the comfort of central heating and cooling, elevator access from the elegant lobby, and garage parking. Live moments from the sand, surf, and vibrant coastal community that make Winthrop one of Boston?s best-kept secrets.

Home for Sale in Winthrop

Winthrop is one of the last undervalued waterfront towns in Greater Boston, and opportunities like this don't sit long. 11 Pearl Ave is a vacant 3-family just a block from the ocean, generating $10,500/month at market rents with zero displacement headaches. Three floors, 11 bedrooms total, 4,032 sq ft of income-producing space on a town where the average days on market keeps shrinking. 3 separate heat systems, and 200-amp electric. Flood insurance runs about $2,600/year. Live in one, rent two, or hold all three. Priced at $1,050,000 with a cap rate that pencils with room for improvement and valuate add. Don't sleep on Winthrop.

Home for Sale in Winthrop

Discover true beachfront living at 129 Strandway, where every day feels like vacation. Step from your back door directly into the sand and enjoy panoramic ocean views from the heated sunroom. The main level offers an updated kitchen with marble counters, a cozy fireplaced living room, two bedrooms, and a convenient beach-entry bath. The spacious second-floor primary suite provides its own private bath and sweeping coastal vistas. The fully finished lower level is one of only ten legal Airbnbs in Winthrop, offering exceptional income potential, or use it as an ideal in-law or au pair suite with its family room, bonus room, full bath, and laundry. Parking is effortless with two off-street spots and additional front potential. Low, transferable flood insurance at $1,138.00. Embrace waterfront living at its best.

Home for Sale in Winthrop

Welcome to the Highlands, Winthrop?s most coveted neighborhood where modern design meets sweeping Boston views. This renovated home rises high on the hill with sunlit interiors, wide white oak floors, and timeless details throughout. The main level offers an open layout with a living room and fireplace, Thermador-Pro kitchen with island, beverage bar, and pantry, plus a dining area that opens to a skyline deck. A first-floor bedroom, full bath, and mudroom add versatility. Upstairs features three bedrooms, including a luxe primary suite with Juliet balcony, walk-in closet, and a spa bath with steam shower, soaking tub, heated floors, and double vanity. The lower level provides a complete one-bedroom living space with its own kitchen, laundry, French doors to the yard, and private entrance ideal for multi-generational living, an au pair, or added flexibility. With a tiered backyard and three-car parking, this home blends sophistication, versatility and unmatched city views.

Home for Sale in Winthrop

Welcome to the Highlands, Winthrop?s most coveted neighborhood- where modern design meets sweeping Boston views. This newly renovated 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 to a skyline deck. A first-floor bedroom, full bath, and mudroom add versatility. Upstairs features three bedrooms, including a luxe primary suite with Juliet balcony, walk-in closet, and spa bath with steam shower, soaking tub, heated floors, and double vanity.The lower-level one-bedroom unit includes its own kitchen, laundry, French doors to the yard, and private entrance?perfect for multi-generational living, au pair, or income. With a tiered backyard, three-car parking, and one of Winthrop?s premier addresses, this home blends sophistication, flexibility, and unmatched city views.

Home for Sale in Winthrop

This offering is about the land and the view. Located in Point Shirley, one of Winthrop?s most sought after waterfront neighborhoods, this shovel ready site sits above the Atlantic with wide open views of the ocean, Boston skyline, and the iconic Winthrop water tower. Walkable to the beach, yacht clubs, Winthrop Landing, and the ferry, with an easy commute back to the city. The existing structure is intended for tear down to provide a clean and cleared plot of land. Zoning Board of Appeals approval has already been granted and the project is fully entitled. A buyer simply needs to pull a building permit and start construction.

Home for Sale in Winthrop

Attention Investors and Contractors ? Prime Opportunity! Four-bedroom home with a third-floor in-law suite ready for its next chapter. Set on a charming tree-lined street, this property offers a solid footprint for renovation along with a detached garage and manageable yard space. Vacant and being sold as-is, this home will require a full rehab. Ideal for investors or owner-occupants looking to renovate and personalize a property to their own style. A great opportunity to transform a well-located property and bring new life to a classic home.