First time on the market in more than 50 years. Enjoy gorgeous water views from this extra spacious 2 family home located in sought after Highlands neighborhood. Unit 1 features 5 rooms, including a large L-shaped living room with fireplace, formal dining room with china cabinet, eat-in kitchen, 2 bedrooms, full bath and front and rear porches. Unit 2 features a big living room with fireplace, formal dining room, open to the eat-in-kitchen. There's 2 spacious bedrooms, a full tiled bath, front and rear porches, and a large, walk-up third floor finished space. Other features include a huge basement, beautiful hardwood floors, high ceilings, loads of natural light, nice yard and a big 4 car driveway. Both units have separate utilities. Unit 2 is vacant. New roof in 2023. House needs work on the interior and the property is being sold as is.Perfect for a condo conversion.
Introducing coastal living in this luxurious two-family home set on one of Winthrop’s most exclusive seaside streets. Just minutes from downtown Boston, this rare offering blends high-end finishes with exceptional investment potential. Additional in-law/guest suite possibilities create the opportunity for a dynamic property with multiple income streams or an elegant multigenerational retreat. Enjoy updated electric, beautiful updated countertops, top-of-the-line appliances, new plumbing fixtures, sun-filled rooms, wood restored fireplaces, front/back porches, fenced in yard and flexible layouts designed for comfort and value. Coastal breezes, nearby beaches, marinas, and shoreline paths capture Winthrop’s coveted seacoast charm. A private 3–4 car driveway completes this versatile property—ideal as a luxury residence, premier investment, or both. Don’t miss this smart investment opportunity. More pictures coming soon!!
OPPORTUNITY KNOCKS.......Two family with large yard is located right on the bus line with a very short ride to the T to Boston. There are 6 off street parking spaces! Some renovations as of 2001. The owner's unit is on the second and third floors with an open floor plan and lots of natural lighting. It contains a living room, dining area, kitchen, bath and one bedroom. The top floor consists of a sprawling main bedroom large enough to become 2 rooms. There are Boston skyline and marina views from the the top floor. The owner's unit has a great layout and good size rooms with lots of windows and laundry area of the kitchen. The first floor unit consists of a living room, kitchen, bath and two bedrooms. THIS IS A GREAT OWNER OCCUPY OR, INVESTMENT PROPERTY!
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.
Winthrop -Hard to Find 3 Family Home - Ocean views from this 3 -Family Home located on quiet one-way street with short walk to the ocean in Winthrop. The first floor unit has kitchen, living room, 2 bedrooms & 1 bath. The second floor unit has kitchen, living room, 3 Bedrooms, 1 bath, washer & dryer in unit. The third floor unit has kitchen, living room, 2 bedrooms, office or den, 1 bath, washer & dryer in unit. All three units have modern kitchens, hardwood floors, porches, plenty of parking for 6+ cars off street, plus new asphalt roof. Just minutes to seaside walking and bike baths on Winthrop Beach.
Traditional two-family home featuring two spacious 3-bedroom apartments. Recently upgraded with a new roof and windows, as well as newer vinyl siding, gas FHA heating units, and updated electrical service. While the interior of both units requires a complete makeover, this property holds immense potential. A similar home just a few doors down recently sold for $885,000. Conveniently located approximately 100 yards from the bus stop offering access to the T for a quick commute to Boston. Situated in Winthrop by the Sea, residents enjoy proximity to Boston via the T, car, or water shuttle. The area boasts a variety of quality restaurants, bistros, coffee shops, a golf course, three yacht clubs, three marinas, newly constructed schools, public beaches, and scenic seaside walking and biking paths. There are numerous public and private sporting activities for children. Ideal for an owner-occupant seeking rental income to offset the mortgage or for an investor looking to capitalize
Just Renovated – Perfect for Owner-Occupants or Investors!Welcome to 50-52 Wilshire Street, a fully updated two-family home located in the picturesque seaside community of Winthrop, Massachusetts. This property has 5 bedrooms and 2 bathrooms. Fresh from a complete renovation, this property blends modern finishes with timeless New England charm, offering unmatched flexibility for both comfortable living and strong rental income. Each unit features a brand-new kitchen with stainless steel appliances, quartz countertops, and custom cabinetry, as well as new PVC flooring, newly renovated bathrooms, stylish lighting, and freshly painted interiors. Updated plumbing, electrical, and energy-efficient windows ensure peace of mind for years to come. Located on a quiet residential street just minutes from Winthrop Beach, local shops, dining, and public transportation to Boston, this home offers the perfect combination of lifestyle and investment potential. Schedule your showing today!
Winthrop is located in Massachusetts.
