Multi-Family Homes for Sale in Winthrop, MA

Home for Sale

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

Rare opportunity to own a spacious waterfront duplex offering versatility, income potential, and breathtaking coastal living just minutes from Boston and Logan Airport. This well-designed property features 4+ bedrooms with finished lower levels on each side, each offering three additional rooms--ideal for extended family, home offices, or flexible living space. With potential for an additional unit ADU(Accessory Dwelling Unit), this property presents an outstanding opportunity for multi-generational living or added rental income(buyer to perform due diligence). Two separate newer boilers , the convenience of a 2 car garage and ample storage, all while taking in serene water views and direct access to the shoreline lifestyle Winthrop is known for. Perfectly located near beaches, marinas, restaurants, and public transportation, this gem combines suburban coastal charm with unbeatable proximity to the city. A truly unique offering with endless possibilities! Floor plans attached MLS

Home for Sale

Outstanding Winthrop investment opportunity offering strong income potential in a highly desirable coastal community. This newly renovated two-family property features two spacious units (2BR and 4BR), ideal for owner-occupants seeking rental income or investors looking to expand their portfolio. Both units provide modern living with off-street parking for four vehicles total. Conveniently located just minutes from major highways, public transportation, shopping, beaches, and local schools, this property combines location, flexibility, and long-term upside in one exceptional offering.1st Open House Sat FEB 28TH (12-2 PM)

Home for Sale

In the sought after Winthrop HIGHLANDS you'll find this quality built THREE FAMILY home. This is your opportunity to become an owner occupied investor! Each unit features a comfortable layout with a generous amount of natural light and functional living spaces. The first floor has three bedrooms, second floor one and the third unit is on two levels with two bedrooms. The property has been well maintained and offers separate utilities, one off street parking space, and a nicely landscaped backyard. You'll enjoy beautiful ocean views and it's just steps to Halford Beach. Pride of ownership is evident throughout. Winthrop by the Sea is just six miles to Boston, has a variety of wonderful restaurants, walk/jog trails, access to the Blue Line and close to Logan Airport - 22 Upland Road is an outstanding opportunity to own a home and collect rental income in one smart investment,

Home for Sale

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.

Home for Sale

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!

Home for Sale

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!!

Home for Sale

Well-located 4-family investment property in the heart of Winthrop?s Cottage Hill neighborhood. 10?12 Charles Street offers four separately metered units totaling 3,688 square feet on a 6,127 sq ft lot, with strong in-place income and upside. The unit mix consists of two larger units and two one-bedroom units, appealing to both long-term renters and owner-occupants seeking supplemental income. Current rents total approximately $8,550 per month, with additional room for optimization over time. The property features off-street parking for six vehicles, a major value driver in this coastal submarket, along with a full unfinished basement ideal for storage and future improvements. Several units have been refreshed, providing a solid balance of immediate cash flow and long-term capital improvement potential. Located just blocks from the ocean, public transportation, schools, and Winthrop Center amenities, this asset benefits from strong rental demand driven by proximity to Boston & Logan.

Home for Sale

Discover an investor?s dream in the heart of Winthrop. Set on a generous lot on a quiet, friendly street, 28 Thornton Park offers a rare opportunity to bring a fully gutted two-unit multifamily back to life. The property has been taken down to the studs and is ready for renovation?perfect for developers, investors, or owner-occupants looking to customize their ideal home while building long-term value. Enjoy the convenience of being just a short walk to Winthrop?s town center, local shops, restaurants, and the beach. Whether you?re envisioning rental income, condo conversion, or a multigenerational layout, the possibilities are endless. A rare find in an unbeatable location!

Home for Sale

Lovely custom built ranch offering endless possibilities! Perfect for multi-generational living or added income with a fully equipped lower level apartment. The main floor features a cherry wood kitchen with granite countertops, a spacious fireplace living room, tiled bath with separate shower and tub, generous bedrooms, den, and a bright sunroom with ocean views. Enjoy central air and an attached garage. The lower level includes a kitchen, family room with sliders to a private yard and in-ground pool, two bedrooms, and a bath. Garage and mudroom could be converted into an ideal ADU for extra income or extended family. Fantastic location public transportation at one end of the street and beach access at the other!