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.
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, two off street parking spaces, 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,
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
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.
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.
