Downtown Winthrop, MA homes for sale & real estate

Downtown Winthrop, MA Homes for Sale

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 d

Downtown Winthrop, MA Homes 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 pa

Downtown Winthrop, MA Homes for Sale

Coastal living in Winthrop! This 2 bed 1 bath condo offers many updates including NEW roof and siding (2025), NEW furnace for gas cooking (2024). Additional conveniences include, in-unit laundry 2023, and 1 off street parking spot! Located just steps away from the shoreline, beaches, local restaurants, and Winthrop's vibrant coastal community. Showings begin at open houses Saturday 12/6 11-1230 and Sunday 12/7 11-1230.

Downtown Winthrop, MA Homes for Sale

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 compl

Downtown Winthrop, MA Homes for Sale

Belle Mer is a newer built 16 unit condo association just on the outskirts of vibrant Winthrop Center, Nearby bountiful dining options, a best of North Shore boutique, coffee shops, fitness studios, book store, and unlimited conveniences. The unit is completely modernized with a timeless aesthetic. Seldom available, modern design 2 level floor plan with oversized windows, dramatic tall ceilings, exquisite appointments, 2 bedrooms, 2 bathrooms, charming window seats and ultimately desired PRIVATE front and back entries and assigned parking space 25. The association has curated wonderful professionally landscaped grounds creating a beautiful ambience nearby Boston Harbor. Hardwood floors, rec

Downtown Winthrop, MA Homes for Sale

Welcome to Unit 405 at The Somerset, a premier boutique condominium community in the heart of Winthrop. This well-designed 1-bedroom residence offers a spacious bedroom with a generous closet and an open-concept kitchen and living area that’s perfect for both entertaining and unwinding. The home features quartz countertops, stainless steel appliances, central A/C, and modern, stylish finishes throughout. Residents of The Somerset enjoy exceptional on-site amenities, including a fitness room, elevator, and a warm, inviting lounge ideal for remote work or casual gatherings. Located near sandy beaches, waterfront parks, and popular local dining—and offering convenient access to dow