Downtown Winthrop
For sale
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Beds/baths
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Downtown Winthrop, MA Homes for Sale
This charming, move-in-ready 2-bed, 1-bath condo in a gorgeous brownstone building offers historic character and modern convenience just minutes from downtown Boston! Beautiful original hardwood floors and bay window add warmth and timeless appeal. Both bedrooms are generously sized and filled with natural light. The second bedroom has a walk-in closet. The spacious, eat-in kitchen features tile flooring, Corian countertops, and direct access to a peaceful, private deck. Two oversized hall closets provide excellent storage options. Additional storage and shared laundry are conveniently located in the basement. Enjoy Ingleside Park at your doorstep, or take a short stroll to Donovan's Beach,
Welcome to 500 Governors Drive Unit 9, a spacious and well-maintained 3-bedroom, first-floor condo located in the beautiful coastal town of Winthrop. This unit features a bright and airy open-concept living and dining area, perfect for both relaxing and entertaining. Vinyl flooring runs throughout the entire home, offering a sleek, low-maintenance finish. Set within a well-managed association, residents enjoy peace of mind and a sense of community. Whether you're a first-time buyer, downsizer, or investor, this unit offers comfort, convenience, and value all in one.
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Tucked away on a quiet street, this home boasts stately features and has been meticulously renovated. From the elegant newel post to the timeless kitchen details, nothing was overlooked. During the condo conversion, preserving the home's original integrity was a priority. The first floor offers 2 bedrooms, laundry, and a full bath with marble tile floors. The sunlit living room, complete with a fireplace, opens to the dining room and the first of two decks, offering ocean views. The second deck is covered, perfect for rainy days. The kitchen features high-end appliances and classic white cabinetry. Upstairs, find 2 more bedrooms, including a primary with a large walk-in closet and full bath
Welcome to Unit 201 at The Somerset—Winthrop’s premier boutique condo community where coastal charm meets modern design. This spacious 2-bed, 2-bath home features an open-concept layout with a large living/dining area perfect for entertaining or relaxing. A generous kitchen island anchors the space and faces the front of the building, inviting natural light and a welcoming flow. Enjoy quartz countertops, stainless steel appliances, central A/C, and stylish finishes throughout. The Somerset offers garage parking, a fitness room, elevator access, and a cozy resident lounge ideal for remote work or casual connection. Close proximity to sandy beaches, waterfront parks, and local res
Endless Potential in Prime Seaside Location – 02152 Welcome to this oversized two-family home located in the highly desirable seaside community of Winthrop, 02152. Perfectly situated on a generous lot, this property offers a rare opportunity for investors, multi-generational living, or owner-occupants looking to customize and create value. Each unit features spacious layouts with room to grow, and the home includes a full unfinished basement—ideal for storage or future expansion. Enjoy the convenience of off-street parking and a private backyard, perfect for outdoor entertaining or quiet relaxation. With its prime location near the ocean, beaches, and all that Winthrop has to of
Prime corner lot in one of Winthrop’s most desirable neighborhoods! This home has great bones and is ready for new owners to make it their own. With an ideal layout, the second floor offers the perfect space for a primary suite with walk-in closet and full bath. The first floor features a spacious living room, with the opportunity to open up the kitchen and dining area for a large island and modern flow. A side entry leads into a generous mudroom with potential for custom storage. The backyard is perfect for a patio, outdoor kitchen, and entertaining. The garage could be connected to the home with a breezeway. Once renovated, this home could be worth $1.2M+. The price reflects the upd
Ideally located just steps from the Winthrop Yacht Club, The Landing, local restaurants, and both Winthrop and Yirrell Beach, this spacious single-family home offers stunning water views and a clear line to Boston’s skyline. The first level features a unique and expansive layout with a formal living and dining room anchored by a double-sided fireplace wrapped in lava-rock, plus two additional rooms perfect for a family room, guest room, or home office. The updated eat-in kitchen includes a convenient half bath with in-unit laundry and plenty of cabinet space with a Wolf Cooktop, Miele dishwasher and newer range. The upstairs offers three spacious bedrooms including an expansive oversi
Highly desirable location this home is only 16 years old built over its original foundation. this 4-bed, 3.5-bath home spans three levels in Winthrop’s Highlands. The first floor offers an open layout ideal for entertaining, with a spacious kitchen featuring white cabinets and updated countertops flowing into the living and dining rooms. French doors lead to a deck and patio overlooking a large, fenced in backyard. The main suite opens to a private side deck and features a primary bath. Enjoy central air, second-floor laundry, a large basement for storage, a newer furnace and water heater (2022). The top floor offers a ocean views, and there's a hidden beach at the end of the street.
Located just 3.5 miles from the game-changing Suffolk Downs redevelopment, this fantastic two-family home offers incredible long-term upside in one of the fastest-growing areas north of Boston. The project promises millions of square feet of new housing, retail, parks, and life science space—adding immense value & convenience to the surrounding neighborhoods. Just steps from the beach, this income-generating property has been a strong rental performer—ideal for investors or owner-occupants. In the last 9 years, the home has seen MAJOR updates including a 200-amp electrical service upgrade, new front deck and revamped rear deck, a full renovation of Unit 2 (kitchen, floorin
Step inside this farmhouse-style gem and feel right at home. The first floor offers a spacious layout featuring a cozy eat-in kitchen with stainless steel appliances, a formal dining room, and a full bath with direct access to the backyard, perfect for easy pool days. Hardwood floors flow throughout, adding warmth and charm to every room. Character shines at every turn with thoughtful details that make everyday living feel extra special. Upstairs, you’ll find three comfortable bedrooms and a second full bath. The primary bedroom features two closets, offering plenty of space to create a private retreat. Outside is where the magic happens, your own private pool oasis awaits. The pool h
Step into a spacious 1-bedroom + den home at The Somerset, Winthrop’s newest boutique condo community blending coastal charm with modern comfort. This thoughtfully designed layout offers an open-concept living space, a versatile den ideal for a home office or guest room, and a walk-in closet in the bedroom. Enjoy upscale finishes throughout—quartz countertops, stainless steel appliances, central A/C, and sleek modern details. This elevator building features a fitness room, resident lounge, and most units include garage parking. Select homes also offer private decks for your own outdoor escape. Located in the heart of Winthrop, just minutes from beaches, neighborhood shops, and