Browse All Winthrop MA Above $1M Properties for Sale

5 Beds ⋅ 4 Baths ⋅ COMING SOON Status ⋅ 73594447 MLS ⋅ 3,686 SqFt.

Truly exceptional waterfront Victorian, with glorious views of Crystal Cove and direct private access to Boston Harbor and beyond, is historic yet fresh, sophisticated yet wonderfully livable! Head out on your boat to explore beaches and islands, restaurants and bars, or relax and enjoy spectacular water views from almost every room. The bespoke water-facing chef's kitchen, with a welcoming island, bar sink and beverage fridge, coffee bar, and suite of Bosch appliances, is an inviting place to gather, cook and linger. Adjacent, the family room beckons, sliding doors bring the outdoors in, and connect to a deck just steps to your own beach. Natural light changes with the day and seasons; the moody grays of winter will be perfectly offset by a cozy fire in the open living room. Naturally there's a dining room, inviting guests for memorable celebrations, family gatherings, and holidays! Upstairs five thoughtfully located bedrooms are paired with more water views, a roof deck, and three tiled baths with elevated finishes. Charming original details go hand-in-hand with the 2026 updates, including ducted heating and cooling, highly efficient replacement windows, on-demand hot water, 400-amp electrical, hardwood flooring, new kitchen and baths, and more. Bonuses include a two car garage awaiting your roof deck and a clean, dry lower level media room w/ high ceilings and potential for expansion! Close to restaurants, Winthrop Yacht Club, Winthrop Golf Course, five minutes to the blue line, 10 minute drive to Logan Airport and Boston. Enjoy coastal living with easy city access! Anticipated completion by November 15th.

119 Washington Ave, Winthrop

$1,250,000

6 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 73588891 MLS ⋅ 3,420 SqFt.

Fantastic 3-Family Opportunity in Winthrop Center! Well-maintained and with recent updates, this multi-family property offers an excellent opportunity for investors and owner-occupants alike. The property features a 1-bedroom lower-level unit, a spacious 2-bedroom unit with two bonus flex rooms, and a 3-bedroom unit with two additional flex spaces. Recent improvements include replacement windows, updated electrical, interior and exterior painting, bathroom upgrades, new fencing, landscaping enhancements, soffit and gutter repairs, heating system updates, and added off-street parking. Select units enjoy private outdoor space and all units offer laundry. Ideally located just moments from Winthrop Center's shops, restaurants, beaches, and public transportation. A turnkey investment with strong income potential in one of Winthrop's most desirable neighborhoods.

23-25 Fremont St, Winthrop

$1,095,000

4 Beds ⋅ 3 Baths ⋅ UNDER AGREEMENT Status ⋅ 73587151 MLS ⋅ 2,910 SqFt.

Stunning home in the heart of Winthrop. This exceptional American Foursquare combines timeless architectural character with extensive renovations and modern finishes throughout. Spacious and sun-filled, the home offers beautifully remodeled interiors, off-street parking, and exceptional indoor/outdoor living while preserving its classic craftsmanship. A newly remodeled mudroom with custom storage, new windows, and recessed lighting opens to a gracious living room with hardwood floors and a gas fireplace with a newly constructed surround. The spacious dining room features traditional wainscoting and an elegant setting for entertaining.The fully remodeled kitchen is the centerpiece of the home, featuring a large center island, custom cabinetry, designer tilework, new flooring, and generous workspace. An expansive Trex deck overlooks the fully fenced, professionally landscaped 6,000 sq. ft. lot, creating an exceptional setting for outdoor dining and entertaining. A full bath completes the main level.The second floor offers three generously sized bedrooms, and fourth bedroom currently being used as a home office. A fully remodeled bath with new finishes and fixtures caps off the second floor. The finished third floor provides flexible bonus space ideal for an office, guest retreat, media room, playroom, or library.The newly finished lower level offers a separate in-law suite with a brand-new kitchenette, second gas fireplace featuring hand-built stonework, half bath, dedicated gym, and laundry area—ideal for extended family, guests, or additional work-from-home space. Short distance to schools, Town Center restaurants and cafés, shops, the library, parks, and beaches, with convenient access to Boston, the Seaport, Financial District, and Logan Airport.

61 Read Street, Winthrop

$1,275,000

4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 73585487 MLS ⋅ 2,599 SqFt.

Welcome to your ultimate beachfront oasis in Winthrop, where every day feels like a permanent getaway with direct access from your back door straight into the sand. This stunning home features an inviting, fireplaced living room, a kitchen boasting sleek marble countertops and tile flooring, a convenient main-floor full bath and an outdoor shower for rinsing off after the beach, and two flexible bedrooms ideal for guests, children, or a home office. Take in breathtaking ocean sunrises over morning coffee from the year-round heated sunroom, and retreat upstairs to a spacious primary suite complete with its own private bath. The finished lower level functions as a fully separate suite—an incredible asset as one of only 10 legal Airbnbs in all of Winthrop, complete with its own family room, bonus space, full bathroom, and laundry. Positioned in an unbeatable location with two off-street parking spots and an EV charger, this property sits less than 1 mile from the Winthrop Landing MBTA ferry for easy transit to Logan, Central Wharf, and the Seaport, perfectly balancing everyday coastal luxury with elite short-term rental potential.

129 Strandway, Winthrop

$1,500,000

4 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 73582288 MLS ⋅ 2,852 SqFt.

The street name—Harbor View Avenue—says it all! A home any sea captain would be proud to call home! Rare opportunity to own a distinctive multi-family property perched at one of Winthrop’s highest elevations, with sweeping panoramic views of the ocean and Boston Harbor and Skyline. Enjoy spectacular sunrises, sunsets, passing boats, and refreshing ocean breezes from this exceptional coastal setting. Classic Hardie Board siding adds timeless New England character, while public stairs just steps away provide convenient access to Yirrell Beach and its shoreline walks. The flexible multi-family layout offers excellent options for an owner-occupant, multi-generational living, or investment income. The current configuration also provides the potential to convert the property into a spacious four-bedroom single-family home. The owner is currently awaiting Massport approval for replacement windows and doors. Elevated location, exceptional ocean and harbor views, beach access, classic coastal character, and versatile living possibilities make this a truly special Winthrop property. Check out our video with the QR code or cut and paste this link: https://tour.vaulted-media.com/63_harbor_view_ave-4103

63 Harbor View Ave, Winthrop

$1,095,000

2 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 73577096 MLS ⋅ 2,649 SqFt.

Welcome to 94 Winthrop Shore Drive, a truly unique home directly across from Winthrop Shore Beach, offering beautiful water views and an incredible coastal setting. The home is highlighted by a dramatic, light-filled main living area with soaring ceilings, expansive windows overlooking the water, hardwood floors, and distinctive architectural details. Generous living and dining spaces provide plenty of room for entertaining, while the flexible floor plan offers multiple possibilities for everyday living, extended family, guests, or a private retreat. Kitchen areas on both the upper and lower levels add convenience and flexibility to the home’s versatile layout. The basement provides valuable storage space along with a private sauna, adding another unique feature to the property. The boiler and water heater were replaced approximately in 2023, and mini-split systems provide cooling in various areas of the home for added comfort and convenience. Enjoy the character, versatility, and coastal lifestyle of this one-of-a-kind home in an exceptional location directly across from the beach and just minutes from Boston.

94 Winthrop Shore Dr, Winthrop

$1,230,000

3 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 73560746 MLS ⋅ 1,913 SqFt.

Experience elevated waterfront living in this stunning 3 bedroom, 3 bath penthouse at the prestigious Seal Harbor III. This exceptional two-level residence features a spacious open-concept floor plan designed to maximize natural light and showcase its spectacular waterfront setting. Entertain effortlessly or simply relax on the massive private deck, offering the perfect space to enjoy ocean breezes and breathtaking views. The kitchen boasts SS appliances, granite counters, Poggenpohl cabinetry and a breakfast bar. Enjoy the beautiful views while cooking. This 2 level unit offers the flexibility of a first floor bedroom and/or office. Nice open staircase. Lovely primary bedroom with en suite. There is a separate jacuzzi room which could become a home office if one chooses to do so. Seal Harbor III offers an unmatched lifestyle with exceptional amenities, including 24/7 concierge, a beautiful fireplaced lobby, an indoor heated pool and hot tub, a recently renovated fitness center, sauna, rooftop deck with panoramic views, outdoor swimming pool, tennis courts and multiple private resident gathering spaces. Additional highlights include a rare heated two-car garage, G9 and G11. Ideally located in the seaside community of Winthrop, you'll enjoy the tranquility of waterfront living while being just minutes from Logan Airport and downtown Boston, providing the perfect balance of coastal charm and city convenience. LUXURY, LOCATION, AND LIFESTYLE come together in this extraordinary waterfront Penthouse.

3 Seal Harbor Rd Unit PH33, Winthrop

$2,100,000

5 Beds ⋅ 6 Baths ⋅ ACTIVE Status ⋅ 73550891 MLS ⋅ 6,224 SqFt.

One of the most coveted locations in Winthrop, 174 Bartlett Rd is your dream costal retreat where luxury meets seaside living. Completely gut renovated, this exceptional home offers over 6,000 sq ft of beautifully designed living space across four expansive levels. The heart of the home is the stunning chefs kitchen with seamless oversized Brazilian Quartzite island surrounded by premium Sub-Zero, Wolf & Miele appliances, & a fully appointed entertaining bar. Anchored by a striking Valor fireplace, the two thoughtfully designed seating areas & expansive dining room create space for intimate or larger-scale entertaining. The Primary suite is a water view retreat with steam shower & BainUltra therapeutic soaking tub, dual walk-in closets, & private laundry. Welcome guests in the lower level suite, enjoy resort style yard with Gunite in-ground pool, basketball court & grilling island, or end days on the roof top deck with incredible views. This thoughtfully crafted home is unforgettable!

174 Bartlett Road, Winthrop

$1,049,900

6 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 73534385 MLS ⋅ 2,949 SqFt.

Multi-family in Winthrop, MA with four apartments and an ocean view, within 1/10 mile of the beach. The mix is a 3-bedroom, 2-bedroom, 1-bedroom and studio, each with 1 full bath, totaling 2,949 sq ft. The third-floor 1-bedroom is leased at $1,500 per month and conveys. The first-floor 3-bedroom and second-floor 2-bedroom are delivered vacant at closing. The second-floor studio with sunroom is listed for rent at $1,700. Rents total $9,300 per month; three of four are projected. All rents include water; the studio and 1-bedroom also include heat, electricity and gas. Heat is gas hot water baseboard on 3 systems, with window AC and town water and sewer. The 1900 building has vinyl siding, an asphalt roof, LVP and hardwood floors, and an unfinished basement with exterior access. The 4,075 sq ft lot has 3 off-street parking spaces. The building department classifies it as 3 units and the assessor as 4; it is used as 4 units. Winthrop Golf Club, Shirley Street and Logan Airport are nearby.

32 Irwin St, Winthrop

$2,250,000

16 Beds ⋅ 14 Baths ⋅ ACTIVE Status ⋅ 73531829 MLS ⋅ 10,000 SqFt.

DEVELOPMENT OPPORTUNITY WITH EXISTING MIXED USE PROPERTY GENERATING $71K NET ANNUAL INCOME.++A rare coastal investment and development opportunity in the heart of Winthrop, Massachusetts. The mixed use property currently consists of a cash-flowing four-unit mixed-use building with stable in-place NOI of 71,300, combined with a Board of Appeals–approved plan to construct a new 12-unit building with podium parking beneath — all on one site steps from the harbor and in the middle of a quaint yet thriving downtown Winthrop. 5-10 min commute to Boston Logan Airport, quick access to the MBTA Blue Line and ferry access to downtown Boston. All dimensions, square footage, parking spaces and building plans are estimated and should be considered for marketing purposes only. Buyers to do all due diligence as this is a development opportunity.

63-69 Putnam St, Winthrop

$2,250,000

ACTIVE Status ⋅ 73490169 MLS

DEVELOPMENT OPPORTUNITY WITH EXISTING MIXED USE PROPERTY GENERATING $71K NET ANNUAL INCOME. A rare coastal investment and development opportunity in the heart of Winthrop, Massachusetts. The mixed use property currently consists of a cash-flowing four-unit mixed-use building with stable in-place NOI of 71,300, combined with a Board of Appeals–approved plan to construct a new 12-unit building with podium parking beneath — all on one site steps from the harbor and in the middle of a quaint yet thriving downtown Winthrop. 5-10 min commute to Boston Logan Airport, quick access to the MBTA Blue Line and ferry access to downtown Boston.

63-69 Putnam St, Winthrop

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Browse All Winthrop MA Above $1M Properties for Sale

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