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$780,000
6 Beds ⋅ 2 Baths ⋅ PRICE CHANGED Status ⋅ 73545756 MLS ⋅ 2,000 SqFt.
Ingleside Park 2-unit with oversized 10,000sqft lot and parking for 2 cars that offers plenty of potential in a central Winthrop location. Property is in need of interior updating and the back yard is ready to become either expanded parking, a beautiful yard space, or more. First floor unit has two bedrooms, one full bath, and a large rear deck. Second floor unit has two levels with four total bedrooms and one full bath. Building has separate electric and gas meters. Located next to Ingleside Park and the new Winthrop Center, and one mile to the MBTA Blue Line direct to Logan airport and Boston.

120 Hermon St, Winthrop
$799,986
6 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 73523937 MLS ⋅ 2,560 SqFt.
Excellent opportunity to own a well-maintained 2-family property in the highly desirable seaside community of Winthrop! Perfect for investors, owner-occupants or multi-generational living, this spacious property offers two large units featuring 3 bedrooms,1 full bathroom, hardwood floors, generous living areas and a bonus office room! Separate utilities and washer/dryer hookups add convenience and value for both owners and tenants. The property also offers plenty off-street parking, a paved driveway, and a private outdoor area. Conveniently located near restaurants, shopping, public transportation, beaches, Logan Airport, and major highways, making commuting into Boston quick and easy. Strong rental demand in the area creates excellent income potential and long-term upside. Whether you are looking to expand your investment portfolio, generate steady rental income or occupy one unit while collecting rent from the other, this property checks all the boxes!

50 Main St, Winthrop
$1,450,000
6 Beds ⋅ 6 Baths ⋅ ACTIVE Status ⋅ 73499355 MLS ⋅ 5,278 SqFt.
Set on a highly desirable corner lot at Sargent & Johnson Ave, this truly one of a kind home offers exceptional space and versatility. Welcoming foyer opens to a spacious living room, while the dining room features a covered porch with ocean views perfect for enjoying sunset evenings. The first floor also includes a bedroom and full bath, plus a kitchen with direct access to the backyard and one of two driveways. Just off the kitchen, a stunning glass walled sitting room overlooks the home’s standout feature: a large 40K gallon indoor in-ground pool. Additional highlights include a generous garage with expansion potential above. Second floor offers multiple baths, including a primary suite with private bath. The third floor functions well as an in-law suite with its own bedroom, full bath, and living area. Previously operated as a successful legal bed and breakfast, this property presents endless possibilities. Updates include roof 2023, newer pool liner. Perfect opportunity for ADU.

100 Sargent Street, Winthrop
$1,650,000
6 Beds ⋅ 6 Baths ⋅ UNDER AGREEMENT Status ⋅ 73489316 MLS ⋅ 4,122 SqFt.
Situated just steps from the sand, 304 Shirley presents a rare opportunity to own a fully occupied 6-unit building in one of Winthrop's most desirable seaside neighborhoods. Each unit is a well-maintained 1-bedroom, offering consistent rental income and strong tenant demand. This beachside property is perfectly positioned near local shops, restaurants, and public transportation, making it a convenient and attractive location for tenants year-round. Unit 2 has the following updates: new flooring, new paint, updated kitchen, new light fixtures.

304 Shirley Street, Winthrop

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