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$979,900
6 Beds ⋅ 3 Baths ⋅ PRICE CHANGED Status ⋅ 73567723 MLS ⋅ 3,263 SqFt.
Stop by our OPEN HOUSE Sunday 9/13 1:00-2:30 for a viewing. A fantastic value for this home. It’s an opportunity to make it your own, and enjoy the quaint town of Winthrop by the sea. Spacious and beautifully updated, 6-bedroom, 2.5-bath home with the perfect blend of classic character & modern efficiency, all located in the wonderful seaside community of Winthrop by the Sea. Featuring gleaming hardwood floors throughout, newer windows 2 fireplaces giving warmth & charm to the living spaces. Extensive updates include all new mechanical systems including elec. wiring, FWA furnace, cent A/C, on-demand HW, mini-split heat pump/AC units, plumbing lighting, all providing peace of mind for years to come. Generous space, new paint & plaster finishes, & a beautifully finished basement for extra-living space, or entertainment. Kitchen has S.S. appliances and convenient 1st fl stacked washer & dryer. Outside large welcoming porch, groomed backyard, newer asphalt driveway, & an updated 2-car garage w/new overhead doors. Energy conscious buyers can assume the term note solar panels.

217 Pleasant Street, Winthrop
$760,000
6 Beds ⋅ 2 Baths ⋅ PRICE CHANGED Status ⋅ 73545756 MLS ⋅ 2,000 SqFt.
Ingleside Park 2-unit with a rare 10,000sqft oversized lot owned by the same family for over 20 years. Bring your ideas to transform this property into your dream investment or income-producing home with the untouched backyard begging to become either an outdoor oasis, additional parking, or more. Featuring off-street parking for 2 or 3 cars with the first floor unit offering two bedrooms, one full bath, and a large rear deck while the second floor unit has two levels with four total bedrooms, one full bath, and a rear sunroom. The building has separate electric and gas meters for each unit. Centrally located next to Ingleside Park and Winthrop Center only one mile to the MBTA Blue Line direct to Logan airport and Boston.

120 Hermon St, Winthrop
$1,100,000
6 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 73534385 MLS ⋅ 2,949 SqFt.
A rare opportunity to own a 3-unit multi-family investment property with a fourth apartment in one of Winthrop's most sought-after coastal locations, just minutes from downtown Boston and Logan Airport. This asset offers an ideal mix for investors and owner-occupants alike. The property features one three-bedroom apartment, one two-bedroom apartment, one one-bedroom apartment, and one studio unit. The one-bedroom apartment is currently rented and will be conveyed with the property. The two-bedroom and three-bedroom apartments will be delivered vacant at closing. The owner is currently marketing the studio for rent. Three off-street parking spaces come with the property. Set on a 4,075± sq ft lot in a supply-constrained market with strong, year-round rental demand, the property delivers a compelling blend of in-place income and future growth potential through both rent increases and value-addition. Steps to the beach, Winthrop Golf Club, and the heart of Shirley Street - come see everything that this property has to offer.

32 Irwin St, Winthrop
$779,986
6 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 73523937 MLS ⋅ 2,560 SqFt.
PRICE REDUCTION! 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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