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$949,000
7 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 73573129 MLS ⋅ 4,251 SqFt.
Welcome to 190 Pleasant Street, a spacious two-family home offering approximately 4,251 square feet of living space across three levels. Featuring 13 total rooms,seven bedrooms, two full bathrooms and two half bathrooms, this property presents an excellent opportunity for an owner-occupant, investor or multigenerational household. Each unit offers generous living space, while the home’s flexible layout provides plenty of potential to customize and add value. Conveniently located near Winthrop’s beaches, local shops, restaurants, public transportation and Boston. Bring your vision and discover everything this well-located two-family property has to offer!

190 Pleasant St, 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
$875,000
4 Beds ⋅ 3 Baths ⋅ UNDER AGREEMENT Status ⋅ 73542949 MLS ⋅ 2,016 SqFt.
Two-family home in a prime Winthrop location, directly across from Ingleside Park and minutes from Winthrop Center. Each unit offers 2 bedrooms, 1 full bath, a bright living room, eat-in kitchen, and private porch. Set on a 0.14-acre lot, the property features a partially fenced backyard—ideal for entertaining, gardening, grilling, or relaxing. The lower level, accessible via a private rear entrance, offers excellent potential for flexible use such as a recreation area, home office, gym, workshop, or storage. Recent updates include a roof replacement in 2021. Just a short stroll to Winthrop Center shops and restaurants, and to Donovan Beach, with bus service connecting to the Blue Line and approximately a 30-minute door-to-door commute to Boston via public transit. Whether you're an owner-occupant looking to live in one unit and offset your mortgage with rental income, or an investor seeking rental income in a desirable coastal location, this is an opportunity you won't want to miss.

126 Brookfield, Winthrop
$1,499,000
5 Beds ⋅ 3 Baths ⋅ UNDER AGREEMENT Status ⋅ 73541145 MLS ⋅ 2,889 SqFt.
Every evening, the harbor turns amber from the west, 516 Pleasant Street has a front-row seat. A one-of-a-kind home set along Winthrop's harbor front with direct water access, a concrete seawall, and a private boat launch, (all outside the flood-zone by the way!!) this residence offers a lifestyle that cannot be assembled from scratch in today's coastal market. The rights to rebuild a pier remain intact, a dormant asset in a harbor where private moorings are nearly impossible to find. The units span 2,889 square feet across three floors, and this home could easily be transformed into the single-family of your dreams. An in-ground pool, roof deck, sunroom with gas stove, and west-facing harbor views complete the picture.Close to logan sirport, Rt 1A, ferry service to Boston, parks, summer farmers market and more!

516 Pleasant St, Winthrop
$699,000
4 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 73539167 MLS ⋅ 1,963 SqFt.
PRICED TO SELL!! Best value in the neighborhood! Charming 1930's two family, originally a seaside cottage, just steps to the beach. This coastal home has been owned by the same family for over 70 years. It offers off street parking and flexible living options. It could be a great single family. Unit 1 is a one bedroom while Unit 2 has three bedrooms. This property is brimming with potential and is priced to reflect the updating needed - an excellent opportunity to create value in a prime location. Don't miss this wonderful chance to become a homeowner.

153 Locust 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
$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
$999,888
5 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 73529063 MLS ⋅ 2,635 SqFt.
NEWLY PRICED! PRICED TO SELL! Rare waterfront two-family in Winthrop's sought-after Cottage Park neighborhood, offering stunning views of the Bay, Harbor, marsh, and ocean, a lifestyle feature you simply can't replicate at this price point. Built in 1920, this classic 2,635 sq ft two-story home sits on a 5,227 sq ft lot just steps from the beach. A perfect opportunity for first-time buyers or savvy investors. Unit 1 rents for $3,100/mo and Unit 2 for $4,000/mo, generating $85,200 in gross annual income with a net of $76,900. Five bedrooms, two full baths, and a versatile layout ideal for extended families. The property features an enclosed porch, deck, fenced yard, professional landscaping, and individually metered electric. Minutes from downtown Boston via Rt. 1A. Don't miss this opportunity; schedule your private showing today!

66 Sunnyside Ave, 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
$849,900
4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 73508827 MLS ⋅ 2,843 SqFt.
Corner Lot Modern 2 family close to the bay next to Mary Kelly Pavilion.1st floor has 4 large rooms & 2 bed.Kitchen has Induction Stove Top Granite Island & Counter Tops.Stainless Steel Induction Wall Microwave & Wall Oven.Top of the line Stainless Steel Refrigerator & Dishwasher.Granite tile floor. Plenty of Cabinet Space. Beautiful Tiger Hardwood Floors & Natural Woodwork Throughout. Crown Moldings & Chair Rails.Wood Fireplace in Living Room. There's a closet from the kitchen that was used as a staircase to the Basement that's finished with a huge full bath washer & dryer, Family Room & bedroom. That can be added in on the room count to 7 rooms 3 beds 2 full baths. 2nd floor 4 Large Rooms & 2 Bed.Plenty of Cabinet Space.Beautifull Hardwood Floors and All Natural Woodwork Throughout. Huge Living room. Dining Room has a spot for wall A/C. 4 Car Parking, Nice Huge Fenced in Yard with a Large Patio. Plenty of Parking Around The House Because of the corner Lot.5year old roof

7 Willis Ave, 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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