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.
Two-Family Opportunity Near the Beach! Located in desirable Winthrop, this two-family property offers an exciting opportunity to build equity in a sought-after coastal community—all for under $600,000. This fixer-upper is ready for someone with vision to bring it back to life and unlock its full potential. Whether you’re an investor looking for your next project or a buyer willing to put in the time and effort to create value, this property offers plenty of possibilities. Enjoy the convenience of being close to the beach, local shops, restaurants, and transportation while taking advantage of the income potential and flexibility a two-family home provides. A great opportunity to renovate, customize, and create lasting value in Winthrop!
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
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!
Capitalize on the tremendous potential of this centrally located multi with a rare 10,000sqft lot located one block from Ingleside Park. The untouched backyard is ready for your ideas - transform it into additional garage parking, an outdoor oasis, or more. Complete with off-street parking for 2-3 cars and additional easy parking on this quiet side street. The first floor unit offers a large deck, two bedrooms, one full bath. The second floor bi-level unit has two beds downstairs with 2 beds upstairs, one full bath, and an extra rear sunroom. The building is equipped with separate electric and gas meters for each unit. Located just a few blocks away from Winthrop Center, Ingleside Park, and only one mile to the MBTA Blue Line direct to Logan airport and Boston.
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.
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.
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!
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.5 year old roof. PROPERTY DELIVERED VACANT!

Winthrop is located in Massachusetts.