Winthrop is one of the last undervalued waterfront towns in Greater Boston, and opportunities like this don't sit long. 11 Pearl Ave is a vacant 3-family just a block from the ocean, generating $10,500/month at market rents with zero displacement headaches. Three floors, 11 bedrooms total, 4,032 sq ft of income-producing space on a town where the average days on market keeps shrinking. 3 separate heat systems, and 200-amp electric. Flood insurance runs about $2,600/year. Live in one, rent two, or hold all three. Priced at $1,050,000 with a cap rate that pencils with room for improvement and valuate add. Don't sleep on Winthrop.
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.
1080 Shirley St presents a rare two-family property with two separate structures, offering exceptional flexibility for owner-occupants or investors seeking strong rental potential. Ideally located just steps from the ocean in Winthrop, the property enjoys beautiful water views and a true coastal setting. The front unit features a spacious sunroom that fills the home with natural light, along with a bright and inviting living area. Originally built in 1930 and well maintained over the years, the property offers a combined 2,278 square feet of living space across both units, providing comfortable living and income potential. Outdoor space offers the perfect place to relax and enjoy the ocean breeze. Located moments from beaches, the marina, parks, restaurants, and local shops, the home also offers convenient access to public transportation and an easy commute to Boston. A rare chance to own a versatile coastal property in one of Winthrop’s most desirable seaside locations.
Introducing coastal living in this luxurious two-family home set on one of Winthrop’s most exclusive seaside streets. Just minutes from downtown Boston, this rare offering blends high-end finishes with exceptional investment potential. Additional in-law/guest suite possibilities create the opportunity for a dynamic property with multiple income streams or an elegant multigenerational retreat. Enjoy updated electric, beautiful updated countertops, top-of-the-line appliances, new plumbing fixtures, sun-filled rooms, wood restored fireplaces, front/back porches, fenced in yard and flexible layouts designed for comfort and value. Coastal breezes, nearby beaches, marinas, and shoreline paths capture Winthrop’s coveted seacoast charm. A private 3–4 car driveway completes this versatile property—ideal as a luxury residence, premier investment, or both. Don’t miss this smart investment opportunity. More pictures coming soon!!
OPPORTUNITY KNOCKS.......Two family with large yard is located right on the bus line with a very short ride to the T to Boston. There are 6 off street parking spaces! Some renovations as of 2001. The owner's unit is on the second and third floors with an open floor plan and lots of natural lighting. It contains a living room, dining area, kitchen, bath and one bedroom. The top floor consists of a sprawling main bedroom large enough to become 2 rooms. There are Boston skyline and marina views from the the top floor. The owner's unit has a great layout and good size rooms with lots of windows and laundry area of the kitchen. The first floor unit consists of a living room, kitchen, bath and two bedrooms. THIS IS A GREAT OWNER OCCUPY OR, INVESTMENT PROPERTY!
Winthrop is located in Massachusetts.
