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!
| Units | 3 |
| Living area | 2,889 sqft |
| Lot size | 8,550 sqft |
| Year built | 1900 |
| Price / sqft | $519 |
| County | Suffolk |
| MLS # | 73541145 |
| Days on market | 32 days |
| Listed on | June 24, 2026 |
| Annual property tax | $12,555 |
| Tax year | 2026 |
| Assessed value | $1,127,000 |
| Zoning | rh6 |
| Total actual rent | $0/mo |
| Stories | 3 |
| Total rooms | 13 |
| Lot size | 0.2 acres |
| Garage spaces | 0 |
| Parking spaces | 4 |
| Parking | Off Street, Driveway |
| Basement | Full, Interior Entry, Unfinished |
| Foundation | Other |
| Roof | Shingle |
| Construction | Frame |
| Flooring | Wood, Tile, Varies |
| Sewer | Public Sewer |
| Water | Public |
| Utilities | for Gas Range |
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Listing courtesy of a MLS PIN member office. Listing data © MLS PIN.
Auto-generated from the listing data — richer AI answers coming with the live site.
It is a 3-unit multi-family property with 2,889 sqft of living area, built in 1900.
516 Pleasant St, Winthrop MA 02152 has been listed for 32 days (since June 24, 2026).
At a list price of $1,499,000 across 3 units, that works out to roughly $499,667 per unit.
Annual property taxes are $12,555 (2026), on an assessed value of $1,127,000.
At $1,499,000 for 2,889 sqft, that's about $519 per square foot.
4 total parking spaces (off street, driveway).
516 Pleasant St, Winthrop MA 02152 is in Winthrop, Suffolk County, MA 02152.

Justin Rollo is a Broker Associate with Signal Real Estate (MA Lic. #9534264) and a lifelong Massachusetts resident. Over 14 years and hundreds of transactions, he has worked investment properties — multi-families and house-hacking — across Greater Boston full-time. Away from real estate, Justin is a proud dad, youth coach and local school-committee member — and a former professional poker player who still loves golf and following local sports.