
516 Pleasant St Winthrop — Photo 1 of 42
Recent Drop: $101,000
$1,499,000
Winthrop, MA 02152
Beds
5
Baths
3
SqFt
2,889
Style
Multi Family
Built
1900
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!
* Analysis is based on 23 actively listed and recently sold comparable properties strictly within Winthrop, MA.
Shopping • Pool • Park • Walk/Jog Trails • Conservation Area • Highway Access
Was $1,600,000
Jul 22, 2026
MLS® 73541145
Jun 24, 2026
MLS® 73541145
18,759
U.S. Census Bureau, ACS 2024 5-Year Estimates (B01003)
$116K
U.S. Census Bureau, ACS 2024 5-Year Estimates (B19013)
43.1%
U.S. Census Bureau, ACS 2024 5-Year Estimates (B25003)
2,527 housing units permitted in the last 12 months (+37% vs the prior 12 months) — 2,269 in 5+ unit buildings
U.S. Census Bureau, Building Permits Survey (through Jun '26)
Listing Agent: Amanda George
Listing Office: Century 21 Shawmut Properties
MLS® Number: 73541145
Explore other active listings in the area.