HomeWinthropMulti Family516 Pleasant St, Winthrop MA 02152
516 Pleasant St, Winthrop MA 02152 — photo 1 of 421 / 42
$1,499,000
516 Pleasant St, Winthrop MA 02152
3 units · 5 bd · 3 ba · 2,889 sqft · $499,667/unit
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INVESTMENT SNAPSHOT

Signal Score pending — we haven't seeded market rents for this ZIP (02152) yet.

About this property

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!

Property details

Units3
Living area2,889 sqft
Lot size8,550 sqft
Year built1900
Price / sqft$519
CountySuffolk
MLS #73541145

Listing status

Days on market32 days
Listed onJune 24, 2026

Taxes & financials

Annual property tax$12,555
Tax year2026
Assessed value$1,127,000
Zoningrh6
Total actual rent$0/mo

Building & lot

Stories3
Total rooms13
Lot size0.2 acres
Garage spaces0
Parking spaces4
ParkingOff Street, Driveway
BasementFull, Interior Entry, Unfinished
FoundationOther
RoofShingle
ConstructionFrame
FlooringWood, Tile, Varies

Utilities & systems

SewerPublic Sewer
WaterPublic
Utilitiesfor Gas Range

Location

More about investing in Winthrop

Listing courtesy of a MLS PIN member office. Listing data © MLS PIN.

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Questions & answers

Auto-generated from the listing data — richer AI answers coming with the live site.

How many units does 516 Pleasant St, Winthrop MA 02152 have?

It is a 3-unit multi-family property with 2,889 sqft of living area, built in 1900.

How long has 516 Pleasant St, Winthrop MA 02152 been on the market?

516 Pleasant St, Winthrop MA 02152 has been listed for 32 days (since June 24, 2026).

What is the price per unit?

At a list price of $1,499,000 across 3 units, that works out to roughly $499,667 per unit.

What are the property taxes on 516 Pleasant St, Winthrop MA 02152?

Annual property taxes are $12,555 (2026), on an assessed value of $1,127,000.

What is the price per square foot?

At $1,499,000 for 2,889 sqft, that's about $519 per square foot.

Is there parking?

4 total parking spaces (off street, driveway).

Where is this property located?

516 Pleasant St, Winthrop MA 02152 is in Winthrop, Suffolk County, MA 02152.

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Justin Rollo, Broker Associate at Signal Real Estate
Justin RolloBroker Associate, Signal Real Estate · MA Lic. #9534264

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.

📞 978-790-4381📍 25 Braintree Hill Park, Suite 200, Braintree, MA 02184
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