HomeWinthropMulti Family190 Pleasant St, Winthrop MA 02152
190 Pleasant St, Winthrop MA 02152 — photo 1 of 201 / 20
$949,000
190 Pleasant St, Winthrop MA 02152
2 units · 4 bd · 4 ba · 4,251 sqft · $474,500/unit
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INVESTMENT SNAPSHOT

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

About this property

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!

Property details

Units2
Living area4,251 sqft
Lot size9,197 sqft
Year built1890
Price / sqft$223
CountySuffolk
MLS #73573129

Listing status

Days on market0 days
Listed onSeptember 8, 2026

Taxes & financials

Annual property tax$10,175
Tax year2026
Assessed value$913,400
ZoningR3
Gross income (actual)$36,000/yr
Net operating income (actual)$36,000/yr
Total actual rent$3,000/mo

Building & lot

Stories3
Total rooms13
Lot size0.21 acres
Garage spaces0
Parking spaces8
ParkingPaved Drive, Off Street
BasementFull
FoundationConcrete Perimeter
RoofShingle
ConstructionFrame
FlooringTile, Carpet, Laminate, Hardwood

Utilities & systems

SewerPublic Sewer
WaterPublic

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 190 Pleasant St, Winthrop MA 02152 have?

It is a 2-unit multi-family property with 4,251 sqft of living area, built in 1890.

How long has 190 Pleasant St, Winthrop MA 02152 been on the market?

190 Pleasant St, Winthrop MA 02152 has been listed for 0 days (since September 8, 2026).

What is the price per unit?

At a list price of $949,000 across 2 units, that works out to roughly $474,500 per unit.

What are the property taxes on 190 Pleasant St, Winthrop MA 02152?

Annual property taxes are $10,175 (2026), on an assessed value of $913,400.

What is the price per square foot?

At $949,000 for 4,251 sqft, that's about $223 per square foot.

Is there parking?

8 total parking spaces (paved drive, off street).

Where is this property located?

190 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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