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!
| Units | 2 |
| Living area | 4,251 sqft |
| Lot size | 9,197 sqft |
| Year built | 1890 |
| Price / sqft | $223 |
| County | Suffolk |
| MLS # | 73573129 |
| Days on market | 0 days |
| Listed on | September 8, 2026 |
| Annual property tax | $10,175 |
| Tax year | 2026 |
| Assessed value | $913,400 |
| Zoning | R3 |
| Gross income (actual) | $36,000/yr |
| Net operating income (actual) | $36,000/yr |
| Total actual rent | $3,000/mo |
| Stories | 3 |
| Total rooms | 13 |
| Lot size | 0.21 acres |
| Garage spaces | 0 |
| Parking spaces | 8 |
| Parking | Paved Drive, Off Street |
| Basement | Full |
| Foundation | Concrete Perimeter |
| Roof | Shingle |
| Construction | Frame |
| Flooring | Tile, Carpet, Laminate, Hardwood |
| Sewer | Public Sewer |
| Water | Public |
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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 2-unit multi-family property with 4,251 sqft of living area, built in 1890.
190 Pleasant St, Winthrop MA 02152 has been listed for 0 days (since September 8, 2026).
At a list price of $949,000 across 2 units, that works out to roughly $474,500 per unit.
Annual property taxes are $10,175 (2026), on an assessed value of $913,400.
At $949,000 for 4,251 sqft, that's about $223 per square foot.
8 total parking spaces (paved drive, off street).
190 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.