NEW PRICE! Fresh Updates! Now Vacant! Exceptional 2-family in desirable Winthrop. Same owner for 20 years! Turnkey opportunity for Investors or Owner-Occupants seeking strong rental income. Great for Multi-Gen living! Both units offer hardwood floors, closets, and spacious Kitchens w/ Pantrys. Windows galore! Gorgeous natural light! Beautifully proportioned rooms, easy floorplans, great storage. Welcoming farmer’s porch, fenced yard, and more! 3 OFF-ST PARKING SPACES. Unit 1 offers 2 BR’s, LR, DR, and huge Kitchen. Upstairs, Unit 2 features 1BR plus a windowed dressing room/WFH office, LR, DR, roomy Kitchen, along with exclusive access to a finished heated attic with 2 sunny bonus rooms ideal for WFH/guests/storage/gym. Unfinished basement with flex space for storage/hobbies. Steps to WINTHROP H.S. Close to parks, beaches, restaurants. Minutes to East Boston, Orient Heights MBTA/Buses, Logan, DT Boston. GPS "Oceanview"
| Units | 2 |
| Living area | 1,924 sqft |
| Lot size | 6,802 sqft |
| Year built | 1886 |
| Price / sqft | $488 |
| County | Suffolk |
| MLS # | 73537801 |
| Days on market | 40 days |
| Listed on | June 17, 2026 |
| Annual property tax | $7,732 |
| Tax year | 2026 |
| Assessed value | $694,100 |
| Zoning | 1040 |
| Gross income (actual) | $39,600/yr |
| Net operating income (actual) | $39,600/yr |
| Total actual rent | $3,300/mo |
| Stories | 3 |
| Total rooms | 10 |
| Lot size | 0.16 acres |
| Garage spaces | 0 |
| Parking spaces | 3 |
| Parking | Off Street, Tandem, On Street, Paved |
| Basement | Full, Interior Entry, Bulkhead, Concrete, Slab, Unfinished |
| Foundation | Concrete Perimeter, Block, Stone |
| Roof | Shingle, Rubber |
| Construction | Frame, Stone |
| Flooring | Wood, Tile, Vinyl, Laminate, Hardwood, Stone/Ceramic Tile |
| Heating | Natural Gas |
| Sewer | Public Sewer |
| Water | Public |
| Utilities | for Gas Range, for Gas Oven, for Electric Dryer, Washer Hookup |
| Appliances | Range, Microwave, Refrigerator |
More about investing in Winthrop →
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 1,924 sqft of living area, built in 1886.
105 Ocean View St., Winthrop MA 02152 has been listed for 40 days (since June 17, 2026).
At a list price of $939,000 across 2 units, that works out to roughly $469,500 per unit.
Annual property taxes are $7,732 (2026), on an assessed value of $694,100.
At $939,000 for 1,924 sqft, that's about $488 per square foot.
3 total parking spaces (off street, tandem, on street, paved).
105 Ocean View 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.