Welcome to 41 Van Winkle Street, a spacious three-family property ideally situated in Dorchester's Ashmont neighborhood. Offering approximately 4,252 square feet of living space with 9 bedrooms and 4 bathrooms, this property provides generous layouts across three levels and plenty of versatility for its next owner. The brick exterior, hardwood flooring, ample living space, and a sizable lot add to this property’s appeal. Location is a major highlight, with Ashmont Station just a short distance away, providing convenient Red Line access into Downtown Boston. Enjoy close proximity to Peabody Square, restaurants, and everyday conveniences, along with easy access to I-93 and other major routes. 41 Van Winkle Street is a property you won’t want to miss, schedule your private showing today!
| Units | 3 |
| Living area | 4,252 sqft |
| Lot size | 9,829 sqft |
| Year built | 1915 |
| Price / sqft | $235 |
| County | Suffolk |
| MLS # | 73591463 |
| Days on market | 0 days |
| Listed on | October 15, 2026 |
| Annual property tax | $13,612 |
| Tax year | 2025 |
| Assessed value | $1,175,500 |
| Zoning | R3 |
| Total actual rent | $0/mo |
| Stories | 3 |
| Total rooms | 13 |
| Lot size | 0.23 acres |
| Garage spaces | 0 |
| Parking spaces | 4 |
| Parking | Paved |
| Basement | Unfinished |
| Foundation | Brick/Mortar |
| Roof | Shingle |
| Construction | Brick |
| Flooring | Wood, Tile, Carpet |
| 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 3-unit multi-family property with 4,252 sqft of living area, built in 1915.
41 Van Winkle St, Boston MA 02124 has been listed for 0 days (since October 15, 2026).
At a list price of $999,999 across 3 units, that works out to roughly $333,333 per unit.
Annual property taxes are $13,612 (2025), on an assessed value of $1,175,500.
At $999,999 for 4,252 sqft, that's about $235 per square foot.
4 total parking spaces (paved).
41 Van Winkle St, Boston MA 02124 is in Boston, Suffolk County, MA 02124.

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.