Rarely available and cherished by the same family for over 30 years, this classic Dorchester two-family home presents an incredible opportunity on the edge of the highly sought-after Savin Hill area. Boasting over 3,200 square feet of multi-level living space, this robust property is perfect for savvy investors looking to add a premier asset to their portfolio, or owner-occupants ready to start their real estate journey off strong with built-in rental income.The building offers grand-scale proportions, highlighted by a massive, unfinished basement featuring impressive 6-foot ceilings that offer immense potential for future expansion (basement square footage is not included in the official total). Situated a short distance from the Savin Hill and JFK/UMass T-stations, local beaches, and vibrant neighborhood favorites like McKenna's Cafe, this is a true urban oasis.Bring your vision to this longtime family gem and anchor yourself in one of Boston's most dynamic markets. (Some photos virtually enhanced for visualization purposes.)
| Units | 2 |
| Living area | 3,204 sqft |
| Lot size | 4,356 sqft |
| Year built | 1928 |
| Price / sqft | $343 |
| County | Suffolk |
| MLS # | 73583097 |
| Days on market | 0 days |
| Listed on | September 27, 2026 |
| Annual property tax | $12,264 |
| Tax year | 2026 |
| Assessed value | $989,000 |
| Zoning | 2F-5000 |
| Total actual rent | $0/mo |
| Stories | 3 |
| Total rooms | 12 |
| Lot size | 0.1 acres |
| Garage spaces | 0 |
| Parking spaces | 2 |
| Basement | Full, Partially Finished, Walk-Out Access |
| Foundation | Block, Stone |
| Roof | Shingle |
| Construction | Frame, Stone |
| 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 3,204 sqft of living area, built in 1928.
66 Pleasant, Boston MA 02125 has been listed for 0 days (since September 27, 2026).
At a list price of $1,100,000 across 2 units, that works out to roughly $550,000 per unit.
Annual property taxes are $12,264 (2026), on an assessed value of $989,000.
At $1,100,000 for 3,204 sqft, that's about $343 per square foot.
2 total parking spaces.
66 Pleasant, Boston MA 02125 is in Boston, Suffolk County, MA 02125.

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.