A rare turnkey 7-unit investment property with cultural significance, 27 Dudley Street was once home to Maurice Starr where New Kids on the Block and New Edition rehearsed and recorded. Fully gut-renovated in 2021, it delivers modern finishes including waterfall quartz countertops, central HVAC, in-unit laundry, hardwood floors, and 8+ off-street parking spaces, ensuring strong tenant demand. Generating $22,825/month with a 6.3% cap rate and a projected 7.3% cap rate by 9/1/26, it combines reliable cash flow with potential Opportunity Zone tax advantages. Positioned near public transit, universities, and Longwood Medical Area, this asset offers cultural legacy, premium quality, and growth potential in one of Boston’s fastest-growing neighborhoods. Ideal for 1031 exchange buyers or investors seeking a stable, high-performing asset with long-term appreciation potential. Full pro forma and unit breakdown available on request.
| Units | 7 |
| Living area | 6,509 sqft |
| Lot size | 8,241 sqft |
| Year built | 1900 |
| Price / sqft | $530 |
| County | Suffolk |
| MLS # | 73478206 |
More about investing in Boston →
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 7-unit multi-family property with 6,509 sqft of living area, built in 1900.
At a list price of $3,625,000 across 7 units, that works out to roughly $517,857 per unit.
At $3,625,000 for 6,509 sqft, that's about $530 per square foot.
27 Dudley St, Boston MA 02119 is in Boston, Suffolk County, MA 02119.

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.