A truly special opportunity to own a piece of Dorchester history. Built in 1910, 25–27 Kenwood Street is a side-by-side two-family situated on a quiet street with convenient access to schools, the T, parks, shopping, and major highways. Offering an exceptional combination of location, scale, and potential, this expansive 4,410-square-foot property features 10 bedrooms and 3 bathrooms across two spacious residences. Rich in original character, highlights include hardwood floors, built-ins, bay windows, porches, and four off-street parking spaces. Unit 1 offers 6 bedrooms and 2 bathrooms, while Unit 2 features 4 bedrooms and 1 bathroom. Each unit benefits from separate utilities and its own gas-fired hot water boiler. With its substantial footprint, historic charm, and versatile layout, this property presents an exciting opportunity to preserve its original character, renovate and reimagine the existing spaces, or explore future possibilities.
| Units | 2 |
| Living area | 4,410 sqft |
| Lot size | 5,883 sqft |
| Year built | 1910 |
| Price / sqft | $226 |
| County | Suffolk |
| MLS # | 73598506 |
| Days on market | 0 days |
| Listed on | November 4, 2026 |
| Annual property tax | $6,915 |
| Tax year | 2027 |
| Assessed value | $1,105,300 |
| Zoning | 0104 |
| Gross income (actual) | $52,800/yr |
| Net operating income (actual) | $52,800/yr |
| Total actual rent | $4,400/mo |
| Stories | 6 |
| Total rooms | 19 |
| Lot size | 0.14 acres |
| Garage spaces | 0 |
| Parking spaces | 4 |
| Parking | Off Street |
| Basement | Partial |
| Foundation | Stone |
| Sewer | Public Sewer |
| Water | Public |
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Listing courtesy of Gibson Sotheby's International Realty — Ashley Perkins. Listing data © MLS PIN.
Answered from the listing data and public map data.
It is a 2-unit multi-family property with 4,410 sqft of living area, built in 1910.
25-27 Kenwood Street, Boston MA 02124 has been listed for 0 days (since November 4, 2026).
At a list price of $995,000 across 2 units, that works out to roughly $497,500 per unit.
Annual property taxes are $6,915 (2027), on an assessed value of $1,105,300.
At $995,000 for 4,410 sqft, that's about $226 per square foot.
4 total parking spaces (off street).
25-27 Kenwood Street, 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.