A unique opportunity to own a desirable two-unit residence in the heart of Cambridgeport, with strong potential for development, flexible floor plans, expansive basement, rooftop deck, private outdoor spaces, off-street parking, and an exceptional location close to the Charles River, Whole Foods, Trader Joe’s, Mass Audubon’s Magazine Beach Nature Center, and prestigious universities. Unit 1 showcases 9’ ceilings with a comfortable and functional layout filled with period detail. The living room and bedroom both have bay windows and hardwood floors. Living room features floor-to-ceiling custom built-ins and a French door. Generously sized bright bedroom features a marble-surround fireplace and ceiling medallion. A good-sized eat-in kitchen with a gas stove and tile flooring, along with a full bathroom, complete the interior. Unit 2, on the 2nd and 3rd floors, offers spacious, airy two-level living with a flexible floor plan, two bedrooms, two full bathrooms, hardwood floors, dedicated home office, and expansive roof deck. The second floor features a welcoming living room, sunny family room, eat-in kitchen with generous cabinets and gas stove, bedroom with large closet, full bathroom, and home office – an ideal setup for a work-from-home lifestyle. The third floor is a private primary bedroom suite, complete with full bathroom and direct access to the private outdoor roof deck. This exceptional deck with views of trees and urban landscape is a unique, much-coveted extension of the home, ideal for relaxing or entertaining. Roof deck offers potential to expand the 3rd floor living space. Property amenities include water filtration system, separate gas heat and hot water systems, laundry, patio and yard space, one deeded off-street parking space. Resident permit parking is also available on the street. The large basement has high ceilings and offers huge development potential. Ideally situated on one of Cambridgeport’s beautiful tree-lined streets, the property is less than ¼ mile from the Charles River, Whole Foods Market, and Trader Joe’s. Minutes to Mass Audubon’s Magazine Beach Nature Center, vibrant restaurants, cafés, parks, and neighborhood amenities. Convenient access to Central and Harvard Square, MIT, Harvard, BU, public transportation, and major commuter routes. A distinctive Cambridgeport property with potential for development, combining two residences, flexible living space, valuable private outdoor areas, parking, and an outstanding location.
| Units | 2 |
| Living area | 2,064 sqft |
| Lot size | 1,959 sqft |
| Year built | 1886 |
| Price / sqft | $775 |
| County | Middlesex |
| MLS # | 73593969 |
| Days on market | 0 days |
| Listed on | October 22, 2026 |
| Annual property tax | $8,702 |
| Tax year | 2026 |
| Assessed value | $1,304,600 |
| Zoning | C |
| Gross income (actual) | $34,200/yr |
| Net operating income (actual) | $29,657/yr |
| Total actual rent | $2,850/mo |
| Insurance expense | $3,143/yr |
| Stories | 3 |
| Total rooms | 8 |
| Lot size | 0.04 acres |
| Garage spaces | 0 |
| Parking spaces | 1 |
| Parking | Off Street, On Street, Deeded, Stone/Gravel |
| Basement | Full, Interior Entry, Unfinished |
| Foundation | Stone |
| Roof | Shingle |
| Construction | Frame |
| Flooring | Tile, Hardwood, Stone/Ceramic Tile |
| Heating | Baseboard, Natural Gas, Individual, Unit Control |
| Cooling | Window Unit(s) |
| Sewer | Public Sewer |
| Water | Public |
| Utilities | for Gas Range, for Gas Dryer, Washer Hookup |
| Appliances | Washer, Dryer, Range, Dishwasher, Disposal, Refrigerator, Water Treatment |
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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 2,064 sqft of living area, built in 1886.
247 Chestnut St, Cambridge MA 02139 has been listed for 0 days (since October 22, 2026).
At a list price of $1,600,000 across 2 units, that works out to roughly $800,000 per unit.
Annual property taxes are $8,702 (2026), on an assessed value of $1,304,600.
At $1,600,000 for 2,064 sqft, that's about $775 per square foot.
1 total parking space (off street, on street, deeded, stone/gravel).
247 Chestnut St, Cambridge MA 02139 is in Cambridge, Middlesex County, MA 02139.

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.