2 Family - 2 Units Up/Down at 247 Chestnut St, Cambridge MA 02139
2 Family - 2 Units Up/Down at 247 Chestnut St, Cambridge MA 02139, photo 2 of 42
2 Family - 2 Units Up/Down at 247 Chestnut St, Cambridge MA 02139, photo 3 of 42
2 Family - 2 Units Up/Down at 247 Chestnut St, Cambridge MA 02139, photo 4 of 42
2 Family - 2 Units Up/Down at 247 Chestnut St, Cambridge MA 02139, photo 5 of 42
2 Family - 2 Units Up/Down at 247 Chestnut St, Cambridge MA 02139, photo 6 of 42
2 Family - 2 Units Up/Down at 247 Chestnut St, Cambridge MA 02139, photo 7 of 42
2 Family - 2 Units Up/Down at 247 Chestnut St, Cambridge MA 02139, photo 8 of 42
2 Family - 2 Units Up/Down at 247 Chestnut St, Cambridge MA 02139, photo 9 of 42
2 Family - 2 Units Up/Down at 247 Chestnut St, Cambridge MA 02139, photo 10 of 42
2 Family - 2 Units Up/Down at 247 Chestnut St, Cambridge MA 02139, photo 11 of 42
2 Family - 2 Units Up/Down at 247 Chestnut St, Cambridge MA 02139, photo 12 of 42
2 Family - 2 Units Up/Down at 247 Chestnut St, Cambridge MA 02139, photo 13 of 42
2 Family - 2 Units Up/Down at 247 Chestnut St, Cambridge MA 02139, photo 14 of 42
2 Family - 2 Units Up/Down at 247 Chestnut St, Cambridge MA 02139, photo 15 of 42
2 Family - 2 Units Up/Down at 247 Chestnut St, Cambridge MA 02139, photo 16 of 42
2 Family - 2 Units Up/Down at 247 Chestnut St, Cambridge MA 02139, photo 17 of 42
2 Family - 2 Units Up/Down at 247 Chestnut St, Cambridge MA 02139, photo 18 of 42
2 Family - 2 Units Up/Down at 247 Chestnut St, Cambridge MA 02139, photo 19 of 42
2 Family - 2 Units Up/Down at 247 Chestnut St, Cambridge MA 02139, photo 20 of 42
2 Family - 2 Units Up/Down at 247 Chestnut St, Cambridge MA 02139, photo 21 of 42
2 Family - 2 Units Up/Down at 247 Chestnut St, Cambridge MA 02139, photo 22 of 42
2 Family - 2 Units Up/Down at 247 Chestnut St, Cambridge MA 02139, photo 23 of 42
2 Family - 2 Units Up/Down at 247 Chestnut St, Cambridge MA 02139, photo 24 of 42
2 Family - 2 Units Up/Down at 247 Chestnut St, Cambridge MA 02139, photo 25 of 42
2 Family - 2 Units Up/Down at 247 Chestnut St, Cambridge MA 02139, photo 26 of 42
2 Family - 2 Units Up/Down at 247 Chestnut St, Cambridge MA 02139, photo 27 of 42
2 Family - 2 Units Up/Down at 247 Chestnut St, Cambridge MA 02139, photo 28 of 42
2 Family - 2 Units Up/Down at 247 Chestnut St, Cambridge MA 02139, photo 29 of 42
2 Family - 2 Units Up/Down at 247 Chestnut St, Cambridge MA 02139, photo 30 of 42
2 Family - 2 Units Up/Down at 247 Chestnut St, Cambridge MA 02139, photo 31 of 42
2 Family - 2 Units Up/Down at 247 Chestnut St, Cambridge MA 02139, photo 32 of 42
2 Family - 2 Units Up/Down at 247 Chestnut St, Cambridge MA 02139, photo 33 of 42
2 Family - 2 Units Up/Down at 247 Chestnut St, Cambridge MA 02139, photo 34 of 42
2 Family - 2 Units Up/Down at 247 Chestnut St, Cambridge MA 02139, photo 35 of 42
2 Family - 2 Units Up/Down at 247 Chestnut St, Cambridge MA 02139, photo 36 of 42
2 Family - 2 Units Up/Down at 247 Chestnut St, Cambridge MA 02139, photo 37 of 42
2 Family - 2 Units Up/Down at 247 Chestnut St, Cambridge MA 02139, photo 38 of 42
2 Family - 2 Units Up/Down at 247 Chestnut St, Cambridge MA 02139, photo 39 of 42
2 Family - 2 Units Up/Down at 247 Chestnut St, Cambridge MA 02139, photo 40 of 42
2 Family - 2 Units Up/Down at 247 Chestnut St, Cambridge MA 02139, photo 41 of 42
2 Family - 2 Units Up/Down at 247 Chestnut St, Cambridge MA 02139, photo 42 of 42
42 photos

$1,600,000

247 Chestnut St, Cambridge MA 02139
Cambridge, MA 02139
Listed by Anne M Kennedy
Bedrooms
3
Bathrooms
3
Living area
2,064 sqft
Year built
1886

About this home

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.

Highlights

Fireplace

Property details

MLS
MLS Property Information Network
MLS #
73593969
Property type
2 Family - 2 Units Up/Down
Subdivision
N/A
Status
Active
Days on market
1
On market date
October 22, 2026
Stories
3
Total bathrooms
3
Garage spaces
N/A
Parking spaces
1
Lot size
0.04 acres
Loading map…

Nearby schools

Within 10 miles. School directory data from the National Center for Education Statistics (NCES), accessed via the Urban Institute Education Data API. Local Score is calculated by INNOVATE Real Estate; where a state rating is shown, it comes from that state's own official school report card.

Elementary
Morse
0.24 mi away · Grades -1-5
Nearest school -- attendance-zone data not available here
5.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
286
Student:teacher ratio
8.2:1
District
Cambridge
Middle
Putnam Avenue Upper School
0.52 mi away · Grades 6-8
Nearest school -- attendance-zone data not available here
5.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
262
Student:teacher ratio
7.5:1
District
Cambridge
High
Cambridge Rindge and Latin
1.02 mi away · Grades 9-12
Nearest school -- attendance-zone data not available here
5.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
1,867
Student:teacher ratio
8.6:1
District
Cambridge

Walkability

Blended score for Cambridge's center, calculated by INNOVATE Real Estate from two sources: the EPA's National Walkability Index (street network, transit, land-use mix) and Google Places amenity data (what's actually reachable on foot from this point). 60% EPA National Walkability Index + 40% nearby-amenity density (Google Places).

90
Highly walkable
out of 100
EPA National Walkability Index
16.7 / 20 -- Most walkable
Google Places amenity density
100 / 100
Restaurants & cafes20
Grocery stores17
Parks20
Schools20
Transit stops20
Pharmacies10

Market position

How this listing compares to current activity in Cambridge, from live MLS data.

On the market 1 days -- 96 fewer days than Cambridge's current average of 97 days.
For reference, the median list price across 1,077 active listings in Cambridge right now is $7,950.

Mortgage calculator

Estimate only - actual rate and payment depend on your lender, credit, and loan program.

$
%
%
Adjust tax / insurance estimates
% / yr
$
/mo
Est. monthly payment
$9,785/mo
$320,000 down
$1,280,000 loan
Principal & interest$8,302
Property tax (est.)$1,333
Home insurance (est.)$150

Similar homes you might like

Data source: Listing information provided by MLS Property Information Network via Trestle/CoreLogic. Last updated 1 days ago.

Information herein deemed reliable but not guaranteed; all measurements, school assignments, HOA fees, taxes, and feature lists are approximate and should be independently verified. Equal Housing Opportunity.