Single Family Residence at 16 Chestnut Street, Boston MA 02129, Boston
Single Family Residence at 16 Chestnut Street, Boston MA 02129, Boston, photo 2 of 39
Single Family Residence at 16 Chestnut Street, Boston MA 02129, Boston, photo 3 of 39
Single Family Residence at 16 Chestnut Street, Boston MA 02129, Boston, photo 4 of 39
Single Family Residence at 16 Chestnut Street, Boston MA 02129, Boston, photo 5 of 39
Single Family Residence at 16 Chestnut Street, Boston MA 02129, Boston, photo 6 of 39
Single Family Residence at 16 Chestnut Street, Boston MA 02129, Boston, photo 7 of 39
Single Family Residence at 16 Chestnut Street, Boston MA 02129, Boston, photo 8 of 39
Single Family Residence at 16 Chestnut Street, Boston MA 02129, Boston, photo 9 of 39
Single Family Residence at 16 Chestnut Street, Boston MA 02129, Boston, photo 10 of 39
Single Family Residence at 16 Chestnut Street, Boston MA 02129, Boston, photo 11 of 39
Single Family Residence at 16 Chestnut Street, Boston MA 02129, Boston, photo 12 of 39
Single Family Residence at 16 Chestnut Street, Boston MA 02129, Boston, photo 13 of 39
Single Family Residence at 16 Chestnut Street, Boston MA 02129, Boston, photo 14 of 39
Single Family Residence at 16 Chestnut Street, Boston MA 02129, Boston, photo 15 of 39
Single Family Residence at 16 Chestnut Street, Boston MA 02129, Boston, photo 16 of 39
Single Family Residence at 16 Chestnut Street, Boston MA 02129, Boston, photo 17 of 39
Single Family Residence at 16 Chestnut Street, Boston MA 02129, Boston, photo 18 of 39
Single Family Residence at 16 Chestnut Street, Boston MA 02129, Boston, photo 19 of 39
Single Family Residence at 16 Chestnut Street, Boston MA 02129, Boston, photo 20 of 39
Single Family Residence at 16 Chestnut Street, Boston MA 02129, Boston, photo 21 of 39
Single Family Residence at 16 Chestnut Street, Boston MA 02129, Boston, photo 22 of 39
Single Family Residence at 16 Chestnut Street, Boston MA 02129, Boston, photo 23 of 39
Single Family Residence at 16 Chestnut Street, Boston MA 02129, Boston, photo 24 of 39
Single Family Residence at 16 Chestnut Street, Boston MA 02129, Boston, photo 25 of 39
Single Family Residence at 16 Chestnut Street, Boston MA 02129, Boston, photo 26 of 39
Single Family Residence at 16 Chestnut Street, Boston MA 02129, Boston, photo 27 of 39
Single Family Residence at 16 Chestnut Street, Boston MA 02129, Boston, photo 28 of 39
Single Family Residence at 16 Chestnut Street, Boston MA 02129, Boston, photo 29 of 39
Single Family Residence at 16 Chestnut Street, Boston MA 02129, Boston, photo 30 of 39
Single Family Residence at 16 Chestnut Street, Boston MA 02129, Boston, photo 31 of 39
Single Family Residence at 16 Chestnut Street, Boston MA 02129, Boston, photo 32 of 39
Single Family Residence at 16 Chestnut Street, Boston MA 02129, Boston, photo 33 of 39
Single Family Residence at 16 Chestnut Street, Boston MA 02129, Boston, photo 34 of 39
Single Family Residence at 16 Chestnut Street, Boston MA 02129, Boston, photo 35 of 39
Single Family Residence at 16 Chestnut Street, Boston MA 02129, Boston, photo 36 of 39
Single Family Residence at 16 Chestnut Street, Boston MA 02129, Boston, photo 37 of 39
Single Family Residence at 16 Chestnut Street, Boston MA 02129, Boston, photo 38 of 39
Single Family Residence at 16 Chestnut Street, Boston MA 02129, Boston, photo 39 of 39
39 photos

$2,850,000

16 Chestnut Street, Boston MA 02129
Boston, MA 02129
Listed by Zachary Endicott
Bedrooms
4
Bathrooms
3.5
Living area
3,446 sqft
Year built
1860

About this home

Perfectly positioned between the Training Field and the Charlestown Navy Yard, this newly renovated single-family brownstone offers four levels of luxury living in one of the neighborhood’s most coveted locations. The home features 4 bedrooms plus a large finished lower level with dedicated storage—ideal for a media room, gym, or playroom. A stunning chef’s kitchen with marble surfaces and Thermador appliances opens to a private patio with a gas grill hookup, perfect for indoor-outdoor entertaining.The primary suite is a true retreat, complete with a steam shower, gas stove, and a dedicated sitting area that opens to a private balcony with breathtaking city views. A second-level south-facing roof deck with a gas fire-pit hookup provides exceptional outdoor living. Beautiful exposed brick, refined finishes, and thoughtful craftsmanship are showcased throughout. This home combines new construction, period detail, historic surroundings, and unmatched Charlestown Walkability.

Highlights

ViewFireplace

Property details

MLS #
73512592
Property type
Single Family Residence
Subdivision
Charlestown
Status
Active
Days on market
156
On market date
May 5, 2026
Stories
N/A
Total bathrooms
3.5
Garage spaces
1
Parking spaces
1
Lot size
0.03 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 (e.g. NC Dept. of Public Instruction, SC Report Card).

Elementary
Harvard-Kent
0.19 mi away · Grades -1-6
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
347
Student:teacher ratio
8.9:1
District
Boston
Middle
Cambridge Street Upper School
1.66 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
279
Student:teacher ratio
7.5:1
District
Cambridge
High
Charlestown High
0.43 mi away · Grades 7-12
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
821
Student:teacher ratio
9.8:1
District
Boston

Walkability

Blended score for Boston'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).

93
Highly walkable
out of 100
EPA National Walkability Index
17.7 / 20 -- Most walkable
Google Places amenity density
100 / 100
Restaurants & cafes20
Grocery stores20
Parks20
Schools20
Transit stops20
Pharmacies14

Market position

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

On the market 156 days -- 38 more days than Boston's current average of 118 days.
For reference, the median list price across 8,536 active listings in Boston right now is $59,000.

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
$17,313/mo
$570,000 down
$2,280,000 loan
Principal & interest$14,788
Property tax (est.)$2,375
Home insurance (est.)$150

Similar homes you might like

Data source: Listing information provided by MLS Property Information Network via Trestle/CoreLogic. Last updated 7 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.