16 Chestnut Street Boston — Photo 1 of 39
Recent Drop: $349,000
$2,850,000
Investment Analysis — 16 Chestnut Street
Boston, MA 02129 — Charlestown
Based on HUD Small Area Fair Market Rent for Boston-Cambridge-Quincy, MA-NH HUD Metro FMR Area, a 4-bedroom in 02129 carries an estimated $5,320/mo in gross rent — about a 0.97% cap rate and $27,657/yr in estimated NOI at the $2,850,000 list price. Adjust every assumption in the calculator below.
Beds
4
Baths
3.5
SqFt
3,446
Style
Single Family
Built
1860
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.
ADU Potential
Massachusetts allows one accessory dwelling unit by right in single-family zoning districts statewide (M.G.L. c. 40A §3; 760 CMR 71.00, effective Feb 2025). Estimated maximum ADU size for this property: 900 sq ft (the lesser of 900 sq ft or half the 3,446 sq ft principal dwelling). Lot size: 1,348 sq ft.
Based on listing data, which indicates the property type — not the zoning district. Local dimensional, septic (Title 5), and historic-district requirements still apply. Not legal advice — verify with the municipality.
Estimates — not financial advice
These figures are illustrative estimates for informational purposes only — not an appraisal, valuation, or guarantee of rent, income, or returns, and not financial, tax, or investment advice. Rent is either the figure reported on the MLS listing — in-place rent that may differ from market and is not verified against the actual leases — or, where the listing reports none, an estimate from HUD Small Area Fair Market Rents, a government benchmark that may differ from actual market rent. Each figure is labelled with its source. Cap rate, NOI, and returns depend on the assumptions shown, which you can change. MLS and other third-party data may be inaccurate or out of date. Verify all figures independently and consult your own financial, tax, and legal advisors before making any investment decision.
Property Details
Financials
Parking
Interior Specifications
Climate & Utilities
Building & Exterior
Property & Lot
Amenities & Appliances
Electric Water Heater • Range • Dishwasher • Disposal • Microwave • Refrigerator • Freezer • Washer • Dryer • ENERGY STAR Qualified Refrigerator • ENERGY STAR Qualified Dryer • ENERGY STAR Qualified Dishwasher • ENERGY STAR Qualified Washer • Range Hood • Oven • Plumbed For Ice Maker
Geography
Floorplan Breakdown
Structural Layout
Living Room
Lvl First17.5 x 15.5
Closet/Cabinets - Custom Built, Flooring - Hardwood, High Speed Internet Hookup, Open Floorplan, Recessed Lighting, Remodeled, Wainscoting, Lighting - Sconce, Lighting - Overhead, Crown Molding, Decorative Molding, Flooring - Engineered Hardwood
Dining Room
Lvl Main,First17.5 x 15.5
Bathroom - Half, Flooring - Hardwood, Cable Hookup, High Speed Internet Hookup, Open Floorplan, Recessed Lighting, Remodeled, Wainscoting, Wine Chiller, Lighting - Pendant, Lighting - Overhead, Crown Molding, Decorative Molding, Flooring - Engineered Hardwood
Kitchen
Lvl Main,First22.5 x 30
Closet/Cabinets - Custom Built, Flooring - Hardwood, Window(s) - Bay/Bow/Box, Dining Area, Pantry, Cabinets - Upgraded, Exterior Access, Open Floorplan, Recessed Lighting, Remodeled, Slider, Stainless Steel Appliances, Sunken, Lighting - Sconce, Lighting - Overhead, Crown Molding, Breezeway, Decorative Molding, Flooring - Engineered Hardwood
Family Room
Lvl Basement13.8 x 26.5
Bathroom - Full, Closet, Open Floorplan, Recessed Lighting, Lighting - Overhead, Crown Molding, Decorative Molding, Window Seat
Property History
$2,850,000
Was $2,999,000
Aug 19, 2026
MLS® 73512592
$2,999,000
Was $3,199,000
Jun 16, 2026
MLS® 73512592
$3,199,000
May 5, 2026
MLS® 73512592
Listing Agent: Zachary Endicott
Listing Office: RE/MAX Encore
MLS® Number: 73512592
