16 Chestnut Street Boston — Photo 1 of 39
Recent Drop: $149,000
$2,850,000
16 Chestnut Street, Boston, MA 02129
Boston, MA 02129 — Charlestown
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.
Key facts
It was listed on May 5, 2026. The price has come down from an original $3,199,000 to $2,850,000 across 2 changes, most recently on August 19, 2026. The annual property taxes are $20,861 (2026 tax year). It sits on a 0.03-acre (1,348 sq ft) lot.
Open Houses
Market Value Analysis
* Analysis is based on 24 actively listed and recently sold comparable properties strictly within Boston, MA.
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 Main,First13.8 x 26.5
Bathroom - Half, Closet, Closet/Cabinets - Custom Built, Flooring - Hardwood, Flooring - Wood, Cable Hookup, Open Floorplan, Recessed Lighting, Remodeled, Wainscoting, Lighting - Sconce, Lighting - Pendant, Lighting - Overhead, Crown Molding, Decorative Molding, Flooring - Engineered Hardwood
Primary Bedroom
Lvl Third20 x 26
Bathroom - Full, Bathroom - Double Vanity/Sink, Wood / Coal / Pellet Stove, Skylight, Cathedral Ceiling(s), Ceiling Fan(s), Vaulted Ceiling(s), Walk-In Closet(s), Closet, Closet/Cabinets - Custom Built, Flooring - Hardwood, Flooring - Wood, Window(s) - Bay/Bow/Box, Balcony / Deck, Balcony - Exterior, Double Vanity, Exterior Access, Recessed Lighting, Steam / Sauna, Wainscoting, Lighting - Sconce, Lighting - Overhead, Decorative Molding, Pocket Door, Flooring - Engineered Hardwood, Window Seat
Bedroom 2
Lvl Second12 x 12
Bedroom 3
Lvl Second13.5 x 13.5
Walk-In Closet(s), Closet, Closet/Cabinets - Custom Built, Flooring - Hardwood, Flooring - Wood, Recessed Lighting, Wainscoting, Lighting - Sconce, Lighting - Overhead, Crown Molding, Decorative Molding, Flooring - Engineered Hardwood
Bedroom 4
Lvl Second9 x 14.6
Closet, Closet/Cabinets - Custom Built, Flooring - Wood, Balcony / Deck, Exterior Access, Recessed Lighting, Slider, Sunken, Lighting - Overhead, Archway, Half Vaulted Ceiling(s)
Bathroom 1
Lvl Basement6.5 x 7
Bathroom - 3/4, Bathroom - Tiled With Shower Stall, Ceiling Fan(s), Flooring - Laminate, Flooring - Wood, Countertops - Stone/Granite/Solid, Cabinets - Upgraded, Recessed Lighting, Lighting - Sconce, Lighting - Overhead
Bathroom 2
Lvl Second18 x 11
Bathroom - Full, Bathroom - Double Vanity/Sink, Bathroom - Tiled With Tub, Bathroom - With Tub, Closet/Cabinets - Custom Built, Flooring - Stone/Ceramic Tile, Countertops - Stone/Granite/Solid, Cabinets - Upgraded, Double Vanity, Lighting - Sconce, Lighting - Overhead, Pocket Door
Bathroom 3
Lvl Third10 x 6
Bathroom - 3/4, Bathroom - Double Vanity/Sink, Bathroom - Tiled With Shower Stall, Cathedral Ceiling(s), Vaulted Ceiling(s), Closet/Cabinets - Custom Built, Flooring - Stone/Ceramic Tile, Window(s) - Bay/Bow/Box, Countertops - Stone/Granite/Solid, Recessed Lighting, Remodeled, Steam / Sauna, Lighting - Overhead, Half Vaulted Ceiling(s)
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
Questions about this home
When was 16 Chestnut Street, Boston listed?
16 Chestnut Street, Boston was listed on May 5, 2026.
Has the price of 16 Chestnut Street, Boston changed?
The price has come down from an original $3,199,000 to $2,850,000 across 2 changes, most recently on August 19, 2026.
What are the property taxes for 16 Chestnut Street, Boston?
The annual property taxes for 16 Chestnut Street, Boston are $20,861 (2026 tax year).
How big is the lot at 16 Chestnut Street, Boston?
16 Chestnut Street, Boston sits on a 0.03-acre (1,348 sq ft) lot.
What is the status of 16 Chestnut Street, Boston?
16 Chestnut Street, Boston is actively listed for sale.
Population
20,032
U.S. Census Bureau, ACS 2024 5-Year Estimates (B01003)
Median Household Income
$157K
U.S. Census Bureau, ACS 2024 5-Year Estimates (B19013)
Renter-Occupied Homes
49.5%
U.S. Census Bureau, ACS 2024 5-Year Estimates (B25003)
New Construction Permits — Suffolk County
2,337 housing units permitted in the last 12 months (+13% vs the prior 12 months) — 2,062 in 5+ unit buildings
U.S. Census Bureau, Building Permits Survey (through Jul '26)
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.
Listing Agent: Zachary Endicott
Listing Office: RE/MAX Encore
MLS® Number: 73512592
