Active
107 Days on market
16 Chestnut Street Boston — Photo 1 of 39
Recent Drop: $349,000
$3,199,000$2,850,000
$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.
Market Value Analysis
This Property
Size (SqFt) →Price →This Property$827/sqft
Local Avg (Boston)$568/sqft
46% AboveMarket Average
* Analysis is based on 24 actively listed and recently sold comparable properties strictly within Boston, MA.
Property Details
Financials
Original Price$3,199,000
Annual Taxes$20,861
Parking
Garage1
Off-Street1
Interior Specifications
Total Rooms10
Fireplaces2
FlooringWood, Tile, Engineered Hardwood
BasementFull, Finished
Climate & Utilities
HeatingCentral, Natural Gas
CoolingCentral Air
WaterPublic
SewerPublic Sewer
Building & Exterior
ConstructionFrame, Brick
RoofShingle, Rubber
FoundationStone, Granite
ZoningR1
Property & Lot
Acres0.03
SqFt Lot1,348
Lot FeaturesLevel
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
First
Living Room
Basement
Family Room
Main,First
Dining RoomKitchen
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
Price Drop
$2,850,000
Was $2,999,000
Aug 19, 2026
MLS® 73512592
Price Drop
$2,999,000
Was $3,199,000
Jun 16, 2026
MLS® 73512592
Listed
$3,199,000
May 5, 2026
MLS® 73512592
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
2,527 housing units permitted in the last 12 months (+37% vs the prior 12 months) — 2,269 in 5+ unit buildings
U.S. Census Bureau, Building Permits Survey (through Jun '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 Provided By
Listing Agent: Zachary Endicott
Listing Office: RE/MAX Encore
MLS® Number: 73512592
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