Active

130 Days on market

16 Chestnut Street Boston — Photo 1 of 39

Recent Drop: $349,000

$3,199,000

$2,850,000

16 Chestnut Street, Boston, MA 02129

Boston, MA 02129 — Charlestown

Beds

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)$600/sqft

38% AboveMarket Average

* Analysis is based on 24 actively listed and recently sold comparable properties strictly within Boston, MA.

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 First

17.5 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,First

17.5 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,First

22.5 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 Basement

13.8 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.

Full Boston, MA market report ZIP 02129 market data

Listing Provided By

Listing Agent: Zachary Endicott

Listing Office: RE/MAX Encore

MLS® Number: 73512592