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16 Chestnut St, Boston, MA, 02129

4beds
4baths
3,446sqft
$2,999,000
$870price/sqft
$19,365/moest. monthly cost
$774,600/yrincome needed

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.

Getting Around

91
WalkingWalker's Paradise
82
TransitExcellent Transit
84
BikeVery Bikeable

Schools

4/10
8/10
3/10
Charlestown High SchoolGrades 7-120.4 mi

Construction

Condition

  • Year built: 1860

Materials

  • Foundation: Stone,Granite
  • Roof: Shingle,Rubber
  • Construction materials: Frame,Brick

Type & Style

  • Home type: SingleFamily
  • Architectural style: Italianate
  • Property subType: Single Family Residence

Interior

Appliances

  • Appliances included: 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
  • Laundry features: Electric Dryer Hookup,Washer Hookup

Basement

  • Has basement: Yes
  • Basement: Full,Finished

Bedrooms & Bathrooms

  • Bedrooms: 4
  • Bathrooms: 4
  • Full bathrooms: 3
  • 1/2 bathrooms: 1

Dining Room

  • Features: 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
  • Level: Main,First
  • Area: 271.25

Family Room

  • Features: Bathroom - Full, Closet, Open Floorplan, Recessed Lighting, Lighting - Overhead, Crown Molding, Decorative Molding, Window Seat
  • Level: Basement
  • Area: 365.7

Features

  • Sauna/Steam/Hot Tub
  • Flooring: Wood,Tile,Engineered Hardwood
  • Number of fireplaces: 2
  • Fireplace features: Living Room
  • Fireplace: Yes
  • Finished area below ground: 883
  • Finished area above ground: 2,563

Heating & Cooling

  • Heating features: Central,Natural Gas
  • Cooling features: Central Air

Interior Area

  • Total structure area: 3,446
  • Total interior livable area: 3,446 sqft

Kitchen

  • Features: 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
  • Level: Main,First
  • Area: 675

Living Room

  • Features: 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
  • Level: First
  • Area: 271.25

Property

Details

  • Parcel number: 0203466000,1280325
  • Attached to another structure: Yes
  • Zoning: R1
  • Exclusions: Stagers Furniture

Features

  • Patio & porch: Deck,Deck - Composite,Patio,Enclosed
  • Exterior features: Deck,Deck - Composite,Patio,Patio - Enclosed,Balcony,Rain Gutters,City View(s),Outdoor Gas Grill Hookup
  • Has view: Yes
  • View description: City,Water,Bay,Dock/Mooring,Harbor,Marina,Ocean
  • Has water view: Yes
  • Water view: Bay,Dock/Mooring,Harbor,Marina,Ocean,Water

Lot

  • Lot size: 1,348 sqft
  • Features: Level

Parking

  • Total spaces: 1
  • Parking features: Detached,Leased
  • Has garage: Yes
  • Attached garage spaces: 1
  • Covered spaces: 1

Climate Risk is Financial Risk

Every home has a financial story beyond the listing price. Below, you’ll see the climate risks that could affect this property — and in Bills & Affordability, how those risks may influence repairs, insurance, utilities, and long-term value.

Biggest Threats for This Home

  • Heat Wave
    Heat WaveModerate
  • Tsunami
    TsunamiInsufficient Data

How This Home’s Risks Compare

Heat Wave
Tsunami

FEMA Declared Disasters Across Massachusetts Counties

Hurricane

Understanding the Costs

Financial advisors generally recommend spending no more than 30% of your gross household income on housing costs. In practice, many households stretch to 35% or beyond — especially in high-cost markets.

Estimated Costs Today

MonthlyAnnual
Mortgage $15,164$181,968
Home Insurance *$620$7,440
Property Taxes $2,902$34,824
Electricity $679$8,154
Total$19,365$232,380
*Does not include cost of any FAIR Plan premiums

Income You'd Need if You Spent...

35% on housing$663,942/yr
40% on housing$580,950/yr
45% on housing$516,400/yr

Massachusetts FAIR Plan Programs

Massachusetts Property Insurance Underwriting Association

Covered
WildfireWildfire
HailHail
WindWind
Visit Website →
Current Policies
Residential: 213,928Commercial: 230
Total Premiums$400.85M
Total Exposure$115.57B

How Costs Could Change Over Time

Climate risk is quickly impacting all of the major home ownership costs. Adjust the growth rates and percentage of income spent on housing below to see how your housing costs could change over the next 10 years — and what income you'd need to keep up.

Insurance Growth Rate5-year average: 7.3%
7.3%
0%30.0%
Electricity Growth Rate10-year average: 7.9%
7.9%
0%15.0%
Property Taxes Growth Rate2-year average: -0.5%
-0.5%
0%15.0%
Income Spent on Housing
30%
30%45%

Comparing Against the Market

Price Per Sq Ft

$870This listing

vs Other Active Listings

Avg $/sqft

ZIP 02129$606
Suffolk County$574

vs Homes Sold Last Month

Median $/sqft

ZIP 02129$833
Suffolk County$453

Current Market Trends

Median Price Per Square Foot

The median price per square foot of homes sold in this area each month. Compare this to this listing's price per square foot to gauge whether the home is priced in line with recent sales.

Historicals for This Listing

Zestimate History ($/sqft)

Price History

DateEventPrice
2026-05-05Listed for sale$3,199,000
2025-05-29Sold$1,375,000
2025-04-07Contingent$1,699,000
2025-04-02Listed for sale$1,699,000
2025-02-24Listing removed$1,699,000
2025-01-12Price change$1,699,000
2024-12-10Price change$1,799,000
2024-11-19Listed for sale$1,999,000

For Sale by Agent

AgentZachary Endicott
BrokerageRE/MAX Encore

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