4 beds3,446 sqft$827/sqft
16 Chestnut St, Boston, MA 02129
Est: $16,225/moGet pre-approved

Description

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....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.
LISTING UPDATED: 08/23/2026 04:09 AM

  1. Listed by Zachary Endicott • RE/MAX Encore

Property Details for 16 Chestnut Street

Status
MLS #
73512592
Days on Market
113
Taxes
$20,861 / year
HOA Fees
-
Property Type
MLS Type
Single Family / Attached
Year Built
1860
Town
Boston
MLS Area
Charlestown
Area
MA-Boston-Charlestown, MA-Boston
Architectural Style
Italianate
Style
Italianate
Garage Spaces
1
Open Parking Spaces
.00
Parking Spaces Total
1

Open Houses

Wednesday, Aug 26th4:30 PM - 6:00 PM

Location

Listing Courtesy of RE/MAX Encore, Zachary Endicott
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Building Information for 16 Chestnut Street

Stories-Year Built1860Building Size-Lot Size0.03 AC / 1,348 SF

Payment Calculator

$16,225 per month

30 year fixed, 6.55% Interest

Principal and Interest

$14,486

Property Taxes

$1,738

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

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Property Information for 16 Chestnut Street

General Details
Property Details
  • Building Area Units: Square Feet
  • Living Area: 3446.0
  • SqFt with Basement: Yes
  • Property Attached: Yes
  • Single Family Type: Attached
  • Waterfront: No
  • Water View: Yes
  • Year Built Details: Renovated Since
  • Year Built Source: Public Records
Location/School
  • Neighborhood: Charlestown
Features
Interior Features
  • 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
  • Basement Features: Full, Finished
  • Num of Baths: 4.0
  • Num of Full Baths: 3
  • Num of Half Baths: 1
  • Bathrooms Total Decimal: 3.50
  • Bathrooms Total Integer: 4
  • FireplaceFeatures: Living Room
  • FireplaceYN: Yes
  • Fireplaces: 2
  • Flooring: Wood, Tile, Engineered Hardwood
  • Interior Features: Sauna/Steam/Hot Tub
  • Interior Features: Sauna/Steam/Hot Tub
  • Laundry Features: Electric Dryer Hookup, Washer Hookup
  • SpaYN: No
Exterior Features
  • Construction: Frame, Brick
  • Exterior Features: Deck, Deck - Composite, Patio, Patio - Enclosed, Balcony, Rain Gutters, City View(s), Outdoor Gas Grill Hookup
  • Exterior Features: City View(s), Balcony, Deck, Deck - Composite, Patio, Porch - Enclosed
  • Lot Description: Level
  • Patio And Porch Features: Deck, Deck - Composite, Patio, Enclosed
  • Roof Material: Shingle, Rubber
  • View: City
  • View: Yes
  • Waterview Features: Bay, Dock/Mooring, Harbor, Marina, Ocean
Parking Features
  • Attached Garage: No
  • Carport: No
  • Covered Spaces: 1.00
  • Garage: Yes
  • Garage Parking: Detached, Leased
  • Parking Features: Detached, Leased
  • Parking Features: Leased
Utilities
  • Cooling: Central Air
  • Cooling: Yes
  • Electric: Circuit Breakers
  • Green Energy Efficient: Thermostat
  • Heating: Central, Natural Gas
  • Heating: Yes
  • Sewer: City/Town Sewer
  • Utility Connections: for Gas Range, for Gas Oven, for Electric Dryer, Washer Hookup, Icemaker Connection, Outdoor Gas Grill Hookup
  • Water: Public
Room Information
Dining Room
  • Dining Room Area: 271.25
  • 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
  • Dining Room Length: 17.5
  • Dining Room Level: Main,First
  • Dining Room Width: 15.5
Family Room
  • Family Room Area: 365.7
  • Family Room Features: Bathroom - Full,Closet,Open Floorplan,Recessed Lighting,Lighting - Overhead,Crown Molding,Decorative Molding,Window Seat
  • Family Room Length: 13.8
  • Family Room Level: Basement
  • Family Room Width: 26.5
Kitchen
  • Kitchen Area: 675.0
  • 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
  • Kitchen Length: 22.5
  • Kitchen Level: Main,First
  • Kitchen Width: 30.0
Living Room
  • Room Living Room Area: 271.25
  • Room 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
  • Room Living Room Length: 17.5
  • Room Living Room Level: First
  • Room Living Room Width: 15.5
Property Information
Property Info
  • Year Round: Yes
  • Farm Land Area Units: Square Feet
  • WARRANTY: No
  • Lot Size Units: Acres
  • Road Surface Type: Paved
Tax Information
  • Tax ID: 0203466000,3356428
  • Assessments: $1,682,400
  • Book: 71456
  • Tax Year: 2026
  • Zoning: R1
Building / Association Information
Living Characteristics
  • Beds Total: 4
Other Building Characteristics
  • Foundation: Stone, Granite
  • Cooling Zones: 3
  • Heat Zones: 3
Complex & Association Information
  • Adult Community: No

Property History for 16 Chestnut Street

DateEvent & SourcePriceAppreciation
Aug 19, 2026

Price Change

MLS PIN #73512592

$2,850,000
Jun 16, 2026

Price Change

MLS PIN #73512592

$2,999,000
May 5, 2026

Listed (Active)

MLS PIN #73512592

$3,199,000
DateEvent & SourcePrice
08/19/2026

Price Change

MLS PIN #73512592

$2,850,000
06/16/2026

Price Change

MLS PIN #73512592

$2,999,000
05/05/2026

Listed (Active)

MLS PIN #73512592

$3,199,000

For completeness, we often displays two records for one sale: the MLS record and the public record.

Public Records for 16 Chestnut Street

Taxable ValueLand$647,500Additions$939,600Total$1,587,100
Tax Record2025$18,379 ($1,532 / month)
Home Facts
Beds4Baths1.5Total Finished SqFt2,090 SqFtAbove Grade Finished SqFt2,090 SqFtStories2Lot Size1,348 SqFtStyleSingle Family ResidenceYear Built1860Year Renovated1860ZoningR1CountySUFFOLKAPNCHAR W:02 P:03466 S:000

Schools near 16 Chestnut Street

This home is within Boston Public Schools.
Rating
School
Type
Grades
Distance
Public - PK to 6
Public - PK to 8
Public - 7 to 12
Public - PK to 8
Rating
School
Distance
Harvard-Kent Elementary School
PublicPK to 6

Warren-Prescott K-8 School
PublicPK to 8

Charlestown High School
Public7 to 12

Eliot K-8 Innovation School
PublicPK to 8

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

Charlestown
Charlestown
A historic city neighborhood with small-town sensibility. A historic Boston neighborhood nestled between the Mystic and Charles Rivers. Families love Charlestown because it feels like a quaint New England town within Boston, the city’s culture and businesses just a bridge away.

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16 Chestnut Street is a single family home for sale in Boston, MA 02129. This property was listed for sale on May 5, 2026 by RE/MAX Encore, it's currently listed at $2,850,000. It has been on the market for a total of 113 days and was last sold on May 29, 2025. This listing's school district is Boston Public Schools. Nearby schools include Harvard-Kent Elementary School, Warren-Prescott K-8 School and Charlestown High School. 16 Chestnut Street is a 4-bed, 4-bath, 3,446 sqft single family home built in 1860.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of any information, descriptions or measurements (including square footage measurements and property condition), such should be independently verified through appropriate means, including, but not limited to, in person inspection and public records, and Compass International Holdings, its subsidiaries, affiliates and independently owned and operated franchisees, and their affiliated agents and associated third parties expressly disclaim any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the seller's discretion. No financial or legal advice provided. Equal Housing Opportunity.

Listing Courtesy of RE/MAX Encore, Zachary Endicott

The property listing data and information, or the images, set forth herein were provided to MLS Property Information Network, Inc., Martha's Vineyard MLS, CCIMLS, Link MLS, and Berkshire County Board of REALTORS from third party sources, including sellers, lessors and public records, and were compiled by MLS Property Information Network, Inc., Martha's Vineyard MLS, CCIMLS, Link MLS, and Berkshire County Board of REALTORS. The property listing data and information, and the images, are for the personal, non-commercial use of consumers having a good faith interest in purchasing or leasing listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing or leasing. MLS Property Information Network, Inc., Martha's Vineyard MLS, CCIMLS, Link MLS, and Berkshire County Board of REALTORS and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the images, set forth herein.