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16 Chestnut Street, Boston MA 02129
16 Chestnut Street, Boston MA 02129
Massachusetts>Boston>Thompson Square - Bunker Hill

16 Chestnut StreetBoston, MA 02129

For Sale

$2,999,000

Smart Buyer Rebate $14,995

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.

Listed by Tina Endicott

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RE/MAX Encore

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978-376-4908

Listed by Zachary Endicott

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RE/MAX Encore

Last updated June 20, 2026

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Source: MLSPin #73512592

Listing Facts

  • TypeSingle-family
  • NeighborhoodThompson Square - Bunker Hill
  • Bedrooms4
  • Bathrooms4
  • Days on Prevu88
  • Taxes$20,861/year
  • Size3,446 sqft
  • Price per sqft$870

Amenities

  • Dishwasher
  • Private Outdoor Space
  • Washer/Dryer
  • Air Conditioning
  • Parking

Location

Mortgage Calculator

Listing History

06/16/2026
Price Decreased
$2,999,000
05/05/2026
Listed by RE/MAX Encore
$3,199,000

Property Details for 16 Chestnut Street

Exterior

Construction

  • Property Attached: Yes
  • Roof: Shingle, Rubber
  • Year Built: 1860
  • Year Built Details: Renovated Since
  • Architectural Style: Italianate
  • Construction Materials: Frame, Brick
  • Exterior Features: Deck, Deck - Composite, Patio, Patio - Enclosed, Balcony, Rain Gutters, City View(s), Outdoor Gas Grill Hookup

Features

  • Patio And Porch Features: Deck, Deck - Composite, Patio, Enclosed
  • View: City

Measurements

  • Building Area Total: 3,446
  • Building Area Units: Square Feet
  • Lot Features: Level
  • Lot Size Acres: 0.03
  • Lot Size Area: 0
  • Lot Size Square Feet: 1,348
  • Lot Size Units: Acres

Financial

Taxes

  • Parcel Number: 0203466000,3356428
  • Tax Annual Amount: $20,861.00
  • Tax Assessed Value: $1,682,400.00
  • Tax Year: 2026

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
  • Fireplace Features: Living Room
  • Fireplace: Yes
  • Fireplaces Total: 2
  • Flooring: Wood, Tile, Engineered Hardwood
  • Interior Features: Sauna/Steam/Hot Tub

Measurements

  • Living Area: 3,446
  • Living Area Source: Public Record

Rooms

  • Basement: Full, Finished
  • Bathrooms Full: 3
  • Bathrooms Half: 1
  • Bathrooms Total Integer: 4
  • Bedrooms Total: 4
  • Rooms Total: 10

Other

Environmental

  • Green Energy Efficient: Thermostat

General

  • Exclusions: Stagers Furniture

Location

  • Subdivision Name: Charlestown

Parking

Parking

  • Covered Spaces: 1
  • Garage Spaces: 1
  • Garage: Yes
  • Parking Features: Detached, Leased
  • Parking Total: 1

Utilities

Equipment

  • Cooling: Central Air
  • Has Cooling: Yes
  • Electric: Circuit Breakers
  • Heating: Central, Natural Gas
  • Has Heating: Yes
  • Laundry Features: Electric Dryer Hookup, Washer Hookup
  • Sewer: Public Sewer
  • Utilities: For Gas Range, For Gas Oven, For Electric Dryer, Washer Hookup, Icemaker Connection, Outdoor Gas Grill Hookup
  • Water Source: Public

Frequently Asked Questions

How many bedrooms and bathrooms does this single-family home have?

There are 4 bedrooms and 4 bathrooms in this single-family home at 16 Chestnut Street.

Does this single-family home have parking?

Yes, there is 1 parking space available for 16 Chestnut Street.

What are the annual taxes for 16 Chestnut Street?

Annual taxes for this single-family home are estimated at $20,861.

How does 16 Chestnut Street compare to other single-family homes in Thompson Square - Bunker Hill?

This single-family home is listed 21% above the average price for single-family homes in Thompson Square - Bunker Hill and has been on the market for 35 more days than the typical home in this area.

What is the square footage on this single-family home?

According to the MLS, this listing is 3,446 sqft.

16 Chestnut Street is a 4-bedroom, 4-bath single-family home for sale in Boston MA 02129. Listed on Prevu for 88 days at $2,999,000. This includes a recent price decrease of $200,000. This property features 3,446 square feet of living space, located in Thompson Square - Bunker Hill. The median listing price for single-family homes in this area is $799,000. The home offers private outdoor space, dishwasher, air conditioning, parking, and washer/dryer. Browse more single-family home listings in Boston.

The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors, landlords and public records, and were compiled by MLS Property Information Network, Inc. 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, leasing or renting 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, leasing or renting. MLS Property Information Network, Inc. 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.

Full MLS Disclaimers

Rebate estimate is indicative only and based on listing price and estimated buyer's agent commission paid by owner, if applicable. Final rebates are subject to Terms of Use and may vary due to final negotiated transaction terms.