Single Family for Sale: 16 Chestnut Street, Boston, MA 02129

4 beds
3 full, 1 half baths
3,446 sqft
$2,850,000
$2,850,000
16 Chestnut Street, Boston, MA 02129
4 beds
3 full, 1 half baths
3,446 sqft
$2,850,000
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Price:
$2,850,000
$149,000 - 08/19/2026

Type Single Family
Style Italianate
Beds 4
Baths 3 full, 1 half baths
Square Feet 3,446 sqft
Garage Spaces 1
Lot Size 0.03 acres
Year Built 1860

City Boston
County Suffolk
Subdivision Charlestown

MLS 73512592
Status Active
DOM 133 days
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.

Room Features

Dining Room 17.5 x 15.5 Main, First Floor
Family Room 13.8 x 26.5 Basement Floor
Kitchen 22.5 x 30 Main, First Floor
Living Room 17.5 x 15.5 First Floor

Lot & Building Features

Appliances ENERGY STAR Qualified Washer, ENERGY STAR Qualified Dryer, ENERGY STAR Qualified Dishwasher, ENERGY STAR Qualified Refrigerator, Plumbed For Ice Maker, Electric Water Heater, Range Hood, Oven, Freezer, Disposal, Dryer, Washer, Microwave, Dishwasher, Refrigerator, Range
Construction Brick, Frame
Cooling Central Air
Heating Central, Natural Gas
Sewer Public Sewer
Tax Year 2026
Taxes Paid $20,861
Water Public
Foundation Granite, Stone
Exterior Features Outdoor Gas Grill Hookup, Patio - Enclosed, City View(s), Balcony, Deck - Composite, Patio, Deck, Rain Gutters
Interior Features Sauna/Steam/Hot Tub
Roof Rubber, Shingle
Full Baths 3
Half Baths 1
Parking Leased, Detached
Total Rooms 10
Basement Feature Finished, Full
Garage Spaces 1
Fireplaces 2
Waterview Marina, Dock/Mooring, Harbor, Bay, Ocean

Price History of 16 Chestnut Street, Boston, MA

Date Name Price Difference
08/19/2026 Price Adjustment $2,850,000 4.97%
06/16/2026 Price Adjustment $2,999,000 6.25%
05/05/2026 Listing Price $3,199,000 N/A
*Information provided by REWS for your reference only. The accuracy of this information cannot be verified and is not guaranteed.

Comparable Properties Sold Near By

Low
$2,400,000
$711 / sqft
Average
$2,905,859
$855 / sqft
High
$3,525,000
$1,053 / sqft

Address City Zip Beds Baths Price Sq. Ft. $/SQFT Sold Date
This Listing Boston 02129 4 3.5 $2,850,000 3,446 $827 N/A
11 West Cedar Street Boston 02108 5 3.0 $2,650,000 3,600 $736 04/17/2026
102 Myrtle Street Boston 02114 3 3.5 $3,525,000 3,346 $1,053 11/25/2025
16 Boston Ave Somerville 02144 4 4.5 $2,400,000 3,374 $711 02/25/2026
30 Harvard Street Boston 02129 4 4.5 $3,400,000 3,294 $1,032 06/18/2026
18 Greene Street Somerville 02143 4 4.5 $2,406,012 3,265 $737 07/06/2026
419 Main Street Boston 02129 5 3.5 $2,760,000 3,300 $836 08/03/2026
73 Francis Avenue Cambridge 02138 4 3.5 $3,200,000 3,605 $888 07/03/2026

Map of 16 Chestnut Street, Boston, MA

Location Map Street View
Listed by RE/MAX Encore, Zachary Endicott
Photo of AJ Waitt
Direct: 603-437-4447
Office
200 Rockingham Road.
Londonderry, NH 03053
603-437-4447
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16 Chestnut Street (MLS #73512592) is a italianate single family home located in Boston, MA. This single family home is 3,446 sqft and on a lot of 1,348 sqft (or 0.03 acres) with 4 bedrooms, 3.5 baths and is 166 years old. This property was listed on 05/05/2026 and has been priced for sale at $2,850,000.

The 4 bedroom single family home at 30 Harvard Street in Boston is nearby and sold for $3,400,000 on 06/18/2026. Another nearby 5 bedroom single family home, 419 Main Street in Boston sold for $2,760,000 on 08/03/2026.

Nearby zip codes are 02109, 02113, 02114, 02116 and 02136. This property neighbors other cities such as Cambridge and Marlborough.

MLS PIN

Listing Last updated . Some properties which appear for sale on this web site may subsequently have sold or may no longer be available. Walk Score map and data provided by Walk Score. Google map provided by Google. Bing map provided by Microsoft Corporation.

All information provided is deemed reliable but is not guaranteed and should be independently verified.

Listing information courtesy of: RE/MAX Encore

The property listing data and information set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information 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. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information set forth herein.