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16 Chestnut Street, Boston MA 02129

Boston, MA 02129 • Charlestown
$3,199,000
$2,850,000
Est. $16,350/month
4
Beds
3.5
Baths
3,446
Sq Ft
$827
Price/Sq Ft
0.03
Acres
1860
Year Built
1
Garage Space
Single Family Residence
Type
121
Days on Market
For Sale Price Drop -$349,000 Listed May 5, 2026 • MLS# 73512592 Copied! • Updated Aug 23, 2026

Track this home for price, status, and open-house alerts.

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.

BMN Estimate

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Recently Sold Nearby

Property History

Market Insights

2
Price Changes
10.9%
Price Range

Property Timeline

↓
Price Reduced
Aug 19, 2026
$2,850,000 $149,000 (-4.97%)
From $2,999,000 to $2,850,000 (-5.0%)
↓
Price Reduced
Jun 16, 2026
$2,999,000 $200,000 (-6.25%)
From $3,199,000 to $2,999,000 (-6.2%)
🏠
Listed for Sale
May 5, 2026
$3,199,000
Original listing
Office: RE/MAX Encore

Tax History

Year Taxes Assessment
2026 $20,861 $1,682,400

Financial Details

Annual Property Tax
$20,861
Tax Year 2026
Assessed Value
$1,682,400

Facts & Features

1 Car Garage
Central AC

Home Facts

Type Residential
Style Single Family Residence
Year Built 1860
Living Area 3,446 sq ft
Lot Size 0.03 acres
Bedrooms 4
Full Baths 3
Half Baths 1
Total Rooms 10

Interior

Heating Central, Natural Gas
Cooling Central Air
Flooring Wood, Tile, Engineered Hardwood
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 Living Room
Fireplaces 2
Basement Full, Finished
Laundry Electric Dryer Hookup, Washer Hookup
Features Sauna/steam/hot Tub

Exterior

Construction Frame, Brick
Architecture Italianate
Roof Shingle, Rubber
Features Deck, Deck - Composite, Patio, Patio - Enclosed, Balcony, Rain Gutters, City View(s), Outdoor Gas Grill Hookup
Pool None
Spa None
Fencing None
Patio/Porch Deck, Deck - Composite, Patio, Enclosed
Garage Spaces 1
Has Garage Yes
Features Detached, Leased
Total Spaces 1
Electric Circuit Breakers
Water Public
Sewer Public Sewer
Gas None
Other For Gas Range, For Gas Oven, For Electric Dryer, Washer Hookup, Icemaker Connection, Outdoor Gas Grill Hookup
Annual Tax $20,861
Assessed Value $1,682,400
Fee Includes None
Amenities None
Optional Fee Includes None
Lead Paint Unknown
Seller Disclosures None
Exclusions Stagers Furniture
Possession None
Accepted Financing None
Structure Type []
Sq Ft Source Public Record
Sq Ft Disclosures Area includes finished Basement
Documents None
County Suffolk
Total market time (incl. prior listings) 121 days

Property Overview

Property Type
Single Family Residence
Listing Type
For Sale
Year Built
1860
Bedrooms
4
Full Bathrooms
3
Half Bathrooms
1
Living Area
3,446 sq ft
Total Rooms
10

Floor Layout

Interior Features

Flooring: Wood, Tile, Engineered Hardwood
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
Interior Features: Sauna/Steam/Hot Tub
Windows:
Basement: Full, Finished
Laundry: Electric Dryer Hookup, Washer Hookup
Security:

Construction & Materials

Style: Italianate
Year Built: 1860
Structure Type:
Exterior Materials: Frame, Brick
Roof: Shingle, Rubber
Foundation: Stone, Granite

Heating, Cooling & Utilities

Heating: Central, Natural Gas
Heating Zones: 3
Cooling: Central Air
Cooling Zones: 3
Hot Water:
Water Source: Public
Sewer: Public Sewer
Energy Features: Thermostat

Exterior & Lot

Exterior Features: Deck, Deck - Composite, Patio, Patio - Enclosed, Balcony, Rain Gutters, City View(s), Outdoor Gas Grill Hookup
Patio & Porch: Deck, Deck - Composite, Patio, Enclosed
Fencing:
Other Structures:
Lot Features: Level
Road Surface: Paved

Parking & Garage

Garage Spaces: 1
Total Parking Spaces: 1
Parking Features: Detached, Leased

Special Features

Fireplaces: 2
Fireplace Type: Living Room
View: Yes
View Type: City
Community Amenities:
School District
Boston School District local
C-
🎓 Where Graduates Go Class of 2021
52% attend college
38% 4-Year 14% 2-Year 7% Out of State 7% Working
⚠ School Safety 2024-25
3.7% Above Average
3.2% Suspensions 0.3% In-School 0.5% Emergency
↓ 1.8% below state avg
E

Elementary Schools

10 schools
C
Harvard-Kent Elementary School
0.2 mi | #594 of 825 | Score: 41.1
Dropped 186 spots from last year
-17.1 below state avg
315 students Very Diverse
Diverse Student Body
Grades PK-06
A-
Warren-Prescott K-8 School
0.4 mi | #86 of 352 | Score: 50.9
Improved 3 spots from last year
-7.3 below state avg
544 students Diverse
Strong Attendance
Grades PK-08
D
Horace Mann School for the Deaf Hard of Hearing
0.6 mi | #374 of 346 | Score: 33.9
Same rank as last year
78 students Diverse
Diverse Student Body
Grades PK-12
A
Eliot K-8 Innovation School
0.6 mi | #47 of 352 | Score: 57.5
Improved 3 spots from last year
-0.7 below state avg
779 students Diverse
Strong Attendance
Grades PK-08
St. John Elementary School
0.8 mi
Grades PK-08
C+
Mario Umana Academy
0.9 mi | #11 of 16 | Score: 26.5
Improved 333 spots from last year
-31.7 below state avg
585 students Less Diverse
Rising School
Grades PK-08
East Boston Central Catholic School
1.0 mi
Grades PK-08
B+
Alighieri Dante Montessori School
1.1 mi | #5 of 12 | Score: 45.2
Improved 124 spots from last year
-13 below state avg
100 students Diverse
Rising School Strong Attendance
Grades PK-06
D
O'Donnell Elementary School
1.1 mi | #784 of 825 | Score: 29.9
Dropped 59 spots from last year
-28.3 below state avg
248 students Less Diverse
Grades PK-06
C-
Kennedy Patrick J Elementary School
1.2 mi | #669 of 825 | Score: 37.4
Improved 48 spots from last year
-20.8 below state avg
285 students Less Diverse
Rising School
Grades PK-06
M

Middle Schools

10 schools
Middle School Academy
2.8 mi
F
Higginson/Lewis K-8 School
3.9 mi | #349 of 352 | Score: 23.2
Improved 3 spots from last year
-35 below state avg
246 students Diverse
Grades 03-08
Nativity Prep School
4.2 mi
Grades 05-08
A
Uncommon Schools - Roxbury Preparatory Dorchester Campus Middle School
4.4 mi | #4 of 16 | Score: 42.5
Improved 187 spots from last year
-15.7 below state avg
1,225 students Diverse
Rising School College Ready Curriculum
Grades 05-08
Dearborn Middle School
4.7 mi
Mother Caroline Academy
4.8 mi
Grades 05-08
Epiphany School
5.6 mi
Grades 05-08
C
Ohrenberger School
9.1 mi | #266 of 352 | Score: 35.0
Improved 19 spots from last year
-23.2 below state avg
458 students Diverse
Diverse Student Body
Grades 03-08
Edwards Middle
0.6 mi
UP Academy
2.8 mi
H

High Schools

10 schools
D
Charlestown High School
0.4 mi | #319 of 346 | Score: 32.9
Improved 52 spots from last year
-25.4 below state avg
646 students Diverse
11 sports • 488 athletes
Early College Program Rising School
Grades 07-12
C-
East Boston High School
1.3 mi | #300 of 346 | Score: 38.2
Improved 36 spots from last year
-20 below state avg
1,181 students Moderate
14 sports • 584 athletes
Early College Program Rising School
Grades 07-12
C
Quincy Upper School
1.9 mi | #279 of 346 | Score: 44.4
Dropped 7 spots from last year
-13.8 below state avg
575 students Very Diverse
12 sports • 208 athletes
Diverse Student Body
Grades 06-12
Newman School
1.9 mi
Grades 07-12
Cathedral High School
2.3 mi
9 sports • 430 athletes
Grades 07-12
A+
Boston Latin School
3.3 mi | #20 of 346 | Score: 73.7
Improved 60 spots from last year
+15.5 above state avg
2,382 students Very Diverse
18 sports • 2,006 athletes
Strong AP Program High Graduation Rate Rising School Strong Athletics
Grades 07-12
A-
O'Bryant School of Math & Science
3.4 mi | #90 of 346 | Score: 61.6
Improved 94 spots from last year
+3.4 above state avg
1,518 students Very Diverse
High Graduation Rate Rising School College Ready Curriculum Diverse Student Body
Grades 07-12
B
Dearborn STEM Academy
3.5 mi | #13 of 25 | Score: 33.4
Improved 356 spots from last year
-24.8 below state avg
565 students Moderate
10 sports • 242 athletes
Early College Program Rising School
Grades 07-12
C
Ruth Batson Academy
4.0 mi | #20 of 25 | Score: 29.1
Improved 345 spots from last year
-29.1 below state avg
584 students Diverse
8 sports • 128 athletes
Early College Program Rising School
Grades 07-12
A+
Boston Latin Academy
4.2 mi | #2 of 25 | Score: 64.9
Improved 214 spots from last year
+6.7 above state avg
1,669 students Very Diverse
17 sports • 1,298 athletes
Strong AP Program High Graduation Rate Rising School Strong Athletics
Grades 07-12
Learn about these ratings
School data provided by BMN Schools

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Year 15
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Location

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Neighborhood

Charlestown

16 Chestnut Street, Boston MA 02129

Boston, MA 02129

Listing Information

Listing Agent Zachary Endicott
Listing Office RE/MAX Encore
Office Phone 978-988-0028
Agent MLS ID CN251093
Office MLS ID B95079
Listing Data Updated Aug 23, 2026 4:05 AM EDT
Listing information is deemed reliable but not guaranteed. Data provided by MLS Property Information Network, Inc. All information should be independently verified.

Contact Us

Steve Novak Real Estate
Steve Novak Real Estate
mail@steve-novak.com
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