51 Chestnut Street, Boston, MA 02129 - Photo 1

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$2,700,000 Just Listed

For Sale
Active
Single Family
4 Beds
3 Full Baths
1 Partial Bath
3,593 Sq. Ft.
0.05 Acres
1 Car Garage
Updated 10 hours ago

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Thursday 6/11 5:00 PM - 6:00 PM

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Property Description

Located on a gas-lit street near Monument Square, this rarely available, 4BR/3.5BA, two-family home offers 3,593+sf and an extraordinary opportunity for an owner occupant, investor/developer, or buyer looking to convert into a spectacular single family home. The grand entrance is defined by soaring ceilings, period moldings, and a sweeping staircase that leads to an impressive formal living room. An elegant dining room flows into a chef's kitchen with luxury finishes and top-tier appliances. A charming family room w/wet bar and gas FP provides an inviting hub for daily living. A spacious primary suite w/FP has ample closet space and marble spa bath. An addt'l bedroom and full bath complete this level. The separate entrance, 1BR rental unit in the rear of the first floor is well maintained. The crown jewel is an expansive 480sf private roof deck, w/head house, wet bar, and panoramic views of the harbor, Monument, and Boston skyline. A lush garden patio completes this special offering.

Full Property Details

Full Property Details for 51 Chestnut St

General

Price: $2,700,000
Taxes: $30,727 (2026)
Status: Active
Type: Single Family
MLS ID: 73532468
Updated: Today (6/9/2026)
Added to Site: Today

Rooms

Bathrooms

Total Bathrooms: 4
Full Bathrooms: 3
Half Bathrooms: 1
Bathroom 1: 5.25 x 8.17, First
Bathroom 2: Second
Bathroom 3: 15.42 x 16.25, Third

Bedrooms

Total Bedrooms: 4
Primary Bedroom: 13.08 x 19.67, Third
Bedroom 2: 13.75 x 16.58, Main, First
Bedroom 3: 13.67 x 15.92, Main, First
Bedroom 4: 9.83 x 14.25, Third

Other Rooms

Living Room: 24.50 x 17.42, Second
Family Room: 15.08 x 19.08, Second
Kitchen: 15.08 x 12.00, Second
Dining Room: 14.25 x 16.42, Second

Parking

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

Location

County: Suffolk

Structural Information

Architectural Style: Italianate
Basement: Yes
Square Feet: 3,593
Year Built: 1865

Lot Features

Lot Size (Acres): 0.05

Financial Considerations

Tax Amount: $30,727.7
Tax Year: 2026

Disclosures and Reports

Exclusions: 2nd Floor Dining Room Brass Uplight.
Disclosures/Rstr.: 4 fireplaces: 1 electric fireplace in entry parlor; 1 gas fireplace in den off kitchen, and the two wood burning fireplaces are in 2nd floor living room and primary bedroom. Neither of these wood FP chimneys are lined. Seller does not use as a result.
Property ID: 2034120003356557

Listed by Gibson Sotheby's International Realty, Nancy Roth and Colin Boylan

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Listing agents

— 51 Chestnut St —

Nancy Roth

Gibson Sotheby's International Realty
Colin Boylan

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Schools

Schools serving 51 Chestnut St

School District:Boston School District

Name	Grades	Distance
Harvard-Kent Elementary School 50 Bunker Hill Street, Boston, MA 02129	PK-5	0.1 mi
Warren-Prescott K-8 School 50 School Street, Boston, MA 02129	PK-8	0.3 mi
Eliot K-8 Innovation School 16 Charter Street, Boston, MA 02113	PK-8	0.7 mi
Charlestown High School 240 Medford Street, Boston, MA 02129	9-12	0.3 mi
East Boston High School 86 White Street, Boston, MA 02128	9-12	1.3 mi
Quincy Upper School 152 Arlington Street, Boston, MA 02116	6-12	1.9 mi
Boston Adult Academy 20 Church St, Boston, MA 02116	9-12	1.9 mi
Snowden Int'L High School 150 Newbury Street, Boston, MA 02116	9-12	2 mi
Excel High School 95 G. Street, Boston, MA 02127	9-12	3 mi

Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 51 Chestnut St Get Price Alerts and Save Property

Date

Details

Price

Change

Source

6/09/2026

Listed

$2,700,000

101.12%

MLS

6/11/2013

Sold

$1,342,500

—

Public Record

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Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History

Tax History for 51 Chestnut St

Year

Property Taxes

Change

Tax Assessment

Change

2025

$27,866

20%

$2,406,400

13%

2024

$23,287

$2,136,400

—

2023

$22,945

$2,136,400

2022

$22,567

$2,074,200

—

2021

$22,132

$2,074,200

2020

$21,567

10%

$2,042,300

10%

2019

$19,533

12%

$1,853,200

11%

2018

$17,451

$1,665,200

2017

$16,604

$1,567,900

2016

$16,145

18%

$1,467,700

30%

2015

$13,648

13%

$1,127,000

17%

2014

$12,074

—

$959,800

—

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Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Estimate the Cost

Estimate the Cost for 51 Chestnut St

51 Chestnut Street, Boston, MA 02129 (MLS# 73532468) is a Single Family property with 4 bedrooms, 3 full bathrooms and 1 partial bathroom. 51 Chestnut Street is currently listed for $2,700,000 and was received on June 09, 2026. Want to learn more about 51 Chestnut Street? Do you have questions about finding other Single Family real estate for sale in Charlestown? You can browse all Charlestown real estate or contact a Coldwell Banker agent to request more information.

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51 Chestnut St Boston, MA 02129