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51 Chestnut Street, Boston MA 02129

$2,700,000

Estimated $19,197/month Calculator

Single Family

4 Bedrooms

Baths

3593

Total Parking: 2 (1 Garage)

2,136 (0.05)

Built in 1865

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.

This home has been viewed 24 times

Last Checked: June 24th, 2026 at 4:38am (Source: MLS PIN #73532468)

Garage Parking

Air Conditioning

Waterview

Lead Paint Free

General Information for 51 Chestnut Street, Boston MA 02129

Listing ID73532468

Property TypeSingle Family / Attached

Price$2,700,000 ($751.46/SqFt)

StyleColonial

CityBoston

CountySuffolk

MLS AreaCharlestown

Neighborhood(s)

Garage Parking1

ZoningMulti-Fam

Year Built1865

Year Built SourcePublic Records

Year Built DetailsActual

Interior Features for 51 Chestnut Street, Boston MA 02129

Approximate Living Area Total3593

Living Area Includes BasementNo

Rooms10

Bedrooms4

Primary En Suite BathroomYes

BasementFull

Cooling1, Split

Fireplaces

AppliancesRange

FlooringTile

Electric

Exterior Features for 51 Chestnut Street, Boston MA 02129

Approximate Lot Size (Acres)0.05

Approximate Lot Size (Square Feet)2136

Total Parking2 (1 Garage)

Garage Parking1

WaterPublic

SewerPublic Sewer

Lot FeaturesGentle Sloping

Parking Features1

Exterior FeaturesPorch

Foundation Materials

Construction MaterialsFrame

Road Frontage Type

Patio & PorchCovered

Roof MaterialAsphalt/fiberglass Shingles

Utility Connections110 Volts

Water ViewsYes

Water Views FeaturesBay

Waterfront0

Waterfront Features

Pool Features

Horse Permitted0

Horse Amenities

Disclosures for 51 Chestnut Street, Boston MA 02129

Lead PaintNone

UFFI

Living Area Includes BasementNo

Living Area Disclosure

Building Area SourcePublic Records

Special Listing Conditions

ExclusionsLighting In Loft Area

Compensation Based On

Financial Information for 51 Chestnut Street, Boston MA 02129

Association Fee

Association Fee Frequency

Association Fee Includes

Real Estate Tax30727.7

Tax Year2026

Assessed Value$2,454,500

Location Information for 51 Chestnut Street, Boston MA 02129

Elementary SchoolBps

Middle SchoolBps

High SchoolBps

Neighborhood(s)

MLS AreaCharlestown

Area AmenitiesWalk/jog Trails

Contact Information for 51 Chestnut Street, Boston MA 02129

Agent

Name: Nancy Roth

Office

Name: Gibson Sotheby's International Realty

Phone: 617-242-4222

Team Members

Name: Colin Boylan

Payment Calculator

, Interest

Property Taxes 2560.64

Principal & Interest 16636.54

HOA Dues

Term

Interest

Home Price

Down Payment

Exclusive Listing Agent

Gibson Sotheby's International Realty

Nancy Roth

Agent Phone

Office Phone

(617) 242-4222

Text Agent Call Agent Call Office

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    [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.
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EXIT

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