51 Chestnut Street, Boston, MA 02129

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51 Chestnut Street, Boston, MA 02129

$2,500,000 (Active)

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Listed by: - Gibson Sotheby's International Realty

$$2,500,000

Active

est.$2,500,000/month.

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4 beds. 3 baths. 2,136 Sqft.

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51 Chestnut Street, Boston, MA 02129

$2,500,000

Active

est.$2,500,000/month.

Start My Approval

4 beds 3.5 baths 2,136 Sq.ft.

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Property details for 51 Chestnut Street, Boston, MA 02129

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.

Listed by: Nancy Roth
Broker details: Gibson Sotheby's International Realty
Co-listing Agent: Colin Boylan
Co-listing Broker: Gibson Sotheby's International Realty

Property Description

MLS Information

Listing: 73573036
Listing Last Modified: 2026-09-08

Property Details

Standard Status: Active
MLS Status: New
Property style: Italianate
Built in: 1865
Subdivision: Charlestown
Lot size area: 0.05 Acres

Geographic Data

County: Suffolk
MLS Area: Charlestown
Directions: Monument Square to Chestnut Street

Features

Interior Features

Flooring: Wood, Tile, Carpet, Marble, Hardwood
Bedrooms: 4
Full baths: 3.5
Half baths: 1
Living area: 3593
Interior Features: Entrance Foyer, Walk-In Closet(s), Recessed Lighting, Ceiling Fan(s), Tray Ceiling(s)
Fireplaces: 4