51 Chestnut Street

Taxes: $30,727.7 (2026)

About this home

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.

Property details

Sewer

Private

Style

Italianate

Water

City/Town Water

Cooling

Central Air

Heating

Forced Air, Electric Baseboard, Hot Air Gravity

Type

Attached

Flooring

Wood, Tile, Wall to Wall Carpet, Marble, Hardwood

Road type

Public

Appliances

Range, Dishwasher, Disposal, Microwave, Refrigerator, Freezer, Washer, Dryer, Vent Hood

Master Bath

Yes

Construction

Conventional (2x4-2x6)

Roof

Rubber

Garage

Detached

Lot

Other (See Remarks)

Parking

Assigned

Basement

Full, Interior Access, Unfinished Basement, Exterior Access

Exterior

Deck - Roof, Patio, Garden Area

Interior

Cable Available

Waterview Features

Harbor