51 Chestnut Street, Boston, MA 02129

• 4 beds |
• 4 baths |
• 3,593 sqft

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 to live in the "owner's unit" and keep a tenant in 1st floor unit; or buyers looking to convert into a spectacular single family home; or a developer/investor to convert into two high-end condos. 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/fireplace 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. An unfinished basement offers future expansion capabilities, and a lush garden patio completes this special offering.

Listing Status:

Active

Date Added:

September 8, 2026

Data Last Updated:

September 13, 2026 at 6:08PM

Listing Office:

Gibson Sotheby's International Realty : 617-242-4222

Listing Agent:

Nancy Roth : 617-429-6396

MLS ID:

73573036

Interior

• General: Bathroom - FullBathroom - Tiled With Shower StallLighting - OverheadDining AreaBeadboardLighting - PendantArchwayVestibuleChair RailBathroomKitchenFoyerLiving/Dining Rm Combo
• Appliances: Gas Water HeaterWater HeaterTankless Water HeaterRangeDishwasherDisposalMicrowaveRefrigeratorFreezerWasherDryerRange HoodStainless Steel Appliance(s)Gas Cooktop
• Laundry: Third Floor
• Basement: FullInterior EntryUnfinished
• Flooring: WoodTileCarpetMarbleHardwoodFlooring - Stone/Ceramic TileFlooring - WoodFlooring - Hardwood
• A/C: Central Air
• Heating: Forced AirBaseboardNatural Gas
• Fireplace: Family RoomLiving RoomMaster BedroomFireplaceFireplaces: 4

Exterior

• General: Deck - RoofPatioGarden
• Style: Italianate
• Parking: DetachedLeasedParking spaces: 1

Construction

• Roofing: Rubber
• General: Conventional (2x4-2x6)Granite

Location

• Road/Access: Public
• Originating MLS: MLS Property Information Network
• County: Suffolk

Lot

• Zoning: Multi-Fam02034120003356557

Utilities

• Utilities: for Gas Range
• Water: Public
• Sewer: Public Sewer

Financial

• Source: MLS Property Information Network
• Exclusions: 2nd Floor Dining Room Brass Uplight.