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Susan Lelansky
REALTOR®
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51 Chestnut Street, Boston, MA 02129

$2,700,000
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New to the Market Active
BEDS4 BATHS3 full 1 partial SQUARE FEET3,593 MLS#73532468
STATUSActive PROPERTY TYPEResidential - Single Family SUBDIVISIONCharlestown

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 chefs 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 addtl 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.

51 Chestnut Street | MLS# 73532468

This single family home located at 51 Chestnut Street, Boston, MA 02129 is currently listed for sale with an asking price of $2,700,000. This property was built in 1865 and has 4 bedrooms and 3 full and 1 partial baths with 3593 sq. ft. Chestnut Street is located in the Charlestown subdivision. Search Charlestown real estate on susanlelansky.masiellogrouprealestate.com today.

Property Features

Property Type: Residential - Single Family
Basement: Yes
Basement: Full, Interior Entry, Unfinished
Cooling: Central Air
Fireplaces: 4
Garage: 1
Heating: Forced Air, Baseboard, Natural Gas
Home Style: Italianate
Lot Size: 0.05 Acres
Roof Type: Rubber
Taxes: $30,727
Year Built: 1865

Amenities

Bathroom - Full
Bathroom - Tiled With Shower Stall
Lighting - Overhead
Dining Area
Beadboard
Lighting - Pendant
Archway
Vestibule
Chair Rail
Bathroom
Kitchen
Foyer
Living/Dining Rm Combo
Deck - Roof
Patio
Garden

Feature Descriptions

Appliances: Gas Water Heater, Water Heater, Tankless Water Heater, Range, Dishwasher, Disposal, Microwave, Refrigerator, Freezer, Washer, Dryer, Range Hood, Stainless Steel Appliance(s), Gas Cooktop
Building Area Total: 3593
Community Features: Public Transportation, Shopping, Pool, Tennis Court(s), Park, Walk/Jog Trails, Medical Facility, Laundromat, Bike Path, Conservation Area, Highway Access, House of Worship, Marina, Private School, Public School, T-Station, University
Compensation Based On: N/A
Compensation Broker Transaction: N/A
Compensation Buyer Agency: N/A
Compensation Sub Agency: N/A
Compensation Sub Agency Offered: N/A
Dining Room: Flooring - Wood, Chair Rail, Recessed Lighting, Lighting - Pendant, Pocket Door, Tray Ceiling(s)
Exclusions: 2nd Floor Dining Room Brass Uplight.
Exterior: Conventional (2x4-2x6)
Family Room: Ceiling Fan(s), Closet, Closet/Cabinets - Custom Built, Flooring - Wood, Recessed Lighting, Lighting - Overhead
Fireplace Features: Family Room, Living Room, Master Bedroom
Fireplace Y/N: Yes
Flooring: Wood, Tile, Carpet, Marble, Hardwood, Flooring - Stone/Ceramic Tile, Flooring - Wood, Flooring - Hardwood
GarageY/N: Yes
HeatingY/N: 1
Kitchen: Flooring - Wood, Countertops - Stone/Granite/Solid, Kitchen Island, Recessed Lighting, Stainless Steel Appliances, Peninsula, Lighting - Pendant
Laundry: Third Floor
Living Room: Flooring - Wood, Recessed Lighting, Lighting - Overhead, Archway
Lot Features: Other
Master Bathroom: Yes
Master Bedroom: Bathroom - Full, Walk-In Closet(s), Closet/Cabinets - Custom Built, Flooring - Wood, Recessed Lighting, Tray Ceiling(s)
Parcel Number: 0203412000,3356557
Parking Features: Detached, Leased
Parking Total: 1
Patio And Porch: Deck - Roof, Patio
Property Attached Y/N: 1
Rooms Total: 10
Sewer: Public Sewer
Utilities: for Gas Range
Water: Public

Room Sizes

Bathroom 1: 5.25 X 8.17 Level - First
Bathroom 3: 15.42 X 16.25 Level - Third
Bedroom 2: 13.75 X 16.58 Level - Main,First
Bedroom 3: 13.67 X 15.92 Level - Main,First
Bedroom 4: 9.83 X 14.25 Level - Third
Dining Room: 14.25 X 16.42 Level - Second
Family Room: 15.08 X 19.08 Level - Second
Kitchen: 15.08 X 12.00 Level - Second
Living Room: 24.50 X 17.42 Level - Second
Primary Bedroom: 13.08 X 19.67 Level - Third

Local Schools

High School: Bps
Middle School: Bps
Elementary School: Bps

Listed By / Shown By

Listed By

Agency Name: Gibson Sotheby's International Realty
Agent Name: Nancy Roth
Agency Phone: 617-242-4222

Shown By

Agent Name: Susan Lelansky
Agent Phone:
Agency Title: Better Homes and Gardens Real Estate The Masiello Group

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Estimated Payment

$ 9,357.11 per month $6,009.03 Principal & Interest $2,560.58 Property Tax $787.50 Homeowner's Insurance

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Disclaimer: All information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) or information provider(s) shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Listing(s) information is provided for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information on this site was last updated 06/09/2026. The listing information on this page last changed on 06/09/2026. The data relating to real estate for sale on this website comes in part from the Internet Data Exchange program of Delta Media Group MLS (last updated Tue 06/09/2026 12:00:20 AM EST) or MLSPIN MLS (last updated Mon 06/08/2026 11:38:25 PM EST) or Prime MLS (last updated Mon 06/08/2026 11:33:17 PM EST) or MREIS (last updated Mon 06/08/2026 11:55:13 PM EST). Real estate listings held by brokerage firms other than Better Homes and Gardens Real Estate The Masiello Group may be marked with the Internet Data Exchange logo and detailed information about those properties will include the name of the listing broker(s) when required by the MLS. All rights reserved.
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