Prevu by reAlpha
BuySellBlogBrowse Listings
51 Chestnut Street, Boston MA 02129
51 Chestnut Street, Boston MA 02129
Massachusetts>Boston>Thompson Square - Bunker Hill

51 Chestnut StreetBoston, MA 02129

For Sale

$2,500,000

Smart Buyer Rebate $12,500

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.

Last updated September 12, 2026

·

Source: MLSPin #73573036

Listing Facts

  • TypeSingle-family
  • NeighborhoodThompson Square - Bunker Hill
  • Bedrooms4
  • Bathrooms4
  • Days on Prevu7
  • Taxes$30,727.7/year
  • Size3,593 sqft
  • Price per sqft$696

Amenities

  • Dishwasher
  • Private Outdoor Space
  • Washer/Dryer
  • Air Conditioning
  • Parking
  • Swimming Pool

Location

Mortgage Calculator

Listing History

09/08/2026
Listed by
$2,500,000
  1. 09/08/2026$2,500,000
    Listed by

Property Details for 51 Chestnut Street

Association

Amenities

  • Community Features: Pool, Tennis Court(s), Park

Exterior

Construction

  • Property Attached: Yes
  • Roof: Rubber
  • Year Built: 1865
  • Year Built Details: Actual
  • Architectural Style: Italianate
  • Exterior Features: Garden

Features

  • Patio And Porch Features: Patio, Deck
  • View: Harbor, Water

Measurements

  • Building Area Total: 3,593
  • Building Area Units: Square Feet
  • Lot Features: Other
  • Lot Size Acres: 0.05
  • Lot Size Area: 0
  • Lot Size Square Feet: 2,136
  • Lot Size Units: Acres

Financial

Taxes

  • Parcel Number: 0203412000,3356557
  • Tax Annual Amount: $30,727.70
  • Tax Assessed Value: $2,454,500.00
  • Tax Year: 2026

Interior

Features

  • 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
  • Fireplace Features: Family Room, Living Room, Master Bedroom
  • Fireplace: Yes
  • Fireplaces Total: 4
  • Flooring: Wood, Tile, Carpet, Marble, Hardwood
  • Interior Features: Entrance Foyer, Walk-In Closet(s), Recessed Lighting, Ceiling Fan(s), Tray Ceiling(s)

Measurements

  • Living Area: 3,593
  • Living Area Source: Public Records

Rooms

  • Basement: Full, Interior Entry, Unfinished
  • Has Basement: Yes
  • Bathrooms Full: 3
  • Bathrooms Half: 1
  • Bathrooms Total Integer: 4
  • Bedrooms Total: 4
  • Main Level Bedrooms: 2
  • Rooms Total: 10

Other

General

  • Exclusions: 2nd Floor Dining Room Brass Uplight.

Location

  • Subdivision Name: Charlestown

Parking

Parking

  • Covered Spaces: 1
  • Garage Spaces: 1
  • Garage: Yes
  • Parking Features: Detached, Leased
  • Parking Total: 1

Schools

Elementary School

  • Elementary School: Bps

High School

  • High School: Bps

Middle or Junior School

  • Middle Or Junior School: Bps

Utilities

Equipment

  • Cooling: Central Air, Zoned
  • Has Cooling: Yes
  • Heating: Natural Gas, Forced Air, Baseboard, Zoned
  • Has Heating: Yes
  • Sewer: Public Sewer
  • Water Source: Public

Frequently Asked Questions

How many bedrooms and bathrooms does this single-family home have?

There are 4 bedrooms and 4 bathrooms in this single-family home at 51 Chestnut Street.

What schools are nearby to 51 Chestnut Street?

Nearby schools include the Bps Elementary School, Bps Middle School, and Bps High School.

Does this single-family home have parking?

Yes, there is 1 parking space available for 51 Chestnut Street.

What are the annual taxes for 51 Chestnut Street?

Annual taxes for this single-family home are estimated at $30,727.

How does 51 Chestnut Street compare to other single-family homes in Thompson Square - Bunker Hill?

This single-family home is listed 1% above the average price for single-family homes in Thompson Square - Bunker Hill and has been on the market for 46 less days than the typical home in this area.

What is the square footage on this single-family home?

According to the MLS, this listing is 3,593 sqft.

51 Chestnut Street is a 4-bedroom, 4-bath single-family home for sale in Boston MA 02129. On Prevu for 7 days at $2,500,000. This property features 3,593 square feet of living space, located in Thompson Square - Bunker Hill. The median listing price for single-family homes in this area is $799,000. Nearby schools include Bps Elementary School, Bps Middle School, and Bps High School. Property amenities include private outdoor space, dishwasher, air conditioning, parking, swimming pool, and washer/dryer. Explore more single-family home listings in Boston.

The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors, landlords and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information, and the Images, are for the personal, non commercial use of consumers having a good faith interest in purchasing, leasing or renting listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing, leasing or renting. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the Images, set forth herein.

Full MLS Disclaimers

Rebate estimate is indicative only and based on listing price and estimated buyer's agent commission paid by owner, if applicable. Final rebates are subject to Terms of Use and may vary due to final negotiated transaction terms.