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Active

142 Chestnut Street #4-5

Boston, MA 02108

$3,900,000
3Bedrooms
4Bathrooms
2,985Square feet
1915Year built

Residential · Active · MLS #73490273
Listing Courtesy of Campion & Company Fine Homes Real Estate | Tracy Campion

MLS PIN data

About this home

Reminiscent of a classic Venetian palazzo, 142 Chestnut is the former Mansion of famed Boston architect Henry Forbes Bigelow and is located on one of the most desirable streets on the Flat of Beacon Hill. A stunning, Italian-Renaissance inspired brick courtyard graces the center of the building and is complete with a water fountain and lush, green plantings. Residence 4-5 is a spectacular 3-bedroom, 3.5-bathroom residence offering just under 3,000 square feet of living space all on one level and featuring direct elevator access. Outstanding features include a gracious formal living room overlooking gaslit Chestnut Street, eat-in kitchen with high-end appliances, butler’s pantry, spacious dining room with courtyard views and a library/home office. The primary suite is complete with a large walk-in closet and lavish marble bath. Steps from the Charles River Esplanade, the Public Garden, and Charles Street, this magnificent property is not to be missed. Rental parking at Brimmer Garage.

Property information

Details at a glance

Interior

Rooms
7
Heating
Forced Air
Cooling
Central Air
Fireplaces
3

Building

Style
Condominium
Year built
1915
Parking
1

Land & utilities

Water
Public
Sewer
Public Sewer
Zoning
0102

Financial

Annual taxes
$43,583
Assessment year
2026
HOA fee
1391.25

Listing history

Price and status timeline

  1. Ter

    $4,250,000 · Sep 2, 2025

  2. Ter

    $4,250,000 · Mar 10, 2025

Property value estimate

An informed starting point

Estimated value$4,105,605

Estimated range $3,349,598$4,861,612

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Automated estimates are not appraisals or guarantees of market value.

Comparable sales

Recent properties for context

Recent comparable sales are not available for this property.

Photo insights

Condition signals

Overall presentationaverage

Generated from listing photography; not a substitute for an inspection.

Local market context

How this home compares in Beacon Hill

MetricThis propertyBeacon Hill
List price$3,900,000$3,550,00010% above local
Price / sq ft$1,307$1,60218% below local
Days on market16569139% above local
Explore homes in Boston

Active neighborhood listing statistics from MLS PIN as of September 7, 2026. Asking prices are not completed-sale values.

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Bean Group guidance

Useful next steps

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Common questions

About 142 Chestnut Street #4-5

Can I schedule a private showing?

Yes. Request a tour of 142 Chestnut Street #4-5 and a Bean Group agent will help coordinate an available time with the listing side.

Can you help me evaluate this property?

Yes. We can discuss condition, comparable sales, offer strategy and the questions worth asking before you decide whether to proceed.

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Availability varies by property and source. Request the documents you need and we will help obtain what is available.