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$3,900,000

142 Chestnut Street # 5, Boston MA 02108
Boston, MA 02108
Listed by Tracy Campion
Bedrooms
3
Bathrooms
3.1
Living area
2,985 sqft
Year built
1915

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.

Highlights

Fireplace

Property details

MLS #
73490273
Property type
Condominium
Subdivision
N/A
Status
Active
Days on market
N/A
On market date
N/A
Stories
1
Garage spaces
N/A
Lot size
N/A
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Nearby schools

Within 10 miles · public school directory data (NCES)

Elementary
Josiah Quincy
0.71 mi away · Grades -1-5
Nearest school -- attendance-zone data not available here
5.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
711
Student:teacher ratio
10.9:1
District
Boston
Middle
Cambridge Street Upper School
1.46 mi away · Grades 6-8
Nearest school -- attendance-zone data not available here
5.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
279
Student:teacher ratio
7.5:1
District
Cambridge
High
Snowden International School at Copley
0.48 mi away · Grades 9-12
Nearest school -- attendance-zone data not available here
4.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
485
Student:teacher ratio
12.8:1
District
Boston

Mortgage calculator

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Est. monthly payment
$23,636/mo
$780,000 down
$3,120,000 loan
Principal & interest$20,236
Property tax (est.)$3,250
Home insurance (est.)$150

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Data source: Listing information provided by MLS Property Information Network via Trestle/CoreLogic. Last updated June 11, 2026.

Information herein deemed reliable but not guaranteed; all measurements, school assignments, HOA fees, taxes, and feature lists are approximate and should be independently verified. Equal Housing Opportunity.