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.
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| Year | Land | Building | Total | Change |
|---|---|---|---|---|
| FY2023 | $0 | $1,493,900 | $1,493,900 | — |
| Date | Price | Book/Page |
|---|---|---|
| May 24, 2022 | $1 | 67693/13 |
| Apr 2, 2021 | $1,700,000 | 65156/179 |
| Jan 1, 2021 | $9 | 99999/999 |
| Dec 18, 2019 | $1,667,000 | 62257/54 |
| Jul 1, 2015 | $480,000 | 54699/163 |
| Jul 30, 2010 | $1,385,000 | 46712/014 |
| Jan 3, 2008 | $2,850,000 | 42933/294 |
| Aug 29, 2006 | $1,340,000 | 40274/220 |
| Aug 29, 2006 | $260,000 | 40274/217 |
| Dec 10, 2001 | $350,000 | 27567/136 |
| Issued | Type / Work | Status | Value |
|---|---|---|---|
| May 14, 2026 |
Short Form Bldg Permit
ROOF
Roofing
Permit #SF1846712
|
Open | $130,750 |
| Apr 9, 2026 |
Electrical Permit
ELECTRICAL
Electrical
Permit #E1833948
|
Open | $15,000 |
| Mar 31, 2026 |
Plumbing Permit
PLUMBING
Plumbing
Permit #PL1834704
|
Open | $20,000 |
| Feb 9, 2026 |
Short Form Bldg Permit
INTREN
Renovations - Interior NSC
Permit #SF1819388
|
Open | $610,000 |
| Nov 21, 2024 |
Electrical Permit
ELECTRICAL
Electrical
Permit #E1670309
|
Open | $4,000 |
| Sep 19, 2024 |
Short Form Bldg Permit
INTEXT
Interior/Exterior Work
Permit #SF1652046
|
Open | $105,000 |
| Apr 27, 2022 |
Plumbing Permit
PLUMBING
Plumbing
Permit #PL1327017
|
Closed | $5,400 |
| Apr 20, 2022 |
Electrical Permit
INTREN
Renovations - Interior NSC
Permit #E1322840
|
Closed | $2,000 |
| Apr 19, 2022 |
Short Form Bldg Permit
INTREN
Renovations - Interior NSC
Permit #SF1315830
|
Closed | $38,390 |
| Mar 15, 2022 |
Short Form Bldg Permit
EXTREN
Renovations - Exterior
Permit #SF1272287
|
Open | $16,249 |
| Feb 11, 2022 |
Certificate of Occupancy
CHGOCC
Change Occupancy
Permit #COO1286204
|
Closed | $173,550 |
| Jan 7, 2022 |
Electrical Fire Alarms
FA
Fire Alarm
Permit #EFA1282039
|
Closed | $3,500 |
| Jan 3, 2022 |
Certificate of Occupancy
CHGOCC
Change Occupancy
Permit #COO1176715
|
Closed | $47,000 |
Discrepancies found between MLS and assessor records.
| Field | Assessor | MLS | Match |
|---|---|---|---|
| Year built | 1,930 | 1,915 | ✗ |
Beacon Hill
142 Chestnut Street # 5, Boston MA 02108
Boston, MA 02108
| Date | Event | Price | Change | $/sqft | Details |
|---|---|---|---|---|---|
| 05/13/2026 | ↓ Price Reduced | $3,900,000 | $250,000 | - | From $4,150,000 to $3,900,000 (-6.0%) |
| 03/23/2026 | 🏠 Listed for Sale | $4,150,000 | - | - | Original listing |
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