Explore by Metro

Explore By Metro

$4,250,000est. $21,490 Mortgage

Date Listed : Sep 2, 2025
Days on HelloCondo: 34

4-5- 142 Chestnut Street , Boston, MA 02108

142 Chestnut St

3 Beds

4 Baths

2985 sqft

Consider nearby listings that may offer more features at a similar price or similar features at a lower price

Listing by: ,,

Source by:

, MLS#: 73424234

HelloCondo last checked: 0 minutes ago

mamlspin/2457d0c039d9204c05efbc0c7f58b3d7.jpg?width=131&height=105&format3=webp

mamlspin/eff197e8e1211a88d554e912291e744f.jpg?width=131&height=105&format3=webp

mamlspin/7244360bc761b10d21e2fac3f8e47dac.jpg?width=131&height=105&format3=webp

mamlspin/fc1ddc15c281792e556a112a1702b999.jpg?width=131&height=105&format3=webp

Description

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 f...

Locker:

Taxes:

$39,905.05 (2025)

Possession:

Building Age:

110 Years old

HOA fees:

$1,391.25 /Monthly

Basement Feature:

Outdoor space:

Price per sqft:

$1423.79

142 Chestnut St Amenities

Parking

Locker

Concierge

Elevator

Central AC

Pool

Fitness Center

Visitors Parking

142 Chestnut St Policies

Pets Allowed

Short-term Rental Allowed

BBQ Permitted

Sublet Allowed

Unit Price History

Date	Status	Price
Unit Price History for this Listing is not available

Source by: MLS PROPERTY INFORMATION NETWORK

Loading similar listings...

Nearby Cities

See MoreSee Less

Buildings

1 Chestnut Condominium

1 Chestnut St

19 Glade Condominiums

24 Commonwealth Ave

24 Commonwealth Ave. 8

585 Revere Beach Pkwy

60 Coppersmith Way

7 Park Ave

Ambasador East Condos

Canal Place 3 Condominium

Ferry Street Court Condomin...

Ferry Street Court Condominium...

Jamaicaway Place

Meridian Street Condos

Seaview Towers

Tba

The Village At Bedford Woods

The Village At Merrimac Landin...

See MoreSee Less

Neighborhoods

Beacon Hill Bridge Street Neck Chinatown

Cottage Hill Court Park Cummingsville Downtown Beverly Nobscot North Faulkner Park Avenue and the Hills Saxonville South Peabody Spring Hill Strawberry Hill Suffolk Square Union Square / Prospect Hill Waterfront West Cambridge West Salem Witchcraft Heights

See MoreSee Less

ZIP Codes

01450 01463 01742

01801 01810 01826 01845 01863 01887 01890 01901 01904 01949 01966 01982 01983 01985 02188 02199 02739

See MoreSee Less

Community

10-14 Park Vale Avenue Apartments 10-14 Sydney Street Condominiums 10-32A Glenville Avenue Apartments

100 Boatswains Way 100 Captains Row 100 Commandants Way 100 High Street Condominiums 100 Main Street 100 Pond Street 100 Riverway 100 Waite Street Condominiums 101 Prince Street 101-107 Winthrop Road 103 Alban Street 105 Beacon Street 105 West 3rd Street 107 Chestnut Street 108 Mount Vernon Street 108 Washington Street 109 Beach Street

See MoreSee Less

Popular Searches

Condos in Fairmount Hill Boston, MA

Condos in Longwood Medical Area Boston, MA

1-Bedroom Condos Under 400k in Fairmount Hill Boston, MA

1-Bedroom Condos Under 500k in Fairmount Hill Boston, MA

3-Bedrooms Condos Under 500k in Fairmount Hill Boston, MA

3-Bedrooms Condos Under 500k in Thompson Square Boston, MA

2-Bedrooms Condos Under 500k in East Codman Hill Boston, MA

1-Bedroom Condos with City View Under 500k in Boston Harbor Boston, MA

2-Bedrooms Condos with City View Under 300k in Boston Harbor Boston, MA

2-Bedrooms Condos with City View Under 350k in Boston Harbor Boston, MA

2-Bedrooms Condos with City View Under 500k in Boston Harbor Boston, MA

3-Bedrooms Condos with City View Under 500k in Boston Harbor Boston, MA

1-Bedroom Condos with City View and Pool Under 400k in Boston Harbor Boston, MA

2-Bedrooms Condos with City View and Pool Under 500k in Boston Harbor Boston, MA

1-Bedroom Condos with City View and Pet Friendly Under 350k in Boston Harbor Boston, MA

1-Bedroom Condos with City View and Pet Friendly Under 400k in Boston Harbor Boston, MA

1-Bedroom Condos with City View and Pet Friendly Under 500k in Boston Harbor Boston, MA

1-Bedroom Condos with City View and Fitness Center Under 350k in Boston Harbor Boston, MA

2-Bedrooms Condos with City View and Fitness Center Under 400k in Boston Harbor Boston, MA

2-Bedrooms Condos with City View and Fitness Center Under 500k in Boston Harbor Boston, MA

See MoreSee Less

HelloCondo Is The #1 Condo Search Platform And Real Estate Recommendation Engine. Search, Find And Buy The Perfect Condo And Get Matched With The Best Agents. Finding A Condo Has Never Been So Easy.

HelloCondo is a division of HelloCasa, LLC