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285 Chestnut Ave Boston, MA 2130

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For Sale
$1,525,000

Turnkey investment property in a prime Boston location.

Type:3 Family - 3 Units Up/Down
Property size:
5,013 SF
Price / SF:
$304/SF
Added:
Apr 9, 2026
Days on Market:
18
Last Refresh:
Apr 20 at 6:48 pm

Property Features for 285 Chestnut Ave

General Information

Standard status
Active
Size
5,013 SF
Property subtype
3 Family - 3 Units Up/Down

Building Details

Year Built
1905

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Listing Contact
Christian Iantosca Team

Listing agent Christian Iantosca Team

Listing office Arborview Realty Inc.

Listing date Apr 9, 2026

Source Lockandkeyre

Displayed information is deemed reliable but is not guaranteed and should be independently verified.

All listing content including descriptions, pricing, images are the copyrighted material of Arborview Realty Inc.


Overview

Spacious Multifamily Residence in Boston

This spacious 3-family residence presents an investment opportunity in a prime location. The building features three units, each with three to five bedrooms and one full bathroom. The first floor was de-leaded four years ago, and the upper units have been updated within the last decade. In-unit laundry is available for the upper floors. The property includes three driveway parking spots and rear decks. Residents can enjoy a large backyard and garden space. Situated in one of Boston’s vibrant neighborhoods, the property is a short walk from the Orange Line at Green Street and the community events on Lamartine Street. It is also minutes from Jamaica Pond and the shops and restaurants along Centre Street. The property generates $10,600 in monthly rent, resulting in a net annual income of $97,514. All units are rented until August 31, 2026. The property is being sold AS-IS, presenting an opportunity for owner renovations to increase future rental income.
Location Intelligence

Current Use by Public Records

Triplexes

Suggested Use

Law Firm Restaurant Real Estate Agency Spa & Massage Center Dental Office Hair Salon Nail Salon Food Market Grocery & Convenience Store Gym & Fitness Center

Zoning and permitted uses should be independently verified with local authorities.

Location Insight

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  • Local Demand
City
Boston
County
Suffolk
State
Massachusetts
Longitude
-71.11005
Latitude
42.31305

FAQs

What type of property is this?
Triplex - Turnkey investment property in a prime Boston location.
Where is this triplex located?
The property is located at 285 Chestnut Ave Boston, MA.
What is the asking price?
The asking price for this property is $1,525,000.
What are key features of this property?
This property features: High monthly rental income of $10,600 and a substantial $97,514 net annual income.; Prime Jamaica Plain location, near the Orange Line (Green Street), Jamaica Pond, Centre Street shops/restaurants, and Lamartine St events.; Spacious 3‑family residence with units featuring 3‑5 beds each.
More about this property
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