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Spacious Multifamily Residence in Boston

285 Chestnut Ave, Boston, MA 02130

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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

HighLights

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.
Turnkey investment opportunity with 45 years of ownership history.
Updated units, including de‑leading of the first floor (4 years ago) and upper unit renovations within the last decade.
In‑unit laundry for upper floors, 3 driveway parking spots, rear decks, and a large backyard with garden space.

We can help!

Listing Contact

Christian Iantosca Team

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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:: 64
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

We can help!

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.

HighLights

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.
Turnkey investment opportunity with 45 years of ownership history.
Updated units, including de‑leading of the first floor (4 years ago) and upper unit renovations within the last decade.
In‑unit laundry for upper floors, 3 driveway parking spots, rear decks, and a large backyard with garden space.

Overview

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.

Local Financial Insights For Multifamily LT 5

Simulate Cap Rate and NOI

NOI Build-Up

Component	$	$/SF
Gross rent	$189.5k	$37.80
− Vacancy	−$8.5k	−$1.70
EGI	$181.0k	$36.10
− OpEx	−$54.3k	−$10.83
NOI	$126.7k	$25.27

5,013 SF · lease $37.80/SF/yr · vacancy 4.50% · expense 30.00%

Alternative Uses

Best Use

Multifamily LT 5

$1.81M

$1.58M – $2.11M (±1% cap)

NOI $126,675 @ 7.0% cap · market cap 8.31%

Second Best

Apartment 5plus

$1.68M

$1.47M – $1.96M (±1% cap)

NOI $117,766 @ 7.0% cap · market cap 7.72%

Theoretical Best

Office A

$3.75M

$3.28M – $4.38M (±1% cap)

NOI $262,761 @ 7.0% cap · market cap 17.23%

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

Location Intelligence

Current Use by Public Records

Triplexes

Suggested Use

Location Insight

Map
Local Demand

City: Boston
County: Suffolk
State: Massachusetts
Longitude: -71.11005
Latitude: 42.31305

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For sale
Triplexes
MA
Boston
02130
285 Chestnut Ave

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.