Prime location Investment Opportunity in JP! This spacious 3-family residence offers a turnkey opportunity with a strong 45-year ownership history, generating $10,600 in monthly rent (Net Income: $97,514/yr). Building features 3 units with 3-5 beds each, 1 full bath, spacious layouts with a de-leaded first floor (4 years ago) and upper units updated within the last decade. Key amenities include in-unit laundry for the upper floors, 3 driveway parking spots, and rear decks. Residents will enjoy the large backyard and garden space in one of Boston’s most vibrant neighborhoods, ideally situated just a short walk from the Orange Line at Green Street and the community events on Lamartine St. The property boasts an exceptional location just minutes from Jamaica Pond and the bustling shops and restaurants along Centre Street. All units rented till Aug 31 2026. Sold AS-IS. Opportunity for owner renovations to increase future rental income. Any offers reviewed Wed 4/15/26 Noontime, make good 24
| Units | 3 |
| Living area | 5,013 sqft |
| Lot size | 6,160 sqft |
| Year built | 1905 |
| Price / sqft | $342 |
| County | Suffolk |
| MLS # | 73499505 |
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Listing courtesy of a MLS PIN member office. Listing data © MLS PIN.
Auto-generated from the listing data — richer AI answers coming with the live site.
It is a 3-unit multi-family property with 5,013 sqft of living area, built in 1905.
At a list price of $1,525,000 across 3 units, that works out to roughly $508,333 per unit.
At $1,525,000 for 5,013 sqft, that's about $342 per square foot.
285 Chestnut Ave, Boston MA 02130 is in Boston, Suffolk County, MA 02130.

Justin Rollo is a Broker Associate with Signal Real Estate (MA Lic. #9534264) and a lifelong Massachusetts resident. Over 14 years and hundreds of transactions, he has worked investment properties — multi-families and house-hacking — across Greater Boston full-time. Away from real estate, Justin is a proud dad, youth coach and local school-committee member — and a former professional poker player who still loves golf and following local sports.