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.
Property Details
Price:
$1,525,000
MLS #:
73499505
Status:
Active
Beds:
10
Baths:
3
Type:
Multi Family
Subtype:
3 Family – 3 Units Up/Down
Neighborhood:
jamaicaplain
Listed Date:
Apr 9, 2026
Finished Sq Ft:
5,013
Total Sq Ft:
5,013
Lot Size:
6,160 sqft / 0.14 acres (approx)
Year Built:
1905
Units:
3
See this Listing
Schools
Interior
Above Grade Finished Area
5013
Bathrooms
3 Full Bathrooms
Flooring
Hardwood
Heating
Forced Air, Oil, Steam, Natural Gas
Levels
3
Exterior
Community Features
Public Transportation, Park, Walk/Jog Trails, Bike Path, T-Station
Exterior Features
Garden
Fencing
Fenced
Lot Features
Other
Open Parking Spaces
3
Parking Features
Off Street, Stone/Gravel
Parking Spots
3
Parking Total
3
Patio And Porch Features
Porch, Deck
Roof
Rubber
Stories
3
Financial
Tax Year
2026
Taxes
$19,960
Map
Community
- Address285 Chestnut Ave Boston MA
- CityBoston
- CountySuffolk
- Zip Code02130
Subdivisions in Boston
- Adams Village
- Ashmont Hill
- Ashmont Hill / Carruth Area
- Back Bay
- Bay Village
- Beacon Hill
- Bellevue Hill
- Boston
- Brighton-Oak Square
- Charlestown
- Chestnut Hill
- Chestnut Hill /Brookline line
- Chestnut Hill Park Condominium
- Clam Point Neighborhood
- Eight Streets Neighborhood
- Ellis South End Neighborhood
- Fairmount Hill
- Fields Corner
- Gas Light District
- Golf Course Neighborhood
- Harbor View
- Harborview
- Highland
- Hyde Park
- Jamaica Plain
- Lower Mills
- Melville Park
- Metropolitan Heights Area
- Metropolitan Hill
- Mission Hill – Longwood Medical
- Oak Square
- Parkway neighborhood
- Roslindale
- Roslindale – WC Bates
- roslindale village
- Roxbury’s Moreland Street Historic District
- Savin Hill: Minutes to Carson Beach/UMass Boston T-Stop
- South Boston
- Suffolk County
- Sumner Hill
- Thomas Park
- Woodbourne
Market Summary
Current real estate data for Multi Family in Boston as of Apr 10, 2026
334
Multi Family Listed
148
Avg DOM
487
Avg $ / SqFt
$2,329,193
Avg List Price
Property Summary
- 285 Chestnut Ave Boston MA is a Multi Family for sale in Boston, MA, 02130. It is listed for $1,525,000 To schedule a showing of MLS#73499505 at 285 Chestnut Ave in Boston, MA, contact your Cornerstone Real Estate agent at 617-238-7400.
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Courtesy of Arborview Realty Inc.. The property listing data and information set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information are for the personal, non-commercial use of consumers having a good faith interest in purchasing or leasing listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing or leasing. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information set forth herein.
285 Chestnut Ave
Boston, MA