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Properties

  • 285 Chestnut Ave, Boston, Massachusetts, 10 Bedrooms Bedrooms, 17 Rooms Rooms,3 BathroomsBathrooms,Residential Income,For Sale,Chestnut Ave,73499505
  • 285 Chestnut Ave, Boston, Massachusetts, 10 Bedrooms Bedrooms, 17 Rooms Rooms,3 BathroomsBathrooms,Residential Income,For Sale,Chestnut Ave,73499505
  • 285 Chestnut Ave, Boston, Massachusetts, 10 Bedrooms Bedrooms, 17 Rooms Rooms,3 BathroomsBathrooms,Residential Income,For Sale,Chestnut Ave,73499505
  • 285 Chestnut Ave, Boston, Massachusetts, 10 Bedrooms Bedrooms, 17 Rooms Rooms,3 BathroomsBathrooms,Residential Income,For Sale,Chestnut Ave,73499505
  • 285 Chestnut Ave, Boston, Massachusetts, 10 Bedrooms Bedrooms, 17 Rooms Rooms,3 BathroomsBathrooms,Residential Income,For Sale,Chestnut Ave,73499505
  • 285 Chestnut Ave, Boston, Massachusetts, 10 Bedrooms Bedrooms, 17 Rooms Rooms,3 BathroomsBathrooms,Residential Income,For Sale,Chestnut Ave,73499505
  • 285 Chestnut Ave, Boston, Massachusetts, 10 Bedrooms Bedrooms, 17 Rooms Rooms,3 BathroomsBathrooms,Residential Income,For Sale,Chestnut Ave,73499505
  • 285 Chestnut Ave, Boston, Massachusetts, 10 Bedrooms Bedrooms, 17 Rooms Rooms,3 BathroomsBathrooms,Residential Income,For Sale,Chestnut Ave,73499505
  • 285 Chestnut Ave, Boston, Massachusetts, 10 Bedrooms Bedrooms, 17 Rooms Rooms,3 BathroomsBathrooms,Residential Income,For Sale,Chestnut Ave,73499505
  • 285 Chestnut Ave, Boston, Massachusetts, 10 Bedrooms Bedrooms, 17 Rooms Rooms,3 BathroomsBathrooms,Residential Income,For Sale,Chestnut Ave,73499505
  • 285 Chestnut Ave, Boston, Massachusetts, 10 Bedrooms Bedrooms, 17 Rooms Rooms,3 BathroomsBathrooms,Residential Income,For Sale,Chestnut Ave,73499505
  • 285 Chestnut Ave, Boston, Massachusetts, 10 Bedrooms Bedrooms, 17 Rooms Rooms,3 BathroomsBathrooms,Residential Income,For Sale,Chestnut Ave,73499505
  • 285 Chestnut Ave, Boston, Massachusetts, 10 Bedrooms Bedrooms, 17 Rooms Rooms,3 BathroomsBathrooms,Residential Income,For Sale,Chestnut Ave,73499505
  • 285 Chestnut Ave, Boston, Massachusetts, 10 Bedrooms Bedrooms, 17 Rooms Rooms,3 BathroomsBathrooms,Residential Income,For Sale,Chestnut Ave,73499505
  • 285 Chestnut Ave, Boston, Massachusetts, 10 Bedrooms Bedrooms, 17 Rooms Rooms,3 BathroomsBathrooms,Residential Income,For Sale,Chestnut Ave,73499505
  • 285 Chestnut Ave, Boston, Massachusetts, 10 Bedrooms Bedrooms, 17 Rooms Rooms,3 BathroomsBathrooms,Residential Income,For Sale,Chestnut Ave,73499505
  • 285 Chestnut Ave, Boston, Massachusetts, 10 Bedrooms Bedrooms, 17 Rooms Rooms,3 BathroomsBathrooms,Residential Income,For Sale,Chestnut Ave,73499505
  • 285 Chestnut Ave, Boston, Massachusetts, 10 Bedrooms Bedrooms, 17 Rooms Rooms,3 BathroomsBathrooms,Residential Income,For Sale,Chestnut Ave,73499505
  • 285 Chestnut Ave, Boston, Massachusetts, 10 Bedrooms Bedrooms, 17 Rooms Rooms,3 BathroomsBathrooms,Residential Income,For Sale,Chestnut Ave,73499505
  • 285 Chestnut Ave, Boston, Massachusetts, 10 Bedrooms Bedrooms, 17 Rooms Rooms,3 BathroomsBathrooms,Residential Income,For Sale,Chestnut Ave,73499505
  • 285 Chestnut Ave, Boston, Massachusetts, 10 Bedrooms Bedrooms, 17 Rooms Rooms,3 BathroomsBathrooms,Residential Income,For Sale,Chestnut Ave,73499505
  • 285 Chestnut Ave, Boston, Massachusetts, 10 Bedrooms Bedrooms, 17 Rooms Rooms,3 BathroomsBathrooms,Residential Income,For Sale,Chestnut Ave,73499505
  • 285 Chestnut Ave, Boston, Massachusetts, 10 Bedrooms Bedrooms, 17 Rooms Rooms,3 BathroomsBathrooms,Residential Income,For Sale,Chestnut Ave,73499505
  • 285 Chestnut Ave, Boston, Massachusetts, 10 Bedrooms Bedrooms, 17 Rooms Rooms,3 BathroomsBathrooms,Residential Income,For Sale,Chestnut Ave,73499505
  • 285 Chestnut Ave, Boston, Massachusetts, 10 Bedrooms Bedrooms, 17 Rooms Rooms,3 BathroomsBathrooms,Residential Income,For Sale,Chestnut Ave,73499505
  • 285 Chestnut Ave, Boston, Massachusetts, 10 Bedrooms Bedrooms, 17 Rooms Rooms,3 BathroomsBathrooms,Residential Income,For Sale,Chestnut Ave,73499505
  • 285 Chestnut Ave, Boston, Massachusetts, 10 Bedrooms Bedrooms, 17 Rooms Rooms,3 BathroomsBathrooms,Residential Income,For Sale,Chestnut Ave,73499505
  • 285 Chestnut Ave, Boston, Massachusetts, 10 Bedrooms Bedrooms, 17 Rooms Rooms,3 BathroomsBathrooms,Residential Income,For Sale,Chestnut Ave,73499505
  • 285 Chestnut Ave, Boston, Massachusetts, 10 Bedrooms Bedrooms, 17 Rooms Rooms,3 BathroomsBathrooms,Residential Income,For Sale,Chestnut Ave,73499505
  • 285 Chestnut Ave, Boston, Massachusetts, 10 Bedrooms Bedrooms, 17 Rooms Rooms,3 BathroomsBathrooms,Residential Income,For Sale,Chestnut Ave,73499505
  • 285 Chestnut Ave, Boston, Massachusetts, 10 Bedrooms Bedrooms, 17 Rooms Rooms,3 BathroomsBathrooms,Residential Income,For Sale,Chestnut Ave,73499505
  • 285 Chestnut Ave, Boston, Massachusetts, 10 Bedrooms Bedrooms, 17 Rooms Rooms,3 BathroomsBathrooms,Residential Income,For Sale,Chestnut Ave,73499505
  • 285 Chestnut Ave, Boston, Massachusetts, 10 Bedrooms Bedrooms, 17 Rooms Rooms,3 BathroomsBathrooms,Residential Income,For Sale,Chestnut Ave,73499505
  • 285 Chestnut Ave, Boston, Massachusetts, 10 Bedrooms Bedrooms, 17 Rooms Rooms,3 BathroomsBathrooms,Residential Income,For Sale,Chestnut Ave,73499505
  • 285 Chestnut Ave, Boston, Massachusetts, 10 Bedrooms Bedrooms, 17 Rooms Rooms,3 BathroomsBathrooms,Residential Income,For Sale,Chestnut Ave,73499505
  • 285 Chestnut Ave, Boston, Massachusetts, 10 Bedrooms Bedrooms, 17 Rooms Rooms,3 BathroomsBathrooms,Residential Income,For Sale,Chestnut Ave,73499505
  • 285 Chestnut Ave, Boston, Massachusetts, 10 Bedrooms Bedrooms, 17 Rooms Rooms,3 BathroomsBathrooms,Residential Income,For Sale,Chestnut Ave,73499505
Property Description

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.

Features
Heating System:
Forced Air, Steam, Oil, Natural Gas
Basement:
Full
Parking:
Stone/gravel, Off Street
Exterior Unit Features:
Garden
Flooring:
Hardwood
Sewer:
Public Sewer
Water:
Public
Disclosure:
nw. hot water heater, maintenance free siding & deck., contingent upon seller finding suitable housing
Electric Feature:
Circuit Breakers, 100 Amp Service
Garage Parking
Lead Paint:
Certified Treated, Yes
Additional Information
Area:
Jamaica Plain
Parking Spaces:
3
Tax Year:
2026
Status:
Active
Price Per Sqft:
$304
Zoning:
0
No Units:
3
Orig Price:
$1,525,000
LEASE:
Yes
Waterfront:
No
MlsStatus:
New
Address Map
City:
Boston
State:
MA
County:
Suffolk
Postal Code:
02130
Longitude:
W72° 53' 23.8''
Latitude:
N42° 18' 47''
  • Google Map

Residential Income

285 Chestnut Ave, Boston, Massachusetts

10 Bedrooms
3 Total Bathrooms
5,013 Sqft
$1,525,000
Listing ID #73499505
Basic Details
Property Type :
Residential Income
Listing Type :
For Sale
Price :
$1,525,000
Bedrooms :
10
Rooms :
17
Total Bathrooms :
3
Full Bathrooms :
3
Square Footage :
5,013 Sqft
Year Built :
1905
Lot Area :
0.14 Acre
Listing ID :
73499505
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Agent info
Robb Enterprises
  • Stephen E. Robb
  • View website
  • 617-212-0251
  • srobb@robbenterprises.com

Contact Agent

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.

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