285 Chestnut Ave

5,013 Sq. Ft.
$304 / Sq. Ft.
5,013
Sq. Ft.
$304
per Sq. Ft.

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...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
  1. Listed by Christian Iantosca Team • Arborview Realty Inc.

Property Details for 285 Chestnut Avenue

Town
Boston
MLS Area
Jamaica Plain
Area
MA-Boston-Jamaica Plain, MA-Boston
Style
Garden
Garage Spaces
0
Open Parking Spaces
3.00
Parking Spaces Total
3
LISTING UPDATED: 04/10/2026 03:00 PM

Property Details for 285 Chestnut Avenue

StatusNew
MLS #73499505
Days on Market3
Taxes$19,960 / year
HOA Fees-
Property TypeMulti Family
MLS TypeMulti-family / 3 Family - 3 Units Up/Down
Year Built1905
CountySuffolk County

Location

Listing Courtesy of Arborview Realty Inc., Christian Iantosca Team
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Building Information for 285 Chestnut Avenue

Stories3Residences3Year Built1905Building Size-Lot Size0.14 AC / 6,160 SF

Payment Calculator

$9,342 per month

30 year fixed, 6.46% Interest

Principal and Interest

$7,679

Property Taxes

$1,663

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

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Property Information for 285 Chestnut Avenue

General Details
Property Details
  • Building Area Units: Square Feet
  • Community Features: Public Transportation, Park, Walk/Jog Trails, Bike Path, T-Station
  • Living Area: 5013.0
  • SqFt with Basement: No
  • Total Units: 3
  • Waterfront: No
  • Year Built Details: Actual
  • Year Built Source: Public Records
Features
Interior Features
  • Basement Features: Full
  • Num of Baths: 3.0
  • Num of Full Baths: 3
  • Num of Half Baths: 0
  • Bathrooms Total Decimal: 3.00
  • Bathrooms Total Integer: 3
  • FireplaceYN: No
  • Fireplaces: 0
  • Flooring: Hardwood
  • SpaYN: No
Exterior Features
  • Exterior Features: Garden
  • Exterior Features: Fenced Yard, Garden Area, Porch, Deck
  • Fencing: Fenced
  • Lot Description: Other
  • Patio And Porch Features: Porch, Deck
  • Roof Material: Rubber
Parking Features
  • Covered Spaces: .00
  • Garage: No
  • Garage Parking: Off-Street, Stone/Gravel
  • Parking Features: Off-Street, Stone/Gravel
  • Parking Features: Off-Street, Stone/Gravel
Utilities
  • Electric: Circuit Breakers, 100 Amp Service
  • Heating: Forced Air, Oil, Steam, Natural Gas
  • Heating: Yes
  • Sewer: City/Town Sewer
  • Water: Public
Property Information
Property Info
  • Farm Land Area Units: Square Feet
  • WARRANTY: No
  • Lot Size Units: Acres
  • Disclosures: Unit #1=de-lead cert. 15yr rubber roof,hw 4yr tank,10yr (2) tankless. Blown-in insulation walls+ceiling. Possible asbestos (pipe insulation) in basement. #1 laundry basement. SOLD AS IS. Seller wishes to leave building materials in basement storage room. Upper front decks access via window.
Tax Information
  • Tax ID: 1349148
  • Assessments: $1,594,700
  • Book: 0
  • Tax Year: 2026
  • Zoning: 0
Building / Association Information
Living Characteristics
  • Beds Total: 10
  • Total Living Levels: 3
Other Building Characteristics
  • Foundation: Other
  • Levels: 3
  • Heat Units: 3
  • Heat Zones: 3
Income / Expenses
  • Electricity: $.00
  • GOI: $127,200.00
  • Gross Scheduled Income: $.00
  • Insurance: $2,264.00
  • GRE: $29,686
  • HTE: $0
  • MGF: $0
  • MSE: $0
  • RFS: $0
  • RME: $4,000
  • NOI: $97,514.00
  • Operating Expense: $29,686.00
  • WSE: $3,960.00
Complex & Association Information
  • Adult Community: No
Unit Information
Unit 1 Description
  • Floor U1: 1
  • Lease U1: Y
  • Levels U1: 1
Unit 2 Description
  • Floor U2: 2
  • Lease U2: Y
  • Levels U2: 1
Unit 3 Description
  • Floor U3: 3
  • Lease U3: Y
  • Levels U3: 1
Rental Info
Rental Info
  • Total Actual Rent: $10,600.00

Property History for 285 Chestnut Avenue

DateEvent & SourcePriceAppreciation
Apr 9, 2026

Listed (Active)

MLS PIN #73499505

$1,525,000—
DateEvent & SourcePrice
04/09/2026

Listed (Active)

MLS PIN #73499505

$1,525,000

For completeness, Compass often displays two records for one sale: the MLS record and the public record.

Public Records for 285 Chestnut Avenue

Taxable ValueLand$627,000Additions$967,700Total$1,594,700
Tax Record2025$18,467 ($1,539 / month)
Home Facts
Baths3Total Finished SqFt5,013 SqFtAbove Grade Finished SqFt5,013 SqFtStories3Lot Size6,160 SqFtStyleTriplexYear Built1905ZoningR3CountySUFFOLKAPNJAMA W:19 P:01040 S:000

Schools near 285 Chestnut Avenue

This home is within Boston Public Schools.
Rating
School
Type
Grades
Distance
Public - PK to 8
Public - 9 to 12
Public - 7 to 12
Public - 7 to 12
Rating
School
Distance
Curley K-8 School
PublicPK to 8

Community Academy
Public9 to 12

Margarita Muniz Academy
Public7 to 12

The English High School
Public7 to 12

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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285 Chestnut Avenue is a multi-family home for sale in Boston, MA 02130. This property was listed for sale on April 9, 2026 by Arborview Realty Inc., it's currently listed at $1,525,000. This listing's school district is Boston Public Schools. Nearby schools include Curley K-8 School, Community Academy and Margarita Muniz Academy. 285 Chestnut Avenue is a 10-bed, 3-bath, 5,013 sqft multi-family home built in 1905.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties expressly disclaims any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the discretion of the seller. No financial or legal advice provided. Equal Housing Opportunity.

Listing Courtesy of Arborview Realty Inc., Christian Iantosca Team

The property listing data and information, or the images, set forth herein were provided to MLS Property Information Network, Inc., Martha's Vineyard MLS, CCIMLS, Link MLS, and Berkshire County Board of REALTORS from third party sources, including sellers, lessors and public records, and were compiled by MLS Property Information Network, Inc., Martha's Vineyard MLS, CCIMLS, Link MLS, and Berkshire County Board of REALTORS. The property listing data and information, and the images, 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., Martha's Vineyard MLS, CCIMLS, Link MLS, and Berkshire County Board of REALTORS and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the images, set forth herein.