Date
Details
Price
Change
Source
4/09/2026
Listed
$1,525,000
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
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$1,525,000 Just Listed
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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.
Full Property Details
Full Property Details for 285 Chestnut Ave
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General
- Price: $1,525,000
- Taxes: $19,960 (2026)
- Status: Active
- Type: Multi-Family
- MLS ID: 73499505
- Updated: Today (4/9/2026)
- Added to Site: Today
Rooms
Bathrooms
- Total Bathrooms: 3
- Full Bathrooms: 3
Bedrooms
- Total Bedrooms: 10
Parking
- Parking Features: Off Street, Stone/Gravel
Location
- County: Suffolk
Structural Information
- Basement: Yes
- Stories/Levels: 3
- Square Feet: 5,013
- Year Built: 1905
Lot Features
- Lot Size (Acres): 0.14
Financial Considerations
- Tax Amount: $19,960
- Tax Year: 2026
Disclosures and Reports
- Exclusions: Tenants Own Curtains.
- Disclosures/Rstr.: 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.
- Property ID: 1349148
Listed by Arborview Realty Inc., Christian Iantosca Team
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Listing agent
— 285 Chestnut Ave —
Christian Iantosca Team
Arborview Realty Inc.
NMLS#: 1598647Get Pre-Approved Today
Schools
Schools serving 285 Chestnut Ave
School District:Boston School District
| Name | Grades | Distance |
|---|---|---|
Mission Hill School 20 Child Street, Boston, MA 02130 | PK-8 | 0.4 mi |
Curley K-8 School 493 Centre St., Boston, MA 02130 | PK-8 | 0.4 mi |
Mendell Elementary School 164 School Street, Boston, MA 02119 | PK-5 | 0.5 mi |
The English High School 144 McBride Street, Boston, MA 02130 | 9-12 | 0.5 mi |
Boston Latin Academy 205 Townsend Street, Boston, MA 02121 | 7-12 | 1.3 mi |
Jeremiah E Burke High School 60 Washington Street, Boston, MA 02121 | 9-12 | 1.5 mi |
Community Academy 25 Glen Road, Boston, MA 02130 | 9-12 | 0.4 mi |
Margarita Muniz Academy 20 Child Street, Boston, MA 02130 | 9-12 | 0.5 mi |
Egleston Community High School 3134 Washington Street, Boston, MA 02130 | 9-12 | 0.6 mi |
Disclaimer:
School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.
Price & Sales History for 285 Chestnut Ave
Tax History
Tax History for 285 Chestnut Ave
Year
Property Taxes
Change
Tax Assessment
Change
2025
$18,467
3%
$1,594,700
-3%
2024
$17,986
1%
$1,650,100
—
2023
$17,722
6%
$1,650,100
7%
2022
$16,777
9%
$1,542,000
7%
2021
$15,377
1%
$1,441,100
—
2020
$15,188
10%
$1,438,300
10%
2019
$13,779
9%
$1,307,300
8%
2018
$12,687
-1%
$1,210,600
—
2017
$12,820
5%
$1,210,600
9%
2016
$12,218
9%
$1,110,700
20%
2015
$11,242
11%
$928,300
15%
2014
$10,122
—
$804,600
—
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
Estimate the Cost
Estimate the Cost for 285 Chestnut Ave
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- Multi-Family
- Active
- Updated 4 days ago
- 3Units
- 9Total Beds
- 0.22Acres
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- Townhouse
- Active
- Updated 11 hours ago
- 2Beds
- 3Total Baths
- 2,415Sq. Ft.
Listed by Kim Douglas (610) 805-0361
- Multi-Family
- Active
- Updated 1 day ago
- 2Units
- 3Total Beds
- 0.05Acres
Co-Listed by Simon Gray (781) 290-7454
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- Multi-Family
- Active
- Updated 21 hours ago
- 3Units
- 10Total Beds
- 0.06Acres
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- Multi-Family
- Closed
- 2Units
- 4Total Beds
- 0.1Acres
Listed by Brenda van der Merwe
285 Chestnut Ave, Boston, MA 02130 (MLS# 73499505) is a Multi-Family property with 3 units containing 10 bedrooms and 3 full bathrooms. 285 Chestnut Ave is currently listed for $1,525,000 and was received on April 09, 2026. Want to learn more about 285 Chestnut Ave? Do you have questions about finding other Multi-Family real estate for sale in Boston? You can browse all Boston real estate or contact a Coldwell Banker agent to request more information.