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$1,800,000 Just Listed

  • For Sale
  • Active
  • Multi-Family
  • 3 Units
  • 10 Total Beds
  • 0.1 Acres
  • Updated 1 hour ago
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Investors, take note! Don't miss this exceptional opportunity to own a three-family property in one of Brookline's most sought-after locations. Situated near Brookline Village, this property is just a 12-minute walk to the Green Line, providing convenient access to Fenway, Downtown Boston, and beyond. The MBTA Route 60 bus to the Longwood Medical Area is just steps from the front door.Enjoy a highly walkable neighborhood with easy access to grocery stores, restaurants, parks, walking trails, and all the amenities that make Brookline such a desirable place to live.The rear porches offer beautiful city views, and with modern updates, this classic property has the potential to truly shine! Major capital improvements completed within the past three years include a new roof, updated electrical, and new heating and hot water systems. Large driveway accommodates multiple cars for easy off street parking. Enjoy the ample yard space for grilling, bonfires, or just taking in the fresh air! Located in a community renowned for its exceptional schools, vibrant neighborhoods, and unbeatable location, this is an investment opportunity you won't want to miss. The property is fully leased through August 31, 2027, providing immediate, stable rental income.

Full Property Details for 86 Chestnut St

General

  • Price: $1,800,000
  • Taxes: $16,475 (2026)
  • Status: Active
  • Type: Multi-Family
  • MLS ID: 73559809
  • Updated: 8/9/2026
  • Added to Site: 5 day(s) ago

Rooms

Bathrooms

  • Total Bathrooms: 4
  • Full Bathrooms: 4

Bedrooms

  • Total Bedrooms: 10

Parking

  • Parking Features: Off Street

Location

  • County: Norfolk

Structural Information

  • Basement: Yes
  • Stories/Levels: 4
  • Square Feet: 3,681
  • Year Built: 1900

Lot Features

  • Lot Size (Acres): 0.1

Financial Considerations

  • Tax Amount: $16,475
  • Tax Year: 2026

Disclosures and Reports

  • Disclosures/Rstr.: All three units are occupied on leases until August 31st. 2027 All three units are up to date on payments and have never been behind. Property is being sold as is. Buyer and buyer agent to do all due diligence.
  • Property ID: M:0316 B:0020 L:0000, 40929

Listed by Red Tree Real Estate, Sarah McIntyre and Jerome Bibuld

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Listing agents

— 86 Chestnut St —

  • Sarah McIntyre

    Red Tree Real Estate

  • Jerome Bibuld

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 86 Chestnut St

School District:Brookline School District, Brookline, MA
NameGradesDistance
William H Lincoln School
19 Kennard Road, Brookline, MA 02445
K-80.3 mi
Brookline High School
115 Greenough Street, Brookline, MA 02445
9-120.5 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 86 Chestnut St Get Price Alerts and Save Property

Date
Details
Price
Change
Source
8/05/2026
Listed
$1,800,000
125%
MLS
4/15/2009
Sold
$800,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 86 Chestnut St

Year
Property Taxes
Change
Tax Assessment
Change
2025
$15,633
—
$1,583,900
-1%
2024
$15,676
3%
$1,604,500
6%
2023
$15,147
3%
$1,519,300
5%
2022
$14,744
8%
$1,446,900
4%
2021
$13,635
6%
$1,391,300
2%
2020
$12,874
6%
$1,362,300
5%
2019
$12,157
6%
$1,297,400
7%
2018
$11,512
3%
$1,216,900
8%
2017
$11,131
4%
$1,126,600
10%
2016
$10,672
7%
$1,024,200
10%
2015
$9,944
-1%
$931,100
6%
2014
$10,012
—
$879,000
—
View All
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 for 86 Chestnut St

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*These costs are estimates, and the interest rates assume exceptional credit standing.

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

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Listed by Red Tree Real Estate, Sarah McIntyre and Jerome Bibuld

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86 Chestnut St, Brookline, MA 02445 (MLS# 73559809) is a Multi-Family property with 3 units containing 10 bedrooms and 4 full bathrooms. 86 Chestnut St is currently listed for $1,800,000 and was received on August 05, 2026. Want to learn more about 86 Chestnut St? Do you have questions about finding other Multi-Family real estate for sale in Brookline? You can browse all Brookline real estate or contact a Coldwell Banker agent to request more information.

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