10 beds3,681 sqft$489/sqft
86 Chestnut St, Brookline, MA 02445
Est: $10,522/moGet pre-approved

Description

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...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.
LISTING UPDATED: 08/05/2026 09:17 PM

  1. Listed by Sarah McIntyre • Red Tree Real Estate
  2. Listed by Jerome Bibuld • Red Tree Real Estate
  3. Listed by Adam Kotkin • Red Tree Real Estate

Property Details for 86 Chestnut Street

Status
MLS #
73559809
Days on Market
1
Taxes
$16,475 / year
HOA Fees
-
Property Type
MLS Type
Multi-family / 3 Family
Year Built
1900
Town
Brookline
Area
MA-Brookline
Garage Spaces
0
Open Parking Spaces
6.00
Parking Spaces Total
6

Open Houses

Saturday, Aug 8th12:30 PM - 2:30 PM
Sunday, Aug 9th11:00 AM - 1:00 PM

Location

Listing Courtesy of Red Tree Real Estate, Sarah McIntyre; Red Tree Real Estate, Jerome Bibuld; Red Tree Real Estate, Adam Kotkin
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Building Information for 86 Chestnut Street

Stories4Residences3Year Built1900Building Size-Lot Size0.10 AC / 4,500 SF

Payment Calculator

$10,522 per month

30 year fixed, 6.55% Interest

Principal and Interest

$9,149

Property Taxes

$1,373

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

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Property Information for 86 Chestnut Street

General Details
Property Details
  • Building Area Units: Square Feet
  • Community Features: Public Transportation, T-Station
  • Living Area: 3681.0
  • Color: White
  • SqFt with Basement: Yes
  • Total Units: 3
  • Waterfront: No
  • Water View: No
  • Year Built Details: Actual
  • Year Built Source: Public Records
Features
Interior Features
  • Appliances: Oven, Dishwasher, Refrigerator, Range
  • Basement Features: Full, Finished
  • Num of Baths: 4.0
  • Num of Full Baths: 4
  • Num of Half Baths: 0
  • Bathrooms Total Decimal: 4.00
  • Bathrooms Total Integer: 4
  • FireplaceYN: No
  • Fireplaces: 0
  • Flooring: Hardwood, Wood
  • Interior Features: Ceiling Fan(s), Pantry, Bathroom With Tub, Studio, Bathroom with Shower Stall, Living Room, Dining Room, Kitchen
  • SpaYN: No
  • Window Features: Insulated Windows
Exterior Features
  • Construction: Frame
  • Exterior Features: Deck - Wood
  • Lot Description: Corner Lot
  • Patio And Porch Features: Deck - Wood
  • Roof Material: Shingle
Parking Features
  • Covered Spaces: .00
  • Garage: No
  • Garage Parking: Off-Street
  • Parking Features: Off-Street
  • Parking Features: Off-Street
Utilities
  • Cooling: None
  • Cooling: No
  • Electric: Circuit Breakers
  • Heating: 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
  • Road Frontage Type: Public
  • Disclosures: 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.
Tax Information
  • Tax ID: M:0316 B:0020 L:0000,40929
  • Assessments: $1,608,900
  • Book: 26548
  • Tax Year: 2026
  • Zoning: M10
Building / Association Information
Living Characteristics
  • Beds Total: 10
  • Total Living Levels: 4
Other Building Characteristics
  • Foundation: Granite
  • Levels: 4
  • Cooling Units: 0
  • Cooling Zones: 0
  • Heat Units: 3
  • Heat Zones: 3
Income / Expenses
  • GOI: $96,000.00
  • NOI: $96,000.00
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
Unit 4 Description
  • Floor U4: 0
  • Lease U4: N
  • Levels U4: 1
Rental Info
Rental Info
  • Total Actual Rent: $8,000.00

Property History for 86 Chestnut Street

DateEvent & SourcePriceAppreciation
Aug 5, 2026

Listed (Active)

MLS PIN #73559809

$1,800,000
Apr 15, 2009

Sold (Public Record)

Public Record #267115564

$800,000
Apr 15, 2009

Sold

MLS PIN #70861287

$800,000
DateEvent & SourcePrice
08/05/2026

Listed (Active)

MLS PIN #73559809

$1,800,000
04/15/2009

Sold (Public Record)

Public Record #267115564

$800,000
04/15/2009

Sold

MLS PIN #70861287

$800,000

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

Public Records for 86 Chestnut Street

Taxable ValueLand$713,400Additions$870,500Total$1,583,900
Tax Record2025$15,633 ($1,303 / month)
Home Facts
Baths3Total Finished SqFt3,681 SqFtAbove Grade Finished SqFt3,681 SqFtUnfinished Basement SqFt874 SqFtStories3Lot Size4,500 SqFtStyleTriplexYear Built1900Year Renovated1974ZoningM10CountyNORFOLKAPNBROO B:316 L:0020 S:0000

Schools near 86 Chestnut Street

This home is within Brookline School District.
Rating
School
Type
Grades
Distance
Public - K to 8
Public - 9 to 12
Private - PK to 12
Private - 1 to 10
Rating
School
Distance
William H Lincoln School
PublicK to 8

Brookline High School
Public9 to 12

Maimonides School
PrivatePK to 12

Language and Cognitive Develop
Private1 to 10

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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86 Chestnut Street is a multi-family home for sale in Brookline, MA 02445. This listing's school district is Brookline School District. Nearby schools include William H Lincoln School, Brookline High School and Maimonides School. 86 Chestnut Street is a 10-bed, 4-bath, 3,681 sqft multi-family home built in 1900.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of any information, descriptions or measurements (including square footage measurements and property condition), such should be independently verified through appropriate means, including, but not limited to, in person inspection and public records, and Compass International Holdings, its subsidiaries, affiliates and independently owned and operated franchisees, and their affiliated agents and associated third parties expressly disclaim 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 seller's discretion. No financial or legal advice provided. Equal Housing Opportunity.

Listing Courtesy of Red Tree Real Estate, Sarah McIntyre; Red Tree Real Estate, Jerome Bibuld; Red Tree Real Estate, Adam Kotkin

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.