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Active

86 Chestnut St

Brookline, MA 02445

$1,800,000
10Bedrooms
4Bathrooms
3,681Square feet
1900Year built

Residential Income · Active · MLS #73559809
Listing Courtesy of Red Tree Real Estate | Sarah Mcintyre

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MLS PIN data

About this home

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! 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.

Property information

Details at a glance

Interior

Rooms
19
Heating
Natural Gas
Cooling
None
Flooring
Hardwood, Wood

Building

Style
3 Family
Year built
1900
Parking
6
Foundation
Granite
Roof
Shingle

Land & utilities

Lot size
0.1 acres
Water
Public
Sewer
Public Sewer
Zoning
M10

Financial

Annual taxes
$16,475
Assessment year
2026

Listing history

Price and status timeline

No additional public listing history was supplied for this property.

Property value estimate

An informed starting point

Estimated value$1,843,495

Estimated range $1,737,433$1,949,556

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Automated estimates are not appraisals or guarantees of market value.

Comparable sales

Recent properties for context

Recent comparable sales are not available for this property.

Photo insights

Condition signals

Overall presentationbelow average

Generated from listing photography; not a substitute for an inspection.

Local market context

How this home compares in Brookline

MetricThis propertyBrookline
List price$1,800,000$2,895,00038% below local
Price / sq ft$489$62622% below local
Days on market255252% below local
Explore homes in Brookline

Active city listing statistics from MLS PIN as of September 6, 2026. Asking prices are not completed-sale values.

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Common questions

About 86 Chestnut St

Can I schedule a private showing?

Yes. Request a tour of 86 Chestnut St and a Bean Group agent will help coordinate an available time with the listing side.

Can you help me evaluate this property?

Yes. We can discuss condition, comparable sales, offer strategy and the questions worth asking before you decide whether to proceed.

Are property documents available?

Availability varies by property and source. Request the documents you need and we will help obtain what is available.