3 Family at 86 Chestnut St, Brookline MA 02445, Brookline
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33 photos

$1,800,000

86 Chestnut St, Brookline MA 02445
Brookline, MA 02445
Listed by Sarah McIntyre
Bedrooms
9
Bathrooms
4
Living area
3,681 sqft
Year built
1900

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 details

MLS #
73559809
Property type
3 Family
Subdivision
N/A
Status
Active
Days on market
51
On market date
August 5, 2026
Stories
3
Total bathrooms
4
Garage spaces
N/A
Parking spaces
6
Lot size
0.1 acres
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Nearby schools

Within 10 miles · public school directory data (NCES)

Elementary
William H Lincoln
0.31 mi away · Grades 0-8
Nearest school -- attendance-zone data not available here
5.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
471
Student:teacher ratio
9.8:1
District
Brookline
Middle
James P Timilty Middle
1.73 mi away · Grades 6-8
Nearest school -- attendance-zone data not available here
5.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
205
Student:teacher ratio
8.2:1
District
Boston
High
Brookline High
0.52 mi away · Grades 9-12
Nearest school -- attendance-zone data not available here
5.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
2,087
Student:teacher ratio
10.9:1
District
Brookline

Walkability

Blended score for Brookline's center: EPA's National Walkability Index (street network, transit, land-use mix) combined with nearby-amenity density. 60% EPA National Walkability Index + 40% nearby-amenity density (Google Places).

87
Highly walkable
out of 100
EPA National Walkability Index
15.5 / 20 -- Most walkable
Nearby-amenity density
100 / 100
Restaurants & cafes20
Grocery stores20
Parks20
Schools20
Transit stops20
Pharmacies6

Market position

How this listing compares to current activity in Brookline, from live MLS data.

On the market 51 days -- 45 fewer days than Brookline's current average of 96 days.
For reference, the median list price across 791 active listings in Brookline right now is $9,500.

Mortgage calculator

Estimate only - actual rate and payment depend on your lender, credit, and loan program.

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Est. monthly payment
$10,990/mo
$360,000 down
$1,440,000 loan
Principal & interest$9,340
Property tax (est.)$1,500
Home insurance (est.)$150

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Data source: Listing information provided by MLS Property Information Network via Trestle/CoreLogic. Last updated 10 days ago.

Information herein deemed reliable but not guaranteed; all measurements, school assignments, HOA fees, taxes, and feature lists are approximate and should be independently verified. Equal Housing Opportunity.