HomeBrookline3 Family86 Chestnut St, Brookline MA 02445
86 Chestnut St, Brookline MA 02445 — photo 1 of 411 / 41
$1,800,000
86 Chestnut St, Brookline MA 02445
3 units · 10 bd · 4 ba · 3,681 sqft · $600,000/unit
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Signal Score pending — we haven't seeded market rents for this ZIP (02445) yet.

About this property

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.

Property details

Units3
Living area3,681 sqft
Lot size4,500 sqft
Year built1900
Price / sqft$489
CountyNorfolk
MLS #73559809

Listing status

Days on market0 days
Listed onAugust 5, 2026

Taxes & financials

Annual property tax$16,475
Tax year2026
Assessed value$1,608,900
ZoningM10
Gross income (actual)$96,000/yr
Net operating income (actual)$96,000/yr
Total actual rent$8,000/mo

Building & lot

Stories4
Total rooms19
Lot size0.1 acres
Garage spaces0
Parking spaces6
ParkingOff Street
BasementFull, Finished
FoundationGranite
RoofShingle
ConstructionFrame
FlooringHardwood, Wood

Utilities & systems

HeatingNatural Gas
CoolingNone
SewerPublic Sewer
WaterPublic
AppliancesOven, Dishwasher, Refrigerator, Range

Location

More about investing in Brookline

Listing courtesy of a MLS PIN member office. Listing data © MLS PIN.

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Questions & answers

Auto-generated from the listing data — richer AI answers coming with the live site.

How many units does 86 Chestnut St, Brookline MA 02445 have?

It is a 3-unit multi-family property with 3,681 sqft of living area, built in 1900.

How long has 86 Chestnut St, Brookline MA 02445 been on the market?

86 Chestnut St, Brookline MA 02445 has been listed for 0 days (since August 5, 2026).

What is the price per unit?

At a list price of $1,800,000 across 3 units, that works out to roughly $600,000 per unit.

What are the property taxes on 86 Chestnut St, Brookline MA 02445?

Annual property taxes are $16,475 (2026), on an assessed value of $1,608,900.

What is the price per square foot?

At $1,800,000 for 3,681 sqft, that's about $489 per square foot.

Is there parking?

6 total parking spaces (off street).

Where is this property located?

86 Chestnut St, Brookline MA 02445 is in Brookline, Norfolk County, MA 02445.

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Justin Rollo, Broker Associate at Signal Real Estate
Justin RolloBroker Associate, Signal Real Estate · MA Lic. #9534264

Justin Rollo is a Broker Associate with Signal Real Estate (MA Lic. #9534264) and a lifelong Massachusetts resident. Over 14 years and hundreds of transactions, he has worked investment properties — multi-families and house-hacking — across Greater Boston full-time. Away from real estate, Justin is a proud dad, youth coach and local school-committee member — and a former professional poker player who still loves golf and following local sports.

📞 978-790-4381📍 25 Braintree Hill Park, Suite 200, Braintree, MA 02184
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