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.
| Units | 3 |
| Living area | 3,681 sqft |
| Lot size | 4,500 sqft |
| Year built | 1900 |
| Price / sqft | $489 |
| County | Norfolk |
| MLS # | 73559809 |
| Days on market | 34 days |
| Listed on | August 5, 2026 |
| Annual property tax | $16,475 |
| Tax year | 2026 |
| Assessed value | $1,608,900 |
| Zoning | M10 |
| Gross income (actual) | $96,000/yr |
| Net operating income (actual) | $96,000/yr |
| Total actual rent | $8,000/mo |
| Stories | 3 |
| Total rooms | 20 |
| Lot size | 0.1 acres |
| Garage spaces | 0 |
| Parking spaces | 6 |
| Parking | Off Street |
| Basement | Full, Finished |
| Foundation | Granite |
| Roof | Shingle |
| Construction | Frame |
| Flooring | Hardwood, Wood |
| Heating | Natural Gas |
| Cooling | None |
| Sewer | Public Sewer |
| Water | Public |
| Appliances | Oven, Dishwasher, Refrigerator, Range |
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Listing courtesy of a MLS PIN member office. Listing data © MLS PIN.
Auto-generated from the listing data — richer AI answers coming with the live site.
It is a 3-unit multi-family property with 3,681 sqft of living area, built in 1900.
86 Chestnut St, Brookline MA 02445 has been listed for 34 days (since August 5, 2026).
At a list price of $1,800,000 across 3 units, that works out to roughly $600,000 per unit.
Annual property taxes are $16,475 (2026), on an assessed value of $1,608,900.
At $1,800,000 for 3,681 sqft, that's about $489 per square foot.
6 total parking spaces (off street).
86 Chestnut St, Brookline MA 02445 is in Brookline, Norfolk County, MA 02445.

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.