86 Chestnut St Brookline — Photo 1 of 33
Recent Drop: $50,000
$1,750,000
86 Chestnut St, Brookline, MA 02445
Brookline, MA 02445
Beds
9
Baths
4
SqFt
3,681
Style
3 Family
Built
1900
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.
Key facts
It was listed on August 5, 2026. The price has come down from an original $1,800,000 to $1,750,000, most recently on October 1, 2026. The annual property taxes are $16,475 (2026 tax year). It sits on a 0.1-acre (4,500 sq ft) lot.
Open Houses
Market Value Analysis
* Analysis is based on 21 actively listed and recently sold comparable properties strictly within Brookline, MA.
Property Details
Financials
Parking
Interior Specifications
Climate & Utilities
Building & Exterior
Property & Lot
Amenities & Appliances
Oven • Dishwasher • Refrigerator • Range
Neighborhood
Public Transportation • T-Station
Geography
Property History
$1,750,000
Was $1,800,000
Oct 1, 2026
MLS® 73559809
$1,800,000
Aug 5, 2026
MLS® 73559809
Questions about this home
When was 86 Chestnut St, Brookline listed?
86 Chestnut St, Brookline was listed on August 5, 2026.
Has the price of 86 Chestnut St, Brookline changed?
The price has come down from an original $1,800,000 to $1,750,000, most recently on October 1, 2026.
What are the property taxes for 86 Chestnut St, Brookline?
The annual property taxes for 86 Chestnut St, Brookline are $16,475 (2026 tax year).
How big is the lot at 86 Chestnut St, Brookline?
86 Chestnut St, Brookline sits on a 0.1-acre (4,500 sq ft) lot.
What is the status of 86 Chestnut St, Brookline?
86 Chestnut St, Brookline is actively listed for sale.
Population
22,560
U.S. Census Bureau, ACS 2024 5-Year Estimates (B01003)
Median Household Income
$140K
U.S. Census Bureau, ACS 2024 5-Year Estimates (B19013)
Renter-Occupied Homes
47.9%
U.S. Census Bureau, ACS 2024 5-Year Estimates (B25003)
New Construction Permits — Norfolk County
1,524 housing units permitted in the last 12 months (+52% vs the prior 12 months) — 1,030 in 5+ unit buildings
U.S. Census Bureau, Building Permits Survey (through Jul '26)
Listing Agent: Sarah Mcintyre
Listing Office: Red Tree Real Estate
MLS® Number: 73559809
