For Sale
Price CutPrice Drop: $50K (10/01)
Open House
House for sale at 86 Chestnut St, Brookline, MA 02445 | MLS# 73559809 | Listing updated on 2026-10-05
Photo 1 of House for sale at 86 Chestnut St, Brookline, MA 02445 | MLS# 73559809 | Listing updated on 2026-10-05
Photo 2 of House for sale at 86 Chestnut St, Brookline, MA 02445 | MLS# 73559809 | Listing updated on 2026-10-05
Photo 3 of House for sale at 86 Chestnut St, Brookline, MA 02445 | MLS# 73559809 | Listing updated on 2026-10-05
Photo 4 of House for sale at 86 Chestnut St, Brookline, MA 02445 | MLS# 73559809 | Listing updated on 2026-10-05
29+
Beds Icon

Street View

$1,750,000

Monthly Est:$8,710

  • Beds Icon9 Beds
  • Beds Icon
    4 Baths
  • Beds Icon3,681sqft

86 Chestnut St, Brookline, MA 02445

$8,710/moEst:

Get Pre-Approved

  • Triplex

  • Built in 1900

  • $-- HOA

  • 0.1 acre lot

  • $475/sq.ft

Description

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.

  • Houzeo last checked: 7 hours ago
  • Listing updated: October 5, 2026 at 7:05 am
  • Listing Provided by: Sarah McIntyre (617) 794-2045 | Red Tree Real Estate (617) 487-8015
  • Source: MLS Property Information Network-MA | MLS#: 73559809 MLS Property Information Network-MA

Part of

Building
86 Chestnut St
No reviews yet

Property Details

  • Status

    Active

  • Type

    Multi Family

  • No. of Stories

    3

  • County

    Norfolk County

  • City

    Brookline

  • Neighborhood

    --

  • Year Built

    1900

  • HOA Fees

    -

  • Finished Area

    3,681 sqft

  • Lot Size

    0.1 acre lot

  • Basement Area

    - sqft

  • MLS Name

    MLS Property Information Network

  • MLS Number

    73559809

  • MLS Status

    Active

  • Days on Market

    64

Open House

Continue Your Journey in App

Find your dream home, receive real-time updates, and many more!

Location

Facts & Features

Rooms

  • Bedrooms & bathrooms

    Bedrooms: 9

    Bathrooms: 4

Interior

  • Sewer

    Public Sewer

  • Interior Features

    Ceiling Fan(s), Pantry, Bathroom With Tub, Studio, Bathroom With Shower Stall, Living Room, Dining Room, Kitchen

  • Appliances

    Oven, Dishwasher, Refrigerator, Range

  • Window Features

    Insulated Windows

  • Flooring

    Hardwood, Wood

  • Cooling

    None

  • Heating

    Natural Gas

Construction

  • Year Built

    Year Built: 1900

  • Home type

    Triplex

  • Foundation Details

    Granite

  • Roof

    Shingle

  • Construction Materials

    Frame

Utilities & Energy

  • Water Source

    Public

  • Basement

    Full, Finished

  • Parking Features

    Off Street

  • Electric

    Circuit Breakers

Other Features

  • Community Features

    Public Transportation, T Station

  • Patio And Porch Features

    Deck Wood

  • Lot Features

    Corner Lot

  • Disclosures

    Property Is Being Sold As Is. Buyer And Buyer Agent To Do All Due Diligence.first Floor Unit #1 Is Metered With The Common Area. Lease For Unit #2 Is Valid Until August 31st. 2027 There Is No Lease In Place For Units #1 & #3 They Are Occupied With Paying Tenants.

Price History

DateEventPrice

10/01/2026

Source: mls_logoMLS Property Information Network-MA #73559809

Price Decreased

$1,750,000 -2.78%

$475/sqft

09/02/2026

Source: mls_logoMLS Property Information Network-MA #73559809

Listed for Sale

$1,800,000

$489/sqft

08/27/2026

Source: mls_logoMLS Property Information Network-MA #73559809

Pending

$1,800,000

$489/sqft

Nearby Homes

Based on information provided to and compiled by MLS Property Information Network, Inc. covering through Oct 09, 2026, 02:30PM. The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. from third-party sources, including sellers, lessors and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information, and the Images, are for the personal, non-commercial use of consumers having a good faith interest in purchasing or leasing listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing or leasing. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the Images, set forth herein. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified. © 2026 MLS Property Information Network, Inc. All Rights Reserved.

Advertising Broker: Derek Greene | The Greene Realty Group