86 Chestnut St, Brookline, MA 02445
Property image
Property image
FOR SALE

$1,800,000

  • 10 Beds
  • 4 Baths
  • 3,681 sqft

86 Chestnut St, Brookline, MA 02445

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Home Highlights

Parking
6 Parking Spaces
Outdoor
Deck
Price/Sqft
$489
Listed
21 days ago
Climate Control
Natural Gas Heating

Local Information

  • Map ViewExplore the area around 86 Chestnut St.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

About this House

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.
Last check for updates: about 5 hours ago
Listing courtesy of Sarah McIntyre, (617) 794-2045
Red Tree Real Estate, (617) 487-8015
Source: MLS PIN, MLS#73559809
Also Listed on MLS PIN.

Home Details for 86 Chestnut St

Interior Features

Interior Details
Basement: Full,FinishedNumber of Rooms: 19
Beds & Baths
Number of Bedrooms: 10Number of Bathrooms: 4Number of Bathrooms (full): 4
Dimensions and Layout
Living Area: 3681 Square Feet
Appliances & Utilities
Appliances: Oven, Dishwasher, Refrigerator, RangeDishwasherRefrigerator
Heating & Cooling
Heating: Natural GasNo CoolingAir Conditioning: NoneHas HeatingHeating Fuel: Natural Gas
Fireplace & Spa
No FireplaceNo Spa
Gas & Electric
Electric: Circuit Breakers
Windows, Doors, Floors & Walls
Window: Insulated WindowsFlooring: Hardwood, Wood
Levels, Entrance, & Accessibility
Number of Stories: 4Floors: Hardwood, Wood

Exterior Features

Exterior Home Features
Roof: ShinglePatio / Porch: Deck - WoodFoundation: Granite
Parking & Garage
Open Parking Spaces: 6No GarageParking Spaces: 6Parking: Off Street
Frontage
Road Frontage: PublicNot on Waterfront
Water & Sewer
Sewer: Public Sewer
Finished Area
Finished Area (above surface): 3181Finished Area (below surface): 500

Days on Market

Days on Market: 21

Property Information

Year Built
Year Built: 1900
Property Type / Style
Property Type: Residential IncomeProperty Subtype: 3 Family
Building
Construction Materials: FrameDoes Not Include Home Warranty
Property Information
Parcel Number: M:0316 B:0020 L:0000, 40929

Price & Status

Price
List Price: $1,800,000Price Per Sqft: $489

Active Status

MLS Status: Active

Location

Direction & Address
City: Brookline

Agent Information

Listing Agent
Listing ID: 73559809

Building

Building Area
Building Area: 3681 Square Feet

Community

Community Features: Public Transportation, T-StationNot Senior Community

Lot Information

Lot Area: 4500 sqft

Rental Terms, Policies & Fees

Rent Includes: Unit 2(Water), Unit 3(Electric, Water)

Miscellaneous

BasementMls Number: 73559809Above Grade Unfinished Area: 3181

Additional Information

Public TransportationT-Station

Around this home

What Locals Say about Brookline

At least 422 Trulia users voted on each feature.

  • 94 % Say there are sidewalks

  • 90 % Say it's dog friendly

  • 87 % Say it's walkable to restaurants

  • 87 % Say it's walkable to grocery stores

  • 84 % Say people would walk alone at night

  • 81 % Say streets are well-lit

  • 67 % Say kids play outside

  • 60 % Say there's holiday spirit

  • 59 % Say there's wildlife

  • 52 % Say parking is easy

  • 51 % Say they plan to stay for at least 5 years

  • 51 % Say it's quiet

  • 48 % Say neighbors are friendly

  • 40 % Say car is needed

  • 39 % Say yards are well-kept

  • 33 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • Rockygranahan
    "A quick and easy walk to the T. Total commute to downtown Boston from Coolidge Corner ranges between 15-25 minutes consistently."
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  • Kai Hsin Chang
    "Very convenient to do grocery and most people live here use public transportation because there’s no street parking. People who want to do street parking should apply for parking permits."
    0
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  • Sydney Reitz
    "Events at the Coolidge corner theatre, Brookline day on Harvard street in Coolidge corner, open holiday meals at the United Parish church"
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  • Sydney Reitz
    "The sidewalks and streets are well-maintained even in inclement weather. Traffic is only bad around the Longwood medical area and major streets around rush hour. Pub trans is easy and safe."
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  • Austin Wozniak
    "Multiple dog friendly, off-leash parks in the community and many great places to walk a dog. The community is very dog friendly. "
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  • Loming1986
    "Only limited (a hand-full) dog parks available, I wish there are more. Many neighbors have dogs and it’s a very dog friendly neighborhood."
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  • Trulia User
    "Clean, safe and quiet. People are very friendly. Access ti public transportation. Love this place very much."
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  • Trulia User
    "The neighborhood is great environment to raise a family. It’s peaceful, clean and quiet. We would love to be here to raise our kids here. "
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  • Trulia User
    "I’v stayed in a hotel in this neighborhood. It is a beautiful area with many shops to explore. Hope to move to this area. "
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  • Trulia User
    "Near everything. Train across the street, restaurants, coffee shops, etc JP is part of Boston. Vibrant community. Diverse. High incomes mixed with low. "
    1
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  • Trulia User
    "Yes, the area has many dog parks, both on and off leash. Most apartment buildings are dog friendly and neighbors have been very accepting. "
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  • Aliana P.
    "It’s a quick commute to downtown, especially if you live on the D line. Very convenient. It’s also a very walkable area with all stores and necessities close by. "
    1
    Flag
  • Juana B.
    "It’s very safe and great school system!! I been leaving here for 11 years and I love it and my kids too"
    2
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  • Jiyoung W.
    "Lots of other friendly dog owners, plus lots of little parks and green space for pups to run around (especially Amory Park!). Lots of businesses in the area have dog treat jars too!"
    1
    Flag
  • Adriana P.
    "It seems let friendly. Lots of parks and spaces for dogs to run. I don’t have a dog but I have friends with dogs"
    0
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  • Archana B.
    "Lived here for 5 years. I highly recommend it. It is getting more expensive. Some areas are more family friendly than others. "
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  • Deiabarroso86
    "Very safe, with a lot of stores around.. Beacon Street is a beautiful street and we have the Reservoir nearby, which is a good place for a walk."
    1
    Flag
  • Josie E.
    "The kids walk to school on a tree-lined street and neighbors know each other. A little oasis in the city "
    4
    Flag
  • Caroline
    "Drive to Watertown or take shuttle provided by my place of employment. Easy access to city via C or D green line. "
    0
    Flag
  • Dma333
    "Diverse, safe, close to everything, friendly neighbors, great schools, playgrounds in walking distance"
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  • Steve L.
    "Hancock Village in Chestnut Hill is a good place to live overall. Sometimes the management office puts together special functions like handing out cider doughnuts in the fall, or flowers to plant - both gratis. (And more as well but too much to detail)."
    4
    Flag
  • Dma333
    "Block party in September Close to a great school Playgrounds nearby Diverse community Easy access to many communities "
    1
    Flag
  • Szonja.ruppert
    "Lots of greens, parks, even bags for dogpoop is put to parks. Not many pet shops in walking distance"
    0
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  • Scottcunha311
    "Halloween’s are very popular especially on clark rd. Great location to Cleveland circle and both bu and bc can take train anywhere or easily get a bus there’s no shortsge of things to do"
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  • Jawaher A.
    "Good schools, no stealing, good neighbors, good place to kids to play, not far away from BU university, there is driving school, all government facilities around us, Uber so expensive but it is available all time, there is ice cream shop and Starbucks around us also a lot of restaurants and malls "
    2
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  • Courtney C.
    "Safe and homey - education is good but property tax is rising. Commute is perfect - only ten minute drive away from my work site. "
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  • Luis B.
    "Lots of commerce within walking distance and easier access to the city by public transportation. Also very good public schools"
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  • Magdalene M.
    "Right by the T and walking distance to Fenway! Blue bikes and scooters near by. Lots of ways to go. "
    0
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  • Jawaher A.
    "I love this area coz its safe and beautiful and the neighbors are nice and kind and there is a lot of great people "
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  • Oliver L.
    "I walk to work in the medical area. T stops make getting to the center easy. It is quite possible to live without a car."
    0
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  • Sophie
    "The community center holds a lot of interesting activities like Mahjong, movies, reading, yoga and concerts. Also we have a greeeat library here!"
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  • Kathy U.
    "Many dog parks around the Coolidge corner area. Many off leash areas too. The dog community it big in this neighborhood "
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  • Heli C.
    "The schools are excellent, and neighbors tend to know each other. We are a ‘suburb’ of Boston but also officially a town with numerous distinct village neighborhoods, most of which are walkable to restaurants and amenities. Brookline has a fairly international mix of people, with families from all over the world coming here to study and work at the nearby Harvard teaching hospitals."
    0
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  • Ptetrault
    "It is a safe, welcoming and peaceful neighborhood. Heath is a great school. Close to T trains and buses."
    0
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  • Pat B.
    "It's dog friendly...there's lots of parks around to take pets."
    0
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  • Pat B.
    "There's some strange people who are around, but they're harmless. There's lots of daycare places, so if someone has a young kid there's lots of options nearby."
    1
    Flag
  • Billy W.
    "There is only one park on this hill, but a short walk can lead you to bigger parks and playgrounds."
    1
    Flag

Market trends in Brookline

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$1.22M
$182KMoM
Sale-to-List Price
99.7%
0.2%MoM
Price per sq ft
$816
$19MoM
Available listings
216
37MoM

Home Value

Trulia Estimate
$1.74M
Since last month
Increased$37K (+2.2%)
Since last year
Decreased$221K (-11.3%)
Since last sale
Increased$941K (+117.6%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value decreased by -6% in the last 10 years
MonthEstimated value
2026
August 2026$1.74M
July 2026$1.7M
June 2026$1.72M
May 2026$2.01M
April 2026$1.98M
March 2026$1.96M
February 2026$1.93M
January 2026$1.9M
2025
2024
2023
2020

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
9 E Milton Rd, Brookline, MA
0.23
Multi-Family Home
$999,999
04/30/26
8
3
3,898
79-81 Moraine St, Jamaica Plain, MA
0.62
Multi-Family Home
$1,800,000
06/02/26
9
3
3,885
65-67 Halifax St, Jamaica Plain, MA
0.61
Multi-Family Home
$1,834,000
12/22/25
7
3
4,460
36-38 Moraine St, Jamaica Plain, MA
0.70
Multi-Family Home
$1,800,000
06/01/26
9
3
4,063
8-10 Perkins St, Jamaica Plain, MA
0.77
Multi-Family Home
$2,300,000
04/02/26
10
4
4,850
589-591 Washington St, Brookline, MA
0.90
Multi-Family Home
$1,800,000
01/13/26
9
4
3,102
19-21 Elm St, Brookline, MA
0.43
Multi-Family Home
$1,800,000
10/31/25
5
2
2,252
9 Oakview Ter, Jamaica Plain, MA
0.83
Multi-Family Home
$1,400,000
04/01/26
6
3.5
3,988
130 Minden St, Jamaica Plain, MA
0.92
Multi-Family Home
$850,000
01/09/26
6
3
2,621

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
92 Chestnut St #2, Brookline, MA 02445
0.02
-
3
2.5
1,679
Off Market
110-110 Chestnut St #A, Brookline, MA 02445
0.05
$699,000
2
1
831
For Sale
261 Cypress St, Brookline, MA 02445
0.05
$1,468,100
3
3.5
2,398
Off Market
91 Chestnut St #4, Brookline, MA 02445
0.03
$598,000
2
1
718
Off Market
263 Cypress St #263, Brookline, MA 02445
0.06
-
3
3.5
2,398
Off Market
244 Cypress St #2, Brookline, MA 02445
0.06
$566,100
2
1
624
Off Market
70 Chestnut St #3, Brookline, MA 02445
0.05
$1,213,400
3
2
1,660
Off Market
124 Chestnut St #1, Brookline, MA 02445
0.09
$932,300
3
1.5
1,243
Off Market
124 Chestnut St #2, Brookline, MA 02445
0.09
$900,000
3
1
1,232
Recently Sold
40 Sargent Beechwood, Brookline, MA 02445
0.08
$3,445,000
4
3.5
4,322
Off Market
68 Chestnut St #2, Brookline, MA 02445
0.05
$720,000
2
1
1,206
Recently Sold

Price and Tax history

DateEventPrice
Aug 5, 2026
Source: MLS PIN #73559809
Listed For Sale
$1,800,000
Jul 6, 2026
Source: Zillow Rentals
ListingRemoved
$2,200
Jun 22, 2026
Source: Zillow Rentals
Listed For Rent
$2,200
May 22, 2018
Source: Agent Provided
ListingRemoved
$2,500
May 12, 2018
Source: Agent Provided
PriceChange
$2,500
Price decreased by 7%

LGBTQ Local Legal Protections

Sarah McIntyre, Red Tree Real Estate, (617) 487-8015
Agent Phone: (617) 794-2045
The property listing data and information 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 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 set forth herein.
The MLS listing information displayed is deemed reliable, but is not guaranteed accurate by the MLS.

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Frequently asked questions about 86 Chestnut St

  • What is the estimated monthly payment for 86 Chestnut St?
    Based on a $1,800,000 list price with 20% down at today's rates, the estimated monthly payment for 86 Chestnut St in Brookline, MA is approximately $10,984 (about $9,379 principal & interest, $1,530 property taxes, and $75 homeowner's insurance). This is an estimate. Actual payment depends on your loan terms.
  • How does the list price for 86 Chestnut St compare to homes in Brookline?
    86 Chestnut St in Brookline, MA is listed at $1,800,000, about 48% above the $1.22M median sale price in Brookline.
  • What do residents say about Brookline?
    Residents describe Brookline, MA as pedestrian-friendly, dog-friendly, and walkable to restaurants. See homes for sale in Brookline, MA.
  • What are the closest schools to 86 Chestnut St?
    The closest schools to 86 Chestnut St in Brookline, MA are Brookline High School (rated 8/10), William H Lincoln School (Elementary/Middle, rated 9/10).
  • Does 86 Chestnut St have parking?
    Yes, 86 Chestnut St in Brookline, MA has on-site parking.
86 Chestnut St, Brookline, MA 02445 is a 10 bedroom, 4 bathroom, 3,681 sqft multi-family built in 1900. This property is currently available for sale and was listed by MLS PIN on Aug 5, 2026. The MLS # for this home is MLS# 73559809.