99 Chestnut St #2, Brookline, MA 02445
Property image
Property image
OFF MARKET

$428,700

Trulia Estimate
  • 1 Bed
  • 1 Bath
  • 599 sqft

99 Chestnut St #2, Brookline, MA 02445

Est. Refi. Payment $2,620/mo*
Refinance Your Home
Currently Off Market - Sold Mar 27, 2020 for $380,000

Home Value

Trulia Estimate
$429K
Since last month
Decreased$7K (-1.6%)
Since last year
Decreased$19K (-4.2%)
Since last sale
Increased$49K (+12.8%)
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 increased by +22% in the last 10 years
MonthEstimated value
2026
August 2026$429K
July 2026$436K
June 2026$440K
May 2026$447K
April 2026$443K
March 2026$445K
February 2026$434K
January 2026$430K
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

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
77 Pond Ave #308, Brookline, MA
0.57
Apartment
$450,000
04/28/26
1
1
720
394 Riverway #10, Boston, MA
0.75
Apartment
$445,000
11/14/25
2
1
903
425 S Huntington Ave #9, Jamaica Plain, MA
0.71
Apartment
$525,000
04/30/26
2
1
950
70 Day St, Jamaica Plain, MA
0.82
Apartment
$697,000
05/18/26
3
1
1,000
10 Jamaicaway #28, Boston, MA
0.72
Apartment
$305,000
06/16/26
1
1
390
514-516 Harvard St #B2, Brookline, MA
1.59
Apartment
$317,000
09/05/25
1
1
526
20 Saint Paul St #2, Brookline, MA
0.88
Apartment
$400,000
10/14/25
2
1
703
18 Pond St #2, Jamaica Plain, MA
0.87
Apartment
$410,000
09/25/25
2
1
787
369 Tappan St #12, Brookline, MA
1.14
Apartment
$500,000
10/17/25
1
1
678
13 Linden St #8, Brookline, MA
0.69
Apartment
$714,474
01/23/26
2
1
1,088
Home facts updated by county records

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
40 Sargent Beechwood, Brookline, MA 02445
0.04
$3,388,100
4
3.5
4,322
Off Market
124 Chestnut St #1, Brookline, MA 02445
0.05
$859,000
3
1.5
1,233
For Sale
124 Chestnut St #2, Brookline, MA 02445
0.05
$900,000
3
1
1,232
Recently Sold
133 Chestnut St #2, Brookline, MA 02445
0.07
$1,725,300
3
3.5
1,925
Off Market
110-110 Chestnut St #A, Brookline, MA 02445
0.03
$699,000
2
1
831
For Sale
105 Franklin St #1, Brookline, MA 02445
0.07
$550,000
2
1
690
Recently Sold
105 Franklin St #3, Brookline, MA 02445
0.07
$649,000
2
1
757
Off Market
91 Chestnut St #4, Brookline, MA 02445
0.03
$599,300
2
1
718
Off Market
92 Chestnut St #2, Brookline, MA 02445
0.03
-
3
2.5
1,679
Off Market
112 Franklin St #3, Brookline, MA 02445
0.09
$907,800
3
1
1,099
Off Market
106 Franklin St #3, Brookline, MA 02445
0.09
$818,800
3
1
985
Off Market
263 Cypress St #263, Brookline, MA 02445
0.06
-
3
3.5
2,398
Off Market

Local Information

  • Map ViewExplore the area around 99 Chestnut St #2.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Apartment
Year Built
1955
Living Area
599 sqft
Price/Sqft
$716

About this House

This apartment is located at 99 Chestnut St #2, Brookline, MA. 99 Chestnut St #2 is in Brookline, MA and in ZIP code 02445. This property has 1 bedroom, 1 bathroom and approximately 599 sqft of floor space. This property was built in 1955.
99 Chestnut St #2, Brookline, MA 02445 is a 1 bedroom, 1 bathroom, 599 sqft apartment built in 1955. It last sold for $380,000 on Mar 27, 2020. More recently, it was listed as a rental in June 2023 with an asking price of $2,200 per month. That rental listing was removed on July 12, 2023. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $428,700, with a rent estimate of $2,975/month.

Home Details for 99 Chestnut St #2

Interior Features

Heating & Cooling
Heating: BaseboardHeating Fuel: Baseboard
Levels, Entrance, & Accessibility
Stories: 1Floors: Hardwood
Interior Details
Number of Rooms: 3

Exterior Features

Exterior Home Features
Roof: Built UpExterior: Brick
Parking & Garage
Parking Space: 1Parking: Off Street

Property Information

Year Built
Year Built: 1955
Property Type / Style
Property Type: ApartmentArchitecture: Other

Community

Units in Building: 8

Additional Information

On Site Laundry Available

Price and Tax history

DateEventPrice
Jul 12, 2023
Source: Zillow Rentals
ListingRemoved
Jun 7, 2023
Source: Zillow Rentals
Listed For Rent
$2,200
Apr 6, 2020
Source: Agent Provided
ListingRemoved
$2,000
Mar 30, 2020
Source: Agent Provided
Listed For Rent
$2,000
Mar 27, 2020
Source: N/A
Sold
$380,000

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

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.
  • Trulia User
    "Very dog friendly "
    0
    Flag
  • Rockygranahan
    "A quick and easy walk to the T. Total commute to downtown Boston from Coolidge Corner ranges between 15-25 minutes consistently."
    0
    Flag
  • 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
    Flag
  • Sydney Reitz
    "Events at the Coolidge corner theatre, Brookline day on Harvard street in Coolidge corner, open holiday meals at the United Parish church"
    0
    Flag
  • 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."
    0
    Flag
  • 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. "
    0
    Flag
  • 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."
    0
    Flag
  • Trulia User
    "Clean, safe and quiet. People are very friendly. Access ti public transportation. Love this place very much."
    0
    Flag
  • 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. "
    0
    Flag
  • 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. "
    0
    Flag
  • 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
    Flag
  • 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. "
    0
    Flag
  • 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
    Flag
  • 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
    Flag
  • Archana B.
    "Lived here for 5 years. I highly recommend it. It is getting more expensive. Some areas are more family friendly than others. "
    0
    Flag
  • 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"
    0
    Flag
  • 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
    Flag
  • 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"
    0
    Flag
  • 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
    Flag
  • 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. "
    0
    Flag
  • Luis B.
    "Lots of commerce within walking distance and easier access to the city by public transportation. Also very good public schools"
    0
    Flag
  • Magdalene M.
    "Right by the T and walking distance to Fenway! Blue bikes and scooters near by. Lots of ways to go. "
    0
    Flag
  • 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 "
    0
    Flag
  • 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
    Flag
  • Sophie
    "The community center holds a lot of interesting activities like Mahjong, movies, reading, yoga and concerts. Also we have a greeeat library here!"
    0
    Flag
  • Kathy U.
    "Many dog parks around the Coolidge corner area. Many off leash areas too. The dog community it big in this neighborhood "
    0
    Flag
  • 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
    Flag
  • Ptetrault
    "It is a safe, welcoming and peaceful neighborhood. Heath is a great school. Close to T trains and buses."
    0
    Flag
  • 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

LGBTQ Local Legal Protections

Frequently asked questions about 99 Chestnut St #2

  • What is 99 Chestnut St #2 estimated to be worth?
    Trulia's estimated value for 99 Chestnut St #2 in Brookline, MA is $428,700.
  • What is the price history for 99 Chestnut St #2?
    99 Chestnut St #2 in Brookline, MA last sold for $380,000 in March 2020.
  • Is Brookline a buyer's or seller's market?
    Brookline is currently a buyer's market, based on recent for-sale activity.
  • What's the median sale price in Brookline?
    The median sale price in Brookline is $1.22M. That is down $182K from the prior month.
  • Does 99 Chestnut St #2 have laundry facilities?
    Yes, 99 Chestnut St #2 in Brookline, MA has laundry facilities.
  • Does 99 Chestnut St #2 have parking?
    Yes, 99 Chestnut St #2 in Brookline, MA has on-site parking.

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Off Market Homes Near 99 Chestnut St #2

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