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

$528,900

Trulia Estimate
as of Sep 3, 2026
  • 2 Beds
  • 1 Bath
  • 718 sqft
  • 2 Beds
  • 1 Bath
  • 718 sqft

105 Chestnut St #2, Brookline, MA 02445

Home Highlights

Property Type
Apartment
Living Area
718 sqft
Price/Sqft
$737

Local Information

  • Map ViewExplore the area around 105 Chestnut St #2.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

About this House

Newly renovated 2 bedroom condo is located on a quiet street in Brookline Village. Walk to BHS and T station. Close to shops and restaurant. Minutes to Jamaica pond and Longwood Medical area. This beautiful bright corner home features an eat-in kitchen with a garbage disposal and dishwasher. HEAT and one parking space are included in the rent. Extra private storage is available. Laundromat is in the building. Pets are on a case-by-base basis. This property offers a chance to shape a living space to your exact desires.

Landlord is responsible for HEAT, water, sewage, and trash removing. Tenant pays electricity. One assigned parking space is included in the rent. Extra private storage is available. Laundromat is in the building. Pets are on a case-by-base basis.
105 Chestnut St #2, Brookline, MA 02445 is a 2 bedroom, 1 bathroom, 718 sqft apartment. It last sold for $189,000 on Nov 1, 2000 (6,532% above the $2,850 asking price). More recently, it was listed as a rental in January 2026 with an asking price of $3,200 per month. That rental listing was removed on April 12, 2026. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $528,900, with a rent estimate of $3,286/month.

Home Details for 105 Chestnut St #2

Property Information

Property Type / Style
Property Type: Apartment

Rental Terms, Policies & Fees

Lease Term: 1 Year

Interior Features

Appliances & Utilities
DishwasherRefrigerator
Levels, Entrance, & Accessibility
Floors: Hardwood, Tile

Exterior Features

Parking & Garage
Parking: Off Street Parking, On Site

Comparable Sales for 105 Chestnut St #2

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
77 Pond Ave #308, Brookline, MA
0.58
Apartment
$450,000
04/28/26
1
1
720 sqft
394 Riverway #10, Boston, MA
0.76
Apartment
$445,000
11/14/25
2
1
903 sqft
20 Saint Paul St #2, Brookline, MA
0.88
Apartment
$400,000
10/14/25
2
1
703 sqft
425 S Huntington Ave #9, Jamaica Plain, MA
0.74
Apartment
$525,000
04/30/26
2
1
950 sqft
18 Pond St #2, Jamaica Plain, MA
0.89
Apartment
$410,000
09/25/25
2
1
787 sqft
13 Linden St #8, Brookline, MA
0.69
Apartment
$714,474
01/23/26
2
1
1,088 sqft
10 Jamaicaway #28, Boston, MA
0.74
Apartment
$305,000
06/16/26
1
1
390 sqft
33 Pond Ave #1207, Brookline, MA
0.58
Apartment
$880,000
10/15/25
2
2
1,300 sqft
70 Day St, Jamaica Plain, MA
0.84
Apartment
$697,000
05/18/26
3
1
1,000 sqft
21 Westbourne Ter #3, Brookline, MA
1.14
Apartment
$580,000
10/30/25
2
1
876 sqft
Home facts updated by county records

Nearby homes

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Rental Market Trends in Brookline

Last updated Sep 2026
Trulia Rent Estimate$3,286/mo
Average rent
$3.98K
$220MoM
Available listings
1807
View rental market trends in Brookline, MA

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

Price and Tax history

DateEventPrice
Apr 12, 2026
Source: Zillow Rentals
ListingRemoved
$2,850
Feb 28, 2026
Source: Zillow Rentals
PriceChange
$2,850
Price decreased by 3%
Jan 5, 2026
Source: Zillow Rentals
PriceChange
$2,950
Price decreased by 8%
Jan 2, 2026
Source: Zillow Rentals
Listed For Rent
$3,200
Jan 2, 2026
Source: MLS PIN #73459096
ListingRemoved
$3,200

Frequently asked questions about 105 Chestnut St #2

  • What is 105 Chestnut St #2 estimated to be worth?
    Trulia's estimated value for 105 Chestnut St #2 in Brookline, MA is $528,900.
  • What is the price history for 105 Chestnut St #2?
    105 Chestnut St #2 in Brookline, MA last sold for $189,000 in November 2000.
  • 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 105 Chestnut St #2 have parking?
    Yes, 105 Chestnut St #2 in Brookline, MA has on-site parking.

Homes for rent near 105 Chestnut St #2

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Affordability

TIP:Try to keep your rent within a third of your gross household income. Learn why in our Renter's Guide.
For this property
PER YEAR
is the suggested income
Win over prospective landlords with your smart budgeting. As a good rule of thumb, ideally you would have at least three times your monthly rent in combined household income.
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