149 Chestnut St, Brookline, MA 02445
Property image
Property image
OFF MARKET

$857,900

Trulia Estimate
  • 3 Beds
  • 2 Baths
  • 1,500 sqft

149 Chestnut St, Brookline, MA 02445

Est. Refi. Payment $5,274/mo*
Refinance Your Home

Home Value

Trulia Estimate
$858K
Since last month
Decreased$44K (-4.9%)
Since last year
Decreased$86K (-9.1%)
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 +7% in the last 10 years
MonthEstimated value
2026
August 2026$858K
August 2026$851K
July 2026$902K
June 2026$886K
May 2026$827K
April 2026$871K
March 2026$878K
February 2026$831K
January 2026$821K
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
71 Highland Rd, Brookline, MA
0.21
Single-Family Home
$950,000
04/30/26
3
1.5
1,000
209 High St, Brookline, MA
0.09
Single-Family Home
$2,150,000
04/16/26
4
3.5
2,332
18 Cushing Rd, Brookline, MA
0.38
Single-Family Home
$1,351,000
01/23/26
2
2
1,230
14-14A Linden Pl, Brookline, MA
0.82
Single-Family Home
$1,750,000
06/23/26
3
1.5
1,380
50 Waverly St, Brookline, MA
0.61
Single-Family Home
$2,445,000
05/12/26
4
2
2,383
236 Walnut St, Brookline, MA
0.34
Single-Family Home
$2,750,000
05/01/26
4
3.5
3,963
11 Furnival Rd, Jamaica Plain, MA
0.93
Single-Family Home
$1,255,000
11/12/25
3
2
1,535
43 Bowditch Rd, Jamaica Plain, MA
0.95
Single-Family Home
$1,151,000
08/28/26
3
1.5
1,457
22 Edge Hill St, Jamaica Plain, MA
0.79
Single-Family Home
$1,175,000
05/13/26
3
2.5
1,235
43 Waverly St, Brookline, MA
0.63
Single-Family Home
$3,350,000
06/30/26
4
2.5
2,676

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
133 Chestnut St #2, Brookline, MA 02445
0.04
$1,737,000
3
3.5
1,925
Off Market
7 Henry St, Brookline, MA 02445
0.03
-
6
2.5
2,328
Off Market
166 Chestnut St #1, Brookline, MA 02445
0.04
$765,000
3
2
1,079
Recently Sold
112 Franklin St #3, Brookline, MA 02445
0.05
$912,700
3
1
1,099
Off Market
12 Henry St #2, Brookline, MA 02445
0.05
-
3
2
1,283
Off Market
12 Henry St #3, Brookline, MA 02445
0.05
-
3
2
1,913
Off Market
12 Henry St #A, Brookline, MA 02445
0.05
-
2
2
1,155
Off Market
11-13 Henry St, Brookline, MA 02445
0.05
-
5
2
2,136
Off Market
124 Chestnut St #1, Brookline, MA 02445
0.07
$859,000
3
1.5
1,233
For Sale
124 Chestnut St #2, Brookline, MA 02445
0.07
$900,000
3
1
1,232
Recently Sold
106 Franklin St #2, Brookline, MA 02445
0.06
$829,300
3
1
985
Off Market
106 Franklin St #3, Brookline, MA 02445
0.06
$819,500
3
1
985
Off Market

Local Information

  • Map ViewExplore the area around 149 Chestnut St.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1953
1,500 sqft
$572/sqft

About this House

AVAILABLE AUGUST 1ST! This bight and sunny duplex style two-family in owner occupied home, is nestled between Brookline Village and lovely Jamaica Pond. Home offers convenient access to the bus to Longwood Medical Center and Kenmore Square, as well as being a short distance to the D line train. Additional features include a modern kitchen with open floor plan to living and dining room with hardwood floors, spacious first floor family room, private laundry in basement with additional partially finished area great for storage, and shared use of a beautifully manicured fenced back yard. Also included in the rent is parking in driveway for two compact cars in tandem. NO pets and NO smoking, please dont ask. Please use email for fastest reply to questions or to set up a viewing, thank you.
149 Chestnut St, Brookline, MA 02445 is a 3 bedroom, 2 bathroom, 1,500 sqft single-family home built in 1953. More recently, it was listed as a rental in May 2017 with an asking price of $2,800 per month. That rental listing was removed on June 7, 2017. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $857,900, with a rent estimate of $4,553/month.

Home Details for 149 Chestnut St

Property Information

Year Built
Year Built: 1953
Property Type / Style
Property Type: Single Family Home

Price and Tax history

DateEventPrice
Jun 7, 2017
Source: Agent Provided
ListingRemoved
$2,800
May 8, 2017
Source: Agent Provided
Listed For Rent
$2,800
May 14, 2015
Source: Agent Provided
ListingRemoved
$2,700
May 5, 2015
Source: Agent Provided
Listed For Rent
$2,700

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
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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"
    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 149 Chestnut St

  • What is 149 Chestnut St estimated to be worth?
    Trulia's estimated value for 149 Chestnut St in Brookline, MA is $857,900.
  • 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.
  • What do residents say about Brookline?
    Residents describe Brookline, MA as pedestrian-friendly, dog-friendly, and walkable to restaurants. See recently sold homes in Brookline, MA.

Explore by feature - Pet Friendly

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