237 Winchester St, Brookline, MA 02446
Property image
Property image
OFF MARKET

237 Winchester St
Brookline, MA 02446

  • 4 Beds
  • 1 Bath
  • 9,999 sqft
  • 4 Beds
  • 1 Bath
  • 9,999 sqft

Home Highlights

Property Type
Apartment
Living Area
9,999 sqft
Parking
Attached Garage

Local Information

  • Map ViewExplore the area around 237 Winchester St.
  • Schools1 Preschool School2 Elementary Schools2 Middle Schools1 High School
  • Shop & Eat
-- mins to
Commute Destination

About this House

Expansive 4-Bed in Prime Brookline w/ Office Nook & 2 Parking Spots

 Bedrooms: Four large bedrooms with generous closet space
 Bathroom: One full bathroom
 Living Space: Huge living area with formal dining space and separate office alcove
 Kitchen: Tons of cabinetry, dishwasher, great for meal prep
 Comfort: Hardwood floors, high ceilings, classic Brookline charm
 Outdoor: Balcony adds a cozy outdoor space
 Laundry: Free in-building laundry
 Parking: Two off-street spaces included
 Location: Quiet Brookline street, blocks from Coolidge Corner
 Transit: Close to B & C Lines
 Nearby: Walk to Trader Joe's, Whole Foods, and many dining options
 Universities: Convenient to Boston University
237 Winchester St, Brookline, MA 02446 is a 4 bedroom, 1 bathroom, 9,999 sqft apartment. It is currently off market. The Trulia Estimate rent is $4,268/month.

Home Details for 237 Winchester St

Property Information

Property Type / Style
Property Type: Apartment

Rental Terms, Policies & Fees

Lease Term: 1 YearAvailable: now

Interior Features

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

Exterior Features

Parking & Garage
Parking: Attached Off Street, On Site

Comparable Sales for 237 Winchester St

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
108 Columbia St #1, Brookline, MA
0.05
Apartment
$877,500
04/30/26
2
1.5
1,206 sqft
36 Bellvista Rd, Brighton, MA
0.14
Apartment
$458,000
06/08/26
1
9,999 sqft
239 Kelton St #41, Allston, MA
0.14
Apartment
$438,000
06/22/26
2
1
690 sqft
194 A Allston St #2, Boston, MA
0.23
Apartment
$590,000
10/29/25
2
1
935 sqft
12 Bellvista Rd #4, Brighton, MA
0.22
Apartment
$465,000
07/27/26
2
1
972 sqft
85 Brainerd Rd #7, Allston, MA
0.09
Apartment
$1,100,000
05/08/26
3
2
-
106 Westbourne Ter #2, Brookline, MA
0.32
Apartment
$3,150,000
10/22/25
3
2
2,044 sqft
3 Woodstock Ave, Brighton, MA
0.24
Apartment
$760,000
08/26/25
6
2.5
1,800 sqft
21 Westbourne Ter #3, Brookline, MA
0.39
Apartment
$580,000
10/30/25
2
1
876 sqft
106 Westbourne Ter #1, Brookline, MA
0.32
Apartment
$1,650,000
10/22/25
2
2
1,470 sqft
Home facts updated by county records

Nearby homes

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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."
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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"
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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
    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. "
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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. "
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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."
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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."
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  • Ptetrault
    "It is a safe, welcoming and peaceful neighborhood. Heath is a great school. Close to T trains and buses."
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  • Pat B.
    "It's dog friendly...there's lots of parks around to take pets."
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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

LGBTQ Local Legal Protections

Frequently asked questions about 237 Winchester St

  • 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.
  • What are the closest schools to 237 Winchester St?
    The closest schools to 237 Winchester St in Brookline, MA are Brookline High School (rated 8/10), Florida Ruffin Ridley School (Pre-K/Elementary/Middle, rated 9/10), Michael Driscoll School (Elementary/Middle, rated 9/10).
  • Does 237 Winchester St have parking?
    Yes, 237 Winchester St in Brookline, MA has on-site parking.

Homes for rent near 237 Winchester St

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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
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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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