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

$2,990,600

Trulia Estimate
  • 6 Beds
  • 5 Baths
  • 3,968 sqft

255 Winchester St, Brookline, MA 02446

Est. Refi. Payment $18,534/mo*
Refinance Your Home
Currently Off Market - Sold Jul 11, 2003 for $925,000

Home Value

Trulia Estimate
$2.99M
Since last month
Increased$32K (+1.1%)
Since last year
Increased$73K (+2.5%)
Since last sale
Increased$2M (+221%)
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 +46% in the last 10 years
MonthEstimated value
2026
September 2026$2.97M
August 2026$2.99M
July 2026$2.94M
June 2026$3.01M
May 2026$2.98M
April 2026$2.97M
March 2026$2.96M
February 2026$2.84M
January 2026$2.76M
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
91 Verndale St, Brookline, MA
0.09
Multi-Family Home
$2,862,500
10/21/25
8
4
4,166
28 Verndale St, Brookline, MA
0.24
Multi-Family Home
$2,250,000
12/12/25
8
5
3,342
126 Westbourne Ter, Brookline, MA
0.31
Multi-Family Home
$2,200,000
06/10/26
6
2
4,369
65 Atherton Rd, Brookline, MA
0.39
Multi-Family Home
$2,650,000
12/12/25
6
3.5
3,277
1572 Beacon St, Brookline, MA
0.43
Multi-Family Home
$2,200,000
02/02/26
5
3
3,978
5 Fiske Ter, Allston, MA
0.26
Multi-Family Home
$1,250,000
12/23/25
5
2
2,644
200 Washington St, Boston, MA
0.69
Multi-Family Home
$1,370,000
04/22/26
6
4
4,342
53 Quint Ave, Allston, MA
0.36
Multi-Family Home
$2,560,000
12/04/25
11
6
4,313
589-591 Washington St, Brookline, MA
0.57
Multi-Family Home
$1,800,000
01/13/26
9
4
3,102
581 Cambridge St, Allston, MA
0.56
Multi-Family Home
$2,450,000
01/13/26
9
6
4,162

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
251 Kelton St #4, Allston, MA 02134
0.05
$520,700
2
1
747
Off Market
289 Corey Rd #6, Boston, MA 02135
0.07
$594,400
2
1
954
Off Market
140 Columbia St, Brookline, MA 02446
0.03
$2,932,700
8
3
4,310
Off Market
140 Columbia St #2, Brookline, MA 02446
0.03
$2,513,200
4
3.5
2,690
Off Market
290 Corey Rd #12, Brighton, MA 02135
0.07
$480,900
2
1
685
Off Market
290 Corey Rd #14, Brighton, MA 02135
0.07
$507,000
2
1
685
Off Market
290 Corey Rd #23, Brighton, MA 02135
0.07
$516,500
2
1
685
Off Market
285 Corey Rd #7, Boston, MA 02135
0.07
$625,700
2
1
916
Off Market
319 Mason Ter, Brookline, MA 02446
0.06
$1,615,100
4
1.5
2,016
Off Market
309 Mason Ter, Brookline, MA 02446
0.07
$1,961,600
4
2.5
2,520
Off Market
245 Kelton St #11, Allston, MA 02134
0.08
$400,000
2
1
690
Recently Sold
245 Kelton St #21, Allston, MA 02134
0.08
$450,000
2
1
690
Recently Sold

Local Information

  • Map ViewExplore the area around 255 Winchester St.
  • Schools1 Preschool School2 Elementary Schools2 Middle Schools1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Multi-Family
Built in 1932
3,968 sqft
$754/sqft
Garage

About this House

This multi-family home is located at 255 Winchester St, Brookline, MA. 255 Winchester St is in Brookline, MA and in ZIP code 02446. This property has 6 bedrooms, 5 bathrooms and approximately 3,968 sqft of floor space. This property has a lot size of 6969 sqft and was built in 1932.
255 Winchester St, Brookline, MA 02446 is a 6 bedroom, 5 bathroom, 3,968 sqft multi-family built in 1932. It last sold for $925,000 on Jul 11, 2003. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $2,990,600, with a rent estimate of $5,510/month.

Home Details for 255 Winchester St

Interior Features

Heating & Cooling
Heating: OilAir ConditioningHeating Fuel: Oil
Levels, Entrance, & Accessibility
Stories: 2
Interior Details
Number of Rooms: 13
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: TileExterior: Brick
Parking & Garage
GarageParking: Garage Attached

Property Information

Year Built
Year Built: 1932Year Updated: 1982
Property Type / Style
Property Type: Multi FamilyArchitecture: Other

Community

Units in Building: 2

Lot Information

Lot Area: 6969 sqft

Price and Tax history

DateEventPrice
Jul 11, 2003
Source: N/A
Sold
$925,000

Market trends in Brookline

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$1.24M
$23.33KMoM
Sale-to-List Price
99.3%
0.4%MoM
Price per sq ft
$811
$6MoM
Available listings
186
30MoM

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 255 Winchester St

  • What is 255 Winchester St estimated to be worth?
    Trulia's estimated value for 255 Winchester St in Brookline, MA is $2,990,600.
  • What is the price history for 255 Winchester St?
    255 Winchester St in Brookline, MA last sold for $925,000 in July 2003.
  • Is Brookline a buyer's or seller's market?
    Brookline is currently a balanced market, based on recent for-sale activity.
  • What's the median sale price in Brookline?
    The median sale price in Brookline is $1.24M. That is up $23.33K from the prior month.

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