255 Dudley St, Brookline, MA 02445
OFF MARKET

255 Dudley St
Brookline, MA 02445

  • 5 Beds
  • 5 Baths
  • 4,300 sqft (on 0.98 acres)

$10,425,900

Trulia Estimate
as of May 24, 2026
Est. Refi. Payment $61,546/mo*
Refinance Your Home

$10,425,900

Trulia Estimate
as of May 24, 2026
Est. Refi. Payment $61,546/mo*
Refinance Your Home
5 Beds
5 Baths
4,300 sqft
(on 0.98 acres)

Local Information

Map showing home location
© Google
-- mins to
Commute Destination

Description

On nearly one level acre in the Country Club section of Brookline, this gracious property offers a peaceful and private setting in a highly desirable neighborhood. The 1927 Colonial consists of 4,300± square feet of living area and has five bedrooms, three full baths, four half-baths, and four fireplaces. Wide pine plank floors, a sunroom overlooking the property, library with built-in bookshelves and fireplace, master bedroom suite with fireplace, bath and dressing room, and an updated eat-in kitchen. The landscaped grounds offer an expansive rear yard with heated pool and pool house.
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources.

Home Highlights

Parking
Garage
Outdoor
No Info
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
No Info

Home Details for 255 Dudley St

Interior Features

Interior Details
BasementNumber of Rooms: 14
Heating & Cooling
Heating: Forced Air, GasAir ConditioningHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 2
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: Wood
Parking & Garage
GarageParking: Garage Attached

Property Information

Year Built
Year Built: 1927Year Updated: 2012
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Community

Units in Building: 1

Lot Information

Lot Area: 0.98 acres

Price History for 255 Dudley St

DatePriceEventSource
11/12/2010$2,275,000Sold
N/A
11/04/2010$2,595,000Listed For SaleAgent Provided
10/02/2010$2,595,000ListingRemovedAgent Provided
07/03/2010$2,595,000PriceChange
Agent Provided
04/21/2010$2,750,000Listed For SaleAgent Provided
06/11/2009$2,900,000ListingRemovedAgent Provided
05/22/2009$2,900,000Listed For SaleAgent Provided
07/18/1990$897,700Sold
N/A
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Property Tax and Assessment

Year2025
Tax$79,396
Assessment$8,044,200
Home facts updated by county records

Comparable Sales for 255 Dudley St

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
235 Warren St, Brookline, MA
0.28
Single-Family Home
$4,300,000
06/27/25
6
5
8,029
372 Warren St, Brookline, MA
0.11
Single-Family Home
$5,700,000
12/08/25
9
7
8,619
382 Lee St, Brookline, MA
0.39
Single-Family Home
$5,500,000
01/16/26
5
5.5
6,841
125 Lee St, Brookline, MA
0.19
Single-Family Home
$4,650,000
08/18/25
7
7
7,147
325 Goddard Ave, Brookline, MA
0.56
Single-Family Home
$5,150,000
08/25/25
5
4.5
5,160
61 Heath St, Jamaica Plain, MA
0.42
Single-Family Home
$8,000,000
09/11/25
5
6
7,000
469 Walnut St, Brookline, MA
0.43
Single-Family Home
$3,625,000
12/04/25
7
4
6,307
33 Leicester St, Brookline, MA
0.53
Single-Family Home
$6,000,000
11/07/25
5
4.5
6,556
385 Lee St, Brookline, MA
0.40
Single-Family Home
$1,900,000
08/04/25
4
3.5
3,094
371 Walnut St, Brookline, MA
0.64
Single-Family Home
$5,250,000
03/02/26
7
5.5
6,193

Nearby homes

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Assigned Schools

These are the assigned schools for 255 Dudley St.
View nearby schools on GreatSchools
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

What Locals Say about Brookline

At least 421 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

  • 39 % 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."
    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
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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."
    0
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  • Trulia User
    "Clean, safe and quiet. People are very friendly. Access ti public transportation. Love this place very much."
    0
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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. "
    0
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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. "
    0
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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
    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
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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
    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.
    "It's dog friendly...there's lots of parks around to take pets."
    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

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255 Dudley St, Brookline, MA 02445 is a 5 bedroom, 5 bathroom, 4,300 sqft single-family home built in 1927. This property is not currently available for sale. 255 Dudley St was last sold on Nov 12, 2010 for $2,275,000. The current Trulia Estimate for 255 Dudley St is $10,425,900.