53 Windsor Rd, Brookline, MA 02445
OFF MARKET

53 Windsor Rd
Brookline, MA 02445

  • 7 Beds
  • 3 Baths
  • 4,664 sqft

$3,094,000

Trulia Estimate
as of Aug 10, 2026
Est. Refi. Payment $18,546/mo*
Refinance Your Home

$3,094,000

Trulia Estimate
as of Aug 10, 2026
Est. Refi. Payment $18,546/mo*
Refinance Your Home
7 Beds
3 Baths
4,664 sqft

Local Information

  • Map ViewExplore the area around 53 Windsor Rd.
  • Schools1 Preschool School2 Elementary Schools2 Middle Schools1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1891
Living Area
4,664 sqft
Price/Sqft
$663

About this House

This single-family home is located at 53 Windsor Rd, Brookline, MA. 53 Windsor Rd is in Brookline, MA and in ZIP code 02445. This property has 7 bedrooms, 3 bathrooms and approximately 4,664 sqft of floor space. This property has a lot size of 10454 sqft and was built in 1891.
53 Windsor Rd, Brookline, MA 02445 is a 7 bedroom, 3 bathroom, 4,664 sqft single-family home built in 1891. It is currently off market. The Trulia Estimate is $3,094,000, with a rent estimate of $7,577/month.

Home Details for 53 Windsor Rd

Interior Features

Interior Details
BasementNumber of Rooms: 12
Heating & Cooling
Heating: Other, OilAir ConditioningHeating Fuel: Other
Levels, Entrance, & Accessibility
Stories: 3
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: Wood

Property Information

Year Built
Year Built: 1891Year Updated: 1963
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Community

Units in Building: 1

Lot Information

Lot Area: 10454 sqft

Market trends in Brookline

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$1.4M
$16.67KMoM
Sale-to-List Price
99.9%
Price per sq ft
$796
$17MoM
Available listings
253
15MoM
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Property Tax and Assessment

Year2025
Tax$28,129
Assessment$2,849,900
Home facts updated by county records

Comparable Sales for 53 Windsor Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
22 Windsor Rd, Brookline, MA
0.07
Single-Family Home
$2,050,000
03/31/26
5
3.5
2,845
85 Williston Rd, Brookline, MA
0.14
Single-Family Home
$3,670,000
01/15/26
5
5.5
5,552
9 Downing Rd, Brookline, MA
0.21
Single-Family Home
$2,480,000
05/06/26
8
5
5,803
189 Clinton Rd, Brookline, MA
0.36
Single-Family Home
$3,318,000
04/23/26
6
4
4,633
333 Clark Rd, Brookline, MA
0.33
Single-Family Home
$2,487,000
12/11/25
5
3.5
3,100
323 Clark Rd, Brookline, MA
0.35
Single-Family Home
$2,995,000
03/04/26
5
4.5
3,370
43 Druce St, Brookline, MA
0.41
Single-Family Home
$3,285,000
05/14/26
5
4.5
3,658
282 Buckminster Rd, Brookline, MA
0.46
Single-Family Home
$4,100,000
04/27/26
6
4.5
5,058
401 Clinton Rd, Brookline, MA
0.53
Single-Family Home
$2,200,000
06/15/26
5
3.5
3,463
34 Hyslop Rd, Brookline, MA
0.53
Single-Family Home
$4,125,000
05/28/26
5
4.5
4,001

Nearby homes

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Assigned Schools

These are the assigned schools for 53 Windsor Rd.
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 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."
    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
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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."
    0
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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. "
    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."
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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
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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. "
    0
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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"
    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"
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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. "
    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
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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. "
    0
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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 "
    0
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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."
    0
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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!"
    0
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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."
    0
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  • Ptetrault
    "It is a safe, welcoming and peaceful neighborhood. Heath is a great school. Close to T trains and buses."
    0
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  • 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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Apartments for Rent

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Explore by feature - Pet Friendly

322 pet-friendly rentals in Brookline, MA

Explore by feature - Garage

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Explore by feature - Outdoor Space

25 rentals with an outdoor space in Brookline, MA

Homes for sale near 53 Windsor Rd

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Off Market Homes Near 53 Windsor Rd

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Frequently asked questions about 53 Windsor Rd

  • What is 53 Windsor Rd estimated to be worth?
    Trulia's estimated value for 53 Windsor Rd in Brookline, MA is $3,094,000.
  • 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 $1.4M. That is down $16.67K 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.
  • How big is the lot at 53 Windsor Rd?
    The lot at 53 Windsor Rd in Brookline, MA is about 0.24 acres (10,454 sq ft).