68-72 Windsor Rd, Brookline, MA 02445
OFF MARKET

$5,236,400

Trulia Estimate
as of Aug 30, 2026
  • 2 Beds
  • 11 Baths
  • 1,000 sqft
  • 2 Beds
  • 11 Baths
  • 1,000 sqft

68-72 Windsor Rd, Brookline, MA 02445

Home Highlights

Property Type
Single-Family Home
Living Area
1,000 sqft
Price/Sqft
$5,236

Local Information

  • Map ViewExplore the area around 68-72 Windsor Rd.
  • Schools1 Preschool School2 Elementary Schools2 Middle Schools1 High School
  • Shop & Eat
-- mins to
Commute Destination

About this House

Beautiful unit on one of the best streets in Brookline, just completely redone! Brand new kitchen with skylight opens up to a separate dining area looking out onto the spacious living room. Two spacious bedrooms and redone bathroom that maintains its distinctive charm.

Unit has a private entrance, located in the carriage house on a beautiful, quiet street that is steps to Washington Square and the C line MBTA train!

Parking spot will be available for 1 car.
68-72 Windsor Rd, Brookline, MA 02445 is a 2 bedroom, 11 bathroom, 1,000 sqft single-family home. It last sold for $2,261,500 on Dec 5, 2008 (59,413% above the $3,800 asking price). This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $5,236,400, with a rent estimate of $3,714/month.

Home Details for 68-72 Windsor Rd

Interior Features

Heating & Cooling
Heating: BaseboardAir ConditioningCooling System: Window UnitHeating Fuel: Baseboard
Appliances & Utilities
DishwasherMicrowaveRefrigerator
Levels, Entrance, & Accessibility
Floors: Hardwood

Property Information

Property Type / Style
Property Type: Single Family Home

Rental Terms, Policies & Fees

Lease Term: 1 YearAvailable: now

Exterior Features

Parking & Garage
Parking: Off Street Parking, On Site

Comparable Sales for 68-72 Windsor Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
22 Windsor Rd, Brookline, MA
0.10
Single-Family Home
$2,050,000
03/31/26
5
3.5
2,845 sqft
24 Selkirk Rd #24-4, Brighton, MA
0.22
Townhouse
$1,648,000
05/21/26
3
3.5
2,760 sqft
129 Sutherland Rd #A, Brighton, MA
0.21
Single-Family Home
$1,000,000
09/30/25
5
4
1,499 sqft
1800 Beacon St, Brookline, MA
0.10
Single-Family Home
$3,750,000
09/02/25
6
6.5
6,005 sqft
123 Nottinghill Rd, Brighton, MA
0.40
Single-Family Home
$1,315,000
04/10/26
3
3.5
2,126 sqft
333 Clark Rd, Brookline, MA
0.31
Single-Family Home
$2,487,000
12/11/25
5
3.5
3,100 sqft
85 Williston Rd, Brookline, MA
0.19
Single-Family Home
$3,670,000
01/15/26
5
5.5
5,552 sqft
323 Clark Rd, Brookline, MA
0.33
Single-Family Home
$2,995,000
03/04/26
5
4.5
3,370 sqft
9 Downing Rd, Brookline, MA
0.26
Single-Family Home
$2,480,000
05/06/26
8
5
5,803 sqft
30 York Ter, Brookline, MA
0.64
Single-Family Home
$2,210,000
04/13/26
3
2.5
1,740 sqft

Nearby homes

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Around this home

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.
  • 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

Price and Tax history

DateEventPrice
Dec 5, 2008
Source: N/A
Sold
$2,261,500

Frequently asked questions about 68-72 Windsor Rd

  • What is 68-72 Windsor Rd estimated to be worth?
    Trulia's estimated value for 68-72 Windsor Rd in Brookline, MA is $5,236,400.
  • What is the price history for 68-72 Windsor Rd?
    68-72 Windsor Rd in Brookline, MA last sold for $2,261,500 in December 2008.
  • 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.
  • Does 68-72 Windsor Rd have air conditioning?
    Yes, 68-72 Windsor Rd in Brookline, MA has air conditioning.
  • Does 68-72 Windsor Rd have parking?
    Yes, 68-72 Windsor Rd in Brookline, MA has on-site parking.

Homes for rent near 68-72 Windsor Rd

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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
PER YEAR
is the suggested income
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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