59 Windsor Rd, Brookline, MA 02445
Property image
Property image
OFF MARKET

$3,722,400

Trulia Estimate
as of Oct 8, 2026
  • 4 Beds
  • 2 Baths
  • 999 sqft

59 Windsor Rd, Brookline, MA 02445

Brighton

Home Highlights

Apartment
999 sqft
$3,726/sqft

Local Information

  • Map ViewExplore the area around 59 Windsor Rd.
  • Schools1 Preschool School2 Elementary Schools2 Middle Schools1 High School
  • Shop & Eat
-- mins to
Commute Destination

About this House

What's unique:Elegant marble tileGleaming hardwood floorsOn-site laundry facilitiesPlenty of cabinet spaceGas stoveLarge eat-in kitchen
Spacious 4-Bedroom with Two Full Bathrooms Prime Location!

 Bedrooms: Four spacious bedrooms with mirrored closets for added storage
 Bathrooms: Two full bathrooms with elegant marble tile
 Heat & Water: Heat and hot water included in rent
 Living Space: Bright and airy central living room and kitchen
 Floors: Gleaming hardwood floors throughout
 Kitchen: Large eat-in kitchen with gas stove, dishwasher & plenty of cabinet space
 Laundry: On-site laundry facilities
 Transit: Just steps from B & C lines, a quick walk to Washington Square
59 Windsor Rd, Brookline, MA 02445 is a 4 bedroom, 2 bathroom, 999 sqft apartment in Brighton. It last sold for $1,600,000 on Aug 9, 2005 (43,736% above the $3,650 asking price). This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $3,722,400.

Home Details for 59 Windsor Rd

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: Off Street Parking, On Site

Comparable Sales for 59 Windsor Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
1865 Beacon St #1A, Brookline, MA
0.28
Apartment
$900,000
11/14/25
3
2
1,226 sqft
106 Westbourne Ter #1, Brookline, MA
0.33
Apartment
$1,650,000
10/22/25
2
2
1,470 sqft
106 Westbourne Ter #2, Brookline, MA
0.33
Apartment
$3,150,000
10/22/25
3
2
2,044 sqft
24 Selkirk Rd #4, Boston, MA
0.24
Apartment
$1,648,000
05/21/26
3
3.5
2,760 sqft
230 Washington St, Brighton, MA
0.58
Apartment
$1,192,000
05/29/26
2
1
999 sqft
21 Westbourne Ter #3, Brookline, MA
0.44
Apartment
$580,000
10/30/25
2
1
876 sqft
5 South St #3, Boston, MA
0.65
Apartment
$585,000
09/30/26
4
1.5
1,170 sqft
194 A Allston St #2, Boston, MA
0.56
Apartment
$590,000
10/29/25
2
1
935 sqft
147 Kelton St #704, Allston, MA
0.61
Apartment
$730,000
09/18/26
2
3
1,440 sqft
369 Tappan St #12, Brookline, MA
0.28
Apartment
$500,000
10/17/25
1
1
678 sqft
Home facts updated by county records

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.

Neighborhood Overview

Brighton
See Local Highlights
Neighborhood stats provided by third party data sources.

What Locals Say about Brighton

This October

Trick-or-Treat Score

Built from what locals say about Brighton.
  • 95% say there are sidewalks
  • 58% say there's holiday spirit
  • 47% say neighbors are friendly
Trulia Trick or TreatStart Ghost Hunt
At least 531 Trulia users voted on each feature.

  • 95 % Say there are sidewalks

  • 92 % Say it's dog friendly

  • 92 % Say it's walkable to restaurants

  • 81 % Say people would walk alone at night

  • 80 % Say streets are well-lit

  • 69 % Say it's walkable to grocery stores

  • 58 % Say there's holiday spirit

  • 54 % Say parking is easy

  • 52 % Say there's wildlife

  • 47 % Say car is needed

  • 47 % Say neighbors are friendly

  • 46 % Say kids play outside

  • 40 % Say it's quiet

  • 37 % Say they plan to stay for at least 5 years

  • 32 % Say yards are well-kept

  • 24 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • Trulia User
    "I've lived here for three years and people are friendly, lot's of cafes nearby and shops"
    0
    Flag
  • Dait87
    "I don’t really know if you guys want me to say about Boston. Bostonis a pretty good place for the most part. The prices are extremely high, but you get a good return on that from safe neighborhoods to schools and higher paying jobs."
    1
    Flag
  • Ynscvb74v4
    "The worst Neighbor hood I have ever lived in. People constantly deficating on our building and shattered glass all around"
    18
    Flag
  • Trulia User
    "There is a feeling of see guidance interactions between children and families grown up in the area of Brighton, myself and my children that have friends in the neighborhood are always busy in a safe environment neighborhood to live in and grow up in , due to my experiences"
    3
    Flag
  • Trulia User
    "The committee parade every summer Food for the less fortunate Very good transportation system and lots of shops and restaurants to choose from "
    3
    Flag
  • Trulia User
    "Safety is the number one key and Brighton is very safe to have your children and to raise them. Job opportunity in the community is very high. School are pretty safe as well. Been in the Brighton area for 18 years and I have no complains. I wish I can purchase a property in this area."
    5
    Flag
  • Trulia User
    "I’ve enjoyed my time in this neighborhood. It’s safe, fun, well maintained, and relatively quiet. I enjoy many of the restaurants here, as well as walking/running in the neighborhood."
    2
    Flag
  • Trulia User
    "My neighborhood is unique for the many schools ,colleges, and park for a young to play and the piece and quiet."
    1
    Flag
  • Trulia User
    "I’ve lived in the neighborhood for more than 3 years and it is very quiet,clean and kid friendly- there is a lot playgrounds in the area for children to have a good time plus the schools are close by. "
    1
    Flag
  • Trulia User
    "Great neighborhood Oak square has restaurant’s, YMCA small businesses all nearby. Public transportation and easy access to highways."
    1
    Flag
  • Trulia User
    "Full of stutends not a bad place for young people. Wish it had more parks and outdoor spaces. Lots of great food anytime of food at that and plenty of things to do. 8 out of 10. Idle for someone in 20’s early 30’s . Would live here again. "
    3
    Flag
  • Trulia User
    "It is homey and there are always people walking around with their dogs. People are friendly and it is a charming area."
    2
    Flag
  • Trulia User
    "I live in the area. almost two years so far. I feel safe, my children are safe. I can let them go outside without being worried that something bad is going to happen to them. I love the scenery, there are tons of restaurants along commonwealth Ave and there are some attractions and retail stores as well."
    0
    Flag
  • Trulia User
    "nice quiet friendly neighborhood where You're away from the inner city. so there's not much crime or hustle and bustle as other locations in Boston "
    0
    Flag
  • Trulia User
    " I think Brighton is the best place to live in Massachusetts. We have a farmer's market in the summer, there's no children in the neighborhood. I hate children. "
    1
    Flag
  • Trulia User
    "It’s clean and a pet friendly neighborhood. Dog owners pickup after their dogs and there’s a park where owners send their dogs to play with others"
    0
    Flag
  • Trulia User
    "The main roads can be quite busy and people drive fast sometimes. I would want to be careful in crosswalks!!"
    1
    Flag
  • Trulia User
    "There's multiple walking trails and parks! some neighbors struggle with cleaning up after their pets, but for the most part other dog owners in the area rock!"
    0
    Flag
  • Trulia User
    " 35 minutes door to door. I work in Back Bay. From Allston St to Hynes convention. Not too bad. Could be better"
    0
    Flag
  • Trulia User
    "I take the B-Line into work from Washington St. to Hynes convention center. I then walk to the prudential."
    0
    Flag
  • Trulia User
    "It’s a very rich area and the school is very highly well kept, it’s clean it’s safe and feels good to be in"
    0
    Flag
  • Trulia User
    "Close to downtown, regular buses, express buses and trolleys. Very convenient to commuters. Can also drive but parking can be a problem."
    0
    Flag
  • Trulia User
    "There are a lot of families that live in this neighborhood. It is a very up and coming area for young families."
    0
    Flag
  • Trulia User
    "Gardening, education for the summer, computer center, restaurants at walking distance. Community works together to keep everything clean and safe. Parks have doggie bags in case someone may need some. "
    0
    Flag
  • Trulia User
    "There are a lot of people who live in this area and have dogs. I’ve never had a problem walking my dog here."
    0
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  • Trulia User
    "The commute is very easy because the green line passes frequently. You can quickly hop on the green line and get into Boston."
    0
    Flag
  • Rourkiekc
    "This area is popular with college students and young professionals. It is a relatively safe neighborhood."
    2
    Flag
  • Strand413
    "People are great! There are parks. There are families. There are other kids. There is cops. There is hospital just in case of injury and emergency. "
    3
    Flag
  • Madeline G.
    "Brighton can be loud at night in some areas. However, the neighborhood is safe and has lots of great restaurants. It’s easy to walk places and friendly enough to right a bike around. "
    1
    Flag
  • Lauren B.
    "Great accessibility to the pike (I-90) and very quick into Boston no matter which way that I’m traveling "
    1
    Flag
  • Trulia User
    "Boston is easily accessible by bus and train making it ideal for commuting in and out of the city. Access to the mass pike is great perk too. "
    1
    Flag
  • Dawne K.
    "My neighborhood has great access to public transportation and is very short commute to downtown Boston."
    0
    Flag
  • Jenna
    "Public transportation is very available and its one of the easier spots in Boston to find parking nearby if you have a resident sticker"
    0
    Flag
  • Lambert G. J.
    "The Ymca is very popular location and there are lots of parks. The city is very close . Access to all major highways in less than 10 minutes depending on traffic. "
    0
    Flag
  • Lacy B.
    "annual Easter egg hunt is a family favorite, movie nights and bands are held in the center. great library and a gem of a museum in the senior center"
    1
    Flag
  • Juancarlos
    "People don’t like when you don’t pick up gaffer you’re dog because I’ve stepped in some PICK UP AFTER YOUR DOG"
    2
    Flag
  • Lorchik_99
    "Very loving area for dogs of all sizes. Even if a passer by doesn’t have a dog themselves, most of them like to say hi to your dog, or at least a smile comes up on their faces when they see a dog. Love that!"
    2
    Flag
  • Ragsara
    "It’s good place to live ... we have a ground nearby in which people of all walks of life come and play together and have some good time"
    1
    Flag
  • Lmtperez
    "Very walkable, friendly neighbors, excellent library, coffee shops, and parks. We are raising our young family here and love it"
    1
    Flag
  • Audrey M.
    "It's within the city limits, so it's close to everything but feels more residential. I love having a backyard in Brighton. It's close to highways and has some great food options."
    1
    Flag

LGBTQ Local Legal Protections

Price and Tax history

DateEventPrice
Aug 9, 2005
Source: N/A
Sold
$1,600,000

Frequently asked questions about 59 Windsor Rd

  • What is 59 Windsor Rd estimated to be worth?
    Trulia's estimated value for 59 Windsor Rd in Brookline, MA is $3,722,400.
  • What is the price history for 59 Windsor Rd?
    59 Windsor Rd in Brookline, MA last sold for $1,600,000 in August 2005.
  • 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 $586K. That is up $63.33K from the prior month.
  • Does 59 Windsor Rd have parking?
    Yes, 59 Windsor Rd in Brookline, MA has on-site parking.

Homes for rent near 59 Windsor Rd

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Affordability

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