59 Windsor Rd, Brookline, MA 02445
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OFF MARKET

59 Windsor Rd
Brookline, MA 02445

Brighton
  • 4 Beds
  • 2 Baths
  • 999 sqft

$3,775,500

Trulia Estimate
as of Aug 12, 2026
Est. Refi. Payment $22,494/mo*
Refinance Your Home

$3,775,500

Trulia Estimate
as of Aug 12, 2026
Est. Refi. Payment $22,494/mo*
Refinance Your Home
4 Beds
2 Baths
999 sqft

Home Value

Trulia Estimate
$3.78M
Since last month
Increased$71K (+1.9%)
Since last year
Increased$134K (+3.7%)
Since last sale
Increased$2M (+135.4%)
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 +59% in the last 10 years
MonthEstimated value
2026
August 2026$3.77M
July 2026$3.75M
June 2026$3.7M
May 2026$3.7M
April 2026$3.63M
March 2026$3.69M
February 2026$3.64M
January 2026$3.63M
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
1865 Beacon St #1A, Brookline, MA
0.28
Apartment
$900,000
11/14/25
3
2
1,226
106 Westbourne Ter #1, Brookline, MA
0.33
Apartment
$1,650,000
10/22/25
2
2
1,470
1824 Beacon St #5, Brookline, MA
0.16
Apartment
$1,187,500
10/07/25
2
1
850
106 Westbourne Ter #2, Brookline, MA
0.33
Apartment
$3,150,000
10/22/25
3
2
2,044
24 Selkirk Rd #4, Boston, MA
0.24
Apartment
$1,648,000
05/21/26
3
3.5
2,760
120 Sutherland Rd #7, Brighton, MA
0.24
Condo
$530,000
09/02/25
2
1
701
3 Woodstock Ave, Brighton, MA
0.43
Apartment
$760,000
08/26/25
6
2.5
1,800
230 Washington St, Brighton, MA
0.58
Apartment
$1,192,000
05/29/26
2
1
999
311 Allston St #11, Brighton, MA
0.29
Apartment
$460,000
04/29/26
2
1
-
21 Westbourne Ter #3, Brookline, MA
0.44
Apartment
$580,000
10/30/25
2
1
876

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
58 Corey Rd, Brookline, MA 02445
0.04
$1,940,500
6
3
2,907
Off Market
63 Corey Rd #2, Brighton, MA 02135
0.06
$456,400
1
1
660
Off Market
110 Evans Rd #2, Brighton, MA 02135
0.08
$549,500
1
1
670
Off Market
114 Evans Rd #5, Brighton, MA 02135
0.08
$460,100
1
1
610
Recently Sold
25 Windsor Rd, Brookline, MA 02445
0.08
$3,340,600
5
4
3,787
Off Market
106 Evans Rd #1B, Brighton, MA 02135
0.08
$523,400
1
1
710
Off Market
106 Evans Rd #6, Brighton, MA 02135
0.08
$506,500
1
1
720
Off Market
22 Windsor Rd, Brookline, MA 02445
0.08
$2,050,000
5
3.5
2,845
Recently Sold
37 Corey Rd #218, Hancock, MA 01237
0.08
$159,900
1
1
500
For Sale
151 Salisbury Rd, Brookline, MA 02445
0.06
$3,308,200
7
3.5
4,721
Off Market
111 Salisbury Rd, Brookline, MA 02445
0.10
$3,877,300
4
3.5
3,259
Off Market
36 Cummings Rd #1, Brighton, MA 02135
0.08
$615,000
2
1.5
975
Recently Sold

Local Information

  • Map ViewExplore the area around 59 Windsor Rd.
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Home Highlights

Property Type
Apartment
Living Area
999 sqft
Price/Sqft
$3,779

About this House

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). It is currently off market. The Trulia Estimate is $3,775,500, with a rent estimate of $4,106/month.

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

Price and Tax history

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

Market trends in Brighton

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$523K
$63.33KMoM
Sale-to-List Price
98.9%
Price per sq ft
$651
$14MoM
Available listings
186
21MoM
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Around this home

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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

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

  • 80 % Say streets are well-lit

  • 80 % Say people would walk alone at night

  • 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
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  • 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
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  • 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
    Flag
  • 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

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Homes for sale near 59 Windsor Rd

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Off Market Homes Near 59 Windsor Rd

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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 $3,775,500.
  • 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 $593K. That is roughly unchanged from the prior month.
  • Does 59 Windsor Rd have parking?
    Yes, 59 Windsor Rd in Brookline, MA has on-site parking.