44 Brookside Ave, Winchester, MA 01890
Property image
Property image
OFF MARKET

44 Brookside Ave
Winchester, MA 01890

  • Studio

$1,958,100

Trulia Estimate
as of Aug 19, 2026
Est. Refi. Payment $11,707/mo*
Refinance Your Home

$1,958,100

Trulia Estimate
as of Aug 19, 2026
Est. Refi. Payment $11,707/mo*
Refinance Your Home
Studio

Home Value

Trulia Estimate
$1.96M
Since last month
Increased$3K (+0.2%)
Since last year
Increased$5K (+0.3%)
Since last sale
Increased$285K (+16.8%)
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 +98% in the last 10 years
MonthEstimated value
2026
August 2026$1.99M
July 2026$1.98M
June 2026$2M
May 2026$2.1M
April 2026$1.96M
March 2026$1.97M
February 2026$1.97M
January 2026$1.91M
2025
2024
2023
2022
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
415-417 Washington St, Winchester, MA
0.40
Multi-Family Home
$1,200,000
11/21/25
5
2
2,610
339-341 Washington St, Winchester, MA
0.56
Multi-Family Home
$980,000
08/11/26
5
2
2,160
353-355 Washington St, Winchester, MA
0.53
Multi-Family Home
$1,025,000
04/02/26
6
2
2,605
46-48 SW Anton St, Winchester, MA
0.67
Multi-Family Home
$1,290,000
01/29/26
6
3.5
3,233
158-160 Swanton St, Winchester, MA
0.71
Multi-Family Home
$1,199,000
11/21/25
12
8
7,645
303 Washington St, Winchester, MA
0.65
Multi-Family Home
$1,367,500
07/24/26
6
2
5,047
60 Harvard St, Winchester, MA
0.51
Multi-Family Home
$899,000
11/25/25
4
3
1,860
846 Main St, Woburn, MA
0.87
Multi-Family Home
$1,150,000
12/11/25
6
5
3,091
62 Richardson St, Winchester, MA
1.01
Multi-Family Home
$1,060,000
06/09/26
5
2.5
2,849
14-16 Garfield Ave, Woburn, MA
1.15
Multi-Family Home
$1,107,500
02/27/26
8
3
2,866

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
28 Garfield Ave, Winchester, MA 01890
0.05
$1,315,400
4
1.5
1,696
Off Market
44 Forest St, Winchester, MA 01890
0.07
$1,195,700
3
1.5
1,906
Off Market
8 Garfield Ave, Winchester, MA 01890
0.06
$1,080,900
3
2
1,536
Off Market
55 Brookside Ave, Winchester, MA 01890
0.04
$657,500
3
1
1,245
Recently Sold
18 Forest St, Winchester, MA 01890
0.11
$1,319,000
3
2.5
2,365
Off Market
18 Brookside Ave, Winchester, MA 01890
0.08
$1,222,900
3
1.5
1,573
Off Market
25 Marion St, Winchester, MA 01890
0.13
$2,195,500
5
4
4,234
Off Market
540-542 Washington St, Winchester, MA 01890
0.13
-
4
2
2,060
Off Market
518 Washington St, Winchester, MA 01890
0.16
$1,178,700
4
2.5
2,302
Off Market
116 Forest St, Winchester, MA 01890
0.14
$1,117,300
4
2.5
2,106
Off Market
571 Washington St, Winchester, MA 01890
0.14
$900,000
3
1
1,425
Recently Sold
17 Cross St, Winchester, MA 01890
0.18
$1,208,100
4
1.5
2,490
Off Market

Local Information

  • Map ViewExplore the area around 44 Brookside Ave.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Multi-Family

About this House

This multi-family home is located at 44 Brookside Ave, Winchester, MA. 44 Brookside Ave is in Winchester, MA and in ZIP code 01890. This property has a lot size of 10585 sqft.
44 Brookside Ave, Winchester, MA 01890 is a studio multi-family. It last sold for $1,700,000 on Jun 7, 2022. It is currently off market. The Trulia Estimate is $1,958,100, with a rent estimate of $3,777/month.

Home Details for 44 Brookside Ave

Property Information

Property Type / Style
Property Type: Multi Family

Community

Units in Building: 2

Lot Information

Lot Area: 10454 sqft

Price and Tax history

DateEventPrice
Jun 7, 2022
Source: MLS PIN #72959844
Sold
$1,700,000
Mar 30, 2022
Source: MLS PIN #72959844
Listed For Sale
$1,450,000
Dec 12, 1995
Source: N/A
Sold
$164,000

Market trends in Winchester

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$1.47M
$62.83KMoM
Sale-to-List Price
101.9%
0.2%MoM
Price per sq ft
$574
$3MoM
Available listings
64
13MoM

Around this home

What Locals Say about Winchester

At least 93 Trulia users voted on each feature.

  • 92 % Say it's dog friendly

  • 88 % Say yards are well-kept

  • 87 % Say people would walk alone at night

  • 85 % Say parking is easy

  • 79 % Say there are sidewalks

  • 79 % Say car is needed

  • 77 % Say it's walkable to restaurants

  • 77 % Say kids play outside

  • 75 % Say streets are well-lit

  • 74 % Say there's holiday spirit

  • 67 % Say they plan to stay for at least 5 years

  • 67 % Say there's wildlife

  • 66 % Say neighbors are friendly

  • 65 % Say it's walkable to grocery stores

  • 64 % Say it's quiet

  • 54 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • Diana P.
    "Winchester is the cutest town, perfect for families. There is Town Say, and Enka, and everything is very family oriented. We even have great pubs/restaurants as well as sub shops, Greek food, nail salons, anything you could want in a home town!"
    7
    Flag
  • Dominic
    "Phenomenal public school system beginning from Kindergarten and extremely welcoming to new residents transferring in."
    0
    Flag
  • Stacie
    "Very family oriented. Not a great neighborhood if you don’t have children. Great, easy commute into the city. Not enough good restaurants that aren’t overpriced though. "
    0
    Flag
  • Yjchoi7
    "Very safe neighborhood.there are often summer events on the common. Teenagers can take train into Boston area fairly easily as there are two stops within Winchester. Fells is a great place for summer walks. "
    2
    Flag
  • Luis B.
    "perfect for my family It is livable stores Closer to me Barbershop computer store Restaurants I will love to buy a house in this area "
    2
    Flag
  • Yjchoiyjchoi
    "It’s very quiet and safe generally. Yet it’s close to Boston and Cambridge city life within a few stops of the commuter from Winchester. "
    0
    Flag
  • Tara
    "I have lived in this neighborhood for 25 years. I love it. Everybody is friendly and kind. The crime is minimal and it’s very quiet. "
    2
    Flag
  • Katie41287
    "I’m not afraid to walk home at 11pm, the town is clean and has plenty of events around town, the people are friendly and it is near public transportation. "
    1
    Flag
  • Anna S.
    "Excellent school Easy commute to Boston Downtown Great parks and pond nearby"
    0
    Flag
  • tod g.
    "Lovely town with easy access to Boston and easy getaway to northern New England."
    0
    Flag
  • jfrancis6
    "Family community built around three streets that form a circle that only has traffic of residents. The area borders the Town of Winchester forest that is great for walks and snow shoeing in winter. All homes are large and attract families were children can safely play and bike in the neighborhood. Many homes have residents who grow up in the neighborhood as children and returned to raise their families. A short walk 4/10 of a mile to train station for those who work in Boston a trip that takes 12 minutes with only one stop. Schools in Winchester are among the best in Massachusetts, a primary attraction to the Town. The Town center is only one mile away and has an addition train station there as well. The Mystic lakes are just beyond the train station with a Town beach and boating opportunities. The Town also borders a 2500 acre forest known as the Fells consisting of the Town water supply and miles of hiking or mountain biking."
    0
    Flag
  • marta3467
    "Can see kids playing ball in street; people walking their dog and Horn Pond and several nice restaurants all within walking distance"
    1
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 44 Brookside Ave

  • What is 44 Brookside Ave estimated to be worth?
    Trulia's estimated value for 44 Brookside Ave in Winchester, MA is $1,958,100.
  • What is the price history for 44 Brookside Ave?
    44 Brookside Ave in Winchester, MA last sold for $1,700,000 in June 2022.
  • Is Winchester a buyer's or seller's market?
    Winchester is currently a balanced market, based on recent for-sale activity.
  • What's the median sale price in Winchester?
    The median sale price in Winchester is $1.47M. That is up $62.83K from the prior month.

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