44 Brookside Ave, Winchester, MA 01890
OFF MARKET

44 Brookside Ave
Winchester, MA 01890

  • Studio

$1,985,600

Trulia Estimate
as of May 20, 2026
Est. Refi. Payment $11,797/mo*
Refinance Your Home

$1,985,600

Trulia Estimate
as of May 20, 2026
Est. Refi. Payment $11,797/mo*
Refinance Your Home
Studio

Local Information

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Description

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.
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources.

Home Highlights

Parking
No Info
Outdoor
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HOA
None
Price/Sqft
No Info
Listed
No Info

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 History for 44 Brookside Ave

DatePriceEventSource
06/07/2022$1,700,000Sold
MLS PIN #72959844
03/30/2022$1,450,000Listed For SaleMLS PIN #72959844
12/12/1995$164,000Sold
N/A
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Property Tax and Assessment

Year2025
Tax$19,728
Assessment$1,778,900
Home facts updated by county records

Comparable Sales for 44 Brookside Ave

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
540-542 Washington St, Winchester, MA
0.13
Multi-Family Home
$1,120,000
08/11/25
4
2
2,060
415-417 Washington St, Winchester, MA
0.40
Multi-Family Home
$1,200,000
11/21/25
5
2
2,610
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
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
24-26 Leonard St, Woburn, MA
0.80
Multi-Family Home
$865,000
06/10/25
5
2
2,464
14-16 Garfield Ave, Woburn, MA
1.15
Multi-Family Home
$1,107,500
02/27/26
8
3
2,866
8-10 Russell Rd, Winchester, MA
0.90
Multi-Family Home
$960,000
04/06/26
4
2
1,800

Assigned Schools

These are the assigned schools for 44 Brookside Ave.
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 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

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44 Brookside Ave, Winchester, MA 01890 is a studio multi-family. This property is not currently available for sale. 44 Brookside Ave was last sold on Jun 7, 2022 for $1,700,000. The current Trulia Estimate for 44 Brookside Ave is $1,985,600.