21 Brookside Ave, Winchester, MA 01890
OFF MARKET

21 Brookside Ave
Winchester, MA 01890

  • 3 Beds
  • 2 Baths
  • 1,550 sqft

$925,200

Trulia Estimate
as of Jun 3, 2026
Est. Refi. Payment $5,421/mo*
Refinance Your Home

$925,200

Trulia Estimate
as of Jun 3, 2026
Est. Refi. Payment $5,421/mo*
Refinance Your Home
3 Beds
2 Baths
1,550 sqft

Local Information

Map showing home location
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-- mins to
Commute Destination

Description

This condo is located at 21 Brookside Ave, Winchester, MA. 21 Brookside Ave is in Winchester, MA and in ZIP code 01890. This property has 3 bedrooms, 2 bathrooms and approximately 1,550 sqft of floor space. This property was built in 1931.
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
No Info
A/C
Heating only
HOA
None
Price/Sqft
No Info
Listed
Less than a day ago

Home Details for 21 Brookside Ave

Interior Features

Interior Details
BasementNumber of Rooms: 7
Heating & Cooling
Heating: Other, GasHeating Fuel: Other
Levels, Entrance, & Accessibility
Stories: 2

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: Other

Property Information

Year Built
Year Built: 1931Year Updated: 2008
Property Type / Style
Property Type: CondoArchitecture: townhouse

Community

Units in Building: 1

Price History for 21 Brookside Ave

DatePriceEventSource
09/18/2014$580,000Sold
N/A
05/15/2007$580,000Sold
N/A
12/17/1998$329,000Sold
N/A

Market trends in Winchester

Last updated April 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
68
15MoM
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Property Tax and Assessment

Year2025
Tax$8,361
Assessment$753,900
Home facts updated by county records

Comparable Sales for 21 Brookside Ave

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
7 Conant Rd #33, Winchester, MA
0.48
Condo
$680,000
03/16/26
2
2
1,532
7 Conant Rd #53, Winchester, MA
0.48
Condo
$745,000
06/02/26
2
2
1,588
7 Conant Rd #34, Winchester, MA
0.50
Condo
$749,900
06/13/25
2
2
1,545
7 Conant Rd #20, Winchester, MA
0.50
Condo
$665,000
11/14/25
2
2
1,168
7 Conant Rd #23, Winchester, MA
0.50
Condo
$680,000
07/17/25
2
2
1,160
9 Charles Rd, Winchester, MA
0.63
Condo
$681,888
03/25/26
3
1.5
968
16 Park Ave #1, Winchester, MA
0.69
Condo
$950,000
12/04/25
3
2
1,535
16 Park Ave #2, Winchester, MA
0.69
Condo
$999,999
11/21/25
3
2
1,756
4 Mason Way, Woburn, MA
0.60
Condo
$336,101
09/08/25
3
3
2,055
22 Oak St, Winchester, MA
0.76
Condo
$452,500
03/30/26
3
2
1,142

Nearby homes

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Assigned Schools

These are the assigned schools for 21 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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21 Brookside Ave, Winchester, MA 01890 is a 3 bedroom, 2 bathroom, 1,550 sqft condo built in 1931. This property is not currently available for sale. 21 Brookside Ave was last sold on Sep 18, 2014 for $580,000. The current Trulia Estimate for 21 Brookside Ave is $925,200.