21 Brookside Ave, Winchester, MA 01890
OFF MARKET

$893,600

Trulia Estimate
  • 3 Beds
  • 2 Baths
  • 1,550 sqft

21 Brookside Ave, Winchester, MA 01890

Est. Refi. Payment $5,374/mo*
Refinance Your Home
Currently Off Market - Sold Sep 18, 2014 for $580,000

Home Value

Trulia Estimate
$894K
Since last month
Decreased$15K (-1.7%)
Since last year
Decreased$5K (-0.5%)
Since last sale
Increased$311K (+53.6%)
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 +39% in the last 10 years
MonthEstimated value
2026
August 2026$891K
July 2026$906K
June 2026$912K
May 2026$925K
April 2026$911K
March 2026$904K
February 2026$875K
January 2026$864K
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
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 #20, Winchester, MA
0.50
Condo
$665,000
11/14/25
2
2
1,168
9 Charles Rd, Winchester, MA
0.63
Condo
$681,888
03/25/26
3
1.5
968
9 Governors Ave #2, Winchester, MA
0.66
Condo
$888,000
06/08/26
3
1.5
1,799
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
17 Charles Rd, Winchester, MA
0.63
Condo
$645,000
06/16/26
2
2
987
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 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
18 Brookside Ave, Winchester, MA 01890
0.03
$1,236,800
3
1.5
1,573
Off Market
571 Washington St, Winchester, MA 01890
0.07
$900,000
3
1
1,425
Recently Sold
116 Forest St, Winchester, MA 01890
0.08
$1,092,700
4
2.5
2,106
Off Market
118 Forest St, Winchester, MA 01890
0.09
$2,182,600
5
3.5
3,866
Off Market
540-542 Washington St, Winchester, MA 01890
0.10
-
4
2
2,060
Off Market
8 Garfield Ave, Winchester, MA 01890
0.08
$1,077,000
3
2
1,536
Off Market
1 Orient St, Winchester, MA 01890
0.12
$1,330,000
3
1.5
2,222
Recently Sold
124 Forest St, Winchester, MA 01890
0.12
$1,539,500
3
2.5
2,534
Off Market
44 Forest St, Winchester, MA 01890
0.11
$1,192,000
3
1.5
1,906
Off Market
28 Garfield Ave, Winchester, MA 01890
0.11
$1,299,100
4
1.5
1,696
Off Market
55 Brookside Ave, Winchester, MA 01890
0.10
$657,500
3
1
1,245
Recently Sold
518 Washington St, Winchester, MA 01890
0.15
$1,174,600
4
2.5
2,302
Off Market

Local Information

  • Map ViewExplore the area around 21 Brookside Ave.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Condo
Year Built
1931
Living Area
1,550 sqft
Price/Sqft
$577

About this House

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.
21 Brookside Ave, Winchester, MA 01890 is a 3 bedroom, 2 bathroom, 1,550 sqft condo built in 1931. It last sold for $580,000 on Sep 18, 2014. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $893,600, with a rent estimate of $3,470/month.

Home Details for 21 Brookside Ave

Interior Features

Interior Details
BasementNumber of Rooms: 7
Heating & Cooling
Heating: GasHeating Fuel: Gas
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 and Tax history

DateEventPrice
Sep 18, 2014
Source: N/A
Sold
$580,000
May 15, 2007
Source: N/A
Sold
$580,000
Dec 17, 1998
Source: N/A
Sold
$329,000

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 21 Brookside Ave

  • What is 21 Brookside Ave estimated to be worth?
    Trulia's estimated value for 21 Brookside Ave in Winchester, MA is $893,600.
  • What is the price history for 21 Brookside Ave?
    21 Brookside Ave in Winchester, MA last sold for $580,000 in September 2014.
  • 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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