25 Brookside Ave, Winchester, MA 01890
OFF MARKET

$1,068,000

Trulia Estimate
  • 4 Beds
  • 2.5 Baths
  • 2,544 sqft

25 Brookside Ave, Winchester, MA 01890

Est. Refi. Payment $6,727/mo*
Refinance Your Home
Currently Off Market - Sold Sep 10, 2014 for $325,000

Home Value

Trulia Estimate
$1.07M
Since last month
Increased$1K (+0.1%)
Since last year
Increased$107K (+11%)
Since last sale
Increased$751K (+231%)
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 +58% in the last 10 years
MonthEstimated value
2026
September 2026$1.08M
August 2026$1.07M
July 2026$1.02M
June 2026$1.04M
May 2026$1.05M
April 2026$1.02M
March 2026$1.01M
February 2026$972K
January 2026$951K
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
1 Orient St, Winchester, MA
0.13
Single-Family Home
$1,330,000
05/28/26
3
1.5
2,222
11 Williams Cir, Winchester, MA
0.27
Single-Family Home
$1,350,000
09/02/26
4
2.5
2,392
10 Bonad Rd, Winchester, MA
0.33
Single-Family Home
$1,620,000
07/06/26
4
2.5
2,233
55 Brookside Ave, Winchester, MA
0.09
Single-Family Home
$657,500
07/17/26
3
1
1,245
40 Englewood Rd, Winchester, MA
0.40
Single-Family Home
$1,218,000
05/20/26
4
2
1,841
18 Grayson Rd, Winchester, MA
0.30
Single-Family Home
$1,738,000
07/28/26
3
2.5
2,992
571 Washington St, Winchester, MA
0.08
Single-Family Home
$900,000
01/05/26
3
1
1,425
162 Forest St, Winchester, MA
0.32
Single-Family Home
$1,280,000
10/03/25
4
1.5
1,900
17 Baldwin St, Winchester, MA
0.32
Single-Family Home
$878,000
09/26/25
3
1.5
1,672
24 Hinds Rd, Winchester, MA
0.29
Single-Family Home
$1,750,000
07/09/26
4
3
2,814

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
8 Garfield Ave, Winchester, MA 01890
0.07
$1,080,300
3
2
1,536
Off Market
18 Brookside Ave, Winchester, MA 01890
0.03
$1,230,000
3
1.5
1,573
Off Market
44 Forest St, Winchester, MA 01890
0.10
$1,198,700
3
1.5
1,906
Off Market
28 Garfield Ave, Winchester, MA 01890
0.10
$1,290,700
4
1.5
1,696
Off Market
55 Brookside Ave, Winchester, MA 01890
0.09
$657,500
3
1
1,245
Recently Sold
540-542 Washington St, Winchester, MA 01890
0.10
-
4
2
2,060
Off Market
116 Forest St, Winchester, MA 01890
0.09
$1,088,700
4
2.5
2,106
Off Market
571 Washington St, Winchester, MA 01890
0.08
$900,000
3
1
1,425
Recently Sold
25 Marion St, Winchester, MA 01890
0.14
$2,144,800
5
4
4,234
Off Market
1 Orient St, Winchester, MA 01890
0.13
$1,330,000
3
1.5
2,222
Recently Sold
118 Forest St, Winchester, MA 01890
0.10
$2,158,300
5
3.5
3,866
Off Market
518 Washington St, Winchester, MA 01890
0.15
$1,178,400
4
2.5
2,302
Off Market

Local Information

  • Map ViewExplore the area around 25 Brookside Ave.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1920
2,544 sqft
$420/sqft
Garage

About this House

This single-family home is located at 25 Brookside Ave, Winchester, MA. 25 Brookside Ave is in Winchester, MA and in ZIP code 01890. This property has 4 bedrooms, 2 bathrooms and approximately 2,544 sqft of floor space. This property has a lot size of 6534 sqft and was built in 1920.
25 Brookside Ave, Winchester, MA 01890 is a 4 bedroom, 2 bathroom, 2,544 sqft single-family home built in 1920. It last sold for $325,000 on Sep 10, 2014. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $1,068,000, with a rent estimate of $4,600/month.

Home Details for 25 Brookside Ave

Interior Features

Interior Details
BasementNumber of Rooms: 7Types of Rooms: Walk In Closet, Breakfast Nook, Family Room, Laundry Room, Master Bath, Mud Room, Office, Pantry, Recreation Room
Heating & Cooling
Heating: Forced Air, GasAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 2Floors: Hardwood
Appliances & Utilities
Cable ReadyDishwasherDisposalDryerMicrowaveRefrigeratorWasher
Fireplace & Spa
FireplaceJetted Bath Tub
Windows, Doors, Floors & Walls
Double Paned Windows
Security
Security System

Exterior Features

Exterior Home Features
Roof: AsphaltDeckExterior: WoodGardenLawnPatioPorchSprinkler System
Parking & Garage
GarageParking Space: 1Parking: Garage Detached

Property Information

Year Built
Year Built: 1920Year Updated: 2026
Property Type / Style
Property Type: Single Family HomeArchitecture: Other

Community

Units in Building: 1

Lot Information

Lot Area: 6534 sqft

Price and Tax history

DateEventPrice
Sep 10, 2014
Source: N/A
Sold
$325,000
Jun 3, 2011
Source: Agent Provided
PriceChange
$579,000
Price decreased by 2%
Apr 29, 2011
Source: Agent Provided
Listed For Sale
$589,000
Aug 27, 2007
Source: N/A
Sold
$368,000

Market trends in Winchester

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
62
2MoM

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 25 Brookside Ave

  • What is 25 Brookside Ave estimated to be worth?
    Trulia's estimated value for 25 Brookside Ave in Winchester, MA is $1,068,000.
  • What is the price history for 25 Brookside Ave?
    25 Brookside Ave in Winchester, MA last sold for $325,000 in September 2014.
  • Is Winchester a buyer's or seller's market?
    Winchester is currently a buyer's market, based on recent for-sale activity.
  • What do residents say about Winchester?
    Residents describe Winchester, MA as dog-friendly, well-kept, and easy to park in. Most residents say you need a car. See recently sold homes in Winchester, MA.
  • Does 25 Brookside Ave have air conditioning?
    Yes, 25 Brookside Ave in Winchester, MA has air conditioning.
  • Does 25 Brookside Ave have laundry facilities?
    Yes, 25 Brookside Ave in Winchester, MA has in-unit laundry.

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Off Market Homes Near 25 Brookside Ave

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