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

39 Brookside Ave
Winchester, MA 01890

  • 5 Beds
  • 3.5 Baths
  • 3,001 sqft (on 0.54 acres)

$1,239,100

Trulia Estimate
as of Aug 23, 2026
Est. Refi. Payment $7,390/mo*
Refinance Your Home

$1,239,100

Trulia Estimate
as of Aug 23, 2026
Est. Refi. Payment $7,390/mo*
Refinance Your Home
5 Beds
3.5 Baths
3,001 sqft
(on 0.54 acres)

Home Value

Trulia Estimate
$1.24M
Since last month
Decreased$12K (-0.9%)
Since last year
Increased$2K (+0.2%)
Since last sale
Increased$290K (+30.6%)
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 +51% in the last 10 years
MonthEstimated value
2026
August 2026$1.24M
July 2026$1.25M
June 2026$1.27M
May 2026$1.28M
April 2026$1.27M
March 2026$1.27M
February 2026$1.22M
January 2026$1.21M
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
95 Irving St #95, Winchester, MA
0.50
Townhouse
$1,350,000
03/06/26
4
3.5
2,490
209 Washington St #209, Winchester, MA
0.90
Townhouse
$1,499,000
12/24/25
5
3.5
3,141
171 Swanton St #5, Winchester, MA
0.49
Townhouse
$900,000
10/20/25
3
2.5
1,843
19 Mason Way #75, Woburn, MA
0.57
Townhouse
$1,339,995
02/12/26
3
3.5
2,909
17 Mason Way #74, Woburn, MA
0.57
Townhouse
$1,349,999
01/28/26
3
3.5
2,909
171 Swanton St #64, Winchester, MA
0.49
Townhouse
$825,000
08/29/25
3
2.5
1,825
12 Mason Way, Woburn, MA
0.59
Townhouse
$1,274,999
08/29/25
3
3.5
2,812
2-02 Mason Way #6524, Woburn, MA
0.61
Townhouse
$1,290,000
03/27/26
3
3.5
2,909
171 Swanton St #21, Winchester, MA
0.49
Townhouse
$770,000
05/05/26
3
2.5
1,834
2 Mason Way, Woburn, MA
0.61
Townhouse
$1,290,000
03/27/26
3
3.5
2,909

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
55 Brookside Ave, Winchester, MA 01890
0.07
$657,500
3
1
1,245
Recently Sold
18 Brookside Ave, Winchester, MA 01890
0.06
$1,236,800
3
1.5
1,573
Off Market
28 Garfield Ave, Winchester, MA 01890
0.09
$1,315,400
4
1.5
1,696
Off Market
8 Garfield Ave, Winchester, MA 01890
0.09
$1,077,000
3
2
1,536
Off Market
571 Washington St, Winchester, MA 01890
0.10
$900,000
3
1
1,425
Recently Sold
44 Forest St, Winchester, MA 01890
0.11
$1,192,000
3
1.5
1,906
Off Market
116 Forest St, Winchester, MA 01890
0.12
$1,100,500
4
2.5
2,106
Off Market
118 Forest St, Winchester, MA 01890
0.13
$2,144,100
5
3.5
3,866
Off Market
540-542 Washington St, Winchester, MA 01890
0.13
-
4
2
2,060
Off Market
18 Forest St, Winchester, MA 01890
0.16
$1,312,200
3
2.5
2,365
Off Market
124 Forest St, Winchester, MA 01890
0.16
$1,539,500
3
2.5
2,534
Off Market
1 Orient St, Winchester, MA 01890
0.15
$1,330,000
3
1.5
2,222
Recently Sold

Local Information

  • Map ViewExplore the area around 39 Brookside Ave.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Townhouse
Year Built
2003
Lot Size
0.54 acres
Living Area
3,001 sqft
Price/Sqft
$413
Parking
Garage

About this House

Spectacular modern aura weaved with a classic flavor describe this high quality, newer home. Oak floors on all 3 living levels set stage for this wonderful 5 bedroom, 3 and one half bath luxury living space. Two car, over sized garage add to the convenience in this family-friendly Muraco district where living is made easy. Cared for, and lovingly maintained, this striking space is proof positive that quality stands out. Striking cherry kitchen, tasteful counter tops, and an upscale stainless suite of appliances are the focus that make this the heart of the home in this open concept floor. Walking distance to Winchester's NEW Cross Street soccer facility, and Leonard Field on Washington Street make it super convenient for weekend sporting events. A straight line to Interstate 93,and all of Woburn's business centers make it easy to get your work responsibilities. Walking distance to Winchester Center, and the commuter rail. Ultra convenient, superb town amenities, New England charm, and value!
39 Brookside Ave, Winchester, MA 01890 is a 5 bedroom, 4 bathroom, 3,001 sqft townhouse built in 2003. It last sold for $949,000 on Dec 12, 2019. It is currently off market. The Trulia Estimate is $1,239,100, with a rent estimate of $6,417/month.

Home Details for 39 Brookside Ave

Interior Features

Interior Details
BasementNumber of Rooms: 8
Heating & Cooling
Heating: Forced Air, GasAir ConditioningHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 4Floors: Hardwood
Appliances & Utilities
DishwasherDisposalDryerMicrowaveRefrigeratorWasher
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: AsphaltDeckExterior: WoodPorch
Parking & Garage
GarageParking Spaces: 2Parking: Garage Attached

Property Information

Year Built
Year Built: 2003
Property Type / Style
Property Type: TownhouseArchitecture: Other

Community

Units in Building: 2

Lot Information

Lot Area: 0.54 acres

Price and Tax history

DateEventPrice
Dec 12, 2019
Source: N/A
Sold
$949,000
Oct 29, 2019
Source: Agent Provided
Pending
$949,000
Oct 23, 2019
Source: Agent Provided
Listed For Sale
$949,000
Jul 13, 2016
Source: N/A
Sold
$815,200
Mar 18, 2016
Source: Agent Provided
Pending
$799,888

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 39 Brookside Ave

  • What is 39 Brookside Ave estimated to be worth?
    Trulia's estimated value for 39 Brookside Ave in Winchester, MA is $1,239,100.
  • What is the price history for 39 Brookside Ave?
    39 Brookside Ave in Winchester, MA last sold for $949,000 in December 2019.
  • 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.
  • Does 39 Brookside Ave have laundry facilities?
    Yes, 39 Brookside Ave in Winchester, MA has in-unit laundry.
  • Does 39 Brookside Ave have a garage?
    Yes, 39 Brookside Ave in Winchester, MA has a garage.

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Off Market Homes Near 39 Brookside Ave

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