39 Brookside Ave, Winchester, MA 01890
OFF MARKET

39 Brookside Ave
Winchester, MA 01890

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

$1,292,000

Trulia Estimate
as of May 25, 2026
Est. Refi. Payment $7,620/mo*
Refinance Your Home

$1,292,000

Trulia Estimate
as of May 25, 2026
Est. Refi. Payment $7,620/mo*
Refinance Your Home
5 Beds
3.5 Baths
3,001 sqft
(on 0.54 acres)

Local Information

Map showing home location
© Google
-- mins to
Commute Destination

Description

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!
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
Garage
Outdoor
Porch, Deck
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
No Info

Home Details for 39 Brookside Ave

Interior Features

Interior Details
BasementNumber of Rooms: 8
Heating & Cooling
Heating: Forced Air, GasAir ConditioningCooling System: OtherHeating 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 History for 39 Brookside Ave

DatePriceEventSource
12/12/2019$949,000Sold
N/A
10/29/2019$949,000PendingAgent Provided
10/23/2019$949,000Listed For SaleAgent Provided
07/13/2016$815,200Sold
N/A
03/18/2016$799,888PendingAgent Provided
03/10/2016$799,888Listed For SaleAgent Provided
08/05/2004$689,900Sold
N/A
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Property Tax and Assessment

Year2025
Tax$12,098
Assessment$1,090,900
Home facts updated by county records

Comparable Sales for 39 Brookside Ave

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
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
171 Swanton St #60, Winchester, MA
0.49
Townhouse
$738,000
09/26/25
3
2.5
1,824

Nearby homes

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Assigned Schools

These are the assigned schools for 39 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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39 Brookside Ave, Winchester, MA 01890 is a 5 bedroom, 4 bathroom, 3,001 sqft townhouse built in 2003. This property is not currently available for sale. 39 Brookside Ave was last sold on Dec 12, 2019 for $949,000. The current Trulia Estimate for 39 Brookside Ave is $1,292,000.