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

14 Brookside Ave
Winchester, MA 01890

  • 4 Beds
  • 3.5 Baths
  • 2,880 sqft

$1,860,400

Trulia Estimate
as of Jul 7, 2026

$1,860,400

Trulia Estimate
as of Jul 7, 2026
4 Beds
3.5 Baths
2,880 sqft

Local Information

  • Map ViewExplore the area around 14 Brookside Ave.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

Lovely! Walk through the front door & see why this should be your next home. With versatile living space & stylish finishes, you'll enjoy a perfect setting for relaxing & entertaining. Entirely renovated in 2014, it offers the best of both worlds--details & an open (or not) floor plan. Custom features include Coffered ceilings, crown moldings & wainscoting. Beautiful entry hall, fireplaced living room, sunlit office & handy half bath. Expansive eat-in kitchen with island, SS appliances, gas cooking & granite countertops. Sliders to the patio where you can be proud to entertain al fresco. Currently, the dining room is being used as a toddler play space--adaptability at its best. Make your way to the second floor where there is a master with ensuite & custom walk-in closet, junior suite with en-suite & custom closet, two additional bedrooms, full bath (total bath count of 3 ½) & laundry. Finished lower level family room with built-in media center. Perfect for kicking back & unwinding.
14 Brookside Ave, Winchester, MA 01890 is a 4 bedroom, 4 bathroom, 2,880 sqft single-family home built in 1929. It last sold for $1,250,000 on Aug 22, 2019. It is currently off market. The Trulia Estimate is $1,860,400, with a rent estimate of $6,177/month.

Home Highlights

Parking
Garage
Outdoor
No Info
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
Less than a day ago

Home Details for 14 Brookside Ave

Interior Features

Interior Details
BasementNumber of Rooms: 9
Heating & Cooling
Heating: Other, GasAir ConditioningHeating Fuel: Other
Levels, Entrance, & Accessibility
Stories: 2
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: Other
Parking & Garage
GarageParking: Garage Detached

Property Information

Year Built
Year Built: 1929Year Updated: 2013
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Community

Units in Building: 1

Lot Information

Lot Area: 8712 sqft

Price History for 14 Brookside Ave

DatePriceEventSource
08/22/2019$1,250,000Sold
N/A
05/26/2019$1,250,000PendingAgent Provided
05/16/2019$1,250,000Listed For SaleAgent Provided
12/18/2014$1,075,000Sold
N/A
10/28/2014$999,000Listed For SaleAgent Provided
04/25/2014$600,000Sold
N/A
04/09/2014$629,900PendingAgent Provided
04/02/2014$629,900Listed For SaleAgent Provided

Market trends in Winchester

Last updated May 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
75
7MoM
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Property Tax and Assessment

Year2025
Tax$17,050
Assessment$1,537,400
Home facts updated by county records

Comparable Sales for 14 Brookside Ave

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
518 Washington St, Winchester, MA
0.12
Single-Family Home
$1,160,000
08/14/25
4
2.5
2,302
1 Orient St, Winchester, MA
0.09
Single-Family Home
$1,330,000
05/28/26
3
1.5
2,222
10 Bonad Rd, Winchester, MA
0.30
Single-Family Home
$1,620,000
07/06/26
4
2.5
2,233
162 Forest St, Winchester, MA
0.29
Single-Family Home
$1,280,000
10/03/25
4
1.5
1,900
8 Ware Rd, Winchester, MA
0.42
Single-Family Home
$1,226,000
07/15/25
3
3
2,534
8 Garfield Ave, Winchester, MA
0.08
Single-Family Home
$1,062,350
08/22/25
3
2
1,536
18 Brookside Ave, Winchester, MA
0.01
Single-Family Home
$1,207,500
07/24/25
3
1.5
1,573
15 Englewood Rd, Winchester, MA
0.36
Single-Family Home
$1,425,000
05/07/26
4
3
1,903
20 Grayson Rd, Winchester, MA
0.27
Single-Family Home
$1,945,000
09/16/25
5
4.5
3,825
40 Englewood Rd, Winchester, MA
0.36
Single-Family Home
$1,218,000
05/20/26
4
2
1,841

Nearby homes

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Assigned Schools

These are the assigned schools for 14 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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Homes for sale near 14 Brookside Ave

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Off Market Homes Near 14 Brookside Ave

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