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

24 Brookside Ave
Winchester, MA 01890

  • 3 Beds
  • 2.5 Baths
  • 2,381 sqft

$1,445,800

Trulia Estimate
as of Jul 24, 2026
Est. Refi. Payment $8,588/mo*
Refinance Your Home

$1,445,800

Trulia Estimate
as of Jul 24, 2026
Est. Refi. Payment $8,588/mo*
Refinance Your Home
3 Beds
2.5 Baths
2,381 sqft

Local Information

  • Map ViewExplore the area around 24 Brookside Ave.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1905
Living Area
2,381 sqft
Price/Sqft
$607

About this House

Newly gut renovated breathtaking single family home in Winchester! Enter into this exquisite modern design containing an inviting living room, formal dining room featuring a stunning modern light fixture and box window, allowing ample natural light to stream through. The gorgeous kitchen contains elegant granite countertops, stainless steel appliances, a breakfast bar overlooking the sun-drenched family room and mudroom with access to the deck, patio and backyard. Enjoy the master suite, with his and her closets and a spa-like master bath featuring a floating double vanity and oversized shower. Two additional bedrooms and another full bath complete the second floor. The lower level is completely finished and offers an open floor layout with a media room, workout room or game room and a large laundry room. With these meticulous details, recessed lighting, stunning granite countertops and hardwood floors throughout; this newly renovated home is everything youâve dreamed of!
24 Brookside Ave, Winchester, MA 01890 is a 3 bedroom, 3 bathroom, 2,381 sqft single-family home built in 1905. It last sold for $1,211,000 on Nov 1, 2022. It is currently off market. The Trulia Estimate is $1,445,800, with a rent estimate of $4,991/month.

Home Details for 24 Brookside Ave

Interior Features

Interior Details
BasementNumber of Rooms: 10
Heating & Cooling
Heating: Forced Air, GasAir ConditioningHeating Fuel: Forced Air
Appliances & Utilities
DishwasherDisposalMicrowave
Levels, Entrance, & Accessibility
Floors: Tile, Hardwood

Exterior Features

Exterior Home Features
Roof: AsphaltDeckExterior: OtherPatioPorch

Property Information

Year Built
Year Built: 1905Year Updated: 2017
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Community

Units in Building: 1

Lot Information

Lot Area: 5540 sqft

Price History for 24 Brookside Ave

DatePriceEventSource
11/01/2022$1,211,000Sold
MLS PIN #73038195
09/27/2022$1,159,000ContingentMLS PIN #73038195
09/19/2022$1,159,000Listed For SaleMLS PIN #73038195
03/15/2019$965,000Sold
N/A
02/08/2019$979,000PendingAgent Provided
01/18/2019$979,000Listed For SaleAgent Provided
11/15/2018$979,000ListingRemovedAgent Provided
10/20/2018$979,000PriceChange
Agent Provided
09/18/2018$999,000PriceChange
Agent Provided
09/03/2018$1,099,000Listed For SaleAgent Provided
03/06/2018$661,000Sold
N/A
01/25/2018$629,000PendingAgent Provided
01/15/2018$629,000Listed For SaleAgent Provided

Market trends in Winchester

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$1.41M
Sale-to-List Price
101.7%
Price per sq ft
$571
Available listings
77
2MoM
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Property Tax and Assessment

Year2025
Tax$13,877
Assessment$1,251,300
Home facts updated by county records

Comparable Sales for 24 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
18 Brookside Ave, Winchester, MA
0.02
Single-Family Home
$1,207,500
07/24/25
3
1.5
1,573
1 Orient St, Winchester, MA
0.10
Single-Family Home
$1,330,000
05/28/26
3
1.5
2,222
8 Garfield Ave, Winchester, MA
0.05
Single-Family Home
$1,062,350
08/22/25
3
2
1,536
10 Bonad Rd, Winchester, MA
0.30
Single-Family Home
$1,620,000
07/06/26
4
2.5
2,233
40 Englewood Rd, Winchester, MA
0.37
Single-Family Home
$1,218,000
05/20/26
4
2
1,841
15 Englewood Rd, Winchester, MA
0.36
Single-Family Home
$1,425,000
05/07/26
4
3
1,903
571 Washington St, Winchester, MA
0.08
Single-Family Home
$900,000
01/05/26
3
1
1,425
17 Baldwin St, Winchester, MA
0.33
Single-Family Home
$878,000
09/26/25
3
1.5
1,672
162 Forest St, Winchester, MA
0.33
Single-Family Home
$1,280,000
10/03/25
4
1.5
1,900

Nearby homes

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Assigned Schools

These are the assigned schools for 24 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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Off Market Homes Near 24 Brookside Ave

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