396 Main St, Winchester, MA 01890
OFF MARKET

396 Main St
Winchester, MA 01890

  • 3 Beds
  • 2 Baths
  • 1,500 sqft

$912,200

Trulia Estimate
as of Aug 3, 2026
Est. Refi. Payment $5,523/mo*
Refinance Your Home

$912,200

Trulia Estimate
as of Aug 3, 2026
Est. Refi. Payment $5,523/mo*
Refinance Your Home
3 Beds
2 Baths
1,500 sqft

Local Information

  • Map ViewExplore the area around 396 Main St.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Townhouse
Year Built
1850
Living Area
1,500 sqft
Price/Sqft
$608

About this House

DOWNTOWN LOCATION! I REPEAT, DOWNTOWN LOCATION! Morning coffee, easy! CVS run, a breeze! Want to grab a pizza for dinner, no problem! 396 Main Street is the ideal property for those who want to take advantage of all that Winchester as a community has to offer. The first level consists of an open concept dining room and kitchen, full bathroom, and living room. The kitchen has been beautifully gut renovated with upgraded cabinetry, stainless appliances, and granite counters. All three bedrooms are found on the second level as well as the 2nd full bathroom. Let's not forget about the 3rd floor play area! All the heavy lifting has been done for you, new central A/C, heating system, and windows! Unpack your bags and make yourself at home. This unit boasts a private driveway and private rear yard with deck. Best of all? 396 Main is located in the Lincoln School District making the grade school, middle school, AND high school all EASILY walkable!

396 Main St, Winchester, MA 01890 is a 3 bedroom, 2 bathroom, 1,500 sqft townhouse built in 1850. It last sold for $580,000 on Apr 20, 2018. It is currently off market. The Trulia Estimate is $912,200, with a rent estimate of $4,017/month.

Home Details for 396 Main St

Interior Features

Interior Details
BasementAdditional StorageNumber of Rooms: 7Types of Rooms: Dining Room, Family RoomStorage
Heating & Cooling
Heating: Forced Air, Other, GasAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 3Floors: Hardwood
Appliances & Utilities
Cable ReadyDishwasherDisposalDryerRefrigeratorWasher
Fireplace & Spa
Fireplace
Windows, Doors, Floors & Walls
Double Paned Windows

Exterior Features

Exterior Home Features
Roof: AsphaltDeckExterior: WoodPorch
Parking & Garage
Parking Spaces: 3Parking: Off Street

Property Information

Year Built
Year Built: 1850
Property Type / Style
Property Type: TownhouseArchitecture: Other

Community

Units in Building: 2

Price History for 396 Main St

DatePriceEventSource
04/20/2018$580,000Sold
N/A
03/11/2018$599,000PendingAgent Provided
03/01/2018$599,000Listed 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$7,944
Assessment$716,300
Home facts updated by county records

Comparable Sales for 396 Main St

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
31 Mystic Ave #31, Winchester, MA
0.14
Townhouse
$1,200,000
05/29/26
4
2
2,129
62 Vine St #62, Winchester, MA
0.50
Townhouse
$800,000
10/24/25
2
2
1,545
50 Lake St #B, Winchester, MA
0.63
Townhouse
$690,000
09/03/25
2
1.5
1,554
13 Nelson St #13, Winchester, MA
0.59
Townhouse
$425,000
03/18/26
3
2.5
1,783
40 Lake St #I, Winchester, MA
0.64
Townhouse
$701,000
06/12/26
2
1.5
1,315
15 Governors Ave #1, Winchester, MA
0.83
Townhouse
$740,000
09/09/25
3
1
1,358
6 Wyman Ct #6, Winchester, MA
0.57
Townhouse
$1,379,000
01/05/26
3
4.5
2,722
22 Grove Pl #4, Winchester, MA
0.79
Townhouse
$770,000
08/11/25
2
1
1,123
4 Wyman Ct #4, Winchester, MA
0.57
Townhouse
$1,399,000
01/05/26
4
4.5
2,500
171 Swanton St #60, Winchester, MA
1.13
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 396 Main St.
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 396 Main St

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