5 Squanto Rd, Winchester, MA 01890
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Property image
OFF MARKET

5 Squanto Rd
Winchester, MA 01890

  • 4 Beds
  • 3 Baths
  • 2,918 sqft

$1,906,700

Trulia Estimate
as of Jul 7, 2026

$1,906,700

Trulia Estimate
as of Jul 7, 2026
4 Beds
3 Baths
2,918 sqft

Local Information

  • Map ViewExplore the area around 5 Squanto Rd.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

Rare opportunity to own a charming center entrance Colonial located in desirable Ambrose School district! This pristine & spacious home features 4 bedrooms with 3 full bathrooms. Many cosmetic updates and a recently renovated chefâs kitchen! Formal dining room w/ fireplace, custom built-ins & hardwood floors throughout. French doors open to a cozy family room perfect for movie watching! The renovated kitchen is every cook and entertainerâs dream! Open to the living room and with plenty of natural sunlight. Custom cabinetry, granite countertops, gas cooking and stainless steel appliances. Exterior door opens to deck great for barbequing & leads to a fully fenced backyard. Full bathroom & laundry complete first level living. Master bedroom w/ renovated en-suite bathroom. Three additional bedrooms with a full bathroom complete the second level. Fully finished lower level with bonus room perfect for a home office/gym/zoom room & additional media room with fireplace. Welcome to Winchester!
5 Squanto Rd, Winchester, MA 01890 is a 4 bedroom, 3 bathroom, 2,918 sqft single-family home built in 1952. It last sold for $1,525,000 on Jul 8, 2021. It is currently off market. The Trulia Estimate is $1,906,700, with a rent estimate of $6,682/month.

Home Highlights

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

Home Details for 5 Squanto Rd

Interior Features

Interior Details
BasementNumber of Rooms: 10Types of Rooms: Dining Room, Family Room
Heating & Cooling
Heating: Other, GasAir ConditioningHeating Fuel: Other
Appliances & Utilities
Cable ReadyDishwasherDisposalDryerMicrowave
Fireplace & Spa
Fireplace
Levels, Entrance, & Accessibility
Floors: Tile, Hardwood

Exterior Features

Exterior Home Features
Roof: AsphaltDeckExterior: Shingle Not WoodPorch
Parking & Garage
GarageParking Spaces: 4Parking: Garage Attached

Property Information

Year Built
Year Built: 1952
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Community

Units in Building: 1

Lot Information

Lot Area: 8250 sqft

Price History for 5 Squanto Rd

DatePriceEventSource
07/08/2021$1,525,000Sold
MLS PIN #72815003
04/24/2021$1,499,000PendingKeller Williams #72815003
04/24/2021$1,499,000ContingentMLS PIN #72815003
04/15/2021$1,499,000Listed For SaleMLS PIN #72815003
03/07/2016$1,001,000Sold
C21 Commonwealth Sold #71944939_01890
01/14/2016$899,999PendingAgent Provided
01/04/2016$899,999Listed For SaleAgent Provided
10/23/2010$889,900ListingRemovedAgent Provided
05/25/2010$889,900Listed For SaleAgent Provided
08/09/1994$357,000Sold
N/A
04/01/1987$270,000Sold
N/A
01/01/1970$1,525,000Sold
N/A

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$17,180
Assessment$1,549,100
Home facts updated by county records

Comparable Sales for 5 Squanto Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
65 High St, Winchester, MA
0.05
Single-Family Home
$1,440,150
06/01/26
6
3
2,658
15 Westland Ave, Winchester, MA
0.16
Single-Family Home
$1,750,000
10/31/25
4
2.5
2,397
28 Emerson Rd, Winchester, MA
0.09
Single-Family Home
$1,475,000
04/29/26
3
2
2,344
32 Oneida Rd, Winchester, MA
0.18
Single-Family Home
$1,627,000
07/31/25
5
4
2,853
34 Robinhood Rd, Winchester, MA
0.33
Single-Family Home
$1,450,000
06/12/26
4
2.5
3,380
6 Samoset Rd, Winchester, MA
0.14
Single-Family Home
$1,987,000
11/18/25
4
3.5
4,731
61 Westland Ave, Winchester, MA
0.32
Single-Family Home
$1,800,000
02/24/26
3
3.5
2,785
10 Blossom Hill Rd, Winchester, MA
0.29
Single-Family Home
$1,678,500
09/25/25
4
2
3,838
5 Thornton Rd, Winchester, MA
0.46
Single-Family Home
$1,525,000
09/12/25
4
3.5
2,755
29 Pilgrim Dr, Winchester, MA
0.36
Single-Family Home
$1,700,000
06/29/26
5
3
3,271

Nearby homes

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Assigned Schools

These are the assigned schools for 5 Squanto Rd.
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 5 Squanto Rd

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