2 Upland Rd, Winchester, MA 01890
Full bathroom
Laundry room
OFF MARKET

2 Upland Rd
Winchester, MA 01890

  • 3 Beds
  • 2 Baths
  • 1,902 sqft

$1,477,000

Trulia Estimate
as of Aug 3, 2026
Est. Refi. Payment $8,896/mo*
Refinance Your Home

$1,477,000

Trulia Estimate
as of Aug 3, 2026
Est. Refi. Payment $8,896/mo*
Refinance Your Home
3 Beds
2 Baths
1,902 sqft

Local Information

  • Map ViewExplore the area around 2 Upland Rd.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1929
Living Area
1,902 sqft
Price/Sqft
$777

About this House

Fully renovated house in desirable Winchester neighborhood. Home boasts custom built eat-in-kitchen w/granite, gas cooking & Bosch appliances. New roof, new windows throughout, marble bathrooms, maintenance free composite deck, new gas hot water heater & gas heating system. Turn key home also features large basement-level bonus room, bright sunroom/office, brand new laundry room, hardwood floors, walk-in closets, professionally landscaped level yard, and is located near schools, bus, and more
2 Upland Rd, Winchester, MA 01890 is a 3 bedroom, 2 bathroom, 1,902 sqft single-family home built in 1929. It last sold for $606,000 on May 25, 2012. It is currently off market. The Trulia Estimate is $1,477,000, with a rent estimate of $5,060/month.

Home Details for 2 Upland Rd

Interior Features

Interior Details
BasementNumber of Rooms: 8Types of Rooms: Walk In Closet, Breakfast Nook, Family Room, Recreation Room
Heating & Cooling
Heating: Other, GasAir ConditioningHeating Fuel: Other
Levels, Entrance, & Accessibility
Stories: 3Floors: Tile, Hardwood
Appliances & Utilities
DishwasherDryerMicrowaveRefrigeratorWasher
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: Wood

Property Information

Year Built
Year Built: 1929
Property Type / Style
Property Type: Single Family HomeArchitecture: Old Style

Community

Units in Building: 1

Lot Information

Lot Area: 8635 sqft

Price History for 2 Upland Rd

DatePriceEventSource
05/25/2012$606,000Sold
N/A
04/27/2012$599,000Listed For SaleAgent Provided
11/02/2011$290,000Sold
N/A
04/27/2007$174,000Sold
N/A

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
Skip to last item
  • Results are loading
Skip to first item

Property Tax and Assessment

Year2025
Tax$14,189
Assessment$1,279,400
Home facts updated by county records

Comparable Sales for 2 Upland Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
9 Sylvester Ct, Winchester, MA
0.07
Single-Family Home
$1,015,000
12/01/25
4
1.5
2,001
136 Sylvester Ave, Winchester, MA
0.13
Single-Family Home
$1,156,000
02/25/26
3
1.5
1,608
149 Horn Pond Brook Rd, Winchester, MA
0.11
Single-Family Home
$1,020,000
06/05/26
5
2
2,331
2 Maria Ct, Woburn, MA
0.35
Single-Family Home
$780,000
04/23/26
2
2
1,824
104 Wendell St, Winchester, MA
0.32
Single-Family Home
$1,100,000
05/28/26
3
1.5
1,675
76 Woodside Rd, Winchester, MA
0.31
Single-Family Home
$1,080,000
05/12/26
4
2
1,552
198 Pond St, Winchester, MA
0.31
Single-Family Home
$1,070,000
05/20/26
4
1.5
1,917
87 Wendell St, Winchester, MA
0.36
Single-Family Home
$1,250,000
05/29/26
4
2
2,046
40 Pickering St, Winchester, MA
0.18
Single-Family Home
$1,330,000
04/14/26
4
2.5
2,454
235 Cross St, Winchester, MA
0.64
Single-Family Home
$868,000
09/04/25
3
1.5
1,931

Nearby homes

Get a sense of prices in the area by checking nearby homes.
Skip to last item
Skip to first item

Assigned Schools

These are the assigned schools for 2 Upland 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

LGBTQ Local Legal Protections

Apartments for Rent

Skip to last item
Skip to first item

Explore by feature - Pet Friendly

11 pet-friendly rentals in Winchester, MA

Explore by feature - Garage

11 rentals with a garage in Winchester, MA

Explore by feature - Air Conditioning

27 rentals with air conditioning in Winchester, MA

Explore by feature - Pool

9 rentals with a pool in Winchester, MA

Explore by feature - Washer/dryer

28 rentals with a washer/dryer in Winchester, MA

Explore by feature - Outdoor Space

11 rentals with an outdoor space in Winchester, MA

Homes for sale near 2 Upland Rd

Skip to last item
Skip to first item

Off Market Homes Near 2 Upland Rd

Skip to last item
Skip to first item