2 Upwey Rd, Wellesley, MA 02481
OFF MARKET

2 Upwey Rd
Wellesley, MA 02481

  • 3 Beds
  • 3 Baths
  • 2,579 sqft (on 0.27 acres)

$1,850,200

Trulia Estimate
as of May 31, 2026
Est. Refi. Payment $10,704/mo*
Refinance Your Home

$1,850,200

Trulia Estimate
as of May 31, 2026
Est. Refi. Payment $10,704/mo*
Refinance Your Home
3 Beds
3 Baths
2,579 sqft
(on 0.27 acres)

Local Information

Map showing home location
© Google
-- mins to
Commute Destination

Description

Great value and a unique home buying opportunity in Wellesley. See a two story addition with amazing space and luxury features that will make your heart sing. Classic colonial home suits traditional tastes but the recent improvements provide the excitement. Outdoor spaces are designed with low maintenance perennial gardens, stone walls and large areas of bluestone patios. Close to Center of town, train to Boston and all schools.
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources.

Home Highlights

Parking
No Info
Outdoor
No Info
A/C
Heating only
HOA
None
Price/Sqft
No Info
Listed
No Info

Home Details for 2 Upwey Rd

Interior Features

Heating & Cooling
Heating: Other, GasHeating Fuel: Other
Levels, Entrance, & Accessibility
Stories: 2
Interior Details
Number of Rooms: 7Types of Rooms: Recreation Room
Fireplace & Spa
Fireplace

Property Information

Year Built
Year Built: 1938
Property Type / Style
Property Type: Single Family HomeArchitecture: Other

Exterior Features

Exterior Home Features
Exterior: Wood

Community

Units in Building: 1

Lot Information

Lot Area: 0.27 acres

Price History for 2 Upwey Rd

DatePriceEventSource
03/06/2015$964,000Sold
N/A
11/08/2014$995,000PriceChange
Agent Provided
10/10/2014$1,050,000Listed For SaleAgent Provided
01/02/2012$939,000ListingRemovedAgent Provided
09/27/2011$939,000PriceChange
Agent Provided
07/05/2011$989,000Listed For SaleAgent Provided
11/16/2004$699,900Sold
N/A
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Property Tax and Assessment

Year2025
Tax$14,248
Assessment$1,386,000
Home facts updated by county records

Comparable Sales for 2 Upwey Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
35 Windemere Rd, Wellesley, MA
0.16
Single-Family Home
$1,275,000
07/30/25
3
2.5
1,774
10 Alba Rd, Wellesley, MA
0.16
Single-Family Home
$1,380,000
02/27/26
3
2
1,566
33 Upwey Rd, Wellesley, MA
0.16
Single-Family Home
$1,850,000
07/31/25
4
2.5
3,346
15 Clifton Rd, Wellesley, MA
0.25
Single-Family Home
$1,635,650
04/16/26
4
2.5
2,112
345 Linden St, Wellesley, MA
0.05
Single-Family Home
$2,600,000
05/29/26
4
3.5
4,016
3 Rockland St, Wellesley, MA
0.34
Single-Family Home
$1,155,000
08/01/25
3
2
2,304
4 Southwick Cir, Wellesley, MA
0.26
Single-Family Home
$1,690,000
11/20/25
3
1.5
2,014
1 Roberts Rd, Wellesley, MA
0.53
Single-Family Home
$1,365,000
10/24/25
3
3
2,499
45 Kingsbury St, Wellesley, MA
0.27
Single-Family Home
$1,913,000
05/20/26
6
3
2,980
22 Kimlo Rd, Wellesley, MA
0.40
Single-Family Home
$830,000
10/01/25
3
2
1,466

Nearby homes

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Assigned Schools

These are the assigned schools for 2 Upwey 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 Wellesley

At least 124 Trulia users voted on each feature.

  • 92 % Say it's dog friendly

  • 87 % Say parking is easy

  • 85 % Say people would walk alone at night

  • 84 % Say yards are well-kept

  • 80 % Say car is needed

  • 79 % Say there are sidewalks

  • 76 % Say kids play outside

  • 75 % Say there's holiday spirit

  • 74 % Say streets are well-lit

  • 73 % Say there's wildlife

  • 72 % Say it's quiet

  • 70 % Say they plan to stay for at least 5 years

  • 67 % Say it's walkable to restaurants

  • 66 % Say neighbors are friendly

  • 65 % Say there are community events

  • 63 % Say it's walkable to grocery stores

Sourced by Trulia users. Learn more about our methodology.
  • Mike Holiday
    "Everyone walks their dogs and lets their dogs say hello, most often. People know each other. It’s a great community"
    0
    Flag
  • Emilyperrottet
    "Nothing. It’s a changing neighborhood with a mix of old and new homes. Most of the homes are old and run down. "
    0
    Flag
  • Emilyperrottet
    "I take the Commuter rail from Wellesley to the T subway. 1.5 hours to Cambridge from south station. "
    0
    Flag
  • Trulia User
    "Lots of trails and other dogs in the area, many pet stores in the area as well. Dogs are well behaved and friendly. "
    0
    Flag
  • Shirley L.
    "The walking paths and yearly town celebrations are wonderful! A great sense of community and great schools. "
    0
    Flag
  • Sdipietro369
    "I am a visitor to this area. The neighborhood seems very nice with Babson College right around the corner. Shops within a close distance. "
    3
    Flag
  • Katrina C.
    "You feel you're kids are safe here in town. Everyone is friendly and we're all neighbors. It's a lovely town with a community feeling. "
    2
    Flag
  • Jamie.solomon1
    "I lived in Weston for two years and it’s a delightful town, with gorgeous land and large houses. Usually at least an acre"
    1
    Flag
  • Cmt138
    "Great access to commuter rail from either Wellesley Square or Wellesley Hills. Easy 10-15 min walk. Better parking from Wellesley Square. Usually takes about 1/2 hour to Back Bay. Driving into Boston can take a little more time with traffic to cross town to Mass Pike."
    2
    Flag
  • Laura M.
    "There are lots of dogs in our neighborhood- people walk them all the time. Dogs are welcome at Morse’s pond in the off season. "
    1
    Flag
  • Bruce C.
    "Lots of other dog owners who walk their dogs all the time. Also plenty of space to run with dogs on a trail or away from streets. "
    1
    Flag
  • Keith S.
    "Lots of trails and public spaces. Nationally acclaimed colleges. Variety of great shops and restaurants."
    0
    Flag
  • Srodousakis
    "Wellesley is a beautiful but very privileged neighborhood. It is very safe and people are friendly. Schools are great! There is a cute downtown and generally it’s a great place to raise kids. "
    0
    Flag
  • Molly R.
    "i love my neighborhood. everyone is so kind and welcoming. we often times have little gatherings or block parties. everyone knows each other and we are a very close community. "
    0
    Flag
  • Victoria V.
    "That I live on route 16 and nobody lets me out of my driveway in the morning and I have to leave for work an hour early just because of that."
    0
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2 Upwey Rd, Wellesley, MA 02481 is a 3 bedroom, 3 bathroom, 2,579 sqft single-family home built in 1938. This property is not currently available for sale. 2 Upwey Rd was last sold on Mar 6, 2015 for $964,000. The current Trulia Estimate for 2 Upwey Rd is $1,850,200.