56 Windemere Rd, Wellesley, MA 02481
OFF MARKET

56 Windemere Rd
Wellesley, MA 02481

  • 3 Beds
  • 3 Baths
  • 3,010 sqft (on 0.31 acres)

$1,829,900

Trulia Estimate
as of May 30, 2026
Est. Refi. Payment $10,644/mo*
Refinance Your Home

$1,829,900

Trulia Estimate
as of May 30, 2026
Est. Refi. Payment $10,644/mo*
Refinance Your Home
3 Beds
3 Baths
3,010 sqft
(on 0.31 acres)

Local Information

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

Description

This sophisticated contemporary home is located in a cul-de-sac. It is within walking distance to the Wellesley Hills train station, Linden Shopping Center, Sprague Elementary School, Wellesley Middle School, and Wellesley High School! An addition was built in 1998 to feature an open floor plan, expanding the living space from 2,298 square feet to 3,010 square feet. This expansion features a fabulous 24-foot x 27-foot family room with a 10-foot ceiling, a custom built-in entertainment center (with pre-wired walls), and a wet bar. The addition also includes a gorgeous over-sized master suite with space for a home office, a sitting area, and a walk-in closet. The Corian/marble master bath comes with both a steam shower and a Jacuzzi tub. Among the renovation is a large kitchen with granite counters and custom cabinetry. The home was professionally updated again in 2008 to feature complete oak/hardwood flooring, new interior paint, and a renovated lower-level bathroom.
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
Garage
Outdoor
Porch, Patio
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
No Info

Home Details for 56 Windemere Rd

Interior Features

Interior Details
BasementAtticIn-law unitNumber of Rooms: 8Types of Rooms: Walk In Closet, Breakfast Nook, Dining Room, Family Room, Laundry Room, Master Bath, Mud Room, Recreation RoomWet Bar
Heating & Cooling
Heating: Forced Air, GasAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 1Floors: Tile, Hardwood
Appliances & Utilities
Cable ReadyDishwasherDisposalDryerMicrowaveRefrigeratorWasher
Fireplace & Spa
FireplaceHot Tub or SpaJetted Bath Tub
Windows, Doors, Floors & Walls
Double Paned Windows
Security
Security System

Exterior Features

Exterior Home Features
Roof: CompositionExterior: Shingle, Wood, BrickGardenLawnPatioPorch
Parking & Garage
GarageParking: Garage Attached

Property Information

Year Built
Year Built: 1957Year Updated: 2008
Property Type / Style
Property Type: Single Family HomeArchitecture: Ranch / Rambler

Community

Units in Building: 1

Lot Information

Lot Area: 0.31 acres

Building

Pool
Sauna

Price History for 56 Windemere Rd

DatePriceEventSource
08/04/2008$854,325Sold
N/A
05/06/2008$889,000Listed For SaleAgent Provided
04/29/1988$264,000Sold
N/A
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Property Tax and Assessment

Year2025
Tax$13,169
Assessment$1,281,000
Home facts updated by county records

Comparable Sales for 56 Windemere Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
35 Windemere Rd, Wellesley, MA
0.06
Single-Family Home
$1,275,000
07/30/25
3
2.5
1,774
33 Upwey Rd, Wellesley, MA
0.06
Single-Family Home
$1,850,000
07/31/25
4
2.5
3,346
4 Arnold Rd, Wellesley, MA
0.13
Single-Family Home
$1,750,000
09/23/25
4
2.5
3,156
15 Clifton Rd, Wellesley, MA
0.26
Single-Family Home
$1,635,650
04/16/26
4
2.5
2,112
30 Audubon Rd, Wellesley, MA
0.27
Single-Family Home
$2,225,000
06/12/25
4
2.5
3,045
10 Alba Rd, Wellesley, MA
0.21
Single-Family Home
$1,380,000
02/27/26
3
2
1,566
500 Worcester St, Wellesley, MA
0.43
Single-Family Home
$1,340,000
08/28/25
4
2.5
3,257
1 Roberts Rd, Wellesley, MA
0.41
Single-Family Home
$1,365,000
10/24/25
3
3
2,499
45 Kingsbury St, Wellesley, MA
0.26
Single-Family Home
$1,913,000
05/20/26
6
3
2,980
22 Kimlo Rd, Wellesley, MA
0.44
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 56 Windemere 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
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  • 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
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  • Emilyperrottet
    "I take the Commuter rail from Wellesley to the T subway. 1.5 hours to Cambridge from south station. "
    0
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  • 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
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  • 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
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  • 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
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  • 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
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  • 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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56 Windemere Rd, Wellesley, MA 02481 is a 3 bedroom, 3 bathroom, 3,010 sqft single-family home built in 1957. This property is not currently available for sale. 56 Windemere Rd was last sold on Aug 4, 2008 for $854,325. The current Trulia Estimate for 56 Windemere Rd is $1,829,900.