56 Windemere Rd, Wellesley, MA 02481
Property image
Property image
OFF MARKET

$1,741,500

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

56 Windemere Rd, Wellesley, MA 02481

Est. Refi. Payment $10,398/mo*
Refinance Your Home
Currently Off Market - Sold Aug 4, 2008 for $854,325

Home Value

Trulia Estimate
$1.74M
Since last month
Decreased$46K (-2.6%)
Since last year
Increased$21K (+1.2%)
Since last sale
Increased$879K (+102.9%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +57% in the last 10 years
MonthEstimated value
2026
August 2026$1.73M
July 2026$1.78M
June 2026$1.81M
May 2026$1.84M
April 2026$1.79M
March 2026$1.79M
February 2026$1.72M
January 2026$1.66M
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
642 Worcester St, Wellesley, MA
0.32
Single-Family Home
$1,177,000
08/06/26
3
2.5
3,129
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
10 Alba Rd, Wellesley, MA
0.21
Single-Family Home
$1,380,000
02/27/26
3
2
1,566
1 Roberts Rd, Wellesley, MA
0.41
Single-Family Home
$1,365,000
10/24/25
3
3
2,499
69 Donizetti St, Wellesley, MA
0.34
Single-Family Home
$1,560,000
06/18/26
3
2
2,786
45 Kingsbury St, Wellesley, MA
0.26
Single-Family Home
$1,913,000
05/20/26
6
3
2,980
10 Kirkland Cir, Wellesley, MA
0.16
Single-Family Home
$2,480,000
08/14/26
4
3.5
3,610
345 Linden St, Wellesley, MA
0.21
Single-Family Home
$2,600,000
05/29/26
4
3.5
4,016
22 Kimlo Rd, Wellesley, MA
0.44
Single-Family Home
$830,000
10/01/25
3
2
1,466

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
38 Upwey Rd, Wellesley, MA 02481
0.03
$2,295,000
4
3.5
3,776
For Sale
33 Upwey Rd, Wellesley, MA 02481
0.06
$1,902,900
4
2.5
3,346
Off Market
560 Worcester St, Wellesley, MA 02481
0.08
$1,395,000
4
2.5
1,800
For Sale
34 Upwey Rd, Wellesley, MA 02481
0.06
$2,242,400
4
3.5
3,286
Off Market
35 Windemere Rd, Wellesley, MA 02481
0.06
$1,311,400
3
2.5
1,774
Off Market
37 Kirkland Cir, Wellesley, MA 02481
0.09
$1,689,500
4
2.5
2,346
Off Market
44 Windemere Rd, Wellesley, MA 02481
0.08
$1,500,000
3
3
2,447
For Sale
17 Upwey Rd, Wellesley, MA 02481
0.10
$2,580,700
3
1.5
1,764
Off Market
4 Arnold Rd, Wellesley, MA 02481
0.13
$1,833,800
4
2.5
3,156
Off Market
31 Alba Rd, Wellesley, MA 02481
0.11
$3,195,000
5
5
5,735
For Sale
10 Kirkland Cir, Wellesley, MA 02481
0.16
$2,480,000
4
3.5
3,610
Recently Sold
61 Kirkland Cir, Wellesley, MA 02481
0.16
$1,692,200
4
2
2,808
Off Market

Local Information

  • Map ViewExplore the area around 56 Windemere Rd.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1957
Lot Size
0.31 acres
Living Area
3,010 sqft
Price/Sqft
$579
Parking
Garage

About this House

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.
56 Windemere Rd, Wellesley, MA 02481 is a 3 bedroom, 3 bathroom, 3,010 sqft single-family home built in 1957. It last sold for $854,325 on Aug 4, 2008. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $1,741,500, with a rent estimate of $7,301/month.

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 and Tax history

DateEventPrice
Aug 4, 2008
Source: N/A
Sold
$854,325
May 6, 2008
Source: Agent Provided
Listed For Sale
$889,000
Apr 29, 1988
Source: N/A
Sold
$264,000

Market trends in Wellesley

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$2.15M
$161KMoM
Sale-to-List Price
100.6%
0.4%MoM
Price per sq ft
$666
$18MoM
Available listings
87
25MoM

Around this home

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
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 56 Windemere Rd

  • What is 56 Windemere Rd estimated to be worth?
    Trulia's estimated value for 56 Windemere Rd in Wellesley, MA is $1,741,500.
  • What is the price history for 56 Windemere Rd?
    56 Windemere Rd in Wellesley, MA last sold for $854,325 in August 2008.
  • Is Wellesley a buyer's or seller's market?
    Wellesley is currently a balanced market, based on recent for-sale activity.
  • What's the median sale price in Wellesley?
    The median sale price in Wellesley is $2.15M. That is up $161K from the prior month.
  • Does 56 Windemere Rd have air conditioning?
    Yes, 56 Windemere Rd in Wellesley, MA has air conditioning.
  • Does 56 Windemere Rd have laundry facilities?
    Yes, 56 Windemere Rd in Wellesley, MA has in-unit laundry.

Explore by feature - Pet Friendly

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Explore by feature - Outdoor Space

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Off Market Homes Near 56 Windemere Rd

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