20 Windemere Rd, Wellesley, MA 02481
OFF MARKET

20 Windemere Rd
Wellesley, MA 02481

  • 4 Beds
  • 2 Baths
  • 2,156 sqft

$1,566,600

Trulia Estimate
as of May 15, 2026
Est. Refi. Payment $9,116/mo*
Refinance Your Home

$1,566,600

Trulia Estimate
as of May 15, 2026
Est. Refi. Payment $9,116/mo*
Refinance Your Home
4 Beds
2 Baths
2,156 sqft

Local Information

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Description

This single-family home is located at 20 Windemere Rd, Wellesley, MA. 20 Windemere Rd is in Wellesley, MA and in ZIP code 02481. This property has 4 bedrooms, 2 bathrooms and approximately 2,156 sqft of floor space. This property has a lot size of 10018 sqft and was built in 1955.
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 20 Windemere Rd

Interior Features

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

Property Information

Year Built
Year Built: 1955
Property Type / Style
Property Type: Single Family HomeArchitecture: Cape Cod

Exterior Features

Exterior Home Features
Exterior: Other

Community

Units in Building: 1

Lot Information

Lot Area: 10018 sqft

Price History for 20 Windemere Rd

DatePriceEventSource
01/16/2013$625,000Sold
N/A
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Property Tax and Assessment

Year2025
Tax$12,336
Assessment$1,200,000
Home facts updated by county records

Comparable Sales for 20 Windemere Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
10 Alba Rd, Wellesley, MA
0.09
Single-Family Home
$1,380,000
02/27/26
3
2
1,566
35 Windemere Rd, Wellesley, MA
0.08
Single-Family Home
$1,275,000
07/30/25
3
2.5
1,774
31 Kingsbury St, Wellesley, MA
0.18
Single-Family Home
$1,350,000
11/12/25
3
1.5
1,372
4 Southwick Cir, Wellesley, MA
0.35
Single-Family Home
$1,690,000
11/20/25
3
1.5
2,014
3 Rockland St, Wellesley, MA
0.44
Single-Family Home
$1,155,000
08/01/25
3
2
2,304
22 Kimlo Rd, Wellesley, MA
0.49
Single-Family Home
$830,000
10/01/25
3
2
1,466
15 Clifton Rd, Wellesley, MA
0.33
Single-Family Home
$1,635,650
04/16/26
4
2.5
2,112
33 Upwey Rd, Wellesley, MA
0.16
Single-Family Home
$1,850,000
07/31/25
4
2.5
3,346
14 Twitchell St, Wellesley, MA
0.43
Single-Family Home
$1,525,000
02/02/26
4
2.5
1,812
26 Kimlo Rd, Wellesley, MA
0.52
Single-Family Home
$1,065,800
12/02/25
3
2
1,505

Assigned Schools

These are the assigned schools for 20 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 123 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

  • 76 % 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

  • 62 % Say it's walkable to grocery stores

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
    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
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  • 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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20 Windemere Rd, Wellesley, MA 02481 is a 4 bedroom, 2 bathroom, 2,156 sqft single-family home built in 1955. This property is not currently available for sale. 20 Windemere Rd was last sold on Jan 16, 2013 for $625,000. The current Trulia Estimate for 20 Windemere Rd is $1,566,600.