36 Skyline Dr, Wellesley, MA 02482
OFF MARKET

36 Skyline Dr
Wellesley, MA 02482

  • 4 Beds
  • 2.5 Baths
  • 3,680 sqft (on 0.81 acres)

$2,516,900

Trulia Estimate
as of Jun 4, 2026
Est. Refi. Payment $14,875/mo*
Refinance Your Home

$2,516,900

Trulia Estimate
as of Jun 4, 2026
Est. Refi. Payment $14,875/mo*
Refinance Your Home
4 Beds
2.5 Baths
3,680 sqft
(on 0.81 acres)

Local Information

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

Description

Just in time for the holiday's! This bright & sunny 4 bedroom, 2.5 bath Colonial style Cape is set on a quiet Cul De Sac that features .81 level acres. First floor master suite has ample closets & and windows that overlook the backyard, brick patio and mature landscaping. Open floor plan living centers around a custom designed kitchen by Weston Kitchens and is complete with farmers sink, stainless steel appliances, breakfast bar and dining area. Abutting the kitchen is a den/office area w/built in desk, shelving & cabinets. A fireplace living room and elegant dining room are ideal for entertaining, each benefitting from wall to wall windows exposing seasonal views. The 2nd floor includes 2 bedrooms as well as a newly renovated room that doubles as a 4th bedroom or home office. Lower level amenities include a fireplace family room & office area as well as a gym. Enjoy all that Wellesley's conveniences have to offer moments from town. Hurry & see for yourself before it's too late!
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
Patio
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
Less than a day ago

Home Details for 36 Skyline Dr

Interior Features

Heating & Cooling
Heating: Forced Air, GasAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 2Floors: Tile, Carpet, Hardwood
Interior Details
Number of Rooms: 7
Appliances & Utilities
Cable ReadyDishwasherDisposalDryerRefrigeratorWasher
Fireplace & Spa
Fireplace
Security
Security System

Exterior Features

Exterior Home Features
Roof: Asphalt, OtherExterior: WoodPatioSprinkler System
Parking & Garage
GarageParking Spaces: 6Parking: Garage Attached

Property Information

Year Built
Year Built: 1953
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Community

Units in Building: 1

Lot Information

Lot Area: 0.81 acres

Building

Fitness & Sports
Tennis Court

Price History for 36 Skyline Dr

DatePriceEventSource
12/15/2020$1,572,500Sold
N/A
11/17/2020$1,575,000PendingAgent Provided
11/06/2020$1,575,000Listed For SaleAgent Provided
06/13/2012$1,010,000Sold
N/A
03/07/2012$1,075,000Listed For SaleAgent Provided
06/20/2003$931,000Sold
N/A
09/15/1998$463,125Sold
N/A
04/03/1989$64,900Sold
N/A

Market trends in Wellesley

Last updated April 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
108
6MoM
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Property Tax and Assessment

Year2025
Tax$21,053
Assessment$2,048,000
Home facts updated by county records

Comparable Sales for 36 Skyline Dr

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
98 Great Plain Ave, Wellesley, MA
0.08
Single-Family Home
$2,400,000
01/30/26
4
4
4,304
15 Great Plain Ave, Wellesley, MA
0.29
Single-Family Home
$1,850,000
04/09/26
4
2.5
3,016
72 Great Plain Ave, Wellesley, MA
0.09
Single-Family Home
$2,400,000
08/29/25
4
4.5
6,373
145 Great Plain Ave, Wellesley, MA
0.30
Single-Family Home
$2,055,000
07/03/25
4
4
3,991
131 Brook St, Wellesley, MA
0.36
Single-Family Home
$2,210,000
07/17/25
4
2.5
3,511
30 Southgate Rd, Wellesley, MA
0.54
Single-Family Home
$2,405,000
11/03/25
4
2.5
3,144
112 Wellesley Ave, Wellesley, MA
0.35
Single-Family Home
$1,625,000
06/06/25
4
1.5
2,452
15 Alden Rd, Wellesley, MA
0.37
Single-Family Home
$2,625,000
04/30/26
4
3.5
3,433
15 Allen Rd, Wellesley, MA
0.46
Single-Family Home
$2,900,000
06/30/25
4
2.5
2,323
61 Eisenhower Cir, Wellesley, MA
0.39
Single-Family Home
$2,475,000
06/30/25
5
4
4,037

Nearby homes

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Assigned Schools

These are the assigned schools for 36 Skyline Dr.
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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36 Skyline Dr, Wellesley, MA 02482 is a 4 bedroom, 3 bathroom, 3,680 sqft single-family home built in 1953. This property is not currently available for sale. 36 Skyline Dr was last sold on Dec 15, 2020 for $1,572,500. The current Trulia Estimate for 36 Skyline Dr is $2,516,900.