36 Skyline Dr, Wellesley, MA 02482
Property image
Property image
OFF MARKET

$2,416,200

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

36 Skyline Dr, Wellesley, MA 02482

Est. Refi. Payment $14,423/mo*
Refinance Your Home
Currently Off Market - Sold Dec 15, 2020 for $1,572,500

Home Value

Trulia Estimate
$2.42M
Since last month
Decreased$53K (-2.1%)
Since last year
Increased$50K (+2.1%)
Since last sale
Increased$844K (+53.7%)
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 +94% in the last 10 years
MonthEstimated value
2026
August 2026$2.42M
July 2026$2.47M
June 2026$2.49M
May 2026$2.51M
April 2026$2.44M
March 2026$2.43M
February 2026$2.32M
January 2026$2.27M
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
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
122 Great Plain Ave, Wellesley, MA
0.17
Single-Family Home
$2,050,000
08/07/26
4
3.5
3,122
30 Southgate Rd, Wellesley, MA
0.54
Single-Family Home
$2,405,000
11/03/25
4
2.5
3,144
26 Hobart Rd, Wellesley, MA
0.44
Single-Family Home
$2,772,000
07/23/26
4
2.5
2,550
117 Forest St, Wellesley, MA
0.52
Single-Family Home
$3,305,000
06/26/26
4
3.5
3,738
15 Alden Rd, Wellesley, MA
0.37
Single-Family Home
$2,625,000
04/30/26
4
3.5
3,433
170 Benvenue St, Wellesley, MA
0.50
Single-Family Home
$2,040,000
06/02/26
5
3
2,465
23 Cottonwood Rd, Wellesley, MA
0.56
Single-Family Home
$1,608,010
12/02/25
4
3
2,396
39 Twitchell St, Wellesley, MA
0.52
Single-Family Home
$1,920,000
11/26/25
4
3
2,475

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
106 Great Plain Ave, Wellesley, MA 02482
0.07
$2,712,400
4
4
5,037
Off Market
98 Great Plain Ave, Wellesley, MA 02482
0.08
$2,400,000
4
4
4,304
Recently Sold
72 Great Plain Ave, Wellesley, MA 02482
0.09
$2,919,300
4
4.5
6,373
Off Market
122 Great Plain Ave, Wellesley, MA 02482
0.17
$2,050,000
4
3.5
3,122
Recently Sold
5 Fieldstone Way #5, Wellesley, MA 02482
0.19
$1,862,100
3
3
3,032
Off Market
130 Great Plain Ave, Wellesley, MA 02482
0.20
$3,561,400
5
5.5
7,162
Off Market
1 Fieldstone Way #1, Wellesley, MA 02482
0.21
$1,611,300
2
3
2,660
Off Market
18 Fieldstone Way, Wellesley, MA 02482
0.24
$1,623,200
2
3
2,660
Off Market
10 Fieldstone Way #10, Wellesley, MA 02482
0.25
$1,900,000
3
3
3,092
Recently Sold
24 Fuller Brook Rd, Wellesley, MA 02482
0.24
$2,181,000
3
2.5
2,157
Off Market
18 Fieldstone Way #18, Wellesley, MA 02482
0.27
$1,699,900
2
3
2,660
Off Market
21 Fuller Brook Rd, Wellesley, MA 02482
0.26
$2,137,700
3
1.5
1,936
Off Market

Local Information

  • Map ViewExplore the area around 36 Skyline Dr.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1953
Lot Size
0.81 acres
Living Area
3,680 sqft
Price/Sqft
$657
Parking
Garage

About this House

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!
36 Skyline Dr, Wellesley, MA 02482 is a 4 bedroom, 3 bathroom, 3,680 sqft single-family home built in 1953. It last sold for $1,572,500 on Dec 15, 2020. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $2,416,200, with a rent estimate of $7,636/month.

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 and Tax history

DateEventPrice
Dec 15, 2020
Source: N/A
Sold
$1,572,500
Nov 17, 2020
Source: Agent Provided
Pending
$1,575,000
Nov 6, 2020
Source: Agent Provided
Listed For Sale
$1,575,000
Jun 13, 2012
Source: N/A
Sold
$1,010,000
Mar 7, 2012
Source: Agent Provided
Listed For Sale
$1,075,000

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 36 Skyline Dr

  • What is 36 Skyline Dr estimated to be worth?
    Trulia's estimated value for 36 Skyline Dr in Wellesley, MA is $2,416,200.
  • What is the price history for 36 Skyline Dr?
    36 Skyline Dr in Wellesley, MA last sold for $1,572,500 in December 2020.
  • 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 36 Skyline Dr have air conditioning?
    Yes, 36 Skyline Dr in Wellesley, MA has air conditioning.
  • Does 36 Skyline Dr have laundry facilities?
    Yes, 36 Skyline Dr in Wellesley, MA has in-unit laundry.

Explore by feature - Pet Friendly

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