39 Skyline Dr, Wellesley, MA 02482
OFF MARKET

$5,043,100

Trulia Estimate
  • 6 Beds
  • 5.5 Baths
  • 7,000 sqft (on 0.76 acres)

39 Skyline Dr, Wellesley, MA 02482

Est. Refi. Payment $29,969/mo*
Refinance Your Home
Currently Off Market - Sold Oct 16, 2020 for $1,194,375

Home Value

Trulia Estimate
$5.04M
Since last month
Decreased$121K (-2.4%)
Since last year
Increased$368K (+8%)
Since last sale
Increased$4M (+316.4%)
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 +334% in the last 10 years
MonthEstimated value
2026
August 2026$4.97M
July 2026$5.09M
June 2026$5.05M
May 2026$5.06M
April 2026$4.96M
March 2026$4.89M
February 2026$4.71M
January 2026$4.61M
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
72 Great Plain Ave, Wellesley, MA
0.11
Single-Family Home
$2,400,000
08/29/25
4
4.5
6,373
98 Great Plain Ave, Wellesley, MA
0.13
Single-Family Home
$2,400,000
01/30/26
4
4
4,304
38 Fuller Brook Rd, Wellesley, MA
0.39
Single-Family Home
$3,135,000
11/05/25
6
5.5
5,991
93 Seaver St, Wellesley, MA
0.41
Single-Family Home
$2,500,000
01/16/26
5
5
5,200
122 Great Plain Ave, Wellesley, MA
0.20
Single-Family Home
$2,050,000
08/07/26
4
3.5
3,122
15 Great Plain Ave, Wellesley, MA
0.30
Single-Family Home
$1,850,000
04/09/26
4
2.5
3,016
10 Clark Rd, Wellesley, MA
0.43
Single-Family Home
$5,100,000
07/23/26
6
7
6,148
32 Twitchell St, Wellesley, MA
0.57
Single-Family Home
$3,150,000
01/08/26
6
5
6,364
30 Hobart Rd, Wellesley, MA
0.49
Single-Family Home
$3,927,995
11/12/25
7
7
6,800
27 Radcliffe Rd, Wellesley, MA
0.56
Single-Family Home
$3,510,000
06/30/26
5
5
6,037

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
72 Great Plain Ave, Wellesley, MA 02482
0.11
$2,919,300
4
4.5
6,373
Off Market
106 Great Plain Ave, Wellesley, MA 02482
0.12
$2,743,700
4
4
5,037
Off Market
98 Great Plain Ave, Wellesley, MA 02482
0.13
$2,400,000
4
4
4,304
Recently Sold
11 Skyline Dr, Wellesley, MA 02482
0.14
$3,600,000
5
6.5
6,511
For Sale
122 Great Plain Ave, Wellesley, MA 02482
0.20
$2,050,000
4
3.5
3,122
Recently Sold
130 Great Plain Ave, Wellesley, MA 02482
0.23
$3,567,900
5
5.5
7,162
Off Market
5 Fieldstone Way #5, Wellesley, MA 02482
0.23
$1,885,000
3
3
3,032
Off Market
1 Fieldstone Way #1, Wellesley, MA 02482
0.24
$1,626,900
2
3
2,660
Off Market
18 Fieldstone Way, Wellesley, MA 02482
0.28
$1,632,800
2
3
2,660
Off Market
10 Fieldstone Way #10, Wellesley, MA 02482
0.28
$1,900,000
3
3
3,092
Recently Sold
24 Fuller Brook Rd, Wellesley, MA 02482
0.30
$2,228,800
3
2.5
2,157
Off Market
15 Great Plain Ave, Wellesley, MA 02482
0.30
$1,850,000
4
2.5
3,016
Recently Sold

Local Information

  • Map ViewExplore the area around 39 Skyline Dr.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
2022
Lot Size
0.76 acres
Living Area
7,000 sqft
Price/Sqft
$720

About this House

Expansive 1955 home, beautifully sited at end of quiet cul-de-sac neighborhood on over 33,000 sq ft of land abutting woods, a truly special property. Bright and sunny with a gracious foyer, each room generously proportioned, includes the eat-in kitchen, living room with fireplace and a sunroom with sweeping views of the deck and spectacular yard. There is hardwood throughout the first and second floors, this flexible floor plan includes a home office with full windows and a separate exterior entrance, along with a walk-up unfinished attic offering a multitude of options. A serene setting with a large play yard, surrounded by mature trees, it has plenty of space for a pool, sports court, outdoor kitchen, fire pit and more. Roof and heating system are in very good condition, so renovate or build new: your dream home awaits!
39 Skyline Dr, Wellesley, MA 02482 is a 6 bedroom, 5 bathroom, 7,000 sqft single-family home built in 2022. It last sold for $1,194,375 on Oct 16, 2020. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $5,043,100, with a rent estimate of $6,941/month.

Home Details for 39 Skyline Dr

Interior Features

Interior Details
BasementAtticNumber of Rooms: 13
Heating & Cooling
Heating: Baseboard, GasAir ConditioningHeating Fuel: Baseboard
Levels, Entrance, & Accessibility
Stories: 2Floors: Hardwood, Linoleum Vinyl
Appliances & Utilities
DishwasherDisposal
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: AsphaltDeckExterior: Stucco, Wood, Brick
Parking & Garage
Parking Spaces: 4

Property Information

Year Built
Year Built: 2022
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Community

Units in Building: 1

Lot Information

Lot Area: 0.76 acres

Price and Tax history

DateEventPrice
Nov 30, 2022
Source: MLS PIN #73035172
ListingRemoved
$4,600,000
Sep 12, 2022
Source: MLS PIN #73035172
Listed For Sale
$4,600,000
Oct 16, 2020
Source: N/A
Sold
$1,194,375
Jul 16, 2020
Source: Agent Provided
PriceChange
$1,349,000
Price decreased by 6%
Jun 9, 2020
Source: Agent Provided
PriceChange
$1,435,000
Price decreased by 4%

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 39 Skyline Dr

  • What is 39 Skyline Dr estimated to be worth?
    Trulia's estimated value for 39 Skyline Dr in Wellesley, MA is $5,043,100.
  • What is the price history for 39 Skyline Dr?
    39 Skyline Dr in Wellesley, MA last sold for $1,194,375 in October 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.
  • How big is the lot at 39 Skyline Dr?
    The lot at 39 Skyline Dr in Wellesley, MA is about 0.76 acres (33,105 sq ft).
  • Does 39 Skyline Dr have parking?
    Yes, 39 Skyline Dr in Wellesley, MA has on-site parking.

Explore by feature - Pet Friendly

16 pet-friendly rentals in Wellesley, MA

Explore by feature - Garage

9 rentals with a garage in Wellesley, MA

Explore by feature - Air Conditioning

23 rentals with air conditioning in Wellesley, MA

Explore by feature - Washer/dryer

28 rentals with a washer/dryer in Wellesley, MA

Explore by feature - Outdoor Space

8 rentals with an outdoor space in Wellesley, MA

Apartments for Rent

Skip to last item
Skip to first item

Off Market Homes Near 39 Skyline Dr

Skip to last item
Skip to first item

Homes for sale near 39 Skyline Dr

Skip to last item
Skip to first item
Skip to last item
  • Results are loading
Skip to first item