39 Skyline Dr, Wellesley, MA 02482
OFF MARKET

39 Skyline Dr
Wellesley, MA 02482

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

$5,088,700

Trulia Estimate
as of May 30, 2026
Est. Refi. Payment $29,466/mo*
Refinance Your Home

$5,088,700

Trulia Estimate
as of May 30, 2026
Est. Refi. Payment $29,466/mo*
Refinance Your Home
6 Beds
5.5 Baths
7,000 sqft
(on 0.76 acres)

Local Information

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

Description

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!
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
Deck
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
No Info

Home Details for 39 Skyline Dr

Interior Features

Interior Details
BasementAtticNumber of Rooms: 13
Heating & Cooling
Heating: Baseboard, Other, 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 History for 39 Skyline Dr

DatePriceEventSource
11/30/2022$4,600,000ListingRemovedMLS PIN #73035172
09/12/2022$4,600,000Listed For SaleMLS PIN #73035172
10/16/2020$1,194,375Sold
N/A
07/16/2020$1,349,000PriceChange
Agent Provided
06/09/2020$1,435,000PriceChange
Agent Provided
05/14/2020$1,489,000Listed For SaleAgent Provided
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Property Tax and Assessment

Year2025
Tax$41,819
Assessment$4,068,000
Home facts updated by county records

Comparable Sales for 39 Skyline Dr

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
15 Sumner Rd, Wellesley, MA
0.38
Single-Family Home
$5,400,000
08/11/25
6
6
7,817
145 Great Plain Ave, Wellesley, MA
0.33
Single-Family Home
$2,055,000
07/03/25
4
4
3,991
91 Seaver St, Wellesley, MA
0.41
Single-Family Home
$2,900,000
08/15/25
5
5
5,500
15 Great Plain Ave, Wellesley, MA
0.30
Single-Family Home
$1,850,000
04/09/26
4
2.5
3,016
61 Eisenhower Cir, Wellesley, MA
0.45
Single-Family Home
$2,475,000
06/30/25
5
4
4,037
32 Twitchell St, Wellesley, MA
0.57
Single-Family Home
$3,150,000
01/08/26
6
5
6,364

Nearby homes

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Assigned Schools

These are the assigned schools for 39 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 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

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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39 Skyline Dr, Wellesley, MA 02482 is a 6 bedroom, 5 bathroom, 7,000 sqft single-family home built in 2022. This property is not currently available for sale. 39 Skyline Dr was last sold on Oct 16, 2020 for $1,194,375. The current Trulia Estimate for 39 Skyline Dr is $5,088,700.