27 Pine Plain Rd, Wellesley, MA 02481
OFF MARKET

27 Pine Plain Rd
Wellesley, MA 02481

  • 3 Beds
  • 1 Bath
  • 1,380 sqft (on 0.27 acres)

$1,471,100

Trulia Estimate
as of May 15, 2026
Est. Refi. Payment $7,533/mo*
Refinance Your Home

$1,471,100

Trulia Estimate
as of May 15, 2026
Est. Refi. Payment $7,533/mo*
Refinance Your Home
3 Beds
1 Bath
1,380 sqft
(on 0.27 acres)

Local Information

Map showing home location
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-- mins to
Commute Destination

Description

Picture perfect Colonial in desirable cul- de -sac neighborhood offers charm and character throughout. This meticulously maintained property features lovely living room with fireplace and beautiful built-ins. Dining room with corner cabinet opens to sun splashed kitchen and inviting family room with exterior access to deck overlooking gorgeous landscaped grounds. Second floor includes three generous bedrooms with hardwood floors and a full bathroom. Lower level playroom/office offers additional space. Pristine property has been lovingly maintained through the years. Beautiful yard is surrounded by mature trees and lush landscaping. Close to Boulder Brook reservation and elementary school. Incredible opportunity to be a part of all that Wellesley has to offer.
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 & Cooling
HOA
None
Price/Sqft
No Info
Listed
No Info

Home Details for 27 Pine Plain Rd

Interior Features

Heating & Cooling
Heating: Other, GasAir ConditioningHeating Fuel: Other
Levels, Entrance, & Accessibility
Stories: 2
Interior Details
Number of Rooms: 7
Fireplace & Spa
Fireplace

Property Information

Year Built
Year Built: 1933
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Exterior Features

Exterior Home Features
Exterior: Other

Community

Units in Building: 1

Lot Information

Lot Area: 0.27 acres

Price History for 27 Pine Plain Rd

DatePriceEventSource
08/31/2017$775,000Sold
N/A
07/20/2017$795,000PendingAgent Provided
07/14/2017$795,000Listed For SaleAgent Provided
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Property Tax and Assessment

Year2025
Tax$13,025
Assessment$1,267,000
Home facts updated by county records

Comparable Sales for 27 Pine Plain Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
45 Mayo Rd, Wellesley, MA
0.37
Single-Family Home
$1,270,000
01/08/26
3
2
1,581
847 Worcester St, Wellesley, MA
0.43
Single-Family Home
$835,000
11/12/25
3
2
1,555
365 Weston Rd, Wellesley, MA
0.26
Single-Family Home
$1,010,000
12/03/25
4
2
1,743
339 Weston Rd, Wellesley, MA
0.35
Single-Family Home
$1,150,000
04/30/26
3
2
2,023
13 Fells Rd, Wellesley, MA
0.52
Single-Family Home
$1,020,000
06/06/25
3
1.5
1,518
20 Garrison Rd, Wellesley, MA
0.29
Single-Family Home
$1,430,000
06/24/25
3
2.5
1,816
11 Durant Rd, Wellesley, MA
0.24
Single-Family Home
$1,480,000
06/30/25
3
3
2,524
56 Pine Plain Rd, Wellesley, MA
0.13
Single-Family Home
$1,530,000
10/30/25
4
3
2,265
109 Elmwood Rd, Wellesley, MA
0.37
Single-Family Home
$1,385,000
08/15/25
3
3
2,081
15 Lafayette Cir, Wellesley, MA
0.59
Single-Family Home
$1,360,000
07/25/25
3
1.5
1,719

Assigned Schools

These are the assigned schools for 27 Pine Plain Rd.
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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
    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
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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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27 Pine Plain Rd, Wellesley, MA 02481 is a 3 bedroom, 1 bathroom, 1,380 sqft single-family home built in 1933. This property is not currently available for sale. 27 Pine Plain Rd was last sold on Aug 31, 2017 for $775,000. The current Trulia Estimate for 27 Pine Plain Rd is $1,471,100.