66 Massasoit Trl, Brewster, MA 02631
OFF MARKET

66 Massasoit Trl
Brewster, MA 02631

  • 2 Beds
  • 2 Baths
  • 1,210 sqft (on 6.53 acres)

$895,000

Trulia Estimate
as of Jun 29, 2026
Est. Refi. Payment $4,939/mo*

$895,000

Trulia Estimate
as of Jun 29, 2026
Est. Refi. Payment $4,939/mo*
2 Beds
2 Baths
1,210 sqft
(on 6.53 acres)

Local Information

  • Map ViewExplore the area around 66 Massasoit Trl.
  • Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

Charming Cape Cod home in a pristine natural setting with miles of trails thru the woods just out the door! The house is sited at the eastern tip of a 6.53 acre parcel which includes over 5 acres designated forever wild as well as a small scenic pond and old cranberry bog at the rear boundary with the Punkhorn Conservation Area! Although the home was custom-built by the current owners to replicate the exterior of those built in the 1770s, it features a modern layout. The main floor offers an open flr plan along with a bedroom, laundry, and ADA bathroom for easy 1 floor living. Upstairs is a 2nd BR, full bath, and attic storage. The walk-out lower level has a workshop space and a large unfin. room with normal windows for expansion possibilities if approved by the town. 3 BR Title V septic. Upgrades: Cedar roof 19, 30yr war, hi-end Burnham boiler and water heater 18, 3 skylights 19, propane range, washer 19, dryer 19, fridge 19, and oil tank 20. Plus, lots of storage, a Rumford wood-burning fireplace, pine flrs, prop. generator, and lrge wh. cedar deck accessed through the primary BR. Truly a once in a lifetime opportunity! Buyers/agents to confirm details.
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 only
HOA
None
Price/Sqft
No Info
Listed
Less than a day ago

Home Details for 66 Massasoit Trl

Interior Features

Interior Details
BasementNumber of Rooms: 4
Heating & Cooling
Heating: Other, OilHeating Fuel: Other
Levels, Entrance, & Accessibility
Stories: 2
Appliances & Utilities
DishwasherMicrowaveRefrigeratorWasher
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: Shake ShingleExterior: Wood

Property Information

Year Built
Year Built: 1990Year Updated: 1997
Property Type / Style
Property Type: Single Family HomeArchitecture: Cape Cod

Community

Units in Building: 1

Lot Information

Lot Area: 6.53 acres

Price History for 66 Massasoit Trl

DatePriceEventSource
05/14/2021$610,700Sold
CCIMLS #22101704
04/15/2021$550,000PendingCCIMLS #22101704
04/09/2021$550,000Listed For SaleMLS PIN #72811906

Market trends in Brewster

Last updated May 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
Sale-to-List Price
Price per sq ft
Available listings
51
5
MoM
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Property Tax and Assessment

Year2025
Tax$5,110
Assessment$742,700
Home facts updated by county records

Comparable Sales for 66 Massasoit Trl

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
0.17
Single-Family Home
$645,000
01/05/26
3
2
1,590
0.34
Single-Family Home
$649,000
03/09/26
3
1.5
1,266
0.62
Single-Family Home
$915,000
10/02/25
2
2
1,681
0.39
Single-Family Home
$815,000
06/05/26
3
2
1,778
0.49
Single-Family Home
$875,000
06/23/26
3
1.5
1,792
0.93
Single-Family Home
$645,000
09/10/25
3
2
1,320
0.52
Single-Family Home
$1,350,000
12/05/25
3
2.5
2,480
0.76
Single-Family Home
$740,000
11/20/25
3
2.5
1,963
0.81
Single-Family Home
$875,000
08/27/25
3
2
1,568
0.51
Single-Family Home
$1,048,625
02/13/26
4
2.5
2,502

Nearby homes

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Assigned Schools

These are the assigned schools for 66 Massasoit Trl.
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 Brewster

At least 52 Trulia users voted on each feature.
  • 93 % Say car is needed

  • 87 % Say parking is easy

  • 87 % Say it's quiet

  • 86 % Say it's dog friendly

  • 83 % Say yards are well-kept

  • 78 % Say people would walk alone at night

  • 76 % Say there's wildlife

  • 66 % Say there's holiday spirit

  • 63 % Say they plan to stay for at least 5 years

  • 57 % Say neighbors are friendly

  • 54 % Say kids play outside

  • 28 % Say there are community events

  • 27 % Say it's walkable to restaurants

  • 24 % Say there are sidewalks

  • 24 % Say streets are well-lit

  • 13 % Say it's walkable to grocery stores

Sourced by Trulia users. Learn more about our methodology.
  • Rheanna Hastings
    "Lots of families and a beautiful safe place to raise children with lots of outdoor space and things to do."
  • Skylar R.
    "Walking your dog and taking them down to the pond for a quick swim is very convenient located right on the bike path which is always a great spot to walk dogs."
  • Rheanna H.
    "The beach! Low tide, the stores, the restaurants and the farmers markets. Cape Cod is a one of a kind place. "
  • Deboravaughan
    "I really like it!! It is clean, friendly and close to the beach. Houses are well maintained and renters during the summer are great."
  • Peloquinbill
    "it is a small quaint neighborhood where everyone is friendly. Neighbors are always visiting and helping each other."
  • scarroll32
    "Ideal Cape Cod location For Golfing or swimming in salt water Cape Cod BAY or one of Brewster fresh water ponds Boating fishing "
  • Rick S.
    "This is a great town. Rural living, close to all the action of Dennis, Yarmouth and Hyannis. Easy access to the loweer Cape too!. "
  • Cathihill
    "Ocean Edge is a great resort community with obtainable membership fees. However, you do not have to be a member to live in a ocean edge. Billington II is the most quiet and least congested of the town home communities at Ocean Edge."
  • Teresa M.
    "Beautiful, quiet, peaceful place to live. The schools are excellent and the recreation areas amazing. The association beaches are beautiful and limited to only 11 families. The pool is a joy."
  • Nj3167
    "Quite, well manacured properties, very little traffic, quant, old historic Sea Captain's Homes restored into B&B's, Resturants,slower pace of life. Great for Retires."

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Apartments for Rent

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Homes for sale near 66 Massasoit Trl

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Off Market Homes Near 66 Massasoit Trl

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66 Massasoit Trl, Brewster, MA 02631 is a 2 bedroom, 2 bathroom, 1,210 sqft single-family home built in 1990. This property is not currently available for sale. 66 Massasoit Trl was last sold on May 14, 2021 for $610,700. The current Trulia Estimate for 66 Massasoit Trl is $895,000.