66 Massasoit Trl
Brewster, MA 02631
- 2 Beds
- 2 Baths
- 1,210 sqft (on 6.53 acres)
2 Beds
2 Baths
1,210 sqft
(on 6.53 acres)
Local Information
-- mins to
Home Highlights
Property Type
Single-Family Home
Year Built
1990
Lot Size
6.53 acres
Living Area
1,210 sqft
Price/Sqft
$721
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.
66 Massasoit Trl, Brewster, MA 02631 is a 2 bedroom, 2 bathroom, 1,210 sqft single-family home built in 1990. It last sold for $610,700 on May 14, 2021. It is currently off market. The Trulia Estimate is $872,900, with a rent estimate of $3,310/month.
Home Details for 66 Massasoit Trl
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Interior Details BasementNumber of Rooms: 4 |
Heating & Cooling Heating: Other, OilHeating Fuel: Other |
Levels, Entrance, & Accessibility Stories: 2 |
Appliances & Utilities DishwasherMicrowaveRefrigeratorWasher |
Fireplace & Spa Fireplace |
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Exterior Home Features Roof: Shake ShingleExterior: Wood |
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Year Built Year Built: 1990Year Updated: 1997 |
Property Type / Style Property Type: Single Family HomeArchitecture: Cape Cod |
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Units in Building: 1 |
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Lot Area: 6.53 acres |
Price History for 66 Massasoit Trl
| Date | Price | Event | Source |
|---|---|---|---|
| 05/14/2021 | $610,700 | Sold | CCIMLS #22101704 |
| 04/15/2021 | $550,000 | Pending | CCIMLS #22101704 |
| 04/09/2021 | $550,000 | Listed For Sale | MLS PIN #72811906 |
Market trends in Brewster
Last updated June 2026
Avg. sale price
$634K
Sale-to-List Price
—
Price per sq ft
$490
Available listings
53
2MoM
Property Tax and Assessment
| Year | 2025 |
|---|---|
| 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 | |
0.58 | Single-Family Home | $744,000 | 06/30/26 | 3 | 2 | 1,983 | |
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 |
Nearby homes
Get a sense of prices in the area by checking nearby homes.Assigned Schools
These are the assigned schools for 66 Massasoit Trl.
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.
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