285 Massasoit Trl, Eastham, MA 02642
Property image
Property image
OFF MARKET

285 Massasoit Trl
Eastham, MA 02642

  • 3 Beds
  • 1.5 Baths
  • 1,868 sqft (on 0.49 acres)

$834,900

Trulia Estimate
as of Jul 7, 2026

$834,900

Trulia Estimate
as of Jul 7, 2026
3 Beds
1.5 Baths
1,868 sqft
(on 0.49 acres)

Local Information

  • Map ViewExplore the area around 285 Massasoit Trl.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

Looking for that special house to call your home? A place you can begin making life long memories with your family? Right here tucked away among the quiet Pines and Oaks, close to Eastham's bests beaches, the Wellfleet Drive In, Cape Cod National Seashore and more you will find that home that will provide the photos that decades from now will be the best memories of your life! Great rental potential, furnished to help you begin the journey, this is a great investment. Plenty of room to add on in the future.......maybe a screened porch, breezeway or garage. Come take a look, be ready to begin your Cape Cod experience.
285 Massasoit Trl, Eastham, MA 02642 is a 3 bedroom, 2 bathroom, 1,868 sqft single-family home built in 1973. It last sold for $399,500 on Jul 20, 2016. It is currently off market. The Trulia Estimate is $834,900, with a rent estimate of $3,709/month.

Home Highlights

Parking
No Info
Outdoor
No Info
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
Less than a day ago

Home Details for 285 Massasoit Trl

Interior Features

Interior Details
BasementNumber of Rooms: 6Types of Rooms: Dining Room, Family Room, Office
Heating & Cooling
Heating: Baseboard, Heat Pump, ElectricAir ConditioningCooling System: OtherHeating Fuel: Baseboard
Levels, Entrance, & Accessibility
Stories: 2Floors: Carpet, Laminate
Appliances & Utilities
DishwasherDryerRefrigeratorWasher
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: Asphalt, OtherExterior: Shingle
Parking & Garage
Parking Spaces: 4

Property Information

Year Built
Year Built: 1973Year Updated: 1985
Property Type / Style
Property Type: Single Family HomeArchitecture: Cape Cod

Lot Information

Lot Area: 0.49 acres

Price History for 285 Massasoit Trl

DatePriceEventSource
07/20/2016$399,500Sold
CCIMLS #21510945
06/06/2016$409,000PendingAgent Provided
05/20/2016$409,000PriceChange
Agent Provided
04/09/2016$414,000PriceChange
Agent Provided
11/28/2015$419,000PriceChange
Agent Provided
10/08/2015$409,000PriceChange
Agent Provided
04/12/2015$429,000Listed For SaleAgent Provided
10/31/2003$375,000Sold
N/A

Market trends in Eastham

Last updated May 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
Sale-to-List Price
Price per sq ft
Available listings
54
16
MoM
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Property Tax and Assessment

Year2025
Tax$6,102
Assessment$791,400
Home facts updated by county records

Comparable Sales for 285 Massasoit Trl

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
0.07
Single-Family Home
$975,000
10/27/25
3
2
1,906
0.23
Single-Family Home
$1,250,000
11/03/25
3
2
2,230
0.16
Single-Family Home
$690,000
11/19/25
4
1
1,152
0.40
Single-Family Home
$690,000
04/17/26
3
1.5
1,282
0.26
Single-Family Home
$726,000
10/15/25
2
2
1,276
0.59
Single-Family Home
$670,000
12/19/25
3
2
1,872
0.43
Single-Family Home
$1,302,000
06/01/26
3
2
1,890
0.12
Single-Family Home
$586,000
08/08/25
2
1
680
0.42
Single-Family Home
$600,000
12/12/25
3
1.5
1,350
0.45
Single-Family Home
$850,500
06/09/26
3
2
1,350

Nearby homes

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Assigned Schools

These are the assigned schools for 285 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 Eastham

At least 27 Trulia users voted on each feature.
  • 100 % Say car is needed

  • 91 % Say yards are well-kept

  • 90 % Say it's dog friendly

  • 89 % Say parking is easy

  • 87 % Say there's wildlife

  • 83 % Say it's quiet

  • 83 % Say people would walk alone at night

  • 78 % Say they plan to stay for at least 5 years

  • 73 % Say there's holiday spirit

  • 53 % Say neighbors are friendly

  • 45 % Say there are community events

  • 38 % Say kids play outside

  • 32 % Say it's walkable to restaurants

Sourced by Trulia users. Learn more about our methodology.
  • karenkeon
    "I live here and love the community and feel safe. The neighbors are amazing and welcoming to all. I wouldn’t want to live anywhere else "
  • Jw
    "The community events that make our neighborhood special are Windmill weekend and the turnip festival."
  • Eljtradke
    "It is quaint New England oceanside town in a rural setting. That is what makes Eastham unique. aaaa!aaaaaaaaaaaaaaaaa"
  • Nfegela234
    "some traffic not too bad, main road gets a lot of beach traffic during prime times in the summer but in winter it’s like a ghost town!"
  • Imkalilly52
    "I no longer have to commute! I’m retired! Lovely, friendly neighborhood with the bay within walking distance "
  • Tomonthecape
    "The neighbors are a community, friendly...we know them on a first name basis, know their families, anda generally get along with everyone"
  • mannytech
    "nice people respect the bikers there a bike trail right next to the house which is awesome there also a library and beach close by. the flea market is so much fun as well as p town. 60 nickerson RD quite clean enjoyable I loved it so did my many friends and family! :)"
  • Skotwyte
    "I live here, and its wonderful"
  • wsitgm
    "Amazing environment of the outer cape....that's why the Federal Government grabbed it to become the National Seashore. While Eastham is a little rustic, it is 5 miles to Orleans and 20 to Hyannis so that creates many opportunities for restaurants, shopping and health care."
  • Skotwyte
    "Great Area, just 1000 feet from the Cape Cod National Seashore National Park, great schools, beaches, and restaurants."

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Apartments for Rent

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Homes for sale near 285 Massasoit Trl

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Off Market Homes Near 285 Massasoit Trl

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