28 Tradewinds Rd, Oak Bluffs, MA 02557
OFF MARKET

28 Tradewinds Rd
Oak Bluffs, MA 02557

  • 2 Beds
  • 1 Bath
  • 800 sqft (on 0.66 acres)

$783,800

Trulia Estimate
as of Apr 26, 2026
Est. Refi. Payment $4,198/mo*

$783,800

Trulia Estimate
as of Apr 26, 2026
Est. Refi. Payment $4,198/mo*
2 Beds
1 Bath
800 sqft
(on 0.66 acres)

Homes for sale near 28 Tradewinds Rd

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Apartments for Rent

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Local Information

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

Description

This single-family home is located at 28 Tradewinds Rd, Oak Bluffs, MA. 28 Tradewinds Rd is in Oak Bluffs, MA and in ZIP code 02557. This property has 2 bedrooms, 1 bathroom and approximately 800 sqft of floor space. This property has a lot size of 0.66 acres and was built in 1975.
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
No Info

Home Details for 28 Tradewinds Rd

Interior Features

Heating & Cooling
Heating: Other, GasHeating Fuel: Other
Levels, Entrance, & Accessibility
Stories: 1

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: Wood

Property Information

Year Built
Year Built: 1975
Property Type / Style
Property Type: Single Family HomeArchitecture: Ranch / Rambler

Community

Units in Building: 1

Lot Information

Lot Area: 0.66 acres
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Property Tax and Assessment

Year2025
Tax$3,356
Assessment$664,600
Home facts updated by county records

Comparable Sales for 28 Tradewinds Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
0.14
Single-Family Home
$800,000
09/04/25
2
1
1,086
0.30
Single-Family Home
$1,000,000
07/31/25
2
1
768
0.10
Single-Family Home
$860,000
02/09/26
2
2
1,232
0.28
Single-Family Home
$982,000
12/19/25
3
1
980
0.49
Single-Family Home
$782,000
03/06/26
2
1
861
0.11
Single-Family Home
$1,000,000
12/30/25
3
1.5
1,136
0.46
Single-Family Home
$975,000
07/02/25
3
1
1,056
0.26
Single-Family Home
$1,290,020
12/05/25
2
3
1,632
0.14
Single-Family Home
$1,900,000
02/09/26
2
2.5
2,137
0.76
Single-Family Home
$650,000
09/10/25
2
0.5
759

Assigned Schools

These are the assigned schools for 28 Tradewinds Rd.
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 Oak Bluffs

At least 18 Trulia users voted on each feature.
  • 96 % Say it's dog friendly

  • 86 % Say kids play outside

  • 83 % Say yards are well-kept

  • 79 % Say it's walkable to restaurants

  • 79 % Say car is needed

  • 78 % Say people would walk alone at night

  • 78 % Say it's walkable to grocery stores

  • 73 % Say there's wildlife

  • 73 % Say they plan to stay for at least 5 years

  • 70 % Say there's holiday spirit

  • 67 % Say it's quiet

  • 62 % Say parking is easy

  • 59 % Say neighbors are friendly

  • 47 % Say there are community events

  • 44 % Say there are sidewalks

  • 36 % Say streets are well-lit

Learn more about our methodology.
  • P5j4f84ncw
    "Local people, well known community,quite,hard working people,solid business,good schools,hospitality,new opportunities,security and safety place to leave. "
  • Adrianalleyne
    "Oak Bluffs has a vibrant history and continues to be a bastion of African American culture. It’s worth checking out some of the many cultural sites in Oak Bluffs and throughout the island "
  • Trulia User
    "Oak Bluffs is a charming town with a bustling summer harbor and lovely shopping district. It’s a beautiful place to live. "
  • Jrheneeb
    "I love it here. It’s beautiful and the people are amazing. It’s a great place To come relax and unwind. "
  • Kayceesmith27
    "I take the bus to and from work . Car for longer distances. Boat to get to the main land which is 45min ride."
  • Andrea H.
    "This is fantasy island. It is not like the real world it's not fast paced. we say we're on island time. there's hardly any crime it's safe for kids. and it's a good community."
  • tkurian
    "I own a property in Oak Bluffs"
  • Kristin Z.
    "We live here year round in what most people think is a vacation paradise for the rich and famous. But in actuality it is one of the best communities to live in terms of caring wonderful neighbors and exciting intellectual stimulation throughout the winter in the form of performances, music groups, communities by interests. "
  • Island R. E.
    "This is a lovely and desirable area close to town and everything the island has to offer."

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Homes for rent near 28 Tradewinds Rd

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Off Market Homes Near 28 Tradewinds Rd

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28 Tradewinds Rd, Oak Bluffs, MA 02557 is a 2 bedroom, 1 bathroom, 800 sqft single-family home built in 1975. This property is not currently available for sale. The current Trulia Estimate for 28 Tradewinds Rd is $783,800.