8 E  Side Rd, Oak Bluffs, MA 02557
Property image
Property image
OFF MARKET

8 E Side Rd
Oak Bluffs, MA 02557

  • 4 Beds
  • 3 Baths
  • 2,232 sqft (on 0.26 acres)

$2,989,800

Trulia Estimate
as of Aug 10, 2026
Est. Refi. Payment $16,534/mo*

$2,989,800

Trulia Estimate
as of Aug 10, 2026
Est. Refi. Payment $16,534/mo*
4 Beds
3 Baths
2,232 sqft
(on 0.26 acres)

Local Information

  • Map ViewExplore the area around 8 E Side Rd.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1958
Lot Size
0.26 acres
Living Area
2,232 sqft
Price/Sqft
$1,340

About this House

Lagoon Waterfront - Wonderful location with breathtaking views of the Lagoon and beyond the Vineyard Haven harbor from most of the rooms in the house. Built in 1958 this two story conventional style home has approximately 50 feet of beach front. The home features an open living, dining, kitchen area, four bedrooms, two and a half baths, family room in the lower level and partial basement with washer & dryer. Detached carport and plenty of parking. Nicely landscaped yard with gardens.

FIRST FLOOR DESCRIPTION
First level consists of three bedrooms, one and a half baths, family room with pot belly stove and work space.

SECOND FLOOR DESCRIPTION
Second floor consists of open living, dining, kitchen area, one bedroom and full bath. Off the living room is a deck with expansive views of the Lagoon. There is also an attic space over the first floor bedrooms.

BASEMENT DESCRIPTION
Partial basement with washer, dryer, furnace, etc.

OTHER BUILDINGS
A two car carport is at the front of the property.

PARKING
Yes, carport for 2 cars and driveway for 2 more cars

To see many more options available for sale, please contact us at 1-800-287-4801 or www.islandrealestatemv.com for more listings.
8 E Side Rd, Oak Bluffs, MA 02557 is a 4 bedroom, 3 bathroom, 2,232 sqft single-family home built in 1958. It last sold for $875,000 on Dec 19, 2008. It is currently off market. The Trulia Estimate is $2,989,800, with a rent estimate of $6,680/month.

Home Details for 8 E Side Rd

Interior Features

Heating & Cooling
Heating: Forced Air, ElectricAir ConditioningHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 2

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: Brick

Property Information

Year Built
Year Built: 1958
Property Type / Style
Property Type: Single Family HomeArchitecture: Old Style

Community

Units in Building: 1

Lot Information

Lot Area: 0.26 acres

Price History for 8 E Side Rd

DatePriceEventSource
12/19/2008$875,000Sold
LINK #17895

Market trends in Oak Bluffs

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

Year2025
Tax$12,290
Assessment$2,433,700
Home facts updated by county records

Comparable Sales for 8 E Side Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
0.07
Single-Family Home
$705,000
04/16/26
4
2
2,123
0.06
Single-Family Home
$1,530,000
01/13/26
3
2
2,015
0.06
Single-Family Home
$1,530,000
01/13/26
3
2
2,015
0.11
Single-Family Home
$1,350,000
08/15/25
3
2
1,864
0.14
Single-Family Home
$1,310,000
08/18/25
3
2
1,964
0.25
Single-Family Home
$1,090,000
01/16/26
3
2
1,428
0.30
Single-Family Home
$880,000
10/17/25
3
2
1,365
0.47
Single-Family Home
$1,450,000
05/04/26
3
1.5
2,448
0.71
Single-Family Home
$999,000
09/04/25
3
2.5
1,996
0.63
Single-Family Home
$1,187,500
06/12/26
4
2
1,764

Nearby homes

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Assigned Schools

These are the assigned schools for 8 E Side 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

Sourced by Trulia users. 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."

LGBTQ Local Legal Protections

Apartments for Rent

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Homes for sale near 8 E Side Rd

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Off Market Homes Near 8 E Side Rd

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Frequently asked questions about 8 E Side Rd

  • What is 8 E Side Rd estimated to be worth?
    Trulia's estimated value for 8 E Side Rd in Oak Bluffs, MA is $2,989,800.
  • What is the price history for 8 E Side Rd?
    8 E Side Rd in Oak Bluffs, MA last sold for $875,000 in December 2008.
  • Is Oak Bluffs a buyer's or seller's market?
    Oak Bluffs is currently a buyer's market, based on recent for-sale activity.
  • What do residents say about Oak Bluffs?
    Residents describe Oak Bluffs, MA as dog-friendly, well-kept, and walkable to restaurants. See recently sold homes in Oak Bluffs, MA.
  • How big is the lot at 8 E Side Rd?
    The lot at 8 E Side Rd in Oak Bluffs, MA is about 0.26 acres (11,326 sq ft).