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

14 E Side Rd
Oak Bluffs, MA 02557

  • 4 Beds
  • 4.5 Baths
  • 3,288 sqft (on 0.76 acres)

$2,371,600

Trulia Estimate
as of Aug 11, 2026
Est. Refi. Payment $13,130/mo*

$2,371,600

Trulia Estimate
as of Aug 11, 2026
Est. Refi. Payment $13,130/mo*
4 Beds
4.5 Baths
3,288 sqft
(on 0.76 acres)

Local Information

  • Map ViewExplore the area around 14 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
2018
Lot Size
0.76 acres
Living Area
3,288 sqft
Price/Sqft
$721
Parking
Garage

About this House

Enjoy spectacular sunsets and views of the outer Vineyard Haven Harbor from this Lagoon-front, year round home. Walk across the broad, sweeping lawn to 150 feet of saltwater shorefront, perfect for swimming, boating and shellfishing. The detached garage is ideal for storing your bikes, boating gear and lawnmower.
14 E Side Rd, Oak Bluffs, MA 02557 is a 4 bedroom, 5 bathroom, 3,288 sqft single-family home built in 2018. It last sold for $1,300,000 on Mar 31, 2010. It is currently off market. The Trulia Estimate is $2,371,600, with a rent estimate of $8,294/month.

Home Details for 14 E Side Rd

Interior Features

Interior Details
BasementTypes of Rooms: Walk In Closet, Breakfast Nook, Dining Room, Family Room, Laundry Room, Master Bath, Office, Pantry, WorkshopCeiling Fan
Heating & Cooling
Heating: Heat Pump, Other, Electric, SolarAir ConditioningCooling System: Refrigerator, SolarHeating Fuel: Heat Pump
Levels, Entrance, & Accessibility
Stories: 2Floors: Hardwood
Appliances & Utilities
DishwasherDryerMicrowaveRefrigeratorWasher
Fireplace & Spa
Fireplace
Windows, Doors, Floors & Walls
Double Paned Windows
Security
Security System

Exterior Features

Exterior Home Features
Roof: Shake ShingleDeckExterior: ShingleGardenLawnPorch
Parking & Garage
GarageParking: Garage Attached, Garage Detached

Property Information

Year Built
Year Built: 2018Year Updated: 2018
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Community

Units in Building: 1

Lot Information

Lot Area: 0.76 acres

Price History for 14 E Side Rd

DatePriceEventSource
03/31/2010$1,300,000Sold
LINK #18149
04/11/2009$1,400,000ListingRemovedAgent Provided
03/11/2009$1,400,000Listed For SaleAgent Provided
06/22/2005$1,550,000Sold
LINK #10519

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$16,432
Assessment$3,253,900
Home facts updated by county records

Comparable Sales for 14 E Side Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
0.11
Single-Family Home
$1,310,000
08/18/25
3
2
1,964
0.04
Single-Family Home
$1,530,000
01/13/26
3
2
2,015
0.04
Single-Family Home
$1,530,000
01/13/26
3
2
2,015
0.10
Single-Family Home
$1,350,000
08/15/25
3
2
1,864
0.08
Single-Family Home
$705,000
04/16/26
4
2
2,123
0.63
Single-Family Home
$1,865,000
12/04/25
4
4
2,820
0.26
Single-Family Home
$1,090,000
01/16/26
3
2
1,428
0.31
Single-Family Home
$880,000
10/17/25
3
2
1,365
0.49
Single-Family Home
$1,450,000
05/04/26
3
1.5
2,448
0.41
Single-Family Home
$1,470,000
10/27/25
3
2.5
1,620

Nearby homes

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Assigned Schools

These are the assigned schools for 14 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 14 E Side Rd

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Off Market Homes Near 14 E Side Rd

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Frequently asked questions about 14 E Side Rd

  • What is 14 E Side Rd estimated to be worth?
    Trulia's estimated value for 14 E Side Rd in Oak Bluffs, MA is $2,371,600.
  • What is the price history for 14 E Side Rd?
    14 E Side Rd in Oak Bluffs, MA last sold for $1,300,000 in March 2010.
  • 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.
  • Does 14 E Side Rd have air conditioning?
    Yes, 14 E Side Rd in Oak Bluffs, MA has air conditioning.
  • Does 14 E Side Rd have laundry facilities?
    Yes, 14 E Side Rd in Oak Bluffs, MA has in-unit laundry.