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

29 E Side Rd
Oak Bluffs, MA 02557

  • 1 Bed
  • 2 Baths
  • 748 sqft

$1,096,200

Trulia Estimate
as of Aug 10, 2026
Est. Refi. Payment $6,110/mo*

$1,096,200

Trulia Estimate
as of Aug 10, 2026
Est. Refi. Payment $6,110/mo*
1 Bed
2 Baths
748 sqft

Local Information

  • Map ViewExplore the area around 29 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
1960
Living Area
748 sqft
Price/Sqft
$1,466

About this House

This single-family home is located at 29 E Side Rd, Oak Bluffs, MA. 29 E Side Rd is in Oak Bluffs, MA and in ZIP code 02557. This property has 1 bedroom, 2 bathrooms and approximately 748 sqft of floor space. This property has a lot size of 10019 sqft and was built in 1960.
29 E Side Rd, Oak Bluffs, MA 02557 is a 1 bedroom, 2 bathroom, 748 sqft single-family home built in 1960. It last sold for $454,000 on Nov 18, 2009. It is currently off market. The Trulia Estimate is $1,096,200, with a rent estimate of $3,298/month.

Home Details for 29 E Side Rd

Interior Features

Heating & Cooling
Heating: Forced Air, ElectricAir ConditioningHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 1
Interior Details
Number of Rooms: 4

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: Wood

Property Information

Year Built
Year Built: 1960Year Updated: 2005
Property Type / Style
Property Type: Single Family HomeArchitecture: Ranch / Rambler

Community

Units in Building: 1

Lot Information

Lot Area: 10018 sqft

Price History for 29 E Side Rd

DatePriceEventSource
11/18/2009$454,000Sold
LINK #18535
08/24/2009$469,000PriceChange
Agent Provided
04/05/2009$479,000Listed For SaleAgent Provided

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$5,411
Assessment$1,071,400
Home facts updated by county records

Comparable Sales for 29 E Side Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
0.07
Single-Family Home
$1,350,000
08/15/25
3
2
1,864
0.35
Single-Family Home
$975,000
09/30/25
3
2
836
0.05
Single-Family Home
$1,530,000
01/13/26
3
2
2,015
0.05
Single-Family Home
$1,530,000
01/13/26
3
2
2,015
0.27
Single-Family Home
$1,090,000
01/16/26
3
2
1,428
0.50
Single-Family Home
$650,000
09/10/25
2
0.5
759
0.04
Single-Family Home
$1,310,000
08/18/25
3
2
1,964
0.11
Single-Family Home
$705,000
04/16/26
4
2
2,123
0.30
Single-Family Home
$880,000
10/17/25
3
2
1,365
0.87
Single-Family Home
$992,500
12/22/25
1
1.5
1,152

Nearby homes

Get a sense of prices in the area by checking nearby homes.
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Assigned Schools

These are the assigned schools for 29 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 29 E Side Rd

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Off Market Homes Near 29 E Side Rd

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Frequently asked questions about 29 E Side Rd

  • What is 29 E Side Rd estimated to be worth?
    Trulia's estimated value for 29 E Side Rd in Oak Bluffs, MA is $1,096,200.
  • What is the price history for 29 E Side Rd?
    29 E Side Rd in Oak Bluffs, MA last sold for $454,000 in November 2009.
  • 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 29 E Side Rd?
    The lot at 29 E Side Rd in Oak Bluffs, MA is about 0.23 acres (10,019 sq ft).