27 E Side Rd, Oak Bluffs, MA 02557
SOLD
JUN 5, 2026

$1,180,000

Trulia Estimate
  • Studio

27 E Side Rd, Oak Bluffs, MA 02557

Est. Refi. Payment $6,924/mo*
Refinance Your Home
Currently Off Market - Sold Jun 5, 2026 for $1,175,000

Home Value

Trulia Estimate
$1.18M
Since last month
$200 (0%)
Since last year
Increased$766K (+184.7%)
Since last sale
Increased$5K (+0.4%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +257% in the last 10 years
MonthEstimated value
2026
September 2026$1.18M
August 2026$1.18M
July 2026$1.18M
June 2026$1.18M
May 2026$616K
April 2026$607K
March 2026$578K
February 2026$510K
January 2026$445K
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
48 Vineyard Ave, Vineyard Haven, MA
0.04
Single-Family Home
$1,530,000
01/13/26
3
2
2,015
48 Vineyard Avenue Ext, Oak Bluffs, MA
0.04
Single-Family Home
$1,530,000
01/13/26
3
2
2,015
9 Bay View Ave, Oak Bluffs, MA
0.26
Single-Family Home
$1,090,000
01/16/26
3
2
1,428
32 Beach Rd, Oak Bluffs, MA
0.36
Single-Family Home
$975,000
09/30/25
3
2
836
15 2nd Ave, Oak Bluffs, MA
0.67
Single-Family Home
$875,000
07/28/26
2
1
520
26 Winne Ave, Oak Bluffs, MA
0.45
Single-Family Home
$1,470,000
10/27/25
3
2.5
1,620
9 Brunswick Ave, Oak Bluffs, MA
0.69
Single-Family Home
$1,275,000
07/31/26
3
1
1,033
5 Johns Way, Oak Bluffs, MA
0.30
Single-Family Home
$880,000
10/17/25
3
2
1,365

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
48 Vineyard Avenue Ext, Oak Bluffs, MA 02557
0.04
$1,530,000
3
2
2,015
Recently Sold
48 Vineyard Ave, Vineyard Haven, MA 02568
0.04
$1,530,000
3
2
2,015
Recently Sold
35 E Side Rd, Oak Bluffs, MA 02557
0.05
$1,346,200
3
2
1,964
Off Market
35 Vineyard Avenue Ext, Oak Bluffs, MA 02557
0.06
$1,537,600
3
2
1,864
Off Market
34 Shirley Ave, Oak Bluffs, MA 02557
0.07
$1,621,300
3
3
2,305
Off Market
33 June Ave, Oak Bluffs, MA 02557
0.07
$1,392,600
3
3.5
1,871
Off Market
30 Shirley Ave, Oak Bluffs, MA 02557
0.07
$1,900,700
3
3.5
2,900
Off Market
2 E Side Rd #&-60, Oak Bluffs, MA 02557
0.13
$1,645,600
3
2
1,594
Off Market
26 Vineyard Avenue Ext, Oak Bluffs, MA 02557
0.10
$952,000
2
2
912
Off Market
13 June Avenue, Oak Bluffs, MA 02557
0.14
$964,900
2
1.5
1,186
Off Market
4 June Ave, Oak Bluffs, MA 02557
0.17
$1,092,300
3
2
1,064
Off Market

Local Information

  • Map ViewExplore the area around 27 E Side Rd.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home

About this House

What's unique:Storage areaCamp style cottageLadder to a loftCozy home
Existing structure torn down - no building data avaiable. New Construction
27 E Side Rd, Oak Bluffs, MA 02557 is a studio single-family home. It last sold for the $1,175,000 asking price on Jun 5, 2026. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $1,180,000, with a rent estimate of $2,304/month.
Last check for updates: about 11 hours ago
Listed by LINK
LINK
Source: LINK, MLS#44607

Home Details for 27 E Side Rd

Interior Features

Appliances & Utilities
Utilities: None
Heating & Cooling
No Cooling
View
Has a ViewView: D/Snd, Res

Exterior Features

Frontage
Not on Waterfront

Property Information

Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family Residence
Property Information
Parcel Number: 7520

Price & Status

Price
List Price: $1,175,000

Active Status

MLS Status: S

Location

Direction & Address
City: Oak Bluffs

Lot Information

Lot Area: 2178 sqft

Offer

Listing Agreement Type: E

Miscellaneous

Mls Number: 44607Water ViewWater View: D/Snd

Price and Tax history

DateEventPrice
Jun 5, 2026
Source: LINK #44607
Sold
$1,175,000
Jul 15, 2024
Source: LINK #41834
Sold
$400,000
Jun 7, 2024
Source: LINK #41834
Pending
$599,000
May 16, 2024
Source: LINK #41834
PriceChange
$599,000
Price decreased by 5%
Apr 12, 2024
Source: LINK #41834
PriceChange
$629,000
Price decreased by 10%

Market trends in Oak Bluffs

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
72
14MoM

Around this home

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.
  • Trulia User
    "Easy to walk dogs"
    0
    Flag
  • P5j4f84ncw
    "Local people, well known community,quite,hard working people,solid business,good schools,hospitality,new opportunities,security and safety place to leave. "
    0
    Flag
  • 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 "
    0
    Flag
  • Trulia User
    "Oak Bluffs is a charming town with a bustling summer harbor and lovely shopping district. It’s a beautiful place to live. "
    0
    Flag
  • Jrheneeb
    "I love it here. It’s beautiful and the people are amazing. It’s a great place To come relax and unwind. "
    0
    Flag
  • Kayceesmith27
    "I take the bus to and from work . Car for longer distances. Boat to get to the main land which is 45min ride."
    0
    Flag
  • 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."
    0
    Flag
  • tkurian
    "I own a property in Oak Bluffs"
    0
    Flag
  • 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. "
    0
    Flag
  • Island R. E.
    "This is a lovely and desirable area close to town and everything the island has to offer."
    1
    Flag

LGBTQ Local Legal Protections

© 2026 LINK, All Rights Reserved. Data last updated: 2026-09-25 11:12:54 PDT. Some properties may no longer be for sale if they have gone under contract, have sold, or are no longer being offered for sale since the last update.

Frequently asked questions about 27 E Side Rd

  • What is 27 E Side Rd estimated to be worth?
    Trulia's estimated value for 27 E Side Rd in Oak Bluffs, MA is $1,180,000.
  • What is the price history for 27 E Side Rd?
    27 E Side Rd in Oak Bluffs, MA last sold for $1,175,000 in June 2026.
  • Is Oak Bluffs a buyer's or seller's market?
    Oak Bluffs is currently a seller'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 27 E Side Rd?
    The lot at 27 E Side Rd in Oak Bluffs, MA is about 0.05 acres (2,178 sq ft).

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