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

$3,354,100

Trulia Estimate
  • 3 Beds
  • 2 Baths
  • 2,302 sqft (on 0.39 acres)

20 E Side Rd, Oak Bluffs, MA 02557

Est. Refi. Payment $20,143/mo*
Refinance Your Home
Currently Off Market - Sold May 16, 2023 for $2,780,000

Home Value

Trulia Estimate
$3.35M
Since last month
Increased$85K (+2.6%)
Since last year
Increased$112K (+3.5%)
Since last sale
Increased$577K (+20.8%)
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 +120% in the last 10 years
MonthEstimated value
2026
September 2026$3.36M
September 2026$3.35M
August 2026$3.27M
July 2026$3.31M
June 2026$3.26M
May 2026$3.2M
April 2026$3.28M
March 2026$3.34M
February 2026$3.24M
January 2026$3.23M
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 Avenue Ext, Oak Bluffs, MA
0.04
Single-Family Home
$1,530,000
01/13/26
3
2
2,015
48 Vineyard Ave, Vineyard Haven, MA
0.04
Single-Family Home
$1,530,000
01/13/26
3
2
2,015
5 Johns Way, Oak Bluffs, MA
0.32
Single-Family Home
$880,000
10/17/25
3
2
1,365
38 Rogers Way, Oak Bluffs, MA
0.50
Single-Family Home
$1,450,000
05/04/26
3
1.5
2,448
9 Bay View Ave, Oak Bluffs, MA
0.27
Single-Family Home
$1,090,000
01/16/26
3
2
1,428
44 Carole Ave, Oak Bluffs, MA
0.09
Single-Family Home
$705,000
04/16/26
4
2
2,123
33 Windemere Rd, Oak Bluffs, MA
0.31
Single-Family Home
$1,700,000
09/14/26
5
2
2,125
58 Munroe Ave, Oak Bluffs, MA
0.87
Single-Family Home
$1,875,000
05/13/26
3
2
2,215
26 Winne Ave, Oak Bluffs, MA
0.43
Single-Family Home
$1,470,000
10/27/25
3
2.5
1,620
35 Stevens Ave, Oak Bluffs, MA
0.60
Single-Family Home
$1,290,020
12/05/25
2
3
1,632

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
14 E Side Rd, Oak Bluffs, MA 02557
0.02
$2,684,700
4
4.5
3,288
Off Market
55 Vineyard Avenue Ext, Oak Bluffs, MA 02557
0.02
-
Studio
-
-
Off Market
28 E Side Rd, Oak Bluffs, MA 02557
0.04
$1,960,900
Studio
2
1,364
Off Market
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
10 E Side Rd, Oak Bluffs, MA 02557
0.04
$1,816,300
2
1
638
Off Market
14 Mae Ave, Oak Bluffs, MA 02557
0.04
$1,074,100
3
2
952
Off Market
27 E Side Rd, Oak Bluffs, MA 02557
0.05
$1,175,000
Studio
-
-
Recently Sold
30 E Side Rd, Oak Bluffs, MA 02557
0.05
$2,039,000
2
2
1,292
Off Market
8 E Side Rd, Oak Bluffs, MA 02557
0.05
$2,924,600
4
3
2,232
Off Market
12 Mae Ave, Oak Bluffs, MA 02557
0.05
$1,584,100
3
2
1,700
Off Market
32 E Side Rd, Oak Bluffs, MA 02557
0.06
$1,884,100
3
2
1,172
Off Market
29 E Side Rd, Oak Bluffs, MA 02557
0.06
$1,114,100
1
2
748
Off Market
23 Mae Ave, Oak Bluffs, MA 02557
0.07
$1,000,000
2
1
700
Off Market
40 Vineyard Avenue Ext, Oak Bluffs, MA 02557
0.07
-
4
4
2,400
Off Market
15 Mae Ave, Oak Bluffs, MA 02557
0.07
$1,276,500
3
3
1,768
Off Market
31 E Side Rd, Oak Bluffs, MA 02557
0.07
$1,702,900
3
2
1,741
Off Market
25 Mae Ave, Oak Bluffs, MA 02557
0.07
$846,600
2
1
995
Off Market
7 E Side Rd, Oak Bluffs, MA 02557
0.07
$970,800
3
1
780
Off Market
34 E Side Rd, Oak Bluffs, MA 02557
0.07
$2,231,600
2
1
1,912
Off Market

Local Information

  • Map ViewExplore the area around 20 E Side Rd.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 2002
0.39 acre lot
2,302 sqft
$1,457/sqft

About this House

What's unique:Expansive lagoon waterfrontCustom glass-front cabinetsFrench doorsGranite countersOpen floor planLarge basement
This single-family home is located at 20 E Side Rd, Oak Bluffs, MA. 20 E Side Rd is in Oak Bluffs, MA and in ZIP code 02557. This property has 3 bedrooms, 2 bathrooms and approximately 2,302 sqft of floor space. This property has a lot size of 0.39 acres and was built in 2002.
20 E Side Rd, Oak Bluffs, MA 02557 is a 3 bedroom, 2 bathroom, 2,302 sqft single-family home built in 2002. It last sold for $2,780,000 on May 16, 2023. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $3,354,100.

Home Details for 20 E Side Rd

Interior Features

Heating & Cooling
Heating: OilAir ConditioningHeating Fuel: Oil
Levels, Entrance, & Accessibility
Stories: 2
Interior Details
Number of Rooms: 6

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: Wood

Property Information

Year Built
Year Built: 2002Year Updated: 2008
Property Type / Style
Property Type: Single Family HomeArchitecture: ranch

Community

Units in Building: 1

Lot Information

Lot Area: 0.39 acres

Price and Tax history

DateEventPrice
May 16, 2023
Source: LINK #40630
Sold
$2,780,000
Apr 5, 2023
Source: LINK #40630
Pending
$2,775,000
Mar 28, 2023
Source: LINK #40630
Listed For Sale
$2,775,000
Dec 17, 2022
Source: LINK #40165
ListingRemoved
$2,900,000
Oct 24, 2022
Source: LINK #40165
PendingToActive
$2,900,000

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

Frequently asked questions about 20 E Side Rd

  • What is 20 E Side Rd estimated to be worth?
    Trulia's estimated value for 20 E Side Rd in Oak Bluffs, MA is $3,354,100.
  • What is the price history for 20 E Side Rd?
    20 E Side Rd in Oak Bluffs, MA last sold for $2,780,000 in May 2023.
  • 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 20 E Side Rd?
    The lot at 20 E Side Rd in Oak Bluffs, MA is about 0.39 acres (16,995 sq ft).

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