Is Oak Bluffs, MA dog-friendly?

As of early 2026, 96% of users say it's dog friendly

Do kids play outside in Oak Bluffs, MA?

As of early 2026, 86% of users say kids play outside

Are yards well-kept in Oak Bluffs, MA?

As of early 2026, 83% of users say yards are well-kept

Is Oak Bluffs, MA walkable to restaurants?

As of early 2026, 79% of users say it's walkable to restaurants

Is a car needed in Oak Bluffs, MA?

As of early 2026, 79% of users say car is needed

Would people walk alone at night in Oak Bluffs, MA?

As of early 2026, 78% of users say people would walk alone at night

Is Oak Bluffs, MA walkable to grocery stores?

As of early 2026, 78% of users say it's walkable to grocery stores

Is there wildlife in Oak Bluffs, MA?

As of early 2026, 73% of users say there's wildlife

Do residents of Oak Bluffs, MA plan to stay at least 5 years?

As of early 2026, 73% of users say they plan to stay for at least 5 years

Does Oak Bluffs, MA show holiday spirit?

As of early 2026, 70% of users say there's holiday spirit

Is Oak Bluffs, MA quiet?

As of early 2026, 67% of users say it's quiet

Is parking easy in Oak Bluffs, MA?

As of early 2026, 62% of users say parking is easy

Are neighbors friendly in Oak Bluffs, MA?

As of early 2026, 59% of users say neighbors are friendly

Are there community events in Oak Bluffs, MA?

As of early 2026, 47% of users say there are community events

Does Oak Bluffs, MA have sidewalks?

As of early 2026, 44% of users say there are sidewalks

Are the streets well-lit in Oak Bluffs, MA?

As of early 2026, 36% of users say streets are well-lit

What is 14 E Side Rd estimated to be worth?

Trulia's estimated value for 14 E Side Rd in Oak Bluffs, MA is $2,684,700 .

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 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 .

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.

OFF MARKET

$2,684,700

Trulia Estimate

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

14 E Side Rd, Oak Bluffs, MA 02557

Est. Refi. Payment $16,138/mo*

Refinance Your Home

Currently Off Market - Sold Mar 31, 2010 for $1,300,000

Home Value

Trulia Estimate

$2.69M

Since last month

$184K (+7.4%)

Since last year

$695K (-20.6%)

Since last sale

$1M (+106.5%)

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 +111% in the last 10 years

Month	Estimated value
2026
September 2026	$2.68M
September 2026	$2.68M
August 2026	$2.5M
July 2026	$2.34M
June 2026	$2.31M
May 2026	$3.53M
April 2026	$3.37M
March 2026	$3.48M
February 2026	$3.4M
January 2026	$3.46M
2025
December 2025	$3.5M
November 2025	$3.36M
October 2025	$3.41M
September 2025	$3.38M
August 2025	$3.37M
July 2025	$3.31M
June 2025	$3.31M
May 2025	$3.12M
April 2025	$3.21M
March 2025	$3.15M
February 2025	$2.19M
January 2025	$2.22M
2024
December 2024	$1.8M
November 2024	$1.87M
October 2024	$2.09M
September 2024	$2.16M
August 2024	$2.15M
July 2024	$2.15M
June 2024	$2.12M
May 2024	$2.02M
April 2024	$1.78M
March 2024	$1.68M
February 2024	$1.48M
January 2024	$1.44M
2023
December 2023	$1.59M
October 2023	$1.28M
September 2023	$1.17M
August 2023	$1.34M
July 2023	$3.39M
June 2023	$3.31M
May 2023	$3.17M
April 2023	$3.1M
March 2023	$3.13M
January 2023	$3.05M
2022
December 2022	$3.07M
November 2022	$3.06M
October 2022	$2.92M
September 2022	$2.73M
August 2022	$2.77M
July 2022	$2.89M
June 2022	$2.98M
May 2022	$3.1M
April 2022	$3M
March 2022	$3.01M
February 2022	$2.78M
January 2022	$2.72M
2021
December 2021	$2.81M
November 2021	$2.78M
October 2021	$2.72M
September 2021	$2.63M
August 2021	$2.61M
July 2021	$2.57M
June 2021	$2.39M
May 2021	$1.87M
April 2021	$1.85M
March 2021	$1.81M
February 2021	$1.8M
January 2021	$1.79M
2020
December 2020	$1.78M
November 2020	$1.76M
October 2020	$1.75M
September 2020	$1.75M
August 2020	$1.73M
July 2020	$1.73M
June 2020	$1.72M
May 2020	$1.73M
April 2020	$1.73M
March 2020	$1.73M
February 2020	$1.72M
January 2020	$1.71M
2019
December 2019	$1.57M
November 2019	$1.52M
October 2019	$1.53M
September 2019	$1.52M
August 2019	$1.54M
July 2019	$1.53M
June 2019	$1.55M
May 2019	$1.53M
April 2019	$1.48M
March 2019	$1.53M
February 2019	$1.45M
January 2019	$1.51M
2018
December 2018	$1.49M
November 2018	$1.49M
October 2018	$1.44M
September 2018	$1.45M
August 2018	$1.46M
July 2018	$1.55M
June 2018	$1.48M
May 2018	$1.4M
April 2018	$1.46M
March 2018	$1.41M
February 2018	$1.12M
January 2018	$1.12M
2017
December 2017	$1.15M
November 2017	$1.14M
October 2017	$1.16M
September 2017	$1.23M
August 2017	$1.24M
July 2017	$1.27M
June 2017	$1.29M
May 2017	$1.21M
April 2017	$1.24M
March 2017	$1.24M
February 2017	$1.22M
January 2017	$1.27M
2016
December 2016	$1.27M
November 2016	$1.27M
October 2016	$1.27M

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
44 Carole Ave, Oak Bluffs, MA	0.08	Single-Family Home	$705,000	04/16/26	4	2	2,123
71 Netock Ave, Oak Bluffs, MA	0.63	Single-Family Home	$1,865,000	12/04/25	4	4	2,820
9 Bay View Ave, Oak Bluffs, MA	0.26	Single-Family Home	$1,090,000	01/16/26	3	2	1,428
5 Johns Way, Oak Bluffs, MA	0.31	Single-Family Home	$880,000	10/17/25	3	2	1,365
38 Rogers Way, Oak Bluffs, MA	0.49	Single-Family Home	$1,450,000	05/04/26	3	1.5	2,448
33 Windemere Rd, Oak Bluffs, MA	0.33	Single-Family Home	$1,700,000	09/14/26	5	2	2,125
26 Winne Ave, Oak Bluffs, MA	0.41	Single-Family Home	$1,470,000	10/27/25	3	2.5	1,620
35 Stevens Ave, Oak Bluffs, MA	0.59	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
20 E Side Rd, Oak Bluffs, MA 02557	0.02	$3,354,100	3	2	2,302	Off Market
10 E Side Rd, Oak Bluffs, MA 02557	0.02	$1,816,300	2	1	638	Off Market
8 E Side Rd, Oak Bluffs, MA 02557	0.03	$2,924,600	4	3	2,232	Off Market
14 Mae Ave, Oak Bluffs, MA 02557	0.04	$1,074,100	3	2	952	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
12 Mae Ave, Oak Bluffs, MA 02557	0.04	$1,584,100	3	2	1,700	Off Market
55 Vineyard Avenue Ext, Oak Bluffs, MA 02557	0.04	-	Studio	-	-	Off Market
7 E Side Rd, Oak Bluffs, MA 02557	0.05	$970,800	3	1	780	Off Market
2 E Side Rd, Oak Bluffs, MA 02557	0.05	$2,313,800	3	2	1,314	Off Market
28 E Side Rd, Oak Bluffs, MA 02557	0.06	$1,960,900	Studio	2	1,364	Off Market
15 Mae Ave, Oak Bluffs, MA 02557	0.06	$1,276,500	3	3	1,768	Off Market
27 E Side Rd, Oak Bluffs, MA 02557	0.06	$1,175,000	Studio	-	-	Recently Sold
60 Bay View Ave, Oak Bluffs, MA 02557	0.06	$1,760,200	Studio	-	-	Off Market
40 Vineyard Avenue Ext, Oak Bluffs, MA 02557	0.07	-	4	4	2,400	Off Market
1 E Side Rd, Oak Bluffs, MA 02557	0.07	$1,342,800	3	2	1,547	Off Market
30 E Side Rd, Oak Bluffs, MA 02557	0.07	$2,039,000	2	2	1,292	Off Market
2 E Side Rd #&-60, Oak Bluffs, MA 02557	0.07	$1,638,200	3	2	1,594	Off Market
58 Bay View Ave, Oak Bluffs, MA 02557	0.07	$2,805,500	4	3	3,000	Off Market
23 Mae Ave, Oak Bluffs, MA 02557	0.07	$1,000,000	2	1	700	Off Market

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

Single-Family Home

Built in 2018

0.76 acre lot

3,288 sqft

$817/sqft

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. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $2,684,700, with a rent estimate of $8,357/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, 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 and Tax history

Date	Event	Price
Mar 31, 2010 Source: LINK #18149	Sold	$1,300,000
Apr 11, 2009 Source: Agent Provided	ListingRemoved	$1,400,000
Mar 11, 2009 Source: Agent Provided	Listed For Sale	$1,400,000
Jun 22, 2005 Source: LINK #10519	Sold	$1,550,000

Year	Property tax	Tax assessment
2025	$16,432	$3,253,900

Additional Cost

Market trends in Oak Bluffs

Last updated August 2026

Avg. sale price

—

Sale-to-List Price

—

Price per sq ft

—

Available listings

14MoM

Around this home

Oak Bluffs Elementary School
PK-8
Public
390 Students
Oak Bluffs School District
7/10
GreatSchools Rating
Parent Rating Average
An excellent school where students seem to be happy, learning and engaged. You can tell the teachers really care about and truly want the best for their students. The new principal is very energetic, involved and approachable and he seems very well-liked by students, parents and the staff (which is everything).
Parent Review
11mo ago
4 Reviews

View nearby schools on GreatSchools

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.

Trulia User
Resident
1mo ago
"Easy to walk dogs"
0
Flag
P5j4f84ncw
Resident
7mo ago
"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
Visitor
1y ago
"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
Resident
2y ago
"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
Visitor
2y ago
"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
Resident
7y ago
"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.
Prev. Resident
8y ago
"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
11y ago
"I own a property in Oak Bluffs"
0
Flag
Kristin Z.
11y ago
"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.
11y ago
"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 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 $2,684,700.
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 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.
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.

Explore by feature - Washer/dryer

FURNISHED
$7,323/mo
Total price
3 bd
2 ba
1,022 sqft
25 Simpson Ave #ID1514679P,
Vineyard Haven, MA 02568
FURNISHED
$11,021/mo
Total price
4 bd
3 ba
2,281 sqft
13 N Meadow Ln #ID1514673P,
Vineyard Haven, MA 02568
APPLY INSTANTLY
FURNISHED
$3,500/mo
Total price
2 bd
2 ba
1,000 sqft
Address Not Disclosed,
Oak Bluffs, MA 02557
APPLY INSTANTLY
PET FRIENDLY
FURNISHED
$6,550/mo
Total price
4 bd
2 ba
1,520 sqft
107 Barnes Rd,
Oak Bluffs, MA 02557
$28,500/mo
Fees may apply
9 bd
6.5 ba
3,500 sqft
9 Tuckernuck Ave,
Oak Bluffs, MA 02557

Apartments for Rent

Skip to last item

Contact for price
1-2 bd
1-2 ba
145 Main St #776f18ccb,
Vineyard Haven, MA 02568
FURNISHED
$7,323/mo
Total price
3 bd
2 ba
25 Simpson Ave #ID1514679P,
Vineyard Haven, MA 02568
FURNISHED
$11,021/mo
Total price
4 bd
3 ba
13 N Meadow Ln #ID1514673P,
Vineyard Haven, MA 02568
APPLY INSTANTLY
FURNISHED
$3,500/mo
Total price
2 bd
2 ba
Address Not Disclosed,
Oak Bluffs, MA 02557
See more homes for rent in
Oak Bluffs
Take a look

Skip to first item

Off Market Homes Near 14 E Side Rd

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SOLD
OCT 2, 2026
$1,836,000
3 bd
2.5 ba
1,902 sqft
81 Leland Ave,
Tisbury, MA 02568
Tea Lane Associates
SOLD
OCT 2, 2026
$2,500,000
6 bd
4.5 ba
3,267 sqft
100 Connies Way,
Tisbury, MA 02568
Wallace & Co. Sotheby's
SOLD
OCT 1, 2026
$3,225,000
3 bd
4.5 ba
3,219 sqft
8 Woodhaven Dr,
Edgartown, MA 02539
Compass | Point B
SOLD
SEP 30, 2026
$3,500,000
98 Farm Neck Way,
Oak Bluffs, MA 02557
Compass LLC
SOLD
SEP 29, 2026
$2,150,000
5 bd
3.5 ba
3,873 sqft
50 Hidden Cove Rd,
Oak Bluffs, MA 02557
Landmarks at TODAY Real Estate
SOLD
SEP 25, 2026
$3,005,000
4 bd
2.5 ba
3,225 sqft
272 Bigelow Rd,
Tisbury, MA 02568
Tea Lane Associates
SOLD
SEP 24, 2026
$2,150,000
4 bd
3.5 ba
3,016 sqft
3 Hidden Cove Rd,
Oak Bluffs, MA 02557
Wendy Harman, Compass
SOLD
SEP 21, 2026
$1,390,000
4 bd
3 ba
1,514 sqft
26 Sea Glen Rd,
Oak Bluffs, MA 02557
Compass | Point B
SOLD
SEP 18, 2026
$1,400,000
1 bd
2.5 ba
1,254 sqft
20 Union Court #C,
Vineyard Haven, MA 02568
Island Real Estate
SOLD
SEP 16, 2026
$1,680,000
4 bd
2.5 ba
2,329 sqft
37 Old Hedge Row,
Tisbury, MA 02568
Landmarks at TODAY Real Estate
See more homes for sale in
Oak Bluffs
Take a look

Skip to first item

Homes for sale near 14 E Side Rd

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1.06 ACRES
$2,579,000
4 bd
2 ba
1,399 sqft
34 Windemere Rd,
Oak Bluffs, MA 02557
Alisan Lohan-Conway Properties
0.43 ACRES
$2,600,000
6 bd
4 ba
2,400 sqft
111 Eastville Ave,
Oak Bluffs, MA 02557
Arrowhead Homes
0.27 ACRES
$2,678,000
4 bd
3.5 ba
2,363 sqft
31 Temahigan Avenue,
Oak Bluffs, MA 02557
Portfolio Properties
0.7 ACRES
$4,050,000
3 bd
4 ba
2,606 sqft
95 Hines Point Rd,
Tisbury, MA 02568
Tea Lane Associates
0.35 ACRES
$1,255,000
3 bd
1.5 ba
912 sqft
11 Stanley Street,
Oak Bluffs, MA 02557
Anchor Realty of MV
0.34 ACRES
$1,755,000
3 bd
3 ba
2,815 sqft
68 Front Street,
Oak Bluffs, MA 02557
Wallace & Co. Sotheby's International Realty
$2,995,000
5 bd
1.5 ba
1,731 sqft
27 Beach Road,
Oak Bluffs, MA 02557
Wallace & Co. Sotheby's International Realty
0.26 ACRES
$1,295,000
3 bd
2 ba
1,260 sqft
4 Periwinkle Ln,
Oak Bluffs, MA 02557
MV Luxury Homes
1.8 ACRES
$4,450,000
5 bd
4 ba
3,650 sqft
217 Barnes Rd,
Oak Bluffs, MA 02557
Tea Lane Associates
$1,100,000
3 bd
2 ba
1,232 sqft
54 Towanticut Ave,
Oak Bluffs, MA 02557
Island Home Realty Inc.
See more homes for sale in
Oak Bluffs
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