356 E Chop Dr, Oak Bluffs, MA 02557
OFF MARKET

356 E Chop Dr
Oak Bluffs, MA 02557

  • 4 Beds
  • 2 Baths
  • 1,720 sqft

$3,390,600

Trulia Estimate
as of Aug 22, 2026
Est. Refi. Payment $18,651/mo*
Refinance Your Home

$3,390,600

Trulia Estimate
as of Aug 22, 2026
Est. Refi. Payment $18,651/mo*
Refinance Your Home
4 Beds
2 Baths
1,720 sqft

Home Value

Trulia Estimate
$3.39M
Since last month
Increased$73K (+2.2%)
Since last year
Increased$228K (+7.2%)
Since last sale
Increased$3M (+402.3%)
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 +134% in the last 10 years
MonthEstimated value
2026
August 2026$3.39M
July 2026$3.32M
June 2026$3.44M
May 2026$3.35M
April 2026$3.2M
March 2026$3.52M
February 2026$3.29M
January 2026$3.2M
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
44 Carole Ave, Oak Bluffs, MA
0.80
Single-Family Home
$705,000
04/16/26
4
2
2,123
67 New York Ave, Oak Bluffs, MA
0.62
Single-Family Home
$1,400,000
01/30/26
3
2
1,629
311 E Chop Dr, Oak Bluffs, MA
0.22
Single-Family Home
$2,850,000
12/16/25
4
2.5
1,800
32 Beach Rd, Oak Bluffs, MA
0.49
Single-Family Home
$975,000
09/30/25
3
2
836
23 Laurel Ave, Oak Bluffs, MA
0.74
Single-Family Home
$1,300,000
12/18/25
4
2
1,248
11 John Wesley Ave, Oak Bluffs, MA
0.70
Single-Family Home
$1,475,000
10/10/25
4
1.5
1,304
78 Winemack St, Oak Bluffs, MA
0.25
Single-Family Home
$2,899,000
10/01/25
4
2
1,889
71 Netock Ave, Oak Bluffs, MA
0.26
Single-Family Home
$1,865,000
12/04/25
4
4
2,820
14 Chapman Ave, Oak Bluffs, MA
0.82
Single-Family Home
$1,775,000
03/02/26
5
2
1,469
114 Park St, Oak Bluffs, MA
0.38
Single-Family Home
$3,067,050
10/22/25
4
3.5
1,872

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
3 Troy Street, Oak Bluffs, MA 02557
0.13
$1,295,000
3
2
1,863
For Sale
0 Temahigan Ave & Dover St, Oak Bluffs, MA 02557
0.14
$1,200,000
-
-
-
For Sale
5 & 7 Lyme St, Vineyard Haven, MA 02568
0.17
$1,629,900
5
3
1,999
Off Market
Temahigan Avenue & Dover St, Oak Bluffs, MA 02557
0.16
$1,049,000
-
-
-
For Sale
31 Temahigan Avenue, Oak Bluffs, MA 02557
0.18
$2,678,000
4
3.5
2,363
For Sale
35 Temahigan Ave, Oak Bluffs, MA 02557
0.19
$2,299,900
5
3
2,069
Off Market
35 Temahigan Ave #5, Oak Bluffs, MA 02557
0.19
-
-
-
-
Off Market
35 Temahigan Ave #6, Oak Bluffs, MA 02557
0.19
-
-
-
-
Off Market
47 Winemack Street, Oak Bluffs, MA 02557
0.22
$1,199,000
3
2
1,302
For Sale
312 E Chop Dr, Oak Bluffs, MA 02557
0.21
$2,295,000
3
2
1,425
For Sale
312 E Chop Drive, Vineyard Haven, MA 02568
0.22
$2,295,000
3
2
1,425
For Sale
311 E Chop Dr, Oak Bluffs, MA 02557
0.22
$2,850,000
4
2.5
1,800
Recently Sold

Local Information

  • Map ViewExplore the area around 356 E Chop Dr.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1910
Living Area
1,720 sqft
Price/Sqft
$1,971

About this House

This single-family home is located at 356 E Chop Dr, Oak Bluffs, MA. 356 E Chop Dr is in Oak Bluffs, MA and in ZIP code 02557. This property has 4 bedrooms, 2 bathrooms and approximately 1,720 sqft of floor space. This property has a lot size of 4791 sqft and was built in 1910.
356 E Chop Dr, Oak Bluffs, MA 02557 is a 4 bedroom, 2 bathroom, 1,720 sqft single-family home built in 1910. It last sold for $675,000 on May 26, 1999. It is currently off market. The Trulia Estimate is $3,390,600, with a rent estimate of $6,087/month.

Home Details for 356 E Chop Dr

Interior Features

Heating & Cooling
Heating: Forced Air, OilAir ConditioningHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 2

Exterior Features

Exterior Home Features
Roof: Shake ShingleExterior: Wood

Property Information

Year Built
Year Built: 1910Year Updated: 1988
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Community

Units in Building: 1

Lot Information

Lot Area: 4791 sqft

Price and Tax history

DateEventPrice
May 26, 1999
Source: N/A
Sold
$675,000

Market trends in Oak Bluffs

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
58
4MoM

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 356 E Chop Dr

  • What is 356 E Chop Dr estimated to be worth?
    Trulia's estimated value for 356 E Chop Dr in Oak Bluffs, MA is $3,390,600.
  • What is the price history for 356 E Chop Dr?
    356 E Chop Dr in Oak Bluffs, MA last sold for $675,000 in May 1999.
  • 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 356 E Chop Dr?
    The lot at 356 E Chop Dr in Oak Bluffs, MA is about 0.11 acres (4,791 sq ft).

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