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

$3,817,600

Trulia Estimate
  • 3 Beds
  • 2 Baths
  • 2,390 sqft (on 1.17 acres)

379 E Chop Dr, Oak Bluffs, MA 02557

Est. Refi. Payment $21,091/mo*
Refinance Your Home

Home Value

Trulia Estimate
$3.82M
Since last month
Increased$50K (+1.3%)
Since last year
Increased$75K (+2%)
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 +44% in the last 10 years
MonthEstimated value
2026
August 2026$3.8M
July 2026$3.75M
June 2026$3.8M
May 2026$3.76M
April 2026$3.66M
March 2026$3.72M
February 2026$3.65M
January 2026$3.46M
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
78 Winemack St, Oak Bluffs, MA
0.25
Single-Family Home
$2,899,000
10/01/25
4
2
1,889
58 Munroe Ave, Oak Bluffs, MA
0.44
Single-Family Home
$1,875,000
05/13/26
3
2
2,215
311 E Chop Dr, Oak Bluffs, MA
0.25
Single-Family Home
$2,850,000
12/16/25
4
2.5
1,800
13 County Rd, Oak Bluffs, MA
0.42
Single-Family Home
$1,000,000
10/02/25
2
1
1,176
71 Netock Ave, Oak Bluffs, MA
0.23
Single-Family Home
$1,865,000
12/04/25
4
4
2,820
48 Vineyard Avenue Ext, Oak Bluffs, MA
0.72
Single-Family Home
$1,530,000
01/13/26
3
2
2,015
48 Vineyard Ave, Vineyard Haven, MA
0.72
Single-Family Home
$1,530,000
01/13/26
3
2
2,015
114 Park St, Oak Bluffs, MA
0.40
Single-Family Home
$3,067,050
10/22/25
4
3.5
1,872
32 Beach Rd, Oak Bluffs, MA
0.47
Single-Family Home
$975,000
09/30/25
3
2
836
67 New York Ave, Oak Bluffs, MA
0.60
Single-Family Home
$1,400,000
01/30/26
3
2
1,629

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
0.10
$1,295,000
3
2
1,863
For Sale
0 Temahigan Ave & Dover St, Oak Bluffs, MA 02557
0.10
$1,049,000
-
-
-
For Sale
5 & 7 Lyme St, Vineyard Haven, MA 02568
0.13
$1,655,000
5
3
1,999
Off Market
31 Temahigan Avenue, Oak Bluffs, MA 02557
0.14
$2,678,000
4
3.5
2,363
For Sale
35 Temahigan Ave, Oak Bluffs, MA 02557
0.15
$2,304,400
5
3
2,069
Off Market
35 Temahigan Ave #5, Oak Bluffs, MA 02557
0.15
-
-
-
-
Off Market
35 Temahigan Ave #6, Oak Bluffs, MA 02557
0.15
-
-
-
-
Off Market
47 Winemack Street, Oak Bluffs, MA 02557
0.20
$1,199,000
3
2
1,302
For Sale
312 E Chop Drive, Vineyard Haven, MA 02568
0.25
$2,195,000
3
2
1,425
For Sale
311 E Chop Dr, Oak Bluffs, MA 02557
0.25
$2,850,000
4
2.5
1,800
Recently Sold
61 Winemack St, Oak Bluffs, MA 02557
0.24
$850,000
2
1
992
For Sale
78 Winemack St, Oak Bluffs, MA 02557
0.25
$2,974,000
4
2
1,889
Off Market

Local Information

  • Map ViewExplore the area around 379 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
1940
Lot Size
1.17 acres
Living Area
2,390 sqft
Price/Sqft
$1,597

About this House

Enjoy the Vineyard as it used to be from this wonderful ocean-front East Chop home. Ideal for families, the large yard lends itself to outdoor entertainment. Enjoy spectacular sunsets from the private beach, memorable meals at the hand crafted mahogany dining table, or simply relax in the hammock. It doesn't get more authentic then this! Once here, you will never want to leave...

Select weeks available in July & August for $6,000/week. Sleeps 11
379 E Chop Dr, Oak Bluffs, MA 02557 is a 3 bedroom, 2 bathroom, 2,390 sqft single-family home built in 1940. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $3,817,600, with a rent estimate of $6,668/month.

Home Details for 379 E Chop Dr

Interior Features

Heating & Cooling
Heating: GasHeating Fuel: Gas
Levels, Entrance, & Accessibility
Stories: 2
Interior Details
Number of Rooms: 5

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: Wood

Property Information

Year Built
Year Built: 1940Year Updated: 1983
Property Type / Style
Property Type: Single Family HomeArchitecture: Old Style

Community

Units in Building: 1

Lot Information

Lot Area: 1.17 acres

Price and Tax history

YearProperty taxTax assessment
2025
$16,020
$3,172,200
Home facts updated by county records

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 379 E Chop Dr

  • What is 379 E Chop Dr estimated to be worth?
    Trulia's estimated value for 379 E Chop Dr in Oak Bluffs, MA is $3,817,600.
  • 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.
  • What are the closest schools to 379 E Chop Dr?
    The closest schools to 379 E Chop Dr in Oak Bluffs, MA are Martha's Vineyard Regional High School (rated 6/10), Oak Bluffs Elementary School (Pre-K/Middle, rated 7/10).
  • How big is the lot at 379 E Chop Dr?
    The lot at 379 E Chop Dr in Oak Bluffs, MA is about 1.2 acres.

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