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

33 E Chop Dr
Oak Bluffs, MA 02557

  • 6 Beds
  • 2 Baths
  • 4,119 sqft (on 0.38 acres)

$5,908,600

Trulia Estimate
as of Aug 19, 2026
Est. Refi. Payment $32,663/mo*
Refinance Your Home

$5,908,600

Trulia Estimate
as of Aug 19, 2026
Est. Refi. Payment $32,663/mo*
Refinance Your Home
6 Beds
2 Baths
4,119 sqft
(on 0.38 acres)

Home Value

Trulia Estimate
$5.91M
Since last month
Decreased$19K (-0.3%)
Since last year
Increased$934K (+18.8%)
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 +118% in the last 10 years
MonthEstimated value
2026
August 2026$5.9M
July 2026$5.92M
June 2026$5.91M
May 2026$5.7M
April 2026$5.53M
March 2026$5.61M
February 2026$5.31M
January 2026$5.08M
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
1 Rowland Ave, Oak Bluffs, MA
0.28
Single-Family Home
$2,025,000
09/30/25
6
3
3,009
14 Chapman Ave, Oak Bluffs, MA
0.12
Single-Family Home
$1,775,000
03/02/26
5
2
1,469
58 Munroe Ave, Oak Bluffs, MA
0.44
Single-Family Home
$1,875,000
05/13/26
3
2
2,215
16 Atlantic Ave, Oak Bluffs, MA
0.56
Single-Family Home
$2,450,000
06/02/26
6
2.5
2,577
48 Brewster Ave, Oak Bluffs, MA
0.43
Single-Family Home
$1,450,000
09/12/25
5
3
3,352
11 John Wesley Ave, Oak Bluffs, MA
0.19
Single-Family Home
$1,475,000
10/10/25
4
1.5
1,304
23 Laurel Ave, Oak Bluffs, MA
0.19
Single-Family Home
$1,300,000
12/18/25
4
2
1,248
22 Greenleaf Ave, Oak Bluffs, MA
0.31
Single-Family Home
$2,100,000
11/07/25
3
2
1,608
67 New York Ave, Oak Bluffs, MA
0.32
Single-Family Home
$1,400,000
01/30/26
3
2
1,629
34 Massasoit Ave, Oak Bluffs, MA
0.45
Single-Family Home
$2,000,000
02/11/26
6
3.5
1,616

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
13 Wayland Ave, Oak Bluffs, MA 02557
0.09
$1,600,000
3
1
1,025
Recently Sold
14 Chapman Ave, Oak Bluffs, MA 02557
0.12
$1,775,000
5
2
1,469
Recently Sold
9 E Chop Drive, Oak Bluffs, MA 02557
0.13
$2,158,600
3
2
1,304
Off Market
23 Laurel Ave, Oak Bluffs, MA 02557
0.19
$1,300,000
4
2
1,248
Recently Sold
11 John Wesley Ave, Oak Bluffs, MA 02557
0.19
$1,510,400
4
1.5
1,304
Off Market
17 John Wesley Ave, Oak Bluffs, MA 02557
0.19
$1,650,000
3
2.5
1,406
For Sale
35 New York Ave, Oak Bluffs, MA 02557
0.23
$3,050,000
7
5
3,880
Recently Sold
91 Dukes County Avenue, Oak Bluffs, MA 02557
0.22
$1,002,400
1
1.5
1,107
Off Market
9 Wendall Ave, Oak Bluffs, MA 02557
0.22
$1,147,300
2
1
1,040
Off Market
23 Circuit Avenue Extension, Oak Bluffs, MA 02557
0.20
$2,450,000
3
1
-
Recently Sold
25 Simpson Ave, Oak Bluffs, MA 02557
0.26
$1,364,100
3
2
1,151
Off Market
8 Circuit Avenue Ext #14, Oak Bluffs, MA 02557
0.23
$522,200
Studio
1
366
Off Market

Local Information

  • Map ViewExplore the area around 33 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
1915
Lot Size
0.38 acres
Living Area
4,119 sqft
Price/Sqft
$1,434

About this House

This single-family home is located at 33 E Chop Dr, Oak Bluffs, MA. 33 E Chop Dr is in Oak Bluffs, MA and in ZIP code 02557. This property has 6 bedrooms, 2 bathrooms and approximately 4,119 sqft of floor space. This property has a lot size of 0.38 acres and was built in 1915.
33 E Chop Dr, Oak Bluffs, MA 02557 is a 6 bedroom, 2 bathroom, 4,119 sqft single-family home built in 1915. It is currently off market. The Trulia Estimate is $5,908,600, with a rent estimate of $7,061/month.

Home Details for 33 E Chop Dr

Interior Features

Heating & Cooling
Heating: OilHeating Fuel: Oil
Levels, Entrance, & Accessibility
Stories: 2
Interior Details
Number of Rooms: 11

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: WoodFoundation Type: Crawl Raised

Property Information

Year Built
Year Built: 1915Year Updated: 2005
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Community

Units in Building: 1

Lot Information

Lot Area: 0.38 acres

Price and Tax history

YearProperty taxTax assessment
2025
$24,019
$4,756,200
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 33 E Chop Dr

  • What is 33 E Chop Dr estimated to be worth?
    Trulia's estimated value for 33 E Chop Dr in Oak Bluffs, MA is $5,908,600.
  • 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 33 E Chop Dr?
    The closest schools to 33 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 33 E Chop Dr?
    The lot at 33 E Chop Dr in Oak Bluffs, MA is about 0.38 acres (16,552 sq ft).

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