233 E Chop Dr, Oak Bluffs, MA 02557
Property image
Property image
FOR SALE
0.46 ACRES

$7,550,000

  • 6 Beds
  • 4 Baths
  • 2,522 sqft (on 0.46 acres)

233 E Chop Dr, Oak Bluffs, MA 02557

Est. Mortgage $41,637/mo*
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Home Highlights

Price/Sqft
$2,994
Listed
46 days ago
Climate Control
Electric Heating

Local Information

  • Map ViewExplore the area around 233 E Chop Dr.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

About this House

Perched high above the East Chop bluffs beside the historic lighthouse, this exceptional waterfront estate offers timeless character, breathtaking views, and an unmatched coastal setting. The main residence has beautifully preserved much of its original charm and features a gracious living room with a fireplace, a sun-filled sunroom, and a wraparound covered porch designed to take in the spectacular surroundings. The main house offers five bedrooms and three-and-a-half baths, while a detached two-car garage includes a private one-bedroom apartment above, ideal for guests or extended family. Nearly every room captures sweeping views of Vineyard Sound, where passing boats, ever-changing seascapes, and unforgettable sunsets create a remarkable backdrop. The beautifully landscaped grounds feature expansive lawns stretching to the edge of the bluffs, providing both privacy and dramatic scenery. Completing this rare offering are private steps to the shoreline, a deep-water pier, and a private mooring, an extraordinary opportunity to enjoy one of Martha’s Vineyard’s most coveted waterfront locations.
Last check for updates: 1 day ago
Listing courtesy of Gerrett Conover
Landvest MV
Source: LINK, MLS#44725
Also Listed on LINK.

Home Details for 233 E Chop Dr

Interior Features

Interior Details
Number of Rooms: 7
Beds & Baths
Number of Bedrooms: 6Main Level Bedrooms: 1Number of Bathrooms: 5Number of Bathrooms (full): 3Number of Bathrooms (half): 2
Dimensions and Layout
Living Area: 2522 Square Feet
Appliances & Utilities
Utilities: CblAppliances: Stove: Yes, Washer: Yes
Heating & Cooling
Heating: ElectricNo CoolingHas HeatingHeating Fuel: Electric
Fireplace & Spa
Fireplace: Yes - 1 - gas
Windows, Doors, Floors & Walls
Flooring: Softwood
Levels, Entrance, & Accessibility
Floors: Softwood
View
Has a ViewView: Res

Exterior Features

Exterior Home Features
Other Structures: 2-car garage with a bedroom, sitting area, full bath and kitchenette aboveExterior: WViews, Deck, Garden, Porch, PvtBchFoundation: Poured concreteGarden
Parking & Garage
No CarportNo GarageNo Attached GarageParking: Yes, driveway parking
Frontage
WaterfrontWaterfront: WaterfrontFrontage Type: WaterfrontOn Waterfront
Water & Sewer
Sewer: Septic Tank

Days on Market

Days on Market: 46

Property Information

Year Built
Year Built: 1872
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family Residence

Price & Status

Price
List Price: $7,550,000Price Per Sqft: $2,994

Active Status

MLS Status: A

Location

Direction & Address
City: Oak Bluffs

Agent Information

Listing Agent
Listing ID: 44725

Building

Building Area
Building Area: 2522 Square Feet

Lot Information

Lot Area: 0.46 acres

Offer

Listing Agreement Type: E

Miscellaneous

Mls Number: 44725

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

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

Home Value

Trulia Estimate
$6.92M
Since last month
Decreased$122K (-1.7%)
Since last year
Increased$2M (+35.5%)
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 +184% in the last 10 years
MonthEstimated value
2026
August 2026$6.91M
July 2026$7.03M
June 2026$5.23M
May 2026$5.16M
April 2026$4.97M
March 2026$5.24M
February 2026$5.11M
January 2026$4.95M
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
16 Atlantic Ave, Oak Bluffs, MA
0.24
Single-Family Home
$2,450,000
06/02/26
6
2.5
2,577
114 Park St, Oak Bluffs, MA
0.17
Single-Family Home
$3,067,050
10/22/25
4
3.5
1,872
311 E Chop Dr, Oak Bluffs, MA
0.33
Single-Family Home
$2,850,000
12/16/25
4
2.5
1,800
48 Brewster Ave, Oak Bluffs, MA
0.34
Single-Family Home
$1,450,000
09/12/25
5
3
3,352
58 Munroe Ave, Oak Bluffs, MA
0.42
Single-Family Home
$1,875,000
05/13/26
3
2
2,215
78 Winemack St, Oak Bluffs, MA
0.37
Single-Family Home
$2,899,000
10/01/25
4
2
1,889
71 Netock Ave, Oak Bluffs, MA
0.59
Single-Family Home
$1,865,000
12/04/25
4
4
2,820
1 Rowland Ave, Oak Bluffs, MA
0.90
Single-Family Home
$2,025,000
09/30/25
6
3
3,009
11 John Wesley Ave, Oak Bluffs, MA
0.60
Single-Family Home
$1,475,000
10/10/25
4
1.5
1,304
14 Chapman Ave, Oak Bluffs, MA
0.80
Single-Family Home
$1,775,000
03/02/26
5
2
1,469

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
222 E Chop Dr, Oak Bluffs, MA 02557
0.05
$4,883,000
6
7
4,500
Off Market
114 Park St, Oak Bluffs, MA 02557
0.17
$3,139,100
4
3.5
1,872
Off Market
4 Pall Mall, Oak Bluffs, MA 02557
0.17
$3,107,300
4
3.5
1,900
Off Market
67 Madison Ave, Oak Bluffs, MA 02557
0.21
$1,920,200
4
2
1,693
Off Market
283 E Chop Dr, Oak Bluffs, MA 02557
0.20
$3,587,800
4
2.5
2,456
Off Market
16 Atlantic Ave, Oak Bluffs, MA 02557
0.24
$2,450,000
6
2.5
2,577
Recently Sold
33 Clay Ave, Oak Bluffs, MA 02557
0.27
$1,717,400
3
3
2,408
Off Market
90 Munroe Ave, Vineyard Haven, MA 02568
0.28
$4,603,500
7
6.5
3,698
Off Market
312 E Chop Drive, Vineyard Haven, MA 02568
0.33
$2,195,000
3
2
1,425
For Sale
311 E Chop Dr, Oak Bluffs, MA 02557
0.33
$2,850,000
4
2.5
1,800
Recently Sold
48 Brewster Ave, Oak Bluffs, MA 02557
0.34
$2,186,700
5
3
3,352
Off Market

Price and Tax history

DateEventPrice
Jul 14, 2026
Source: LINK #44725
Listed For Sale
$7,550,000

LGBTQ Local Legal Protections

Gerrett Conover, Landvest MV
© 2026 LINK, All Rights Reserved. Data last updated: 2026-08-28 12:37:49 PDT. Some properties may no longer be for sale if they have gone under contract, have sold, or are no longer being offered for sale since the last update.

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Frequently asked questions about 233 E Chop Dr

  • What is the estimated monthly payment for 233 E Chop Dr?
    Based on a $7,550,000 list price with 20% down at today's rates, the estimated monthly payment for 233 E Chop Dr in Oak Bluffs, MA is approximately $42,912 (about $39,691 principal & interest, $3,146 property taxes, and $75 homeowner's insurance). This is an estimate. Actual payment depends on your loan terms.
  • What do residents say about Oak Bluffs?
    Residents describe Oak Bluffs, MA as dog-friendly, well-kept, and walkable to restaurants. See homes for sale in Oak Bluffs, MA.
  • What are the closest schools to 233 E Chop Dr?
    The closest schools to 233 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).
  • What is 233 E Chop Dr estimated to be worth?
    Trulia's estimated value for 233 E Chop Dr in Oak Bluffs, MA is $6,915,300.
  • How big is the lot at 233 E Chop Dr?
    The lot at 233 E Chop Dr in Oak Bluffs, MA is about 0.46 acres (20,037 sq ft).
  • Does 233 E Chop Dr have a garage?
    Yes, 233 E Chop Dr in Oak Bluffs, MA has a garage.
233 E Chop Dr, Oak Bluffs, MA 02557 is a 6 bedroom, 5 bathroom, 2,522 sqft single-family home built in 1872. This property is currently available for sale and was listed by LINK on Jul 14, 2026. The MLS # for this home is MLS# 44725.