283 East Chop Drive, Oak Bluffs, MA 02557
Property image
Property image
OFF MARKET

$3,189,000

Trulia Estimate
  • 4 Beds
  • 2.5 Baths
  • 2,456 sqft (on 0.31 acres)

283 East Chop Drive, Oak Bluffs, MA 02557

Est. Refi. Payment $17,630/mo*
Refinance Your Home
Currently Off Market - Sold Jul 31, 2015 for $1,544,250

Home Value

Trulia Estimate
$3.19M
Since last month
Decreased$14K (-0.4%)
Since last year
Increased$295K (+10.2%)
Since last sale
Increased$2M (+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 +21% in the last 10 years
MonthEstimated value
2026
August 2026$3.19M
August 2026$3.18M
July 2026$3.2M
June 2026$3.34M
May 2026$3.29M
April 2026$3.36M
March 2026$3.2M
February 2026$3.34M
January 2026$2.93M
2025
2024

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
311 E Chop Dr, Oak Bluffs, MA
0.13
Single-Family Home
$2,850,000
12/16/25
4
2.5
1,800
114 Park St, Oak Bluffs, MA
0.13
Single-Family Home
$3,067,050
10/22/25
4
3.5
1,872
58 Munroe Ave, Oak Bluffs, MA
0.43
Single-Family Home
$1,875,000
05/13/26
3
2
2,215
48 Brewster Ave, Oak Bluffs, MA
0.44
Single-Family Home
$1,450,000
09/12/25
5
3
3,352
78 Winemack St, Oak Bluffs, MA
0.27
Single-Family Home
$2,899,000
10/01/25
4
2
1,889
16 Atlantic Ave, Oak Bluffs, MA
0.40
Single-Family Home
$2,450,000
06/02/26
6
2.5
2,577
71 Netock Ave, Oak Bluffs, MA
0.48
Single-Family Home
$1,865,000
12/04/25
4
4
2,820
11 John Wesley Ave, Oak Bluffs, MA
0.66
Single-Family Home
$1,475,000
10/10/25
4
1.5
1,304
1 Rowland Ave, Oak Bluffs, MA
0.92
Single-Family Home
$2,025,000
09/30/25
6
3
3,009
67 New York Ave, Oak Bluffs, MA
0.72
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
311 E Chop Dr, Oak Bluffs, MA 02557
0.13
$2,850,000
4
2.5
1,800
Recently Sold
312 E Chop Drive, Vineyard Haven, MA 02568
0.14
$2,195,000
3
2
1,425
For Sale
4 Pall Mall, Oak Bluffs, MA 02557
0.13
$3,163,800
4
3.5
1,900
Off Market
114 Park St, Oak Bluffs, MA 02557
0.13
$3,139,100
4
3.5
1,872
Off Market
233 E Chop Dr, Oak Bluffs, MA 02557
0.21
$7,550,000
6
4
2,522
For Sale
222 E Chop Dr, Oak Bluffs, MA 02557
0.23
$4,789,200
6
7
4,500
Off Market
78 Winemack St, Oak Bluffs, MA 02557
0.27
$2,974,000
4
2
1,889
Off Market
33 Clay Ave, Oak Bluffs, MA 02557
0.27
$1,717,400
3
3
2,408
Off Market
67 Madison Ave, Oak Bluffs, MA 02557
0.29
$1,920,200
4
2
1,693
Off Market
90 Munroe Ave, Vineyard Haven, MA 02568
0.33
$4,603,500
7
6.5
3,698
Off Market

Local Information

  • Map ViewExplore the area around 283 East Chop Drive.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1900
Lot Size
0.31 acres
Living Area
2,456 sqft
Price/Sqft
$1,298

About this House

Absolutely stunning waterfront home set right on the water's edge in East Chop. Enjoy immediate views of boats in Vineyard Haven harbor, spectacular sunsets over Vineyard Sound and the Elizabeth Islands, and dropping off your back deck to refresh at your private waterfront. The spacious, beachy home has been well-maintained and upgraded through the years and includes beautiful water views from nearly every room. Hardwood floors and high ceilings throughout. Located within one mile to East Chop Beach Club, East Chop Yacht Club, and East Chop Tennis Club. A definite must see for waterfront in Oak Bluffs.
283 East Chop Drive, Oak Bluffs, MA 02557 is a 4 bedroom, 3 bathroom, 2,456 sqft single-family home built in 1900. It last sold for $1,544,250 on Jul 31, 2015 (12% below the $1,750,000 asking price). This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $3,189,000, with a rent estimate of $7,734/month.
Last check for updates: about 1 hour ago
Listed by Alyssa M Halisky, (508) 525-2584
Wallace & Co. Sotheby's International Realty
Bought with: Hope E O'Brien, Anchor Realty of MV
Source: CCIMLS, MLS#21509318

Home Details for 283 East Chop Drive

Interior Features

Interior Details
Number of Rooms: 8
Beds & Baths
Number of Bedrooms: 4Number of Bathrooms: 3Number of Bathrooms (full): 2Number of Bathrooms (half): 1
Appliances & Utilities
Appliances: Other
Heating & Cooling
Heating: OtherHas Heating
Fireplace & Spa
Number of Fireplaces: 1
Windows, Doors, Floors & Walls
Flooring: Wood
Levels, Entrance, & Accessibility
Stories: 2Floors: Wood

Exterior Features

Exterior Home Features
Roof: AsphaltPatio / Porch: Deck, Porch
Parking & Garage
No GarageNo Attached GarageParking: Off Street
Frontage
WaterfrontWaterfront: Salt, Waterview, WaterfrontOn Waterfront

Days on Market

Cumulative Days on Market: 329

Property Information

Year Built
Year Built: 1900
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family Residence
Building
Construction Materials: Shingle SidingDoes Not Include Home Warranty
Property Information
Parcel Number: 1100

Price & Status

Price
List Price: $1,750,000

Active Status

MLS Status: Closed

Location

Direction & Address
City: Oak Bluffs

Building

Building Area
Building Area: 2456 Square Feet

HOA

No HOA

Lot Information

Lot Area: 0.31 acres

Listing Info

Special Conditions: Standard

Miscellaneous

Mls Number: 21509318Showing Requirements: Appointment Required, Call Listing Agent

Price and Tax history

DateEventPrice
Jul 31, 2015
Source: CCIMLS #21509318
Sold
$1,544,250

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

All data relating to real estate for sale on this page comes from the Broker Reciprocity (BR) of the Cape Cod & Islands Multiple Listing Service, Inc. Detailed information about real estate listings held by brokerage firms other than CC&I Assoc. of REALTORS®, Inc. includes the name of the listing company. Neither the listing company nor CC&I Assoc. of REALTORS®, Inc. shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. The Broker providing this data believes it to be correct, but advises interested parties to confirm any item before relying on it in a purchase decision. This site was last updated 2026-09-02 12:53:15 PDT. All properties are subject to prior sale, changes, or withdrawal. Copyright 2026© Cape Cod & Islands Multiple Listing Service, Inc. All rights reserved.

Frequently asked questions about 283 East Chop Drive

  • What is 283 East Chop Drive estimated to be worth?
    Trulia's estimated value for 283 East Chop Drive in Oak Bluffs, MA is $3,189,000.
  • What is the price history for 283 East Chop Drive?
    283 East Chop Drive in Oak Bluffs, MA last sold for $1,544,250 in July 2015.
  • 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 283 East Chop Drive?
    The lot at 283 East Chop Drive in Oak Bluffs, MA is about 0.31 acres (13,503 sq ft).
  • Does 283 East Chop Drive have parking?
    Yes, 283 East Chop Drive in Oak Bluffs, MA has on-site parking.

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