311 E Chop Dr, Oak Bluffs, MA 02557
Property image
Property image
SOLD
DEC 16, 2025

$2,908,000

Trulia Estimate
  • 4 Beds
  • 2.5 Baths
  • 1,800 sqft (on 0.25 acres)

311 E Chop Dr, Oak Bluffs, MA 02557

Est. Refi. Payment $16,531/mo*
Refinance Your Home
Currently Off Market - Sold Dec 16, 2025 for $2,850,000 (5% below list price)

Home Value

Trulia Estimate
$2.91M
Since last month
Increased$22K (+0.8%)
Since last year
Increased$191K (+7%)
Since last sale
Increased$66K (+2.3%)
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 +36% in the last 10 years
MonthEstimated value
2026
August 2026$2.92M
August 2026$2.91M
July 2026$2.89M
June 2026$2.89M
May 2026$2.9M
April 2026$2.87M
March 2026$2.89M
February 2026$2.88M
January 2026$2.86M
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
114 Park St, Oak Bluffs, MA
0.21
Single-Family Home
$3,067,050
10/22/25
4
3.5
1,872
78 Winemack St, Oak Bluffs, MA
0.23
Single-Family Home
$2,899,000
10/01/25
4
2
1,889
71 Netock Ave, Oak Bluffs, MA
0.39
Single-Family Home
$1,865,000
12/04/25
4
4
2,820
58 Munroe Ave, Oak Bluffs, MA
0.43
Single-Family Home
$1,875,000
05/13/26
3
2
2,215
16 Atlantic Ave, Oak Bluffs, MA
0.49
Single-Family Home
$2,450,000
06/02/26
6
2.5
2,577
11 John Wesley Ave, Oak Bluffs, MA
0.68
Single-Family Home
$1,475,000
10/10/25
4
1.5
1,304
67 New York Ave, Oak Bluffs, MA
0.69
Single-Family Home
$1,400,000
01/30/26
3
2
1,629
48 Vineyard Avenue Ext, Oak Bluffs, MA
0.96
Single-Family Home
$1,530,000
01/13/26
3
2
2,015
48 Vineyard Ave, Vineyard Haven, MA
0.96
Single-Family Home
$1,530,000
01/13/26
3
2
2,015

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
312 E Chop Drive, Vineyard Haven, MA 02568
0.02
$2,195,000
3
2
1,425
For Sale
283 East Chop Drive, Oak Bluffs, MA 02557
0.13
$3,189,000
4
2.5
2,456
Off Market
283 E Chop Dr, Oak Bluffs, MA 02557
0.14
$3,620,500
4
2.5
2,456
Off Market
4 Pall Mall, Oak Bluffs, MA 02557
0.21
$3,163,800
4
3.5
1,900
Off Market
114 Park St, Oak Bluffs, MA 02557
0.21
$3,139,100
4
3.5
1,872
Off Market
78 Winemack St, Oak Bluffs, MA 02557
0.23
$2,974,000
4
2
1,889
Off Market
51 Winemack St #&-0, Oak Bluffs, MA 02557
0.28
$2,045,000
2
2
1,048
For Sale
3 Troy Street, Oak Bluffs, MA 02557
0.30
$1,295,000
3
2
1,863
For Sale
33 Clay Ave, Oak Bluffs, MA 02557
0.30
$1,717,400
3
3
2,408
Off Market
47 Winemack Street, Oak Bluffs, MA 02557
0.30
$1,100,000
3
2
1,302
For Sale
233 E Chop Dr, Oak Bluffs, MA 02557
0.33
$6,900,000
6
4
2,522
For Sale

Local Information

  • Map ViewExplore the area around 311 E Chop Dr.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1900
0.25 acre lot
1,800 sqft
$1,583/sqft
Garage

About this House

Arrive by land or sea to 311 East Chop Drive, a truly rare offering that combines panoramic water views in nearly every direction. Perfectly positioned between Vineyard Haven Harbor, Vineyard Sound, and Crystal Lake, this iconic East Chop residence—known as “The Sandpiper”—offers 100 feet of private beach, a 125-foot dock, and an additional mooring, all just minutes from the restaurants, shops and attractions of Oak Bluffs and Vineyard Haven. Completely renovated from top to bottom, this two-story waterfront haven blends the charm of its 125-year history with the modern conveniences of today. Expansive glass sliders and bay windows capture the ever-changing seascape, while hardwood floors, whitewashed beadboard, and a beach-stone fireplace infuse timeless coastal character. With four bedrooms and two and a half baths, the home offers generous space for family and friends. The fully appointed kitchen with breakfast bar invites casual dining and easy gatherings, flowing effortlessly to multiple outdoor spaces designed for relaxation and entertaining. A fenced beach-stone patio and brick terraces lead to a car barn with expansion potential, an outdoor shower, and seaside gardens blooming with rosa rugosa and native grasses. Whether arriving by boat or by car, 311 East Chop Drive offers an unparalleled combination of privacy, convenience, and coastal beauty—an exceptional Vineyard retreat where every day feels like a seaside escape.
311 E Chop Dr, Oak Bluffs, MA 02557 is a 4 bedroom, 3 bathroom, 1,800 sqft single-family home built in 1900. It last sold for $2,850,000 on Dec 16, 2025 (5% below the $3,000,000 asking price). This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $2,908,000, with a rent estimate of $7,864/month.
Last check for updates: about 17 hours ago
Listed by Dawn Bellante Holand, 508.524.1601
Sandpiper Realty
Bought with: Dawn Bellante Holand, 508.524.1601, Sandpiper Realty
Source: LINK, MLS#43858

Home Details for 311 E Chop Dr

Interior Features

Interior Details
Basement: Crawl SpaceNumber of Rooms: 8
Beds & Baths
Number of Bedrooms: 4Main Level Bedrooms: 2Number of Bathrooms: 3Number of Bathrooms (full): 2Number of Bathrooms (half): 1
Dimensions and Layout
Living Area: 1800 Square Feet
Appliances & Utilities
Utilities: CblAppliances: Stove: Yes, Washer: Yes
Heating & Cooling
Heating: OtherNo CoolingHas Heating
Fireplace & Spa
Fireplace: Beach Stone Fireplace with Wood Stove Insert
Windows, Doors, Floors & Walls
Flooring: Wood, Tile, and Carpet
Levels, Entrance, & Accessibility
Floors: Wood, Tile, And Carpet
View
Has a ViewView: Harbor

Exterior Features

Exterior Home Features
Exterior: PvtBch, Porch, PatioFoundation: Block
Parking & Garage
No CarportHas a GarageNo Attached GarageParking: Garage + Driveway
Frontage
WaterfrontWaterfront: Ocean FrontFrontage Type: OceanfrontOn Waterfront
Water & Sewer
Sewer: Septic Tank

Property Information

Year Built
Year Built: 1900Year Renovated: 1989
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family Residence
Property Information
Parcel Number: 0

Price & Status

Price
List Price: $3,000,000Price Per Sqft: $1,583/sqft

Active Status

MLS Status: S

Location

Direction & Address
City: Oak Bluffs

Building

Building Area
Building Area: 1800 Square Feet

Lot Information

Lot Area: 10890 sqft

Offer

Listing Agreement Type: E

Rental Terms, Policies & Fees

Furnished

Miscellaneous

BasementMls Number: 43858Water ViewWater View: Harbor

Price and Tax history

DateEventPrice
Dec 16, 2025
Source: LINK #43858
Sold
$2,850,000
Nov 25, 2025
Source: Martha's Vineyard MLS #32500356
Pending
$3,000,000
Nov 6, 2025
Source: Martha's Vineyard MLS #32500356
Contingent
$3,000,000
Oct 18, 2025
Source: Martha's Vineyard MLS #32500356
Listed For Sale
$3,000,000
Oct 8, 2025
Source: LINK #43084
ListingRemoved
$3,000,000

Market trends in Oak Bluffs

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
72
14MoM

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

© 2026 LINK, All Rights Reserved. Data last updated: 2026-09-12 15:57:40 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.

Frequently asked questions about 311 E Chop Dr

  • What is 311 E Chop Dr estimated to be worth?
    Trulia's estimated value for 311 E Chop Dr in Oak Bluffs, MA is $2,908,000.
  • What is the price history for 311 E Chop Dr?
    311 E Chop Dr in Oak Bluffs, MA last sold for $2,850,000 in December 2025.
  • Is Oak Bluffs a buyer's or seller's market?
    Oak Bluffs is currently a seller'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 311 E Chop Dr?
    The lot at 311 E Chop Dr in Oak Bluffs, MA is about 0.25 acres (10,890 sq ft).
  • Does 311 E Chop Dr have a garage?
    Yes, 311 E Chop Dr in Oak Bluffs, MA has a garage.

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