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

239 E Chop Dr
Oak Bluffs, MA 02557

  • 8 Beds
  • 5 Baths
  • 3,618 sqft (on 0.85 acres)

$9,116,800

Trulia Estimate
as of May 20, 2026
Est. Refi. Payment $50,166/mo*

$9,116,800

Trulia Estimate
as of May 20, 2026
Est. Refi. Payment $50,166/mo*
8 Beds
5 Baths
3,618 sqft
(on 0.85 acres)

Local Information

Map showing home location
© Google
-- mins to
Commute Destination

Description

Classic 1800's shingle style with quite incredible, panoramic views over Nantucket Sound to Cape Cod...located on a high point of East Chop, near the lighthouse and offering over 175' of waterfront...stone steps to the water and dock potential exists.. Original oak paneling, staircases, fireplaces....there has been no corruption of the authentic detail...nearly 4,000sf on 3 full floors with multiple living spaces, high ceilings, large windows... An historical masterpiece, in 3rd generation ownership, period photos are available to provide new owner with original exterior architecture to re-capture the elegance of another era.
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources.

Home Highlights

Parking
No Info
Outdoor
Porch, Patio, Deck
A/C
Heating only
HOA
None
Price/Sqft
No Info
Listed
No Info

Home Details for 239 E Chop Dr

Interior Features

Heating & Cooling
Heating: Forced Air, ElectricHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 3Floors: Hardwood
Interior Details
Number of Rooms: 12Types of Rooms: Family Room, Office
Appliances & Utilities
DishwasherDryerRefrigeratorWasher
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: Shake ShingleDeckExterior: WoodLawnPatioPorch
Parking & Garage
Parking Spaces: 2

Property Information

Year Built
Year Built: 1900Year Updated: 2020
Property Type / Style
Property Type: Single Family HomeArchitecture: Victorian

Community

Units in Building: 1

Lot Information

Lot Area: 0.85 acres

Price History for 239 E Chop Dr

DatePriceEventSource
10/18/2011$2,400,000Sold
LINK #21261
10/07/2011$2,499,000Listed For SaleAgent Provided
10/19/2010$2,750,000ListingRemovedAgent Provided
05/05/2010$2,750,000PriceChange
Agent Provided
02/13/2010$3,500,000Listed For SaleAgent Provided
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Property Tax and Assessment

Year2025
Tax$45,575
Assessment$9,024,700
Home facts updated by county records

Comparable Sales for 239 E Chop Dr

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
0.17
Single-Family Home
$3,067,050
10/22/25
4
3.5
1,872
0.38
Single-Family Home
$2,899,000
10/01/25
4
2
1,889
0.36
Single-Family Home
$1,450,000
09/12/25
5
3
3,352
0.33
Single-Family Home
$2,850,000
12/16/25
4
2.5
1,800
0.60
Single-Family Home
$1,865,000
12/04/25
4
4
2,820
0.92
Single-Family Home
$2,025,000
09/30/25
6
3
3,009
0.63
Single-Family Home
$1,475,000
10/10/25
4
1.5
1,304
1.70
Single-Family Home
$3,925,000
09/24/25
8
4.5
3,954
0.82
Single-Family Home
$1,775,000
03/02/26
5
2
1,469
1.39
Single-Family Home
$1,699,000
06/20/25
4
4.5
2,954

Assigned Schools

These are the assigned schools for 239 E Chop Dr.
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

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.
  • P5j4f84ncw
    "Local people, well known community,quite,hard working people,solid business,good schools,hospitality,new opportunities,security and safety place to leave. "
  • 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 "
  • Trulia User
    "Oak Bluffs is a charming town with a bustling summer harbor and lovely shopping district. It’s a beautiful place to live. "
  • Jrheneeb
    "I love it here. It’s beautiful and the people are amazing. It’s a great place To come relax and unwind. "
  • Kayceesmith27
    "I take the bus to and from work . Car for longer distances. Boat to get to the main land which is 45min ride."
  • 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."
  • tkurian
    "I own a property in Oak Bluffs"
  • 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. "
  • Island R. E.
    "This is a lovely and desirable area close to town and everything the island has to offer."

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Apartments for Rent

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Homes for sale near 239 E Chop Dr

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Off Market Homes Near 239 E Chop Dr

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Homes for rent near 239 E Chop Dr

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239 E Chop Dr, Oak Bluffs, MA 02557 is a 8 bedroom, 5 bathroom, 3,618 sqft single-family home built in 1900. This property is not currently available for sale. 239 E Chop Dr was last sold on Oct 18, 2011 for $2,400,000. The current Trulia Estimate for 239 E Chop Dr is $9,116,800.