150 E Chop Dr
Oak Bluffs, MA 02557
8 Beds
8 Baths
8,170 sqft (on 0.64 acres)
8 Beds
8 Baths
8,170 sqft
(on 0.64 acres)
We estimate this home will sell faster than 83% nearby.
Local Information
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Description
BIG BLUFF- Recognized for its architectural significance and featured in leading design publications, this home stands as one of the Vineyard’s most notable coastal residences. Set along the prestigious shoreline of East Chop, this estate represents a rare convergence of architectural pedigree, craftsmanship, and irreplaceable setting. Designed by Hutker Architects, built by J.G. Early, and landscape designed by Dan Gordon Landscape Architects, the home reflects a level of design and craftsmanship virtually impossible to replicate today. Originally conceived as a generational estate, the residence pairs exceptional craftsmanship with modern construction designed to withstand decades of coastal exposure. From artisan millwork to landscapes seamlessly integrated into the natural surroundings, every element was purposefully considered. Spanning over 8,000+ square feet with eight bedrooms, the property offers expansive, light-filled living spaces oriented toward sweeping ocean views and effortless indoor-outdoor living. Ideally located just moments from the East Chop Beach Club, East Chop Tennis Club, and East Chop Yacht Club, this home places you at the center of one of the island’s most established and desirable enclaves.
We estimate this home will sell faster than 83% nearby.
Home Highlights
Parking
No Info
Outdoor
No Info
A/C
Heating only
HOA
None
Price/Sqft
$1,089
Listed
2 days ago
Home Details for 150 E Chop Dr
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Interior Details Basement: A thoughtfully designed 1, 498 sq. ft. finished basement offers exceptional additional living space, featuring a dedicated media room, a fully equipped gym area, and a convenient half bath. This level also includes an oversized pantry for ample storage, as well as well-organized utility spaces.Number of Rooms: 16 |
Beds & Baths Number of Bedrooms: 8Main Level Bedrooms: 1Number of Bathrooms: 9Number of Bathrooms (full): 7Number of Bathrooms (half): 2 |
Dimensions and Layout Living Area: 8170 Square Feet |
Appliances & Utilities Utilities: CblAppliances: Stove: THERMADOR, Washer: LG |
Heating & Cooling Heating: Heat PumpNo CoolingHas HeatingHeating Fuel: Heat Pump |
Fireplace & Spa Fireplace: 5 |
Windows, Doors, Floors & Walls Flooring: 3 |
Levels, Entrance, & Accessibility Floors: 3 |
View Has a ViewView: Ocean |
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Exterior Home Features Other Structures: A 576 sq. ft. attached garage offers generous space for vehicles, storage, and seasonal equipment, with convenient direct access to the home for added ease and functionality.Exterior: ScrPorch, Porch, Patio, WViews, GymFoundation: Poured concrete |
Parking & Garage No CarportNo GarageNo Attached GarageParking: Private parking court |
Frontage Frontage Type: NoneNot on Waterfront |
Water & Sewer Sewer: Septic Tank |
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Days on Market: 2 |
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Year Built Year Built: 2018 |
Property Type / Style Property Type: ResidentialProperty Subtype: Single Family Residence |
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Price List Price: $8,900,000Price Per Sqft: $1,089 |
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MLS Status: A |
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Direction & Address City: Oak Bluffs |
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Listing Agent Listing ID: 44397 |
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Building Area Building Area: 8170 Square Feet |
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Lot Area: 0.64 acres |
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Listing Agreement Type: E |
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BasementMls Number: 44397Water ViewWater View: Ocean |
Last check for updates: about 9 hours ago
Listing courtesy of Andrew McElhinney
Compass LLC
Source: LINK, MLS#44397
Also Listed on LINK.
Price History for 150 E Chop Dr
| Date | Price | Event | Source |
|---|---|---|---|
| 05/07/2026 | $8,900,000 | Listed For Sale | LINK #44397 |
| 04/29/2026 | $8,900,000 | ListingRemoved | MLS PIN #73386607 |
| 10/09/2025 | $8,900,000 | PriceChange | MLS PIN #73386607 |
| 07/23/2025 | $9,900,000 | PriceChange | MLS PIN #73386607 |
| 06/05/2025 | $12,400,000 | Listed For Sale | MLS PIN #73386607 |
| 06/02/2025 | $13,200,000 | ListingRemoved | LINK #42039 |
| 03/21/2025 | $13,200,000 | PendingToActive | Martha's Vineyard MLS #32400128 |
| 03/05/2025 | $13,200,000 | Contingent | Martha's Vineyard MLS #32400128 |
| 05/27/2024 | $13,200,000 | Listed For Sale | Martha's Vineyard MLS #32400128 |
| 04/26/2017 | $2,550,000 | ListingRemoved | Agent Provided |
| 03/07/2017 | $2,550,000 | Pending | Agent Provided |
| 03/07/2017 | $2,550,000 | Listed For Sale | Agent Provided |
| 10/23/2015 | $2,695,000 | Sold | CCIMLS #21504982 |
| 07/15/2015 | $2,550,000 | ListingRemoved | Agent Provided |
| 05/26/2015 | $2,550,000 | Listed For Sale | Agent Provided |
| 11/02/2014 | $2,650,000 | ListingRemoved | Agent Provided |
| 06/05/2014 | $2,650,000 | Listed For Sale | Agent Provided |
| 11/02/2013 | $2,875,000 | ListingRemoved | Agent Provided |
| 05/22/2013 | $2,875,000 | Listed For Sale | Agent Provided |
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Property Tax and Assessment
| Year | 2025 |
|---|---|
| Tax | $59,616 |
| Assessment | $11,805,100 |
Home facts updated by county records
Comparable Sales for 150 E Chop Dr
Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
0.16 | Single-Family Home | $1,450,000 | 09/12/25 | 5 | 3 | 3,352 | |
0.39 | Single-Family Home | $3,067,050 | 10/22/25 | 4 | 3.5 | 1,872 | |
0.48 | Single-Family Home | $2,899,000 | 10/01/25 | 4 | 2 | 1,889 | |
0.65 | Single-Family Home | $1,865,000 | 12/04/25 | 4 | 4 | 2,820 | |
0.70 | Single-Family Home | $2,025,000 | 09/30/25 | 6 | 3 | 3,009 | |
0.59 | Single-Family Home | $2,850,000 | 12/16/25 | 4 | 2.5 | 1,800 | |
0.38 | Single-Family Home | $1,475,000 | 10/10/25 | 4 | 1.5 | 1,304 | |
0.56 | Single-Family Home | $1,775,000 | 03/02/26 | 5 | 2 | 1,469 | |
0.94 | Single-Family Home | $2,000,000 | 02/11/26 | 6 | 3.5 | 1,616 | |
0.54 | Single-Family Home | $1,300,000 | 12/18/25 | 4 | 2 | 1,248 |
Assigned Schools
These are the assigned schools for 150 E Chop Dr.
- Oak Bluffs Elementary School
- PK-8
- Public
- 390 Students
7/10GreatSchools RatingParent Rating AverageAn excellent school where students seem to be happy, learning and engaged. You can tell the teachers really care about and truly want the best for their students. The new principal is very energetic, involved and approachable and he seems very well-liked by students, parents and the staff (which is everything).Parent Review6mo ago - Martha's Vineyard Regional High School
- 9-12
- Public
- 703 Students
6/10GreatSchools RatingParent Rating AverageStandards for academic engagement are ON THE FLOOR at this school. The “c1” courses are equivalent to a special ed class in any other school, and an honors class to a typical c1 course. Very, very low expectations for C1 students, often no homework at all, or just one assignment per week, and very little in class work. Many teachers in the school are just blatantly bad at their jobs. The school is not able to address it due to a lack of new teachers, but also because they refuse to train teachers properly. I will admit, many teachers are incredible, but it is unacceptable that the academic standards are so incredibly low and how the administration allows teachers to get by without being able to teach the curriculum during the school year. Specifically, this school and the school system on the island in general is notorious for its awful math program. The school is now having to extend the math period for freshmen because of the amount of failing students (likely more changes to come). The administration has also consistently shown disregard for the opinions of students and families, particularly about the new phone policy. Many valid arguments were simply dismissed or never addressed or answered prior to the establishment of the policy. The administration is also very unaware of what is actually happening (particularly the former principal) in the student body, as a very, very small percentage of students are actually following the policy—the vast majority sticking to the old rule of just not having phones out in class, while the administration continually brags about how well the implementation of the policy has gone. Hopefully as the former principal is now gone some of these issues will be addressed, but it is important to note that there are many issues with this school.Student Review8mo ago 
Check out schools near 150 E Chop Dr.
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
Learn more about our methodology.
LGBTQ Local Legal Protections
LGBTQ Local Legal Protections
Andrew McElhinney, Compass LLC
© 2026 LINK, All Rights Reserved. Data last updated: 2026-05-08 14:38:44 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.
150 E Chop Dr, Oak Bluffs, MA 02557 is a 8 bedroom, 9 bathroom, 8,170 sqft single-family home built in 2018. This property is currently available for sale and was listed by LINK on May 7, 2026. The MLS # for this home is MLS# 44397.