Big Bluff: $12.4M Martha's Vineyard Waterfront Compound Sets Oak Bluffs Record

A newly constructed Colonial-style shingle home named "Big Bluff" has been listed for $12.4 million, establishing a new benchmark as the most expensive property for sale in Oak Bluffs, Martha’s Vineyard. The 8,560-square-foot waterfront mansion, a complete rebuild that pays homage to the original 1928 structure, offers eight bedrooms, nine bathrooms, and sweeping views of the Vineyard Sound. Based on current construction costs, rebuilding a comparable property would likely exceed $15 million, positioning this listing as a significant opportunity in the premium island real estate market.

What Is the History and Location of This Oak Bluffs Property?

Located on the northernmost tip of Oak Bluffs, the property is just a ten-minute walk from the ferry terminal, providing access to Nantucket, Cape Cod, and mainland Massachusetts. The current owners, a commercial real estate brokerage founder and his wife, purchased the land in 2015 for $2.156 million. The original 88-year-old house was determined to be a candidate for a gut rehabilitation, a process involving stripping a structure down to its frame and rebuilding the interior. However, a cost-assessment revealed that a full teardown and rebuild was more financially viable than a renovation. The old house was demolished in 2016, and the new, larger home was completed in 2018.

How Does the Design Honor the Home's Original Character?

Working with architect Mark Hutker and builder J.G. Early, the owners adhered to a traditional Colonial design—an architectural style characterized by symmetry and classical elements—while significantly expanding the living space. A key objective was to preserve the property's history. Salvaged elements from the original house were thoughtfully integrated, including several sinks, fieldstone used to construct a dual-sided fireplace, and original shutters repurposed in a bunk room. The home's name, "Big Bluff," was also retained as a nod to its long-standing presence.

What Are the Key Features and Amenities of the Home?

The interior is bright and airy, featuring beamed ceilings and wood floors throughout. The floor plan includes two primary suites, with the second-story suite serving as the main retreat complete with two dressing rooms, a fireplace, and two balconies, one featuring an outdoor shower. In total, the property boasts three outdoor showers. The main level's great room flows into a screened, three-season porch that features one side of the dual-sided fieldstone fireplace. The home's front porch overlooks the Vineyard Sound, and while there is no private beach, one is accessible within walking distance. A significant advantage is that East Chop Drive, which runs in front of the property, is restricted to pedestrians and cyclists, ensuring minimal traffic noise.

For prospective buyers in the premium Martha's Vineyard market, this property represents a unique combination of new construction quality, historical charm, and an unparalleled waterfront location. The $12.4 million price point reflects not only the custom build and high-end finishes but also the scarcity of such large, well-positioned parcels in Oak Bluffs.