Real Estate Confidential: The Chops of Martha’s Vineyard


Real Estate Confidential is a biweekly chit-chat about new listings, sales, or other insider information on the Martha’s Vineyard Real Estate market, presented by Fred Roven, owner/broker of Martha’s Vineyard Buyer Agents. It appears every other Friday in The Minute.

A chop is defined as the entrance to a harbor; in the case of East and West Chop, this is the entrance from Vineyard Sound to Vineyard Haven harbor on through the drawbridge to the Lagoon. This week, there are homes of all types and price ranges. From a three-bedroom, two-bath contemporary on the outer border of West Chop priced at $995,000, to a waterfront commercial investment property on East Chop that includes multiple boat slips, docks, and apartments priced at $11,000,000.

East Chop, also known as the Vineyard Highlands, is a residential area on the north end of the Island. It is a peninsula that features the high, prominent bluffs that gave Oak Bluffs its name. A lighthouse, East Chop Light, stands at the north end of the chop on Telegraph Hill. East Chop became a popular summer resort in the late 19th century with regular ferry traffic from the mainland, and a horse railroad connected it to the village of Cottage City, later renamed Oak Bluffs.

Across Vineyard Haven harbor is West Chop, a residential area located in Vineyard Haven on the north end of the Island. It is a peninsula surrounded on the north and west by Vineyard Sound and on the east by Vineyard Haven harbor. A lighthouse, West Chop Light, stands at the north end of the chop. West Chop is about a mile stroll to town, with its many restaurants, movies, shopping, and parkland. The West Chop historic district represents a well-preserved, planned, summer resort community of the late 19th century, with many rambling waterfront mansions with spectacular views.

The contemporary home at 73 Leonard Circle on the outskirts of West Chop is perfect for residents and vacationers alike. It has been thoughtfully renovated over the years, and it’s the perfect space for entertaining guests, hosting barbecues, or simply enjoying a quiet cup of coffee while soaking in the serene surroundings. The fully fenced-in yard provides the ideal backdrop for outdoor activities, offering both privacy and security. The property has potential for up to four bedrooms, it’s a short distance to the town beach, and it has easy access to downtown Tisbury shopping and dining.

Built in 1893 and representing one of the classic Grand Dames of West Chop is the waterfront property at 1115 Main Street. A sensitive and well thought-out renovation was completed, honoring all of the home’s character and charm. There are large windows everywhere, with awe-inspiring North Shore sunset views. There are expansive water views from nearly every room in the house, as well as from a wrap-around porch and balcony. The home is within close proximity to the West Chop Club, Mink Meadows Golf Course, and downtown Vineyard Haven.

The East Chop home at 67 Madison Avenue is a vintage, two-story summer home with all the charm of a bygone era. With its screened porch and stone patio, the home is the perfect place to enjoy a quiet setting, and the large lot gives the opportunity for up to six bedrooms. The home is only one block from the East Chop Tennis Club and two blocks from the East Chop Lighthouse and gorgeous bluff views. East Chop is a quintessential, close-knit community only a short distance from the harbor and downtown Oak Bluffs.

From the East Chop home at 15 Mill Square, you will have unparalleled views of Woods Hole and Cape Cod across the Sound, Chappaquiddick, and beyond. In addition, there are active harbor views, ferry crossings, boating of all varieties, and beaching at your fingertips. The home is an elegant version of an oversized farmhouse, and it provides ocean views from every window. An enormous front porch adds living space, holding extra seating, a full dining area, or any number of other configurations. There is a town beach and boat landing close by, and downtown is a short stroll around the harbor.

Click here for a list of other East Chop and West Chop homes.

For more Real Estate Confidentials, click here.