Real Estate Confidential: The home buyer’s guide to Vineyard Haven

The Captain Dexter House, in-town Vineyard Haven, at 92 Main Street.

Weekly chit-chat about new listings, sales or other insider info on the Martha’s Vineyard real estate market, by Fred Roven, Martha’s Vineyard Buyer Agents

In the current real estate market, with fewer properties available and prices on highly desirable properties going up, downtown Vineyard Haven currently offers the best price and investment opportunity for luxury in-town homes on the Vineyard. I understand the draw of Edgartown, with its stately homes — many of them carefully restored sea captains’ homes, and Oak Bluffs with a wonderful and active harbor and along Sea View Avenue, some of the Island’s most incredible ocean vistas.

According to a new survey from the National Association of Realtors, 53 percent of Americans prefer to live in communities containing houses with small yards but within an easy walking distance of the community’s amenities, rather than living in communities with houses that have large yards but they have to drive to all amenities. A majority of Americans have shown a preference for walkable communities.  

As the main transportation and commercial hub for the entire Island of Martha’s Vineyard, Vineyard Haven is a beautifully preserved town dating back to the mid-1600s that is alive with history and small-scale commerce. “VH” is protected by East Chop and West Chop, and due to this geographical anomaly and its strategic location on shipping routes, the town, also known as Tisbury, was once one of the busiest ports in the world.

The town of Tisbury is home to only about 2,000 year-round residents, with a much greater influx of tourists in the summer. If you’re one of the lucky ones who have the opportunity to buy a home in Tisbury, you’ll be able to experience the scenic beauty of Vineyard Haven, along with its local historic charm and tight-knit community all year round.

Homes for Sale in Vineyard Haven

Vineyard Haven is home to a wide variety of residential properties. There are historic homes on Main and William Streets, as well as cottages and land for sale on Lake Tashmoo, the Lagoon, Vineyard Sound, and West Chop.

The NAR study found buyers either with young children or “empty nesters” are looking for walk to town properties in increasing numbers. That attribute is common to the following properties.  

First is the stately Captain Dexter House (see photo above), a perfect blend of historic charm and modern amenities. Built in 1843 and fully restored to its original grandeur in 2004 with a gourmet kitchen, a private staircase to the third floor master suite with views across Vineyard Haven Harbor to East Chop Lighthouse and, of course, five fireplaces.

Proximity to town and the water. Courtesy Martha’s Vineyard Buyer Agent

Proximity to Ramble Trail preserve, a Lagoon boat access, and a rural setting yet walking distance to town makes the location of this next property (see photo above) ideal for in-town living. The home sits on over 1 acre with 4500 square feet of space on three levels with a peak of the harbor from the third floor.


212 Skiff Ave., Vineyard Haven. Courtesy Martha’s Vineyard Buyer

Another walk to town opportunity is a home that’s perfect for year-round living, a vacation rental income property or a second home and is being offered furnished and essentially “turnkey.” The home has a well designed open floor plan that accommodates today’s casual and active lifestyle and consists of a chef’s kitchen, living and dining area with views of the Lagoon and a great room with fireplace.


Sights to See Around Town

Owen Park, off Main Street in the center of town, dates back to 1911; its beach is a great place to watch the ships come in and get a feel for the pulse of life in Tisbury. The park also has a bandstand and small playground. Other scenic public beaches in the area include Tisbury Town Beach and Lake Tashmoo Town Beach.

The Old Schoolhouse Museum, built in 1828, has served as a carpentry shop, a school, and a Congregational Church. In front of the museum stands the tall white Liberty Pole, commemorating the revolutionary act of three young women who inserted gunpowder into the town’s liberty pole in 1778 and blew it up, to keep it from being used as a spar for a British warship.  The Vineyard Playhouse on Church Street, built in 1833 as a Methodist meeting house, is home to the Island’s only year-round professional theater company.


Nearby Amenities

In addition to its many historic landmarks, Tisbury has many excellent shops, fine restaurants, and small art galleries. The Art Cliff Diner is a classic New England diner serving, among other favorites, pecan pancakes with rum raisins, stuffed French toast, and sweet potato crepes. For something upscale for dinner try La Soffitta Italian Restaurant, or the waterfront dining room at Garde East. And how can you possibly leave Martha’s Vineyard without the famous Black Dog t-shirt for everyone back home?

A complete list of homes for sale in Vineyard Haven can be found at Martha’s Vineyard Real Estate. I would love to get suggestions for future columns that would be of interest to readers.  Please write me at