Choosing the Location that’s Right for You

It might sound elementary, but a good look at a map is the best first step toward mastering the Island’s quirky geography. The three most densely populated towns, Vineyard Haven, Oak Bluffs, and Edgartown, are referred to as “down-Island.” They are home to roughly three-quarters of the Island’s year-round population of 16,500 people. The more rural, agrarian towns of West Tisbury, Chilmark, and Aquinnah are known collectively as “up-Island.”

The easiest way to narrow your home search, according to Alan Schweikert, owner/broker at Ocean Park Realty in Oak Bluffs, is to invest your time before your money. “I always encourage people to look around the Island independently,” Alan says.

Budget often ultimately dictates location, says broker Shakti Reynolds of Wallace & Co. Sotheby’s International Realty in Edgartown and Chilmark. “Lots of people would love to live in Chilmark,” she explains. “But in the $700,000 price range, there may be only one or two houses. You’ll get larger acreage but a lot less house than you would down-Island. It’s a trade-off.”

As for the merits of each town, you’ll find that opinions vary as much as the weather on any given Vineyard day.

Towns at a glance

Vineyard Haven (Tisbury): The Island’s most populated year-round community and main ferry port, its bustling Main Street features a movie theater, restaurants, shops, and galleries – all just a short stroll to live theater, town parks, and a harbor populated with classic wooden boats.

Oak Bluffs: With lively shops, restaurants, and two seasonal movie theaters, Circuit Avenue is where the younger crowd goes to strut their stuff on summer nights. Colorful gingerbread cottages encircle the historic Tabernacle, an open-air venue for community gatherings, and a thriving arts district hosts summer gallery strolls.

Edgartown: The Island’s first English settlement and center of the world’s nineteenth-century whaling industry is home to historic sea captains’ houses and an upscale summer scene. Main and North Water streets offer chic boutiques, lodging, dining, and a two-screen movie theater. Crashing waves at South Beach lure the adventurous.

West Tisbury: Gateway to up-Island, acres of woodland, rich farmland, fields, ponds, and conservation properties form the agricultural heartland of the Island. It’s home to weekly summer farm markets and artisans festivals, as well as the annual Agricultural Fair each August.

Chilmark: Old stone walls, rolling fields, and sweeping water views of the Atlantic remain unchanged, though the town’s sheep-farming legacy has largely been replaced by costly homes on large parcels of land. Menemsha’s fresh seafood markets and sunsets draw hundreds of visitors each summer day.

Aquinnah: Formerly known as Gay Head, the Island’s smallest and most remote town is home to fewer than four hundred year-round residents who treasure its dramatic clay cliffs (a protected national landmark), isolated beaches, and the beauty of 485 acres of Wampanoag tribal land.

Real estate Q&A

Q: What is a buyer’s agent?

A: In the past, real estate professionals were required by law to represent first and foremost the interests of the seller in any real estate transaction, even if they were already working with a potential buyer and were not themselves listing the property for sale.

In 2005, however, Massachusetts became the last state in the U.S. to enact “buyer’s agency” laws to guard against possible conflicts of interest. Today, all agents must disclose up front whether they represent the buyer or seller, or whether they’ll act as a “dual agent” representing both parties in a transaction.

For additional clarity and protection, a prospective buyer and real estate agent may sign an agreement that spells out the particulars. While most licensed real estate agents, including those who list property for sale, may act as dedicated buyer agents, some choose to specialize as “exclusive” buyer agents, professionals who neither list property for sale nor represent a seller’s interest.

Fred Roven, principal broker at Martha’s Vineyard Buyer Agents, has served as a buyer’s broker for twelve years. “I saw potential conflicts and wanted it to be clear who I was representing,” he explains. “People who work with me never have to worry about...whose interest I really have in mind.”

There is typically no extra fee to either buyer or seller when a buyer’s agent is involved in a transaction, Fred explains, since the participating agents are usually compensated for their services from the proceeds of the sale. But because every transaction is unique and the terms of service are negotiable, prospective buyers should establish those parameters with their agents prior to viewing property together.