You could say that preserving traditional Nantucket architecture is in Chip Webster's blood.

Webster is the go-to architect if you want to build a home that fits into traditional Nantucket—given the island's strict architectural review guidelines, there is almost no other kind—and it's almost as if fate chose Webster for this role. His forebears were one of the five families that first settled the island some 300 years ago. He's done a lot of roaming around—travelled around the world, spent two years doing film and videos, restored a home in Cambridge—but he finally came home to roost in 1991 because he sensed that Nantucket was going to "catch the recovery wave." At the time, the country was experiencing a recession, but Webster says Nantucket is a leading indicator of the real estate market. 

"In 1991 the island started coming back really strong," he says, which prompted him to move his architectural practice to Nantucket from Cambridge.

Now he leads a double life: the man who knows how to do Nantucket traditional on Nantucket, and the man who travels to do innovative contemporary in places like Aspen, Colorado.

He was in charge of restoring one of Nantucket's prime landmarks, Greater Light, which was built in 1791 to house livestock and later became the 1920s home of Hanna and Gertrude Monaghan, prominent members of that decade's Nantucket artist colony. (The name was taken from Genesis 1:16; the sisters were very religious). The place was a wreck when he started the project, having been uninhabited for a decade. "It is a building that would be impossible to recreate today, given current regulations and requirements," Webster says.

Then there's the other side of his talent. "We do a lot of ski- and beach-vacation homes," he says. (For the record, he lives in a mixed-use building—home, office, and community spaces—just outside Nantucket town.)

But would-be Nantucketers come to Webster because knowing how to do traditional on Nantucket is more than being an architect.

"Working on Nantucket is arguably one of the most restrictive places on the planet," he says, referring to the island's Historic District Commission, established in 1955 to ensure that the island's downtown core would not turn into Malibu-like exercises in vanity architecture. 

This actually began to happen in Madaket in the '70s, architecture that Webster calls "triangular masses." The Board subsequently extended its purview to the entire island—"Even a lunch patio or a trim color has to be approved," says Webster—but he sees its worth. "The downtown core has one of the best collections of pre-Civil-War houses in the country," he says, in a tip of the hat.

"Usually the road to success in architecture is to create a very identifiable style," he says (and one thinks immediately of Gehry or Calatrava).

But Webster is a nuancier: Consistent doesn't have to mean homogeneous, he explains. And he has also become a bit of a Historic District Commission mind-reader. The Commission generally wants the same thing, but without tassels, a swag, or a new detail.

"Generally speaking," he says, “The Board is not looking for symmetry and balance. If you go in with the dead symmetrical house, you're going to have a hard time."

And you can sometimes over-game the situation. "It can backfire on you. You put in something a little bizarre thinking you'll take it out, but then they like it," he says. So he no longer puts up bargaining chips, and he admits that the Board's demands produce an interesting architectural vernacular within established boundaries that are appropriate to the island.

“Houses on Nantucket today are built to last 100 years and anthropologists will be able to date them exactly."


Fly to Nantucket with Tradewind Aviation, offering scheduled shuttles and private charters from across the Northeast, including New York.

*All photos courtesy of Chip Webster Architecture