Phil Regan always knew he would be an architect. “I liked to draw,” he said. “I had always been in art classes and I liked those classes the most.”

A drafting course at the Martha’s Vineyard Regional High School was the first crisp, clean line on Mr. Regan’s own career blueprint.

“I knew this was it. I wanted to study architecture,” he said.

After narrowing down a list of colleges to warm weather schools with both an architecture program and a baseball team, Mr. Regan selected the University of Miami. And in December of 1987, during his senior year, when he was getting ready to pack up and head home for Christmas break, he read an article in his hometown newspaper.

“The Gazette would show up in my dorm, it would get handed around. People really loved it because it was different, the size of it and all the quotes,” Mr. Regan said. His mother was a librarian for the Vineyard Gazette. Sixteen hundred miles from home, something in the newspaper caught his eye.

“It was an article about the Oak Bluffs Inn being renovated,” said Mr. Regan. “Mark Hutker was quoted in it.”

Mark A. Hutker, an architect on Martha’s Vineyard, had bought Dunn Brady Associates in 1985 and renamed it in 1987, calling it Hutker Architects.

Mr. Regan had never planned to pursue architecture on the Island, mainly because the topography and commercial architecture he learned about in school was so different from that in his hometown. But while visiting his parents for Christmas he met Mr. Hutker and that summer, after graduation, Mr. Regan began working at Hutker Architects as just a summer employee. It would be the same office he would work at for the next 25 years. The same company where he would eventually hold the title of Principal and Senior Project Designer for Hutker Architect’s Vineyard office. But he didn’t know that then. After all, this was just a summer job.

“I thought I would never stay the winter,” said Mr. Regan. But being an Island kid came in handy as he began his career. He already knew about building permits and development restrictions. And, of course, he knew his way around the Island. But the Vineyard was atypical in terms of the architecture field because it is mainly residential.

“When I was in school they didn’t talk about residential architecture because you couldn’t make a living,” said Mr. Regan. But things have changed now. “And if you’re interested in residential architecture, Martha’s Vineyard is the place to be.”

And what is unique about the design of Vineyard homes?

“There is very different architecture five miles apart from one another,” said Mr. Regan. And the Vineyard is very casual. People like to be laid back when they come to the Vineyard, he added. This leaves a lot of choice for clients interested in designing a home.

Hutker Architects has designed homes “all over the map.” And there is a lot to choose from. “An ultra-modern house in Chilmark or a very traditional house in Edgartown,” said Mr. Regan.

Mr. Regan describes residential architecture in two words: “It’s personal.”

“We talk with clients often and meet with them throughout the entire process. When people have an idea of what they want I always ask, ‘why?’”

These initial conversations lead to patterns in housing desires.

“In the late 90s there were lots of rich guys who wanted to build a house on Martha’s Vineyard just because they could,” he recalled. But in the early 2000s that bubble burst and clients had a new desire. “Everyone wanted a house that would attract their extended family. A home is a very personal thing. We like to think of a home like an heirloom.”

Hutker Architects’ mission, which is stated on their website, confirms this: “We use honest, simple materials to create homes worthy of preservation.”

Recently, Mr. Regan met with an older couple he designed a house for decades ago. They were moving off-Island because their lifestyle was changing and they were getting older. “They weren’t going to the beach every day anymore, it was just time for them to move. This is what they don’t prepare you for in school,” he said of the personal relationship.

“They called me and wanted to meet with me because they just wanted to tell me why.”