THERE’S A COMMON belief among many longtime New Yorkers that, in order to love the city, you have to leave it regularly. For the minimalist residential and commercial architect Robert Finger, 57, that’s long meant escaping to his family’s Cape Cod cottage, built circa 1918 in the dunes along the Atlantic Ocean in Wellfleet, Mass., which he first visited when he was a month old. Every summer, his parents and two older sisters would drive up from Bethesda, Md., for “two months of never wearing shoes,” he recalls over a late breakfast on the house’s weathered gray deck. “ ‘Sunblock’ wasn’t a word I understood, and I remember the feeling at the end of summer: Putting on proper clothes felt so harsh.”

After inheriting the home two decades ago from his mother, who inherited it from her own mother three decades before that, he seeks that barefoot feeling whenever he can, much to the surprise of the people with whom he works. His employees sometimes ask whether the un-air-conditioned place is uncomfortable — “miserable” is their word of choice — to which he says, “Yeah.” His clients, many of whom are Manhattan real estate developers with more comfortable second homes, don’t believe him when he describes the cabin or shows them pictures. “They have an impression of me as someone who does exquisite, refined work, and they see what looks like clutter everywhere,” he says. “But I need a balance, a separation — that’s why you get out of the city so often.”

The shack was all but invented for escaping society’s expectations. It was constructed more than a century ago by Finger’s great-aunt Adelaide Newhall, who after graduating from Smith in 1906 decided that, instead of getting married or having children, she would become a teacher and artist. When she was growing up in Worcester, Mass., her family would take a summer rental nearby: This region, known as the Outer Cape, is mostly protected national seashore, meaning that the only view you have from the house is of a high, seagrass-covered sand embankment leading down to a chilly ocean that, despite the increasing presence of sharks, is more or less your own. Newhall chose the spot because it was ideal for creating the plein-air paintings that established her alongside her teachers Charles Hawthorne and Jerry Farnsworth as part of the Cape Cod School of Art, whose naturalist folk works have recently become desirable in certain American collecting circles.