Interior designer Jocelyn Chiappone strikes a balanced chord between the historic past of Edgartown and an active family’s future.

The bespoke village of Edgartown is truly a haven of charm and character redolent of a bygone era. Majestic sea captains’ homes, clad in frothy white clapboard and punctuated with droplets of color provided by shutters accented with period-appropriate working hardware, are set back behind white picket-fencing from the tree-lined streets that allow for leisurely evening strolls after a sun-soaked day on the water. When the opportunity arose for one very busy family to create their own Vineyard retreat, it became apparent that a blank canvas actually involved a myriad of countless decisions, that the homeowner—who accomplished all of the design of her home in Wellesley, and originally wanted to be at the helm of their new undertaking—quickly realized she should enlist the help of the best professionals she could find. That short list included Patrick Ahearn, FAIA and Newport’s own Digs Design Company.

“The history of Edgartown really resonated with these clients, so for us, the question became how do we create a new old house—a house with a sense of implied history, that would take cues from houses in the historic district that they appreciated so much,” says Ahearn. The result became a Greek Revival cottage designed by Ahearn and Project Architect Francesca Gordini that looks as though it could have been a mid-1800s captain’s house, complete with period-appropriate details that imbue the home with the patina of age even though it’s all new construction. “All of the layers on the exterior—the heavily articulated cornice boards, corner columns and oversailing eaves—plus smaller details like copper gutters and authentic lanterns and louvered shutters—all come together to indicate a house that could...