An Aquinnah Home is Updated by Digs Design Company

With the door system fully retracted, the great room opens entirely to the deck. “The shining moment was opening up that entire side of the house,” says designer Jocelyn Chiappone. “You feel like you’re outside.”

The cedar-shingled facade reads simply from this vantage, while dormers and folding doors hint at the renovation within.

In the living room, a traditional Oushak rug from Loom & Co softens tailored seating layered with patterned textiles. Art above the fireplace is by Dallas-based painter Arienne Lepretre, whose luminous palette subtly echoes the water beyond.

A cerused Highland House dining table is paired with Chaddock chairs upholstered in lively embroidery, balancing tradition with ease.

Painted oak cabinetry by Jutras Woodworking defines the kitchen. A leathered quartzite island with bronze inserts to hide the slab’s seams anchors the space beneath sculptural Swedish pendants; Palecek stools line the counter. The open plan ensures sight lines from prep space to dining and deck, reinforcing the home’s easy indoor-outdoor flow.

In the powder room, Scalamandré palm-print wallpaper nods to Isabelle’s Florida upbringing, enriched by moody black trim.

Thibaut wallpaper wraps the primary bedroom in a layered blue pattern, while tailored upholstery introduces subtle notes of pink—an unexpected warmth within the cool palette—and expansive windows frame nearly 180 degrees of water.

In the primary bath, an arched alcove frames the sculptural tub against mosaic tile.

A guest bedroom layers shiplap with playful pattern and upholstered comfort.

The reworked rear elevation stretches toward the horizon, dormers and folding doors maximizing water views while respecting Aquinnah’s light-pollution regulations.

Century counter stools upholstered in Sister Parish fabric line the generous kitchen pass-through.

Clad in Alaskan yellow cedar, the screened porch layers gray-washed wicker seating with blue patterned fabrics and a traditional hanging swing.

When Isabelle inherited her family’s Martha’s Vineyard home, she found herself holding more than a set of keys. The Aquinnah property—purchased by her great-grandfather in 1939—had passed quietly through generations. Now, in her mid-twenties, it was her turn.

“Because I was so young when we started, I was very cognizant of making it evolve with me,” she says. “I wanted it to feel young and bright—but not trendy.”

Interior designer Jocelyn Chiappone of Digs Design Company understood the balance immediately. “When I first arrived, I was met with the most breathtaking water views,” she says. “I knew instantly this was going to be special.”

The assignment was layered: honor the history, open the interiors to the landscape, and create something that would feel as right decades from now as it does today.

Architect Christopher W. Arner refined rather than reinvented the structure. “The bones were good,” he says. Folding door systems replaced standard windows on the water side, dormers reshaped the roofline, and the second floor became a true primary suite. Aquinnah’s light-pollution regulations limited expanses of glass, but the team pushed openings as far as permitted.

The interiors carry the emotional weight. “The view is the star,” Chiappone says. “So we pivoted toward neutrals and greens and let the landscape lead.”

In the great room, a traditional Oushak rug anchors a pair of softly tailored sofas layered with patterned pillows. A caned coffee table and woven bench introduce texture without fuss. “It’s about coming in, sitting down, and exhaling,” the designer says.

In the dining area, a cerused table is paired with embroidered chairs that feel lively but not precious. Custom cabinetry displays Isabelle’s grandmother’s china—a quiet bridge between generations. “The silhouettes are traditional,” Chiappone says, “but nothing feels fussy.”

The screened porch, clad in Alaskan yellow cedar, threads old Vineyard charm with modern ease. Patterned lounge chairs and counter stools gather near a kitchen pass-through that dissolves the boundary between indoors and out. “The swing was nonnegotiable,” Chiappone says. “It feels historic, but when you turn back into the kitchen, it feels completely current.”

Builder Matt Stedman calls the setting “one of the most incredible on the Vineyard,” overlooking Menemsha Pond with views stretching from the Elizabeth Islands to the Atlantic. “The essence of the house is to live inside and outside,” he says. Radiant heat and integrated lighting ensure it works year-round.

His brother, Zack, adds, “The feeling when you walk in and see that view completely transforms you. And Isabelle trusted Jocelyn to bring in color and personality. A lot of homes here go neutral—this one has energy.”

Upstairs, Chiappone allowed more personality to emerge. Isabelle’s favorite color—blue—guides the primary suite, where Thibaut wallpaper feels traditional yet fresh. In the bath, an arched alcove frames the tub against a mosaic tile backdrop, turning a daily ritual into something quietly theatrical.

“Though she was young, Isabelle has an old soul,” Chiappone says. “We guided her toward materials and details that will age beautifully. Nothing in this house is trying too hard.”

For Isabelle, that restraint feels right. “I wanted the house to grow with me,” she adds. “And I think it will.”

 Project Team
Architecture: CWA Architect
Interior design: Digs Design Company
Builder: Stedman Construction
Landscape design: Contemporary Landscapes