A young family moves from the big city to Martha’s Vineyard. For many people, this might sound like a dream come true. But husband and wife Sean Roach and Heather Dyas-Fried had never even considered it until Ms. Dyas-Fried’s father, longtime Vineyard Haven resident Chris Fried, began showing signs of cognitive decline as the result of severe Lyme disease.

“We had a really tough decision to make about leaving everything,” Mr. Roach said.

In the Philadelphia area the couple had built thriving careers and established their family. But in 2017, with son Everest, now 9, and daughter Opal, now 5, the family moved to Mr. Fried’s sunlit home near Lagoon Pond.

A painter, sculptor and actor—as well as an amateur musician—Mr. Roach quickly became involved in the local art scene, hand-painting the winsome full-page illustrations for Rebecca Loescher’s 2018 children’s book The Mermaid of Martha’s Vineyard.

Mr. Roach is now stepping out as an artist in his own right. In his current one-man show of paintings, though April 4 in the Lobby Art Space of the Martha’s Vineyard Playhouse in Vineyard Haven, he explores the world above the waves with still lives, landscapes and human subjects that spark the viewer’s imagination.

Sean Roach and his black cat Baby Pop. — Louisa Hufstader

“His work is so special,” said playhouse director MJ Bruder Munafo. “His painting skills are exquisite. I think the light is beautiful, and the imagery is so strong.”

Mr. Roach used his son as the model for Capitol Hill, which views the back of a young boy holding an older man’s hand as they look at the Capitol dome in Washington, D.C.

The centerpiece and largest work in the playhouse exhibition, titled Boys, depicts seven boys in a leafy glade, toting a flag and some toy guns. Five of them are gazing at the pages of what appears to be a girlie magazine (only the women’s faces are visible).

One youngster is looking up in apparent disbelief at what he’s witnessing, and the last is watching anxiously to make sure they don’t get caught.

“I paint very literally,” Mr. Roach said. But, he added, he’s not trying to send a specific message in works like Boys and Legacy of Violence, another large canvas that hangs in the family’s home.

“I don’t like to think in those terms,” he said. “I love that [a painting] sparks conversation. I enjoy hearing people’s ideas of what they think it means.”

In Legacy of Violence, three young men stand in a woodland stream as one reverently lifts a dripping automatic rifle from the water. In the foreground, the stream disappears over the edge of a waterfall. Three girls watch from beneath the trees.

“I was trying to create a piece that evokes the emotional state I was feeling—the darkness around gun violence in this country and the obsession with guns. We pass that down to the next generation,” Mr. Roach said.

“Some people see it as a celebration of guns,” recognizing the AR-15 model weapon in the painting, he added.

Mr. Roach used his son as the model for Capitol Hill. — Louisa Hufstader

“I’m not interested in passing judgment.”

Mr. Roach studied fine arts at Temple University’s Tyler School of Art, but after graduating decided to pack up all his painting supplies and try life as an actor.

“I auditioned for every part I could,” he said, and met his future wife in a production of Noises Off.

He went on to host two children’s television programs, Noodle & Doodle and the Sunny Side Up Show on the Sprout channel, and developed a career creating sculptural set pieces for stage shows and other applications.

One of his earliest sculptures was a life-sized Mr. Peanut, for the 100th anniversary of Planters, which occupied a bench on the Atlantic City boardwalk for several years.

Mr. Roach also created a nine-foot-tall sculpture of the Boston Calling music festival logo, a nattily-dressed Boston terrier, for the 2018 event. On the Vineyard, he’s just finished restoring the weatherbeaten sign for Cronig’s Real Estate. In gleaming whites and colors, the decades-old sign now looks brand new.

Trained in theatre at Bloomsburg University, Ms. Dyas-Fried co-founded and remains artistic director of a Pennsylvania-based nonprofit theatre company called Equalogy, Inc., which visits Eastern college campuses performing pieces about partner violence and acquaintance rape.

On the Vineyard, she’s working part-time in marketing with Ms. Bruder Munafo at the playhouse.

Along with their children and Mr. Fried, who has his own apartment in the passive-solar home he designed in the 1980s, Mr. Roach and Ms. Dyas-Fried’s family includes Baby Pop, an affectionate black cat that moved with them from Philadelphia.

“He’s kind of like a dog. He goes for walks with us, he rides in the kayak with me. He loves it here. He’s very happy,” Mr. Roach said.

The Sean Roach exhibition of paintings is open during regular playhouse box office hours. For more information, visit mvplayhouse.org or seanroacharts.com.