This Magical House On Martha’s Vineyard Includes Its Own Speakeasy

The Obamas have an estate nearby. Jackie Kennedy rode horses here. Steven Spielberg shot Jaws on this island 50 years ago, and the locals still talk about it. Edgartown, on Martha’s Vineyard, is a place that has seen a few things — and learned not to make a fuss about any of them. So when the new owners of a certain cottage on Upper Main Street turned their dining room into a stylish speakeasy, no one raised an eyebrow.

Who dreamed up this act of rebellion on Edgartown’s most historic and proper thoroughfare? Meet Dallas art collectors Jennifer and Tom Karol.

The Karols purchased the cottage in 2020, a white clapboard charmer with a deep front porch and picket fence that sits comfortably among Upper Main Street’s storied old whaling cottages. Never mind that it was built in 2010. It is a picture of Edgartown propriety and looks as if it has been there for centuries.

Tom Karol, a Boston native, knew Martha’s Vineyard well. But where most first-time buyers are drawn to the island’s dramatic oceanfront cliffs and secluded beaches, Jennifer Karol fell for the conviviality of Upper Main Street — the historic houses, the restaurants, the shops.

“I knew it the second I walked in,” she says. “This house is mine.” Back in Dallas, she texted her interior designer: “Do you want to make some magic happen?”

Corbin See had designed the Karols’ Dallas home — a collaboration that began almost 20 years ago.

“We just call it an ongoing conversation,” Jennifer Karol says. “It’s never really stopped.” See knew just how to conjure the enchantment Karol was seeking: Why not turn the cottage’s formal dining room into a bar?

As a partner in Duro Hospitality, the force behind The Charles and a raft of other Dallas restaurants, Corbin See had spent years thinking about how people inhabit social spaces. The dining room, he argued, was wasted square footage — especially in a place where everyone eats al fresco from Memorial Day through September.

He wanted to turn it into something more alive: a bar lounge, a salon, a room with hospitality at its center. Corbin’s wife Sara See — a partner in the design firm with a focus on textiles — was equally convinced.

“I think Jennifer knew that the room was going to be badass — something no one had ever seen before on the island,” Sara See says.

The design brief for this island retreat had an unexpected turn. “I want it to be pattern upon pattern upon pattern upon pattern,” Jennifer Karol told Sara See. Her Dallas home is collected and a little edgy — the interiors of a sophisticate with a fearless sense of personal style. This was her chance to do something looser and more joyful — and Sara See was the perfect accomplice. While Corbin handles the furniture and spatial architecture of a room, fabrics are Sara’s domain.

“She gave me a long leash,” Sara See tells PaperCity.

The result is what Corbin calls tailored maximalism — and somehow, despite the layers of pattern and color and antiques and irreverent objects, the whole thing feels as laidback and fun-loving as Martha’s Vineyard itself.

Embracing the Martha’s Vineyard Ethos and an Unexpected Choice

Jennifer Karol came to the project with a vision of the island’s colors — sky blue, ocean blue, the classic coastal palette. Corbin See suggested something different: “a little bit cheerful, but pulled back,” he says. Jennifer Karol spent some time being uncertain about it.

“It turns out he’s always right, which I hate,” she laughs. As Sara See notes, the quieter paint color was precisely what gave them permission to be fearless with everything else: “That became the restraint that allowed the textiles to follow,” she says.

The main living space is anchored by a large custom sectional sofa (“wildly upholstered,” as Sara See puts it) — a decision that set the tone for the rest of the room. Made by Marroquin Custom Upholstery, the sectional’s bold pink and green stripes do the heavy lifting, with layers of pattern building across the room’s two distinct territories. One side given over to the sofa and a Nickey Kehoe wingback chair. The other, organized around a game table ringed by coral-printed chairs with aqua contrast seats.

Sara See chose Roman shades in a subtle stripe by Carolina Irving to create continuity between the two spaces without overpowering. A shark carved from small blocks of wood — abstract, almost pixelated — hangs above the fireplace, a jolt of wit in an already spirited room. It was spotted by Jennifer Karol and Corbin See on a shopping trip, both rounding a corner at the same moment.

“We looked at each other and said, ‘We have to get that,’” Jennifer Karol remembers. Given that Jaws was filmed on Martha’s Vineyard, the discovery felt like fate.

Jennifer Karol claimed a small alcove off the main bedroom as her private retreat — somewhere to read, put on makeup and slip away when all five kids descend on the house. The inspiration came from a trip to Marrakesh, where Jennifer had toured Villa Oasis, Yves Saint Laurent and Pierre Bergé’s legendary Moorish-style home, with built-in banquettes tucked into every nook and cranny. The rooms were alive with intense color and layered pattern — and Jennifer wanted all of that. 

Sara See’s answer was Schumacher Modern Toile in indigo, designed by Johnson Hartig of Libertine — a large-scale, room-enveloping pattern based on Renaissance drawings, its mystical imagery populated with nude figures and sun faces.

“It’s got a little bit of edge to it,” Jennifer Karol says. In a space this small, Sara See reasoned, full commitment was the only option, with walls, ceiling and built-in banquettes wrapped in the same blue-and-white pattern with red trim.

“It is my room and my room only,” Jennifer says.

Making a House Complete

The finishing touches came together the same way much of the house did: by instinct, and often by accident. Sara See found the reeded bamboo desk on a subsequent trip Martha’s Vineyard, stumbling across it while shopping for something else entirely. It fit the niche perfectly.

The antique shell mirror, found at Nick Brock Antiques in Dallas, made the long journey to the island in one piece, which Sara See describes as something of a miracle. The mirror, along with other small nautical touches — a rope sconce and a shell-shaped pewter sconce by the English brand Collier Webb — moor the room to its island setting.

The dressing room is an immersive world unto itself, but the former dining room is what truly transports. When Jennifer Karol first started inviting people over, they would make their way through the house — and pause at the sight of the dimly lit bar.

“Oh my gosh, Jennifer has a speakeasy,” they would say, amazed. The room has since acquired a proper name: Bar Karol, coined by Jennifer’s friend and PaperCity Dallas editor in chief Billy Fong on a visit. The name is now immortalized on a book of matches. 

The mood is set by Iksel for Schumacher Romantic Bosphorus, a sweeping panoramic wallpaper in deep blues and greens that evokes the glamour of a grand European hotel. Corbin See found a 19th-century English gentlemen’s table — a low horseshoe-shaped bar for tasting port that was often used in manor houses after a fox hunt. He had lion’s-paw legs made for it, raising it to bar height, and Sara See wrapped the base in a vintage tartan fabric she’d held onto for years.

“For me, the narrative was Vivienne Westwood — traditional English design turned to punk,” Corbin See says.

Three portraits of Abraham Lincoln by Hunt Slonem, which Jennifer collected through the years, give the room a sly Americana undercurrent. On the opposite wall hangs a painting from Obsolete in Los Angeles — a man and woman in formal dress, the latter portly and jovial, martini in hand.

“There’s a story to almost everything,” Jennifer Karol says. “This whole house is just magic.”