Can we take a peek?

Trespassing on the best Island properties (with permission).


After a few missed turns down wrong dirt roads, I found Jamie Curtis’ and Jason Colin’s Chilmark home. It was around 4 o’clock, when the light starts to soften, casting pure gold on the up-Island town. Jamie’s and Jason’s house sits at the end of a long pebble driveway on a grassy well-kept lawn. The smooth, sleek, natural cedar boards vertically line the exterior of the home, knitted closely together, each driftwood-colored panel seamlessly blending into the next. Black trim details the windows that pepper the home with simple, geometric symmetry. 

“I wanted it to look like a rustic old farmhouse,” Jamie said. “I also wanted a house that could absorb a lot of family and friends. Never saying no to the kids wanting to bring friends up, or friends deciding they want to come last-minute.” 

Jamie and Jason split their time between Martha’s Vineyard, New York City, and East Hampton. Jamie is a lawyer and real estate broker, and Jason is a marketing consultant and real estate investor. Both have a knack for interior design, and won’t shy away from the reins when it comes to building and designing homes.

“I knew I wanted to build a post-and-beam style barn house,” Jamie said. After buying the raw land in 2014, the couple chose Yankee Barn Home, a custom home builder based in New Hampshire, to construct their up-Island vision. “This [house] came in like 20 truck loads,” Jamie said. “It’s actually much less expensive to build. It’s really energy efficient and goes up really quickly.”

The entire home was built inside a climate-controlled facility in New Hampshire. After breaking ground and building the foundation in April 2014, the house was up and ready for its first of many gatherings by the first week of December. “All of the scraps of wood were either reused or given back to [Yankee Home] employees for wood burning,” Jamie said. 

Jamie and Jason love to entertain — that’s why they went with 6 bedrooms, 6.5 bathrooms, and a totally open-floor plan. 

“There’s a lot of space for people to have privacy in the house, but when they come out, they’re all part of the same action,” Jamie said. “Kitchen, dining room, family room, living room, deck, pool — everything’s all one open area.” 

In the kitchen, Jamie liked the idea of an island that “just kind of disappeared,” he said. He and Jason chose soapstone countertops, black appliances, quarter sawn cabinetry, barn board, and wide-plank oak flooring. “A blacksmith shop kind of feel,” Jamie said. During floor installation, Jamie asked the builders to put a nickel in-between the floorboards every so often. “The builders said, ‘You’re crazy. Then the floorboards will have gaps between them — that’s not going to look good.’ And I said, ‘That’s exactly the look I want. Like an old rustic farmhouse,’” Jamie said.

Jamie and Jason tag-teamed the home’s interior design. “Jason gave me an idea to make the windows bigger — as big as they can be — and he was absolutely right,” Jamie said. “That brought in a lot of southern light. It’s a great passive solar-type thing.”

Most of the furniture is from Design Within Reach, a company based in Stamford, Conn.  Custom-colored red chairs surround a dark, raw, wooden dining table, bringing out pops of red and orange on a wall-sized canvas painted by artist Marie-Louise Rouff. “It’s a funny story,” Jamie said. “Jason was in Vineyard Haven and said he found the perfect piece for the dining room. I said, ‘Jason, art is really important to me, and I want to be really careful with what we put there.’ I had recently gone into an art gallery myself and found what I thought would be the exact right painting. It turns out, we were talking about the same work of art.” 

Art is a huge fixture for the up-Island home. Much of it is either by a Vineyard artist, or by an artist who spends time on the Island, Jamie said. There are pieces by Alan Whiting, Jennifer Pisano, Lucy Mitchell, Rez Williams, Kate Feiffer, and Lizzy Taft, among others.

Jamie used to work at Sotheby’s Real Estate as a specialist in the print department. He also used to own a photo gallery and a small interior design business in New York City. Some of Jamie’s own drawings and paintings are framed and front lit throughout the house. “Lighting is really important for artwork,” Jamie said. 

Bedrooms are ‘dormitory style’ and close-off as standalone ensuites with private bathrooms. Dark furniture and mahogany detail pop against white painted walls. Bedrooms are basically uniform throughout the house. Stainless steel cables line the staircase leading to the second level. The master bedroom, and both Jamie’s daughter’s and son’s bedrooms, are situated on the second floor. Two balconies, detailed with the same steel cabling, overlook their sprawling plot of land.  

We made our way back downstairs and out the screened-in porch, which includes a glass dining table, stone fireplace, and seating area. The screened-in porch leads to an outdoor deck. “The deck is where we spend most of our time,” Jamie said. It overlooks the ozone filtration pool and property’s lower guesthouse and garage. The guesthouse is a one-bedroom, half-bathroom, also built by Yankee Barn Homes. 

The property maintains the natural beauty of the area — the home blends right into its environment. The Island, to Jamie and Jason, feels like a bit of a work of art itself. “The natural beauty of the Island is really spectacular,” Jamie said. “Everywhere you turn, you see a different vista. The people are really nice — it’s such a self-sustaining community, and I find that really unusual and so heartening. “Agriculture, farm-to-table food, and the fact that there are so many artists here — the Island is a haven for so many writers and creative, like-minded people. 

“Many people that live here appreciate how beautiful it is, but it’s not until you go away and then come back that you realize it’s a truly special place.”
We toasted to that over a glass of rosé.  


Have a home you’re curious about? Email, and we’ll see if we can make the connection and take a peek.