The first time Annie Sullivan Cobb visited Shelter Island, New York, in her early 20s, she was overcome with nostalgia. It’s only 90 miles from Manhattan, but she had traveled by bicycle, bus, and ferry to get there. Once on the island, she walked to her friend’s rental in the historic Heights neighborhood. “There was something with the smells, how lush it was, how the houses felt…you know that visceral feeling when you’re like, this is my place?” recalls Cobb.
Her British husband felt the same. Over the years, they visited together, sometimes staying at the Chequit, other times with friends. And on their morning coffee walks, they would pass by the same sweet Victorian house, peering into the side garden to admire the sprawling hydrangeas. “It just seemed like a fantasy; it was the most enchanted place,” says Cobb. In true fairy-tale fashion (at least the real-estate kind), the home eventually came on the market. In 2012, just before the couple’s daughter turned 1, they bought the circa-1880 property.
For the first few years, Cobb admits they didn’t go east much. Their life with two small children in Brooklyn, where they still live full-time, got busy, so they rented out the Shelter Island house. Plus it took time to build a community of friends and neighbors there—something their kids’ summer camps eventually helped with.
A decade later, they embarked on an extensive renovation, adding central air-conditioning and a patio, plus a mudroom and breakfast nook off the galley kitchen. For Cobb, it was an exciting challenge: Just a few years earlier, she and a friend of a friend, Saara Matthews, launched an interior design business, Sullivan Matthews. While some rooms called for wallpaper and others modern lighting, she kept much of the home’s adorable gingerbread Victorian details intact, from the intricate gable trim to the floors.
“I feel like this house lends itself to an English country aesthetic, so we pushed in on that,” she says. After visiting a friend’s home in London, Cobb was turned on to DeVol’s classic Shaker cabinetry and unlacquered brass accessories (pot rack included). She even opted for British brand Farrow & Ball’s Sardine, a blue hue, for the floors, color-matched by Kirby’s Paints, a company out of Maine that makes marine-grade (read: superdurable) finishes for boats.
The fun in renovating a summer house during the summertime is that guests can weigh in on design decisions. For example, when Cobb’s designer friend Starrett Hoyt Ringbom popped by for a visit and spotted a closet between the kitchen and dining room, she suggested they turn it into a bar. “Oh, that’s genius!” Cobb exclaimed.
Cobb then dedicated three weekends to painting the nook, first swathing it in a blue-green color before deciding that it looked too similar to the kitchen floor. She started over with Sulking Room Pink and topped the wine fridge–slash–ice maker with Beata Heuman’s bow handle.
Meanwhile, her husband worked on painting a nearby closet in Farrow & Ball’s Churlish Green. “A friend said it looks like Shrek,” Cobb says with a laugh, “but I think it’s a very English color.” If the bar is Cobb’s domain (she makes a mean gin and tonic), its pair is certainly her husband’s: The shelves are stocked with his record collection, and at the heart of it is a vintage turntable dropped into the soapstone counter.
His hi-fi obsession extends into the living room, where two discreet KLH Model 6 speakers from the 1960s (still with their original grille cloths) set the stage for summer gatherings. “Now that we have central air, when people come over, they want to hang out inside our house,” says Cobb. When Shelter Island quiets down in the winter, the couple will hole up there for family time. “The summer is amazing, but it’s extremely social,” she shares. “We love to hide away and cook stews, put the fire on, and play games.”
Back in 1880, residents didn’t think much about built-in storage, leaving Cobb to get creative with their extra blankets and clothes. In Cape Cod, where antiquing “is like a sport,” the designer scooped up a decorative trunk for spare linens. “I got it thinking I would paint it, because I thought the flowers were sort of cheesy, but now I’m kind of into it,” she says. Instead, she lent her DIY skills to the bed, wrapping a basic IKEA headboard in foam and a Moroccan wedding blanket to give it a cushy feel.
When the couple upgraded their nightstands to sleek round Componibili storage units, they carried the old Victoria bedside tables down to the porch, where they now serve as pedestals for potted ferns. “We started going crazy with plants during COVID and now it’s almost an obsession,” she says. During the warmer months, tropical trees crowd the new seating Cobb bought at Beall & Bell in Greenport.
There’s even more room for greenery now that she’s moved the dining table to the new patio in the garden for privacy. Previously, when strangers passed by and saw the family eating on their porch, they’d ask if the place was a restaurant. “I always joke that you can never walk around our house naked,” she says—it’s that public.
Most of the time, though, they don’t mind the extra bit of foot traffic or the well-meaning snooper. After all, she and her husband used to spy on the house before it belonged to them. “The neighbors have kids the same ages as ours. I’ll be making pancakes and see these little faces peering in the window, and I’ll be like, ‘Come on in!’” says Cobb. “It feels very old-fashioned in that way.”
