Encompassed in 29 square miles, more than half of which is water, Shelter Island may be the East End’s most geographically intriguing with its mix of woodlands, salt marshes, fresh and saltwater ponds, beaches, and elevated hills in an otherwise flat landscape. Preservation of land and culture has been critical to the close-knit community of 2,400 year-round residents on the island, whose population is five times as much in the summer. Rife with history, natural in its beauty and relaxed in atmosphere, Shelter Island has maintained its simple way of life, which is why so many have sought paradise here.
The peaceful Manhanset tribe inhabited the “island sheltered by islands” until the mid-1650s when English settlers planted roots of their own. History is immortalized today with the Shelter Island Historical Society and its Havens House Museum, and Sylvester Manor Educational Farm. Described by The Nature Conservancy as “a museum of life in progress,” Mashomack Preserve is a 2,000-acre sanctuary for protected ecosystems. The coastal nature preserve offers five public land trails and one marine water trail with 20 miles of varying lengths and difficulty. Stick to the trails to explore nature at its best while respecting the flora and fauna inhabiting this peaceful preserve.
It is this peace and quiet that has long served as an attraction to second homeowners seeking the East End lifestyle but without the dense traffic and fuss of the North Fork and Hamptons. The real estate market on Shelter Island had a slow start this year, much of which may be weather related with a lot of rainy weekends early on. Though later in the season, activity is picking up and the island is now chock full of people.
Linda McCarthy, Licensed Real Estate Salesperson with Daniel Gale Sotheby’s International Realty, says most of what is moving are waterfront properties in the $1.5 – 2.2 million range and some below that price point. “Inventory is fairly low below the million-dollar mark,” she shares. “That’s driving prices a little bit. Lower end properties are able to ask for a little bit more. A big change is people are mostly buying homes that are turnkey, homes they can move right into that were maybe recently renovated, have a chef’s kitchen and a pool already in place.”
Saying that these homes are modern and beachy, McCarthy shares that many are done nicely and ready to move-in now. Her listing at 6 Quail Hedge Lane for example meets the criteria of what people are looking for. On the market for $1.57 million, the impeccably maintained home has four bedrooms, three-and-a-half bathrooms, a chef’s kitchen, pool and pool house, and areas to entertain. McCarthy says the home has a lot of value for the asking price.
As for why people come to Shelter Island, McCarthy shares it is a family-oriented community that is still preserved and so far, immune to overpopulation even in the summer. “Once people come here it’s like, ‘Well, I’m glad I finally found it,’” she explains, adding the ferries limit the amount of people. “Now the island is busy but it’s still a place where you can get away. It’s a pace that’s still quiet but has nightlife and a lot of restaurants. It’s changing still.”
On an island that has managed to maintain its old charm, there have been some recent changes in the dining scene, however subtle. Somewhat of an institution, The Dory has been around since Prohibition. It is casual, classic, and unfussy in aesthetics and offerings and owner Jack Kiffer can still be found behind the bar. What’s new is Chef Andrea Cinus Napolitano taking over the kitchen, breathing new life into the classic dive bar-esque menu with some Italian-inspired updates.
Caci, which first opened in Southold, now has a second location inside the Shelter Island House. “After several discussions regarding both businesses, it became apparent that Caci taking over restaurant operations at Shelter Island House would be a winning collaboration and a complement for both Caci and the Shelter Island House brands, and happened at just the right time for us to expand,” said owner Anthony Cacioppo in a press statement. “We have always loved visiting Shelter Island, and the historic charm of this graciously restored inn really attracted us to the opportunity to have our second location here.”
The seasonally inspired northern Italian fare by Umbrian-born chef Marco Pellegrini is simplistic yet inventive with fresh, local, and house-made ingredients. “I am inspired by the agriculture and aquaculture the North Fork offers and believe that the access to these fresh ingredients provides me the opportunities to create an unforgettable dining experience,” the chef explained in a statement. “I am really looking forward to bringing this unique menu, as well as tastes of Central and Northern Italy, to Shelter Island.”
Dining on Shelter Island is always a culinary adventure and often is representative of the local bounty. The beautifully situated Ram’s Head Inn is tucked away on Ram Island and overlooks Coecles Harbor. Guests can enjoy a seasonally-focused farm-to-table menu in and outdoors all-season long. Vine Street Café is another staple that also has a new Manhattan outpost called Harwood on Hudson.
There’s more to the island than food, of course. There is sailing, fishing, 10K races and charity fundraisers. For the active – and those that wish to be – Shelter Island Pilates and Barre is an ideal place to take a journey to your core with group and private Pilates, yoga and barre classes. Founder and owner Suzette Smith guides students in connecting mind, body, and spirit through thoughtful and powerful workouts.
Shelter Island is slowly starting to follow suit of its neighboring East End towns. “There is more of a year-round population with a younger generation buying more homes and they’re coming here on weekends and holidays throughout the year,” McCarthy explains. “It’s an escape. It is a place to come for peace.”