Shelter Island is the kind of place that’s easy to romanticize. A roughly 20-square-mile island with rocky peninsulas large and small, this community is surrounded by the sea. In that aspect, it has more in common with an island in the Maine archipelago or a fictional community in a Hallmark movie. The island’s resemblance to this trope is only strengthened by the fact that the tiny community is accessible only by ferry. “There’s one grocery store, so everybody knows everybody,” says Marika Kaasik, a licensed real estate salesperson at Daniel Gale Sotheby’s International Realty who grew up on the island and has been in real estate there since the 1980s. “If you just moved here this week, within a couple of weeks you’re going to know a lot of people.” But being entirely cut off from the rest of civilization by water is what makes living on Shelter Island require a lot of dedication. It’s also exactly what draws many residents to it. “Besides being beautiful, surrounded by water, it feels very safe here,” Kaasik says. “There’s not a lot of hoopla here. I think people like that, too, where it’s just really peaceful.”
Accessible by ferry, the population of Shelter Island was 3,253 as of 2020.
Shelter Island Country Club is a popular public golf course.
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A lifestyle that changes with the seasons
Life on the island slows down considerably when the weather begins to turn cold. Although essential shops like the grocery store and coffee shops stay open through the winter, some of the restaurants close, and most residents close up their houses and leave for their primary homes — although, Kaasik says, that is changing. “When I was growing up, there was never anybody up here after Labor Day,” she says. “We used to call Labor Day Tumbleweed Tuesday because you didn’t see anything but the tumbleweeds going down the road. But now, with people working from home and with homes becoming so expensive that people want to enjoy them more, they stay here for longer seasons.” The residents that do leave, Kaasik says, often rent their island homes on Airbnb to help offset the cost of ownership.
Sylvester Manor, now a farm, is a historic manor on Shelter Island.
Shelter Island is around 8000 acres in size, much of which is protected wetlands.
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Swimming at Sunset Beach, hiking through Mashomack Preserve
With water on all sides, beaches ring Shelter Island’s coast. “You have these nice ocean-water beaches, but you don’t have to worry about big waves,” Kaasik says. “But the beaches aren’t that crowded. On weekends, they can be kind of busy, but not like you see over off the island, it gets more popular.” One of the most popular of these is Sunset Beach. Swimming, kayaking, boating and other water sports are all popular here, with marinas also dotting the coast. Heading inland, huge swaths of nature also leave plenty of space for hobbies like hiking and birdwatching. “One-third of the island is preserved by the Nature Conservancy,” says Linda McCarthy, a licensed real estate salesperson for Daniel Gale Sotheby’s and longtime resident. “Mashomack Preserve is a wonderful 2,000-acre space with woods, marshes, bays and inlets and miles of well-maintained hiking trails.” A variety of wildlife, including deer, muskrats and over 200 species of birds can be found there, and its more inland habitats are ringed by its 11 miles of coastline. Golfers head to the Shelter Island Country Club or Gardiner’s Bay Country Club, and many boaters join organizations like the Shelter Island Yacht Club.
Shelter Island's beaches on Peconic Bay are calm and family friendly.
Mashomack Preserve allows visitors opportunities to take a stroll.
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Island homes start at $1.3 million
Homes on Shelter Island often have spacious yards of at least an acre. Colonials are common, often with wood shingles, but ranch-style homes, Victorians and the occasional modern-style or 2020s contemporary home also make appearances. When it comes to cost, Kaasik says, there’s nothing available for less than $1 million. Three-bedroom homes typically start at more like $1.3 million, and large waterfront homes with private pools or houses with acreage at the edge of the preserve can climb to $10 million. Taxes are lower than in other areas of Eastern Long Island, but flood insurance is a must for many, and homebuyers pay a 2.5% tax after the first $400,000 when they purchase their home. This money goes to the preservation of the island’s land and nature. Still, demand for homes is high. “There’s very little inventory,” McCarthy says. “Prices are holding high and when houses present well, they go quickly.” The CAP Index crime score is 1 out of 10, which is below the national average of 4.
Shelter Island is ringed with impressive waterfront homes.
Shelter Island Heights is known for its Victorian homes.
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Annual craft fair, 10K and school plays
For 60 years, Shelter Island has held an Arts & Crafts Fair during the summer, which Kaasik says attracts a large number of participants. Another popular, long-running event is the island’s annual 10K in June, which features awards and live music after the race. “The school puts on an annual play that people look forward to once a year,” Kaasik says.
Thousands of people are drawn to the Greenport Maritime Festival near Shelter Island.
The Big Black Canoe is taking the lead in the Cardboard Boat Race.
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Shopping and dining on Shelter Island
Despite its small size, the dining scene on Shelter Island is vibrant, especially during the summer — so much so that Kaasik says some people come to the island specifically to eat at some of its restaurants. Stars Café bakes fresh pastries in the mornings and offers organic coffee and a lunch men, and Vine Street Café is a local favorite. “That’s been on the island for many, many years,” Kaasik says. “They’re very consistent and they run a really nice restaurant, a tight ship.” SALT Waterfront Bar & Grill is known for its lobster roll, waterfront views and lively atmosphere thanks to live music that plays nearly every day they’re open. Even many of the hotels dotting the island house popular restaurants, including The Sunset Beach Bar and Hotel. “It’s this crazy, wild place on the sand beach over there, and they’re packed all the time,” Kaasik says. “People come from all over to go there. They don’t have many rooms for the hotel, but they’ve got a really cool vibe there.” When it comes to shopping, Shelter Island has the essentials — there’s an IGA Supermarket near its center for groceries, a few fish markets and a seasonal farmers market, plus Black Cat Books has secondhand books and records. Kaasik also owns a little furniture boutique on the island, Marika’s Eclectic Boutique. There’s no hospital on Shelter Island.
Sunset Beach Hotel and Bar is a hopping spot on Shelter Island.
The Shipwreck is an outdoor bar that is part of SALT Waterfront Bar and Grill on Shelter Island.
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Small classes at Shelter Island School
Shelter Island School, which Niche gives a B-plus, is the only academic school on the island. Even teaching kindergarten through 12th grade, the school has only about 175 students and a student-teacher ratio of 4-to-1. Kaasik says her graduating class had fewer than 15 students, which is typical for the school. Also on the island is The Perlman Music Program, established by Toby Perlman, wife of the famed violinist Itzhak Perlman. The school is anchored by its summer camp for young string musicians but features a variety of workshops and programs with partners across the country.
Shelter Island School has 172 students in grades PK-12.
Shelter Island School is convenient to locals due to its centralized location in Shelter Island.
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Mail delivery, ferry to Long Island
Shelter Island has so little traffic that there’s not a single traffic light on the island. Living on an island isn’t without its downsides, though, and with the ferry, one of the biggest is accessibility. There’s no mail delivery on the island — which also lacks garbage pickup — so locals need to head to one of its two post offices to get their mail. According to Kaasik, getting package deliveries from Amazon can even be a little tricky, as sometimes sellers will say they don’t deliver to her address. The South Ferry takes residents to and from the North and South Fork of Long Island. It runs every 10 or 15 minutes from 5:20 a.m. to 1:45 a.m. in the summer and 11:45 p.m. in the winter, with the trip taking between five and 15 minutes, depending on where the ferry is heading. From there, residents may drive about two hours to New York City or take the Long Island Rail Road.
Reliable ferry services connects Shelter Island to the North and South Forks of Long Island.
Shelter Island's post office connects the island with the rest of the world via mail service.
Mike Carroll is a veteran RE/MAX professional who has been part of the network for over 30 years. He is a savvy real estate professional who understands markets and trends. Mike has been a Sales leader on Long Island since 1989 and has previously been in the Re/Max top 10 salespeople in the Country He works closely with many lenders, attorneys, financial advisors, accountants, and fellow real estate professionals to sell Long Island properties quickly.
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