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.
The IGA on Shelter Island is its main grocery store.
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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.
Shelter Island is ringed with impressive waterfront homes.
Bliss' Department Store is the go-to for basics on Shelter Island.
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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 is known for its beautiful, calm beaches with views of Peconic Bay.
Along a hiking path, visitors can rest at a gazebo to observe wildlife.
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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 Heights is known for its Victorian homes.
Intimate inland ranches offer serene views of the woods and privacy on Shelter Island.
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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.
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.
Marika's Eclectic Boutique on Shelter Island is a great resource for vintage furniture.
Black Cat Books on Shelter Island has an extensive array of used books and records.
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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 about 175 students in pre-k through 12th grade.
The Perlman Music Program is a world renowned school on 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.
Whatever time of year, Shelter Island's ferries run frequently and efficiently.
Shelter Island's post office connects the island with the rest of the world via mail service.
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Interested in learning more about homes in this area?
Reach out to
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an experienced agent in this neighborhood.
Parks in this Area
Mashomack Preserve
Picnic Area
Trails
Visitor Center
Cedar Point County Park
Picnic Area
Trails
Beach
Fiske Field
Baseball/Softball
Basketball
Multi-Purpose Field
Founders Landing Park
Old Schoolhouse Park
Inlet Pond County Park
Trails
Transit
Airport
Tweed/New Haven
189 min drive
Reviews
Niche Reviews
4.02 Reviews
4.0Current Resident
12/28/2019Niche Review
The Town of Shelter Island is a secluded island between the forks of eastern Long Island. It is much less Hampton when placed in comparison to that of the surrounding Hamptons. The locals are very welcoming and helpful and prideful of their small town. A must visit...
Immerse yourself in the serene charm of 7 Gazon Road, a Zen-inspired retreat tucked away on Shelter Island. This waterfront sanctuary offers the perfect balance of modern luxury and tranquil living. With three bedrooms and two-and-a-half baths, you can choose between a first or second-floor primary suite, each thoughtfully updated to exude sophistication and comfort. Nestled on 1.6 acres of lush
Welcome to this stunning 6-Bedroom, 4-Bath Home with Water Views on Shelter IslandThis expansive 6-bedroom, 4-bathroom home, nestled in one of Shelter Island’s most sought-after locations, offers a perfect blend of luxury and comfort. Featuring a grand primary suite and a versatile junior suite, it’s ideal for both relaxation and hosting guests.The very large dining room is perfect
Nestled off the road for added privacy this updated home offers Chase Creek water views. Featuring 2 bedrooms and 2 renovated bathrooms, the layout includes an office perfect for remote work or creative pursuits. The open-concept living and dining area is bright and inviting, flowing into the renovated kitchen with modern finishes and storage. Step out onto the back deck thru sliders from the
This well located 3 bedroom, 2 bath contemporary ranch has a lovely open living room with stone fireplace, beamed ceiling and dining room both of which have access to bilevel decks overlooking a beautifully landscaped and fenced back yard with cute little art studio. Just off the dining area is a well equipped kitchen with breakfast bar. The primary bedroom has an ensuite bath. The two
Set on a peaceful street in Shelter Island’s historic Heights neighborhood, this mid-century modern home has everything you need for an easy, laid-back summer. There’s plenty of room to spread out, a spacious deck for lounging or dining outside, and a gas grill ready for summer cookouts. You’re just a few blocks from shops, restaurants, and all the local action. As a bonus, you’ll have access to
Debra Von Brook BinderDaniel Gale Sothebys Intl Rlty
Welcome to Sandpoint, an exclusive Shelter Island retreat recently built on 1.4 acres, just a stone's throw from a sandy beach and across from a 12-acre preserve. This stunning home features five bedrooms, including two master suites and one room with twin beds. Sunlit and spacious, the heart of the home is a well-equipped kitchen with an oversized island overlooking a large pool and landscaped
Interested in learning more about homes in this area?
Reach out to
Deborah Pirro,
an experienced agent in this neighborhood.
Average Home Value
Source: Public Records
Property Mix - Square Feet
This Neighborhood Has More Owners
Demographics
Total Population
3,004
Median Age
55
Population Density
1 person/acre
Population under 18
16.2%
Below the national average
23.8%
Population over 65
33.1%
Above the national average
19.1%
Finances
Median Household Income
$107,839
Significantly above the national average
$71,702
Average Household Income
$137,823
Education and Workforce
High School Graduates
94.4%
College Graduates
59.7%
Significantly above the national average
34.1%
Advanced Degrees
31.3%
Above the national average
13.3%
% Population in Labor Force
52%
Weather
Annual Precipitation
47''
Average Winter Low Temperature
20°F
Average Summer High Temperature
80°F
Annual Snowfall
35''
Area Factors
Car-Dependent
Walk Score®
26/ 100
Source: Walk Score
Source: Walk Score
Sound Score® measures the noise level of any address. Transit Score® measures access to public transit. Bike Score® measures the bikeability of any address.
Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. Our sources include: Accuweather, Public Records and Neustar. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.
