SILVER BEACH · SHELTER ISLAND, NY
Shelter Island Family Oasis
A family home with a private heated pool, a quiet street, and the water at the end of the road.
A family home with a private heated pool, a quiet street, and the water at the end of the road.
The pool is where every stay seems to settle in. It is a heated salt water pool, set in the fenced yard of a one-acre lot, and ringed by a stone deck with sun loungers and plenty of umbrellas for shade. The big back deck has a grill, an outdoor dining table for the whole group, and a fire table for evenings, so long summer days run straight into dinner.
“The pool was beyond compare.” Steven, August 2026
“A beautiful heated pool that was even better than the photos.” Meredith, August 2024
“Our toddler grandchild loved the pool (which has a big shallow end!).” Hallie, June 2024
Three bedrooms are upstairs and three are down. Guests tell us the layout works: kids can sleep on one side of the house while the grown-ups stay up in the sunny family room on the other.
The kitchen is fully stocked, with a big island and a farmhouse table that seats everyone. There’s a dishwasher, three ways to make coffee (drip, Keurig, and French press), a washer and dryer, and a gas grill on the deck. Dual-zone central air keeps upstairs and downstairs comfortable on their own settings. There’s a second living room at the center of the house, away from the TV, for conversation, reading, or a quiet drink. Board games, books, and a front porch fill the rainy days.
“We loved the sunny and bright family/TV room. We had a few “chefs” in our group and they loved working in the kitchen.” Kathleen, June 2025
“I loved the three bedrooms on one side of the house with the TV on the opposite side. It allowed our grandkids to sleep well and the rest of us to have fun.” Beth, August 2025
A split-rail fence, a red maple, and a front porch made for morning coffee.
“Two porches (one off the primary bedroom) to enjoy our morning coffee.” Joann, July 2024
The house isn't on the water, but there's water at both ends of the street, and a short walk in almost any direction brings you to it. Our road has minimal through traffic, so it's quiet and safe for bikes and long walks. Spring through fall, two tandem kayaks wait at the North Silver Beach landing, with paddles, seats, and life jackets for everyone hanging by the house.
“Kayaking to Shell Beach was magical, as we had the beach to ourselves.” Hallie, June 2024
“A stone’s throw away from the ocean (in both directions!).” Guillaume, December 2020
Salt marsh at low tide, ferry crossings, farm fields, and long golden evenings on the water. Shelter Island moves at its own slower pace, and that is the whole point.
“It was also a beautiful place to stargaze!” Neva, September 2024
Photos in this section show the island, not the property.
Our family has been coming here for generations. These are the places and rituals we return to every summer.
Our favorite ritual: pack a cooler of sundowners, launch the kayaks from the end of our street, and paddle over to Shell Beach for happy hour as the sun goes down.
Some of the best sunsets on the island. Bring your own drinks to the sand, or if you feel like being a little fancier, grab a cocktail at the Sunset Beach Hotel or settle onto the lawn at the Pridwin.
Well-marked trails through marshes, creeks, and forest. Wear plenty of bug spray.
At the Shelter Island Historical Society, Saturdays 9 to noon, with events all summer.
Rent bikes at Piccozzi’s Bike Shop. The island is made for slow, scenic rides.
Kayak from the launch by the house to SALT at the Island Boatyard for a drink or dinner on the water. A very doable, moderate paddle. Just don’t forget your wallet.
Two tandem kayaks wait at the North Silver Beach landing. Explore West Neck, Menantic, and Dickerson Creeks right from the end of our street.
A long spit of sand about a 10–15 minute walk or a 3–5 minute bike ride away. Swimming, shells, and calm water.
Right here in Silver Beach. A stony beach for picnics and shell collecting, plus a little tidal “river” kids love to splash in as the tide turns.
A long sandy beach with lifeguards, ideal for families.
Cast a line from the point on Ram Island.
Mini golf and ice cream, a summer-evening classic.
Kids love playing in the shallow tidal channel as the water flows in and out.
A great children’s program. Check their calendar when you arrive.
A working farm with a market and events through the season.
Ice cream on North Menantic Road.
A folding wooden crib and a high chair, board games, children’s books, a large fenced yard, and an automatic pool cover for peace of mind.
A beautiful bar and indoor/outdoor restaurant. Take your drink to the lawn for pétanque or cornhole with the kids.
Cocktails or dinner on the big porch over Crescent Beach. Book ahead in summer.
Country-chic, local ingredients, and an island favorite.
At the Island Boatyard. Indoor and outdoor seating, a kids’ menu, good cocktails, and live music. You can even paddle there: it’s a very doable, moderate kayak trip straight from the launch by the house. Just don’t forget your wallet.
A sports bar downstairs (get the smash burger) and finer dining upstairs, with cocktails around the fire pit.
Our pick for a casual cup of coffee and a great selection of sandwiches, right in the center of town next to the pharmacy and the post office.
A gourmet grocer with pastries and light meals. Eat on the back deck overlooking Dering Harbor.
Pancakes and milkshakes at the Islander Diner, or a retro counter breakfast at the Pharmacy Diner.
A short ferry ride away. Ride the classic carousel, then try Lucharitos for tacos and margaritas, the upper deck at Anker, a dockside drink at Crabby Jerry’s, or seafood at Claudio’s.
Our current favorites are The Old Field Vineyards and Rose Hill Vineyards.
The South Ferry puts you minutes from Sag Harbor. The Children’s Museum of the East End in Bridgehampton is a great rainy-day outing.
The easiest way: take the Hampton Jitney from Manhattan’s East Side to Greenport, about two and a half hours. It drops you right by the North Ferry. Walk on, then get picked up on the Shelter Island side or take a local taxi to the house.
From Greenport on the North Fork. Boats run every 10 to 15 minutes from early morning until after midnight.
From North Haven, near Sag Harbor. Boats run every 10 to 15 minutes, with late boats on Friday and Saturday nights.
Walk facing traffic and bike single file with traffic. The island gets busy with cyclists and walkers in summer. Local taxis run between the ferries and the North Fork.
A full welcome guide with house details and check-in instructions is shared after booking. We’re happy to pass along trusted contacts for cleaners, caterers, and other local help, arranged before your stay or once you’re on the island.
Many of our guests come back summer after summer.
“Well equipped for our family ages 5 to 75.”
“This was our second stay. We all love the house, pool and location.”
“The walk out to Shell Beach was just spectacular.”
Our family has loved Shelter Island for generations, and we come back every year. We hope you will too.
All bookings and messages go through VRBO. Questions about the house? Message us there and we’ll be happy to help.