Shelter Island

This secluded island offers a peaceful reprieve from the everyday hustle and bustle of city.

Shelter Island Real Estate

The quiet, laid back, and boating-inspired island known for its charming, serene setting
Shelter Island offers a completely different environment from the Hamptons that feels more relaxed, quiet, and laid back. This secluded island offers a peaceful reprieve from the everyday hustle and bustle of city life complete with pristine beaches, serene hiking trails, cozy cafés, and endless boating with all of the charming and picturesque scenery you expect from the East End but with none of the crowds.

What to Love 

  • Spending the night at SEVEN: the cute, yet modern bed and breakfast
  • Spending the day on Crescent Beach with lunch and cocktails at Sunset Beach
  • Exploring the greenery, coastal views, and wildlife along Mashomack Preserve
  • Sipping craft brews at the Shelter Island Brewery

Local Lifestyle 

The secluded, 8,000-acre island is a five-minute ride from the Hamptons, the vacation destination of choice among wealthy New Yorkers. Known as the "un-Hamptons" for its quiet, charming, and serene setting, Shelter Island offers more of a laid-back vibe than a thriving and entertaining nightlife.

Dining, Entertainment & Shopping

Sunset Beach Hotel offers just twenty guest rooms, each one with a private porch looking out onto the water. Discover sensational food and drinks inside the European-style restaurant that hosts some of the area's best DJs. Enjoy endless activities with easy access to the beach complete with complimentary bikes, beach chairs, paddleboards, and boats to water-ski, fish, or explore the area by water. And don’t forget to watch the sunset.

Ready to feel part of an exclusive, old-world club? Ram’s Head Inn is the iconic Shelter Island waterfront destination rich with farm/sea-to-table dining, a beach with moorings, live music, private event spaces, spa services, and guest rooms scattered across 4.5 beautifully landscaped acres.

Vine Street Cafe offers food with integrity, delivering only the highest quality ingredients and perfect layers of flavor while taking zero shortcuts along the way. Discover seasonally influenced menus inspired by time-honored culinary techniques complete with food made intensely from the ground up with bounty supplied by the great resources among local farmers, fishermen, and winemakers. 

Dreaming of sunny days on the porch of the oldest continuously used public building on Shelter Island? Check out the online reservation system to book your stay with Chequit Inn this summer when the new owner completes his renovation vision consistent with its storied past as the social center of the summer community. 

Things to Do

There is no better beach club membership in town than Shelter Island Heights, where fishing, firepits, tennis, a kids program, and other key summer perks connect you with the rich history, distinctive and quaint character, and natural environment known to the community-favorite spot.

Need a place that’s private, discrete, and perfect for settling in? Dering Harbor offers scenically situated pristine heated swimming pools, a fitness center with tennis courts, a dock, and over seven acres of walkabout space to relax, reflect and rejuvenate. Slow to the Shelter Island pace rightfully referred to as the "un-Hamptons” in an area walking distance from village restaurants, bars, markets, shops, and bike rentals.

If the natural wonders of 11 miles of coastline and acres of creeks, woodlands, and fields are  more your speed, then Mashomack Preserve is the place for you. Or maybe you’re the parent of a young string player of rare and special talent itching to join the unparalleled musical training at Itzhak Perlman Music Camp.


Shelter Island is home to Hayground School, the distance learning program using this unusual time as an opportunity to revisit on-campus learning and segue into a more authentic at-home learning experience for students. 

  • Shelter Island Union Free School District - K through 12


Other Neighborhoods


Are you considering moving to this gorgeous island? Contact the Jonathan Milioti Team to explore Shelter Island real estate now!

Browse Properties in the Area


As a real estate investors, owners, and landlords, we have made a career of our passion. With decades of professional and personal experience, we are experts in the process of buying, selling, and renting homes.

Contact Us