Shelter Island

$695,000 Prime 1.2-acre buildable lot on the desirable south side of Shelter Island with water views and room for a pool. Approved building plans available. A rare opportunity to build your dream island home. Listed by Debra Von Brook-Binder, Daniel Gale Sotheby’s International Realty. View Full Listing Details Read more...

$4,750,000  |  5 Bed  |  4 Bath Stunning 5-bedroom waterfront property with panoramic views of Dering Harbor and Greenport. Deep water dock, heated pool, expansive lawns, and a renovated chef’s kitchen. One of the premier waterfront offerings on Shelter Island. Listed by Debra Von Brook-Binder, Daniel Gale Sotheby’s International Realty. View Full Listing Details Read more...

$1,295,000  |  3 Bed  |  2 Bath A beautifully maintained 3-bedroom cottage in Shelter Island Heights with an open floor plan, updated kitchen, wrap-around porch, and a short walk to the beach. This classic island home blends vintage character with modern comfort. Listed by Debra Von Brook-Binder, Daniel Gale Sotheby’s International Realty. View Full Listing Details Read more...

Annual Memorial Day ceremony honoring veterans with a community parade and remembrance service on Shelter Island. A solemn and meaningful tradition paying tribute to those who served. Read more...

Annual community holiday tree lighting ceremony in Shelter Island Heights with carols, hot cocoa and festive cheer. A beloved winter tradition that brings the island community together during the holiday season. Read more...

Community adult recreation sports programs at the Shelter Island School including softball, basketball and volleyball. Seasonal programs organized by the town recreation department for island residents. Read more...

Public meetings of the Shelter Island Town Board held on the 1st and 3rd Friday of each month. Open to all residents and property owners. Stay informed about town governance, zoning decisions, and community issues. Read more...

Year-round programming at the Shelter Island Public Library including author talks, book clubs, children’s programs, movie screenings, art exhibitions and community events. The library serves as a cultural hub for island residents. Read more...

Free classical and chamber music concerts throughout the summer on Shelter Island. Nine performances featuring acclaimed musicians in intimate settings across the island. A cultural highlight of the Shelter Island summer season. Read more...

Nature education programs for children at Mashomack Preserve including guided hikes, wildlife identification and outdoor activities. A wonderful way for kids to connect with nature on Shelter Island during the summer months. Read more...