Head of the Harbor, NY

Tucked along the scenic waters of Stony Brook Harbor on Long Island's North Shore, Head of the Harbor is a quiet, picturesque village within the Town of Smithtown. Home to around 1,500 residents, the community is known for its winding, tree-lined roads, spacious properties, and preserved coastal landscapes. Daily life here blends seamlessly with neighboring Stony Brook and St. James, giving locals a peaceful, semi-rural setting with convenient access to nearby shops, restaurants, and train stations.

ATTRDougtone / CC BY-SA 2.0

For families, school assignments depend on where you live in the village, with students attending either the Smithtown Central School District or Brookhaven's Three Village Central School District. A strong commitment to historic preservation and open space helps the area retain its timeless charm. You will find historic landmarks like the 1845 Deepwells Farm estate alongside great outdoor spots, including the scenic walking trails at Avalon Nature Preserve right along the harbor.