Head of the Harbor is located in Suffolk County on Long Island’s North Shore, overlooking the Long Island Sound.

The Nissequogue River is a main attraction here, in addition to the 543-acre Caleb Smith State Park and historic sites like the Franklin O. Arthur Farm. The area has attracted young buyers for decades—its child-friendly environment and affordable, high-quality homes make it ideal for families.

Smithtown itself has a “real” downtown. The village of Nissequogue is also a coveted area with beautiful luxury homes on the Sound as well as golf and country clubs, the Nissequogue River State Park and Sunken Meadow State Park with six miles of public trails. 

The Smithtown school district is noted for its schools, parks, and natural beauty as well as for its classic, well-kept downtown district at the heart of the surrounding waterfront estates of Fort Salonga and the low-key suburbs and large older homes and beach houses of San Remo. Within its boundaries are five miles of publicly-owned shoreline and more open space and recreation area than most Long Island communities, and it borders one of the island's few rivers.

Head of the Harbor is a short distance from the destination and recreation spots that Long Island is known for: The North Fork vineyards, the neighborhoods of central Long Island and the Hamptons and beaches of the South Fork as well as the quieter residential communities of Stony Brook, Huntington and Old Field. The area is a 90-minute commute to New York City on the Long Island Railroad and is accessible major highways and the Sunken Meadow Parkway.