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Head of Harbor NY Real Estate & Homes for Sale

Head of Harbor NY Homes for Sale

Head of the Harbor is a village in the Town of Smithtown in Suffolk County, Long Island, New York. It is an upper-middle class residential community in a densely-treed waterfront setting, blanketed by plenty of tulips and maple trees. It has shared a rich and complex history with Nissequogue Village and the neighborhood of Saint James for over three centuries.

Local Area Information

Head of the Harbor is an incorporated village in Suffolk County’s Town of Smithtown on the North Shore of Long Island, New York. It is a coastal community adjacent to Stony Brook, Saint James, the hamlet of Smithtown, and the village of Nissequogue, which is practically its mirror image. Its northwestern edges are bordered by the waters of Stony Brook Harbor.

Incorporated in 1928, Head of the Harbor enforced strict zoning regulations to retain the neighborhood’s historic characteristic and rustic charm. The place only allows single-family homes, most of which are on two-acre zoned lots, maintaining the wide spaces between the residences and creating a more suburban appearance as a consequence.

The homes tucked away in the woods are a mix of 1960s colonials, 1980s contemporaries, a few split-level ranches, and a number of stately 19th-century estates and luxury homes with a pool modestly hidden by hedges. Many of the homes are waterfront properties with spectacular water views and membership to small homeowner associations, which take care of such community resources as the stairs descending to the beaches.

Head of the Harbor may be lacking a commercial district, but shopping is not entirely nonexistent as strip malls and interstate roads are nearby. The neighborhood is generally considered a safe place by national and state standards and is served round-the-clock by uniformed members of the Village of Head of the Harbor Police Department. Along with the hamlet of St. James, the village is protected by the St. James Volunteer Fire Department.

Manhattan, around 52 miles southwest in New York City, can be reached via the Long Island Rail Road’s Port Jefferson Branch with trains from St. James Station to Penn Station running daily on weekdays. Driving to or from the city takes around an hour and 22 minutes to a couple of hours via the Long Island Expressway or Northern State Parkway.

General Information

Township: Town of Smithtown | Smithtown, New York

County: Suffolk County

Population: 1,520 (2020)

Classification: Incorporated Village

LIRR Train Station/Schedule:
The LIRR serves Head of Harbor via the St. James Station.
Travel time to Manhattan, Penn Station is about
1 hour 31 minutes to 1 hour 50 minutes.

Head of Harbor, NY suburban home with front porch


Water District
Suffolk County Water Authority

Gas Company(s)
PSEG Long Island
National Grid

Electric Company(s)
PSEG Long Island

Cable/ Phone/ TV/ Internet Provider(s)
Verizon Fios


Head of Harbor, NY Listings

Beaches & Parks

The nearby Avalon Park & Preserve in Stony Brook is a 140-acre oasis for nature lovers and has natural habitats for various forest animal and plant species. Sometimes referred to as the “Stony Brook Duck Pond,” the arboretum features a pond, five habitats, a wildflower meadow, over 80 acres of nature trails, a labyrinth, boardwalk and benches. The park is just across from Stony Brook Grist Mill and is located on Harbor Road, off Main Street, and is open year round from dawn to dusk for free to the public.

Cordwood Park of the Town of Smithtown is a pocket park that offers scenic views of the sunset or sunrise over Stony Brook Harbor, picnic opportunities, and access to the waters of the harbor for fishing, canoeing, kayaking or paddleboarding for those who have the equipment, or simply taking a quiet walk along the shoreline. There are picnic tables and benches on the park grounds and wooden fences around the viewing area.

The Schools

Most Head of the Harbor village students are served by the Smithtown Central School District, which has 12 public schools. Students within the district start off at Saint James Elementary School, then go to Nesaquake Middle School after, and Smithtown High School East next.

A smaller segment of the student populace in the northeastern area is served by the Three Village Central School District, which has eight public schools. District students in the village attend Minnesauke Elementary School, Paul J. Gelinas Junior High School and Ward Melville Senior High School.

Also located within the village is the Harbor Country Day School, a private educational institution for pre-K through eighth grade, accredited by the NYS Association of Independent Schools.


Head of Harbor, NY

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Communities In The Township Of Smithtown