Head of the Harbor
Discover Head of the Harbor: Secluded Sophistication on the North Shore
Nestled along the scenic coastline of Long Island’s North Shore, Head of the Harbor is a hidden haven of luxury, tranquility, and natural beauty. With its rolling hills, panoramic waterfront views, and estate-style homes, this incorporated village in the Town of Smithtown offers an exclusive lifestyle steeped in elegance and privacy.
Estate Living in a Coastal Setting
Head of the Harbor features:
Gated estates and custom-built homes on multi-acre lots
Colonial, Mediterranean, and contemporary architectural styles
Properties with horse stables, private docks, and sweeping water views
Quiet, winding roads framed by ancient oaks and stone walls
Neighborhood Highlights:
✔ Panoramic views of Stony Brook Harbor and Long Island Sound
✔ Minutes from Stony Brook Village shops, dining, and marina
✔ Access to hiking trails, beaches, and Avalon Park & Preserve
✔ Zoned for the acclaimed Smithtown Central School District
The Head of the Harbor Lifestyle
Morning: Coffee on your veranda overlooking the harbor
Afternoon: Horseback riding, kayaking, or gardening on your estate
Evening: Private dinners under the stars or hosting at-home concerts
Weekends: Gallery hopping in nearby villages or sailing on the Sound
Why Discerning Buyers Choose Head of the Harbor
• Ultra-private, low-density community with luxury acreage
• Unspoiled nature and open space with high-end amenities nearby
• Proximity to renowned hospitals, universities, and cultural hubs
• A retreat for those seeking North Shore grandeur without pretense
Note: Many properties here are custom or legacy homes—off-market listings are common.
For buyers looking to escape into refined coastal seclusion, Head of the Harbor offers timeless beauty, unmatched privacy, and rare North Shore prestige.
Contact us today for exclusive listings and estate tours in Head of the Harbor.
