89 Harbor Road, Head Of The Harbor, NY 11780

$1,999,000 · 5 bed · 4 bath · 4,600 sq ft · built 1974 · MLS# 1054624 · Active

A Rare Waterfront Sanctuary in the Village of Head of the Harbor. For the first time since it was built more than half a century ago, this remarkable waterfront property is being offered for sale. Privately set on 2.75 acres overlooking Stony Brook Harbor, 89 Harbor Road has remained under its original ownership since its creation and is defined by privacy, natural beauty and an extraordinary connection to the surrounding landscape. With 200 feet of waterfront, sweeping views extend across the pristine harbor toward Nissequogue, and Long Island Sound beyond,…

Single-family homes in the Smithtown Central School District sold for a median of $845,000 (typically $735,000–$995,000) across 440 recorded sales between Oct 6, 2025 and Oct 2, 2026, up 5% on the 12 months before. This home's $1,999,000 list price sits in the luxury single-family tier for the Smithtown Central School District.

ZIP 11780 has about 3.6 months of single family inventory — seller's market. Demand is outpacing supply, so homes sell quickly with firm pricing and limited room to negotiate.

At about $39,785 a year, this home's property tax runs roughly 165% above the $15,000 typical for Smithtown Central School District. Suffolk bills combine town, school and special-district levies, so two homes at the same price in neighboring districts can carry materially different taxes. Exemptions such as STAR, Senior or Veteran move the number as well — a new owner's bill is often not the same as the seller's.

OneKey MLS (recorded LI sales, trailing 12mo) + actual tax