38 Landing Meadow Road, Smithtown, NY 11787

$3,995,000 · 7 bed · 6 bath · 6,000 sq ft · built 1828 · MLS# 1022766 · Active

Welcome to 38 Landing Meadow Road, Smithtown. Nestled on almost 23 picturesque and serene waterfront acres overlooking the renowned Nissequogue River this is a truly extraordinary North Shore retreat. Driving down the long private driveway your senses are alive to the possibilities of what is to appear. Surrounded by breathtaking natural beauty, the property includes agricultural land adjoining approx. 60 acres of protected preserve, creating an unmatched sense of privacy and tranquility. Wide open vistas, emerald lawns, magnificent mature trees and the grand nature of this idyllic scene are unmatched.…

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 $3,995,000 list price sits in the luxury single-family tier for the Smithtown Central School District.

ZIP 11787 has about 2.7 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 $37,095 a year, this home's property tax runs roughly 147% 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