21 Wilderness Road, Nissequogue, NY 11780

$1,419,999 · 4 bed · 4 bath · 2,905 sq ft · built 1965 · MLS# 1027742 · Active

Welcome to 21 Wilderness Road, an exceptional Colonial set on two private acres in the Village of Nissequogue, where timeless design and thoughtful updates come together in a private, serene setting. Offering 4 bedrooms and 4 bathrooms, this residence delivers generous living spaces, refined finishes, and effortless everyday comfort. Hardwood floors, detailed crown molding, and an inviting floor plan create a warm yet elegant atmosphere throughout. The updated kitchen is appointed with granite countertops, abundant cabinetry, and flows seamlessly into the main living areas, making it ideal for both entertaining…

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 $1,419,999 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 $20,775 a year, this home's property tax runs roughly 39% 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