20 Hillside Road, Southampton, NY 11968

$4,495,000 · 4 bed · 5 bath · 3,853 sq ft · built 1987 · MLS# 914642 · Active

Private, Park-Like Estate in Southampton - Welcome to 20 Hillside Road, a serene estate set on over 4 acres of beautifully-manicured grounds. This custom-built home has been meticulously cared for over three decades, and offers an exceptional blend of privacy, tranquility, and natural beauty. Inside, graciously-proportioned rooms, vaulted ceilings, and large windows create a bright, airy ambiance that serves as a canvas for your lifestyle. Step outside to enjoy a suite of resort-like amenities, including a gunite pool with cabana, tennis court, and acres of lush grounds. Just under five…

Single-family homes in the Tuckahoe Common School District sold for a median of $2,040,000 (typically $1,490,000–$3,500,000) across 33 recorded sales between Oct 30, 2025 and Oct 2, 2026, down 0.5% on the 12 months before.

ZIP 11968 has about 10.8 months of single family inventory — strong buyer's market. A heavily oversupplied market — buyers hold the upper hand, and sellers often offer price cuts or concessions to compete.

At about $12,476 a year, this home's property tax runs roughly 56% above the $8,000 typical for Tuckahoe Common 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