18 Chestnut Hill Drive, Upper Brookville, NY 11771

$4,980,000 · 7 bed · 9 bath · 8,925 sq ft · built 1992 · MLS# 1061600 · Active

Set on five magnificent acres of sprawling, level grounds along one of Long Island’s most coveted residential streets, this extraordinary contemporary estate, designed by acclaimed architectural firm Mojo Stumer, represents a sophisticated expression of modern luxury, architectural innovation, and resort-inspired living. Distinguished by dramatic proportions, soaring ceilings, expansive walls of glass, and a seamless connection between indoor and outdoor spaces, the residence offers an exceptional combination of architectural significance, privacy, and grand-scale entertaining. A grand entrance foyer introduces interiors defined by remarkable volume and natural light, leading to a breathtaking…

Single-family homes in the Locust Valley Central School District sold for a median of $1,230,000 (typically $815,000–$2,400,000) across 141 recorded sales between Oct 7, 2025 and Oct 1, 2026, down 12.2% on the 12 months before. This home's $4,980,000 list price sits in the luxury single-family tier for the Locust Valley Central School District.

ZIP 11771 has about 5.4 months of single family inventory — balanced market. Supply and demand are roughly even, so buyers and sellers share leverage with fair, predictable pricing.

At about $52,121 a year, this home's property tax runs roughly 207% above the $17,000 typical for Locust Valley Central School District. Nassau assessments run on a multi-year cycle, so the assessed value behind this bill can lag what the home actually sells for today. A sale does not automatically reset it, and 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