31 Chestnut Hill Drive, Upper Brookville, NY 11771

$7,850,000 · 6 bed · 1 bath · 7,639 sq ft · built 1989 · MLS# 1061123 · Active

Introducing 31 Chestnut Hill Drive, an extraordinary contemporary estate situated on five private acres at the end of a prestigious cul-de-sac in Upper Brookville. Originally designed by renowned architect Gary Gallagher and comprehensively reimagined from 2023 to 2026 by award-winning architect Stuart Narofsky, this exceptional residence seamlessly blends striking modern architecture with sophisticated design, cutting-edge technology, and resort-style amenities. Spanning over 10,000 square feet, the home features six bedrooms, six full and four half bathrooms, including a luxurious first-floor primary suite. Dramatic architectural details, including two custom floating staircases with…

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 $7,850,000 list price sits in the luxury single-family tier for the Locust Valley Central School District.

ZIP 11771 has about 6 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 $53,464 a year, this home's property tax runs roughly 214% 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