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31 Chestnut Hill Drive

Upper Brookville, NY, 11771

$7,850,000
6Bedrooms
10Bathrooms
7,639Interior sq ft
5Acres
1989Year built

AN INTRODUCTION

A closer look.

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 glass railings, expansive walls of glass, porcelain flooring, and polished white oak floors, create a remarkable sense of openness and light. Thoughtfully designed living and entertaining spaces are complemented by a state-of-the-art chef's kitchen featuring custom cabinetry, integrated Thermador appliances, specialty quartz countertops, and an expansive center island. The home's extensive accommodations include multiple home offices, a library, and beautifully appointed guest suites. The fully finished lower level offers an exceptional collection of recreational and wellness amenities, including a Dolby Atmos home theater, custom wine room and tasting area, wet bar, fitness room, Finnish sauna, and dedicated yoga and massage space. Outdoors, the estate unfolds into a private resort-like setting, complete with a newly rebuilt heated saline pool and spa, expansive porcelain patios, and a fully renovated guest/pool house with its own kitchen. An outdoor kitchen and beautifully landscaped grounds provide an ideal setting for both intimate gatherings and large-scale entertaining. Additional highlights include a heated four-car garage, five-zone energy-efficient climate control, whole-house generator, and comprehensive smart-home technology managing lighting, security, motorized shades, and numerous additional systems. Offering exceptional privacy, architectural distinction, and an extraordinary level of modern luxury, 31 Chestnut Hill Drive represents a rare opportunity to experience contemporary estate living on Long Island's Gold Coast.

Property overview

Property type
Single Family Residence
Architecture
Contemporary, Modern
Condition
Actual
Year built
1989
Lot size (sq ft)
217,800
Status
Active
Listed
2026-10-15
MLS number
KEY1061123

Interior & comfort

Interior features
First Floor Bedroom, First Floor Full Bath, Built-in Features, Central Vacuum, Chefs Kitchen, Double Vanity, Eat-in Kitchen, Entrance Foyer, Formal Dining, High Ceilings, High Speed Internet, His and Hers Closets, Kitchen Island, Open Floorplan, Primary Bathroom, Master Downstairs, Quartz/Quartzite Counters, Recessed Lighting, Sauna, Smart Thermostat, Soaking Tub, Walk-In Closet(s), Wet Bar
Appliances
Dishwasher, Dryer, Electric Cooktop, Electric Oven, Exhaust Fan, Microwave, Refrigerator, Washer
Heating
Electric, Forced Air
Cooling
Central Air
Basement
Partial, Walk-Out Access
Fireplaces
2

Outdoors & amenities

Exterior features
Balcony, Gas Grill, Lighting, Mailbox
Parking
Attached, Driveway, Garage, Garage Door Opener, Heated Garage
Garage spaces
4
Pool
Fenced, In Ground, Pool Cover, Salt Water, Tile
Views
Trees/Woods

Schools & location

Postal town
Upper Brookville
County
Nassau County
School district
Locust Valley
Elementary school
Ann Macarthur Primary School
Middle school
Locust Valley Middle School
High school
Locust Valley High School

Taxes & utilities

Annual property taxes
$53,464
Tax year
2026
Association
Yes
Association fee
$1,500
Fee frequency
Annually
Water
Public
Sewer
Cesspool

Listing courtesy of Daniel Gale Sothebys Intl Rlty · 516-626-7600
MLS #KEY1061123 · Active

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