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18 Chestnut Hill Drive

Upper Brookville, NY, 11771

$4,980,000
7Bedrooms
9Bathrooms
8,925Interior sq ft
5Acres
1992Year built

AN INTRODUCTION

A closer look.

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 double-height great room anchored by a striking marble fireplace. Expansive windows frame picturesque views of the surrounding landscape, enhancing the home's connection to its private, park-like setting. The thoughtfully designed main level features an elegant formal dining room, spacious eat-in kitchen, inviting family room, and sophisticated lounge with a wet bar. A powder room and first-floor laundry provide additional convenience. Occupying a private wing of the main level, the luxurious first-floor primary suite offers an exceptional retreat, complete with a generous his and her walk-in closet and a beautifully appointed bathroom featuring a steam shower. An additional first-floor bedroom with a full bathroom provides ideal accommodations for guests or extended family. The second level features four generously proportioned guest bedrooms complemented by two full bathrooms. Additionally an expansive loft with its own balcony and full bathroom offers a versatile space ideally suited for a private office, additional lounge, or secluded retreat. Designed for recreation, wellness, and entertaining, the expansive lower level features a dramatic double-sided fireplace connecting the game room and entertainment spaces. A spacious recreation area with a wet bar provides the perfect setting for gatherings, while a substantial private gym with its own full bathroom creates a dedicated fitness retreat. Additional accommodations include a staff or guest bedroom and another full bathroom. Beyond the residence sits a remarkable private resort featuring a swimming pool, hot tub, and tennis court. A substantial poolside cabana offers a full indoor kitchen, outdoor wet bar, comfortable lounge, full bathroom, and dedicated laundry facilities. A built-in outdoor grill completes the exceptional entertaining amenities, providing an effortless transition between indoor luxury and outdoor leisure. A four-car garage further complements the estate, providing generous space for automobiles and storage. The property presents a remarkable opportunity to experience architectural distinction, privacy, and an uncompromising lifestyle.

Property overview

Property type
Single Family Residence
Architecture
Contemporary
Year built
1992
Lot size (sq ft)
217,800
Status
Active
Listed
2026-10-12
MLS number
KEY1061600

Interior & comfort

Interior features
First Floor Bedroom, First Floor Full Bath, Cathedral Ceiling(s), Chefs Kitchen, Eat-in Kitchen, Entrance Foyer, Formal Dining, Granite Counters, High Ceilings, His and Hers Closets, Kitchen Island, Marble Counters, Open Floorplan, Pantry, Primary Bathroom, Master Downstairs, Sauna, Sound System, Stone Counters, Storage, Walk-In Closet(s), Wet Bar
Appliances
Convection Oven, Cooktop, Dishwasher, Dryer, Electric Cooktop, Electric Range, Exhaust Fan, Freezer, Microwave, Oven, Range, Refrigerator, Stainless Steel Appliance(s), Washer
Heating
Forced Air
Cooling
Central Air
Basement
Finished, Full

Outdoors & amenities

Parking
Attached, Garage
Garage spaces
4

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
$52,121
Tax year
2025
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 #KEY1061600 · Active

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