Active
18 Chestnut Hill Drive
Upper Brookville, NY, 11771
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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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