18 Chestnut Hill DR Upper Brookville, NY 11771 New

UPDATED: 10/13/2026 09:01 AM ON MARKET: 4 days on market

$4,980,000

7 Beds9 Baths8,925 SqFt

Key Details

Property Type Single Family Home

Sub Type Single Family Residence

Listing Status Active

Purchase Type For Sale

Square Footage 8,925 sqft

Price per Sqft $557

MLS Listing ID 1061600

Style Contemporary

Bedrooms 7

Full Baths 8

Half Baths 1

HOA Fees $1,500/ann

HOA Y/N Yes

Rental Info No

Year Built 1992

Annual Tax Amount $52,120

Lot Size 5.000 Acres

Acres 5.0

Property Sub-Type Single Family Residence

Source onekey2

Location

State NY

County Nassau County

Rooms

Basement Finished,Full

Interior

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

Heating Forced Air

Cooling Central Air

Fireplace No

Appliance Convection Oven,Cooktop,Dishwasher,Dryer,Electric Cooktop,Electric Range,Exhaust Fan,Freezer,Microwave,Oven,Range,Refrigerator,Stainless Steel Appliance(s),Washer

Exterior

Parking Features Attached,Garage

Garage Spaces 4.0

Utilities Available Cable Connected,Electricity Connected,Water Connected

Garage true

Private Pool Yes

Building

Sewer Cesspool

Water Public

Structure Type Wood Siding

Schools

Elementary Schools Ann Macarthur Primary School

Middle Schools Locust Valley Middle School

High Schools Locust Valley

School District Locust Valley

Others

Senior Community No

Special Listing Condition None

Property Description

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.

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