18 Chestnut Hill Drive
Upper Brookville, NY, 11771 $ 4,980,000
Bedrooms7 Baths8.1 Sq 8,925 Monthly Estimate*
$ 34,396
for $4,980,000 with 7 bedrooms and 8 full baths, 1 half bath. This 8,925 square foot home was built in 1992 on a lot size of 5.
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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FeaturesInteriorInterior Amenities 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 Coun
Basement Finished Full
Basement Features Finished Full
Basement (Y/N) Y
Fireplace Y/N Y
Half Baths 1
Total Bedrooms 7
Total Baths 9
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GeneralSewer Cesspool
Heating Forced Air
Cooling Central Air
Utilities Cable Connected Electricity Connected Water Connected
Appliances Convection Oven Cooktop Dishwasher Dryer Electric Cooktop Electric Range Exhaust Fan Freezer Microwave Oven Range Refrigerator Stainless Steel Appliance(s) Washer
HOA Fee 1500
Garage Spaces 4
Association Fee Includes Other
Architectural Style Contemporary
Construction Materials Wood Siding
Year Built 1992
Property Subtype Single Family Residence
Tax Year 2025
Parcel Number 2427-24-E-00-1052-0
Assoc Fee Paid Per Annually
County Nassau County
Property Type Residential
HOA Y
Garage Y/N Y
Total Rooms 13
Full Baths 8
High School Locust Valley High School
City Oyster Bay
Senior Community Y/N N
High School District Locust Valley
Carport Y/N N
Spa Features Bath
Elementary School Ann Macarthur Primary School
Property Attached Y/N N
Tax Annual Amount 52120.72
Middle/Junior High School Locust Valley Middle School
Building Area Units Square Feet
Standard Status Active
Middle/Junior School District Locust Valley
Elementary School District Locust Valley
Tax Assessed Value 3225
Virtual Tour https://youtu.be/og-iu48sFLQ?si=U92lp1vLYuSMIOZe
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ExteriorParking Features Attached Garage Attached Garage
Water Source Public
Building Area Total 8925
Waterfront Y/N N
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* Excluded FeaturesList ByJason P. FriedmanListing Agent
Daniel Gale Sothebys Intl RltyBroker
Affordability Calculator
- Monthly Principal & Interest
- $34,396
- Monthly Property Taxes
- $4,343
- Monthly Home Insurance
- --
Default based on a 30-year fixed rate of 7.375% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
Learn more about how to save NearbySingle family listings in Upper Brookville, NY
Average List Price $6,250,250
Percent of Sale Price 26%
About Upper Brookville, NY 1,754 Population
-1% Since 2002
$ 182,142 Median Income
38.43 Median Age
40% Households with Children
Trends Information provided by ATTOM Data Solutions.
4099815 Elementary School
4099618 Middle School
Locust Valley High School High School
Pricing History| Date | Price | Price Change | Description |
|---|
| 10/12/2026 | $4,980,000 | | Listed Price |