18 Chestnut Hill Drive Upper Brookville, NY $ 4,980,000
18 Chestnut Hill Drive
$ 4,980,000
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18 Chestnut Hill Drive

Upper Brookville, NY, 11771
$ 4,980,000
Bedrooms7 Baths8.1 Sq 8,925

Monthly Estimate*

$ 34,396

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Single Family Home for sale in Upper Brookville, NY

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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Single Family Active

Price

$ 4,980,000

Bedrooms

7

Full Bath

8

Half Bath

1

Property Type

Single Family

Taxes

$ 52,120

Style

Contemporary

Lot Size

5

Year Built

1992

Town/City

Upper Brookville

County/Region

Nassau

MLS | Web ID

1061600

Features
Interior
Interior 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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General
Sewer 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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Exterior
Parking Features Attached Garage Attached Garage
Water Source Public
Building Area Total 8925
Waterfront Y/N N
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Internal Only
Street Number 1 18
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* Excluded Features
List By
Jason P. Friedman

Listing Agent

Daniel Gale Sothebys Intl Rlty

Broker

516-626-7600

Contact

Affordability Calculator

$38,739
Per Month
89%
11%
0%
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.
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Nearby
4099815 Elementary School
4099618 Middle School
Locust Valley High School High School
Pricing History
DatePricePrice ChangeDescription
10/12/2026$4,980,000 Listed Price

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18 Chestnut Hill Drive, Upper Brookville, NY, 11771 is a Single Family Home for sale at $4,980,000 with 8,925 sqft and a lot size of 5. 18 Chestnut Hill Drive has 7 bedrooms, 8.1 baths, and was built in 1992. The property's zip code is 11771 which is in Upper Brookville, NY