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7 Beds
9 Baths
8,925 sqft

$4,980,000

18 Chestnut Hill Drive, Upper Brookville NY, 11771

Price per sqft$557.98
Built in1992
Property size8,925 sqft
Property typeResidential

Overview

Active

Listed Oct 11, 2026

Updated 5 days ago

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.

$33,132/mo

Est. mortgage payment based on a $4,980,000 home price.

All estimates are provided by Luxury Presence for informational purposes only. Actual amounts may vary.

Additional information

MLS® ID
1061600
Available since
October 11, 2026

Interior Features

Bedrooms
7
Bathrooms
9
Basement
No

Exterior Features

Lot Size
5 Acres

Other Property Details

Taxes
$52,121
Tax Frequency
Annually
Garage
Yes

 Courtesy of Jason Friedman | Daniel Gale Sotheby's International Realty

Based on information from DASH - Sotheby's International Realty (SIR) as of 10/13/2026. This information is for your personal, non-commercial use and may not be used for any purpose other than to identify prospective properties you may be interested in purchasing. The display of MLS data is usually deemed reliable but is NOT guaranteed accurate by the MLS. Buyers are responsible for verifying the accuracy of all information should investigate the data themselves or retain appropriate professionals. Information from sources other than the Listing Agent may have been included in the MLS data. Unless otherwise specified in writing, Broker/Agent has not and will not verify any information obtained from other sources. The Broker/Agent providing the information contained herein may or may not have been the Listing and/or Selling Agent. 

©2026 DASH - Sotheby's International Realty (SIR). All rights reserved. 

Data last updated 4:03 AM UTC, 10/13/2026

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