$4,980,000
 $26,734 est/mo Sourced by Back At You

18 Chestnut Hill Drive,Upper Brookville, NY 11771

Upper Brookville, NY 11771

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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.

Details

MLS #1061600
Listing TypeFor Sale
StyleHouse
HOA Dues$1,500
Sub-TypeResale
StatusActive
Year1992
Days On Site32
Listing Provided ByDaniel Gale Sothebys Intl Rlty | Jason P. Friedman

Features

Bed(s)7
Bath(s) 9 Total
SQ Feet8,925
Garage4
BasementY
PoolYes
Acreage5.00

Interior

CoolingCentral Air
HeatingForced Air
Interior FeaturesFirst 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
AppliancesConvection Oven, Cooktop, Dishwasher, Dryer, Electric Cooktop, Electric Range, Exhaust Fan, Freezer, Microwave, Oven, Range, Refrigerator, Stainless Steel Appliance(s), Washer

Exterior

Construction MaterialsWood Siding

Parking

Garage Yes / NoYes
Parking FeaturesAttached, Garage

Utilities

UtilitiesCable Connected, Electricity Connected, Water Connected
SewerCesspool

Taxes

Tax Year2025
Tax Assessed Value3225
Tax Annual Amount52120.72

Area Information

StateNY
CountyNassau County
CityUpper Brookville
Zip Code11771
School DistrictLocust Valley High School
Elementary SchoolAnn Macarthur Primary School
High SchoolLocust Valley High School
Listing VS Median (in 11771)
Price:
$4,980,000
low | high
Med:
$1,325,000
100% of Average
sqft:
8,925
low | high
Med:
2,716
100% of Average
$ / sqft:
$558
low | high
Med:
$488
62.569090796174% of Average
On site:
32
low | high
Med:
190
16.842105263158% of Average
Sourced by Back At You

Market Activity 11771

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Learn More About This Property

StateNY
CountyNassau County
CityUpper Brookville
Zip Code11771
School DistrictLocust Valley High School
Elementary SchoolAnn Macarthur Primary School
High SchoolLocust Valley High School
Listing VS Median (in 11771)
Price:
$4,980,000
low | high
Med:
$1,325,000
100% of Average
sqft:
8,925
low | high
Med:
2,716
100% of Average
$ / sqft:
$558
low | high
Med:
$488
62.569090796174% of Average
On site:
32
low | high
Med:
190
16.842105263158% of Average
Sourced by Back At You
Nearby Listings (Within 1/2 mile)
Price: $3.735M - $6.225M
sqft: 6,500 - 11,000
Nearby Listings Property ImageNearby Listings Details
7 Fairway Court Property Photo 1
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10 Laurel Woods Drive Property Photo 1
$4,200,000
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Upper Brookville, NY 11771
Listing Updated: October 13, 2026 at 4:07:16 AM PDT