$7,850,000
 $42,140 est/mo Sourced by Back At You

31 Chestnut Hill Drive,Upper Brookville, NY 11771

Upper Brookville, NY 11771

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Description

Introducing 31 Chestnut Hill Drive, an extraordinary contemporary estate situated on five private acres at the end of a prestigious cul-de-sac in Upper Brookville. Originally designed by renowned architect Gary Gallagher and comprehensively reimagined from 2023 to 2026 by award-winning architect Stuart Narofsky, this exceptional residence seamlessly blends striking modern architecture with sophisticated design, cutting-edge technology, and resort-style amenities. Spanning over 10,000 square feet, the home features six bedrooms, six full and four half bathrooms, including a luxurious first-floor primary suite. Dramatic architectural details, including two custom floating staircases with glass railings, expansive walls of glass, porcelain flooring, and polished white oak floors, create a remarkable sense of openness and light. Thoughtfully designed living and entertaining spaces are complemented by a state-of-the-art chef's kitchen featuring custom cabinetry, integrated Thermador appliances, specialty quartz countertops, and an expansive center island. The home's extensive accommodations include multiple home offices, a library, and beautifully appointed guest suites. The fully finished lower level offers an exceptional collection of recreational and wellness amenities, including a Dolby Atmos home theater, custom wine room and tasting area, wet bar, fitness room, Finnish sauna, and dedicated yoga and massage space. Outdoors, the estate unfolds into a private resort-like setting, complete with a newly rebuilt heated saline pool and spa, expansive porcelain patios, and a fully renovated guest/pool house with its own kitchen. An outdoor kitchen and beautifully landscaped grounds provide an ideal setting for both intimate gatherings and large-scale entertaining. Additional highlights include a heated four-car garage, five-zone energy-efficient climate control, whole-house generator, and comprehensive smart-home technology managing lighting, security, motorized shades, and numerous additional systems. Offering exceptional privacy, architectural distinction, and an extraordinary level of modern luxury, 31 Chestnut Hill Drive represents a rare opportunity to experience contemporary estate living on Long Island's Gold Coast.

Details

MLS #1061123
Listing TypeFor Sale
StyleHouse
HOA Dues$1,500
Sub-TypeResale
StatusActive
Year1989
Days On Site19
Listing Provided ByDaniel Gale Sothebys Intl Rlty | Jason P. Friedman

Features

Bed(s)6
Bath(s) 10 Total
SQ Feet7,639
Garage4
BasementY
PoolYes
Acreage5.00
Property ViewTrees, Woods

Interior

CoolingCentral Air
HeatingElectric, Forced Air
Interior FeaturesFirst Floor Bedroom, First Floor Full Bath, Built-in Features, Central Vacuum, Chefs Kitchen, Double Vanity, Eat-in Kitchen, Entrance Foyer, Formal Dining, High Ceilings, High Speed Internet, His and Hers Closets, Kitchen Island, Open Floorplan, Primary Bathroom, Master Downstairs, Quartz/Quartzite Counters, Recessed Lighting, Sauna, Smart Thermostat, Soaking Tub, Walk-In Closet(s), Wet Bar
Window FeaturesCasement, Double Pane Windows, Floor to Ceiling Windows, New Windows, Oversized Windows
AppliancesDishwasher, Dryer, Electric Cooktop, Electric Oven, Exhaust Fan, Microwave, Refrigerator, Washer

Exterior

Exterior FeaturesBalcony, Gas Grill, Lighting, Mailbox
Security FeaturesBuilding Security, Fire Alarm, Security Gate, Security Lights, Security System, Smoke Detector(s), Video Cameras
Construction MaterialsFrame
Lot FeaturesBack Yard, Cul-De-Sac, Landscaped, Sprinklers In Front, Sprinklers In Rear

Parking

Garage Yes / NoYes
Parking FeaturesAttached, Driveway, Garage, Garage Door Opener, Heated Garage

Utilities

UtilitiesElectricity Connected, Propane, Trash Collection Private
SewerCesspool

Taxes

Tax Year2026
Tax Annual Amount53464

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:
$7,850,000
low | high
Med:
$1,325,000
100% of Average
sqft:
7,639
low | high
Med:
2,716
100% of Average
$ / sqft:
$1,028
low | high
Med:
$488
100% of Average
On site:
19
low | high
Med:
180
10.555555555556% 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:
$7,850,000
low | high
Med:
$1,325,000
100% of Average
sqft:
7,639
low | high
Med:
2,716
100% of Average
$ / sqft:
$1,028
low | high
Med:
$488
100% of Average
On site:
19
low | high
Med:
180
10.555555555556% of Average
Sourced by Back At You
Listing Updated: October 16, 2026 at 12:52:20 PM PDT