31 Chestnut Hill Drive Upper Brookville, NY $ 7,850,000
31 Chestnut Hill Drive
$ 7,850,000
Recently Listed
Share Save

31 Chestnut Hill Drive

Upper Brookville, NY, 11771
$ 7,850,000
Bedrooms6 Baths6.4 Sq 7,639

Monthly Estimate*

$ 54,218

31 Chestnut Hill Drive, Upper Brookville, NY 11771 - Image 1
31 Chestnut Hill Drive, Upper Brookville, NY 11771 - Image 2
31 Chestnut Hill Drive, Upper Brookville, NY 11771 - Image 3
31 Chestnut Hill Drive, Upper Brookville, NY 11771 - Image 4
31 Chestnut Hill Drive, Upper Brookville, NY 11771 - Image 5
31 Chestnut Hill Drive, Upper Brookville, NY 11771 - Image 6
31 Chestnut Hill Drive, Upper Brookville, NY 11771 - Image 7
31 Chestnut Hill Drive, Upper Brookville, NY 11771 - Image 8
31 Chestnut Hill Drive, Upper Brookville, NY 11771 - Image 9
31 Chestnut Hill Drive, Upper Brookville, NY 11771 - Image 10
31 Chestnut Hill Drive, Upper Brookville, NY 11771 - Image 11
31 Chestnut Hill Drive, Upper Brookville, NY 11771 - Image 12
31 Chestnut Hill Drive, Upper Brookville, NY 11771 - Image 13
31 Chestnut Hill Drive, Upper Brookville, NY 11771 - Image 14
31 Chestnut Hill Drive, Upper Brookville, NY 11771 - Image 15
31 Chestnut Hill Drive, Upper Brookville, NY 11771 - Image 16
31 Chestnut Hill Drive, Upper Brookville, NY 11771 - Image 17
31 Chestnut Hill Drive, Upper Brookville, NY 11771 - Image 18
31 Chestnut Hill Drive, Upper Brookville, NY 11771 - Image 19
31 Chestnut Hill Drive, Upper Brookville, NY 11771 - Image 20
31 Chestnut Hill Drive, Upper Brookville, NY 11771 - Image 21
31 Chestnut Hill Drive, Upper Brookville, NY 11771 - Image 22
31 Chestnut Hill Drive, Upper Brookville, NY 11771 - Image 23
31 Chestnut Hill Drive, Upper Brookville, NY 11771 - Image 24
31 Chestnut Hill Drive, Upper Brookville, NY 11771 - Image 25
31 Chestnut Hill Drive, Upper Brookville, NY 11771 - Image 26
31 Chestnut Hill Drive, Upper Brookville, NY 11771 - Image 27
31 Chestnut Hill Drive, Upper Brookville, NY 11771 - Image 28
31 Chestnut Hill Drive, Upper Brookville, NY 11771 - Image 29
31 Chestnut Hill Drive, Upper Brookville, NY 11771 - Image 30
31 Chestnut Hill Drive, Upper Brookville, NY 11771 - Image 31
31 Chestnut Hill Drive, Upper Brookville, NY 11771 - Image 32
31 Chestnut Hill Drive, Upper Brookville, NY 11771 - Image 33
31 Chestnut Hill Drive, Upper Brookville, NY 11771 - Image 34
31 Chestnut Hill Drive, Upper Brookville, NY 11771 - Image 35
31 Chestnut Hill Drive, Upper Brookville, NY 11771 - Image 36
31 Chestnut Hill Drive, Upper Brookville, NY 11771 - Image 37
31 Chestnut Hill Drive, Upper Brookville, NY 11771 - Image 38
31 Chestnut Hill Drive, Upper Brookville, NY 11771 - Image 39
31 Chestnut Hill Drive, Upper Brookville, NY 11771 - Image 40
31 Chestnut Hill Drive, Upper Brookville, NY 11771 - Image 41
31 Chestnut Hill Drive, Upper Brookville, NY 11771 - Image 42
31 Chestnut Hill Drive, Upper Brookville, NY 11771 - Image 43
31 Chestnut Hill Drive, Upper Brookville, NY 11771 - Image 44
31 Chestnut Hill Drive, Upper Brookville, NY 11771 - Image 45
31 Chestnut Hill Drive, Upper Brookville, NY 11771 - Image 46
31 Chestnut Hill Drive, Upper Brookville, NY 11771 - Image 47
31 Chestnut Hill Drive, Upper Brookville, NY 11771 - Image 48
31 Chestnut Hill Drive, Upper Brookville, NY 11771 - Image 49

Single Family Home for sale in Upper Brookville, NY

for $7,850,000 with 6 bedrooms and 6 full baths, 4 half baths. This 7,639 square foot home was built in 1989 on a lot size of 5.

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.

See more

Single Family Active

Price

$ 7,850,000

Bedrooms

6

Full Bath

6

Half Bath

4

Property Type

Single Family

Taxes

$ 53,464

Style

Contemporary,Modern

Lot Size

5

Year Built

1989

Town/City

Upper Brookville

County/Region

Nassau

MLS | Web ID

1061123

Features
Interior
Interior Amenities First 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 Close
Basement Partial Walk-Out Access
Flooring Hardwood Other
Total Fireplaces 2
Basement Features Partial Walk-Out Access
Basement (Y/N) Y
Window Features Casement Double Pane Windows Floor to Ceiling Windows New Windows Oversized Windows
Fireplace Y/N Y
Half Baths 4
Total Bedrooms 6
Total Baths 10
See more
General
Sewer Cesspool
Heating Electric Forced Air
Cooling Central Air
Utilities Electricity Connected Propane Trash Collection Private
Appliances Dishwasher Dryer Electric Cooktop Electric Oven Exhaust Fan Microwave Refrigerator Washer
HOA Fee 1500
Garage Spaces 4
Association Fee Includes Snow Removal
Patio/Porch Features Patio
Architectural Style Contemporary Modern
Pool Features Fenced In Ground Pool Cover Salt Water Tile
Security Features Building Security Fire Alarm Security Gate Security Lights Security System Smoke Detector(s) Video Cameras
Construction Materials Frame
Exclusions Ask listing agent
Year Built 1989
View Trees/Woods
Property Subtype Single Family Residence
Tax Year 2026
Parcel Number 2427-24-E-00-1046-0
Assoc Fee Paid Per Annually
County Nassau County
Property Type Residential
HOA Y
Facing Direction West
Garage Y/N Y
Other Structures Guest House Outdoor Kitchen Pool House
Total Rooms 12
Full Baths 6
Directions Chicken Valley to Chestnut Hill Drive
High School Locust Valley High School
City Oyster Bay
Senior Community Y/N N
High School District Locust Valley
Carport Y/N N
Elementary School Ann Macarthur Primary School
Property Attached Y/N N
Tax Annual Amount 53464
Middle/Junior High School Locust Valley Middle School
Property Condition Actual
Building Area Units Square Feet
Standard Status Active
Middle/Junior School District Locust Valley
Elementary School District Locust Valley
Year Built Effective 2025
See more
Exterior
Exterior Amenities Balcony Gas Grill Lighting Mailbox
Parking Features Attached Driveway Garage Garage Door Opener Heated Garage Attached Driveway Garage Garage Door Opener Heated Garage
Water Source Public
Spa Y
Building Area Total 10109
Waterfront Y/N N
Other Equipment Dehumidifier Generator Pool Equip/Cover
See more
Internal Only
Street Number 1 31
See more
* Excluded Features
List By
Jason P. Friedman

Listing Agent

Daniel Gale Sothebys Intl Rlty

Broker

516-626-7600

Contact

Affordability Calculator

$58,673
Per Month
92%
8%
0%
Monthly Principal & Interest
$54,218
Monthly Property Taxes
$4,455
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

Discover how much house you can afford

Your dream home may be within reach.

Learn More about how to save

The time to sell is now
THE TIME TO SELL IS NOW! What's my home worth?
Nearby
4099815 Elementary School
4099618 Middle School
Locust Valley High School High School
Pricing History
DatePricePrice ChangeDescription
10/15/2026$7,850,000 Listed Price

Map


See all

31 Chestnut Hill Drive, Upper Brookville, NY, 11771 is a Single Family Home for sale at $7,850,000 with 7,639 sqft and a lot size of 5. 31 Chestnut Hill Drive has 6 bedrooms, 6.4 baths, and was built in 1989. The property's zip code is 11771 which is in Upper Brookville, NY