Jacob Loope
Licensed Associate Real Estate Broker
REALTOR®
Liverpool, NY
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31 Chestnut Hill Drive, Upper Brookville, NY 11771

New - 24 Hours Ago
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Property 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.

31 Chestnut Hill Drive | MLS# 1061123

This single family home located at 31 Chestnut Hill Drive, Upper Brookville, NY 11771 is currently listed for sale with an asking price of $7,850,000. This property was built in 1989 and has 6 bedrooms and 6 full and 4 partial baths with 7639 sq. ft. Chestnut Hill Drive is located within the Locust Valley school district. Search Upper Brookville real estate on jacob-loope.coldwellbankerprime.com today.

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Property Features

Property Type: Residential - Single Family
Basement: Yes
Basement: Partial, Walk-Out Access
Cooling: Central Air
Fenced: Yes
Fireplaces: 2
Garage: 4
Heating: Electric, Forced Air
Home Style: Contemporary, Modern
Lot Size: 5.00 Acres
Taxes: $53,464
Year Built: 1989

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 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
Balcony
Gas Grill
Lighting
Mailbox

Feature Descriptions

Appliances: Dishwasher, Dryer, Electric Cooktop, Electric Oven, Exhaust Fan, Microwave, Refrigerator, Washer
Association Fee: $1500/Annually
Association Fee Includes: Snow Removal
Building Area Total: 10109
Days on Site: 1
Exclusions: Ask listing agent
Exterior: Frame
Fireplace Y/N: Yes
Flooring: Hardwood, Other
Formal Dining: Yes
GarageY/N: Yes
Heating Zones: 5
House Faces: West
Laundry: Laundry Room
Lot Features: Back Yard, Cul-De-Sac, Landscaped, Sprinklers In Front, Sprinklers In Rear
Number Of Kitchens: 2
On Market Date: 2026-10-15
Other Structures: Guest House, Outdoor Kitchen, Pool House
Parcel Number: 2427-24-E-00-1046-0
Parking Features: Attached, Driveway, Garage, Garage Door Opener, Heated Garage
Patio And Porch: Patio
Pool Features: Fenced, In Ground, Pool Cover, Salt Water, Tile
Rental Term: Monthly
Rooms Total: 12
Sauna: Yes
Security: yes
Security Features: Building Security, Fire Alarm, Security Gate, Security Lights, Security System, Smoke Detector(s), Video Cameras
Sewer: Cesspool
Spa Y/N: Yes
Special View Info: Trees/Woods
Swimming Pool: Yes
Utilities: Electricity Connected, Propane, Trash Collection Private
Water: Public
Window Features: Casement, Double Pane Windows, Floor to Ceiling Windows, New Windows, Oversized Windows

Local Schools

High School: Locust Valley High School
Middle School: Locust Valley Middle School
Elementary School: Ann Macarthur Primary School
School District: Locust Valley

Estimate Your Payment

Estimated Payment

$ 24,215.61 per month $17,470.70 Principal & Interest $4,455.33 Property Tax $2,289.58 Homeowner's Insurance

Change Payment Information

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yearly (est.)
(Payments are an estimate and may vary by lender)

Demographics

Listed By / Shown By

Listing By

Agency Name: Daniel Gale Sothebys Intl Rlty
Agency Contact: 516-626-7600

Shown By

Agent Name: Jacob Loope
Agent Phone: (315) 884-0868 Cell
Agency Title: Coldwell Banker Prime Properties

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Disclaimer: All information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) or information provider(s) shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Listing(s) information is provided for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information on this site was last updated 10/16/2026. The listing information on this page last changed on 10/16/2026. The data relating to real estate for sale on this website comes in part from the Internet Data Exchange program of Delta Media Group MLS (last updated Fri 10/16/2026 12:19:56 AM EST) or Global MLS (last updated Fri 10/16/2026 12:07:42 AM EST) or New York State Alliance MLS (last updated Fri 10/16/2026 12:15:07 AM EST) or Hudson Valley Catskill Region MLS (last updated Fri 10/16/2026 12:11:18 AM EST) or Berkshire MLS (last updated Thu 10/15/2026 8:13:58 PM EST) or OneKey MLS (last updated Fri 10/16/2026 12:14:26 AM EST). Real estate listings held by brokerage firms other than Coldwell Banker Prime Properties may be marked with the Internet Data Exchange logo and detailed information about those properties will include the name of the listing broker(s) when required by the MLS. All rights reserved.

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