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31 Chestnut Hill Drive
Upper Brookville, NY, 11771
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AN INTRODUCTION
A closer look.
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.
Property overview
- Property type
- Single Family Residence
- Architecture
- Contemporary, Modern
- Condition
- Actual
- Year built
- 1989
- Lot size (sq ft)
- 217,800
- Status
- Active
- Listed
- 2026-10-15
- MLS number
- KEY1061123
Interior & comfort
- Interior features
- 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
- Appliances
- Dishwasher, Dryer, Electric Cooktop, Electric Oven, Exhaust Fan, Microwave, Refrigerator, Washer
- Heating
- Electric, Forced Air
- Cooling
- Central Air
- Basement
- Partial, Walk-Out Access
- Fireplaces
- 2
Outdoors & amenities
- Exterior features
- Balcony, Gas Grill, Lighting, Mailbox
- Parking
- Attached, Driveway, Garage, Garage Door Opener, Heated Garage
- Garage spaces
- 4
- Pool
- Fenced, In Ground, Pool Cover, Salt Water, Tile
- Views
- Trees/Woods
Schools & location
- Postal town
- Upper Brookville
- County
- Nassau County
- School district
- Locust Valley
- Elementary school
- Ann Macarthur Primary School
- Middle school
- Locust Valley Middle School
- High school
- Locust Valley High School
Taxes & utilities
- Annual property taxes
- $53,464
- Tax year
- 2026
- Association
- Yes
- Association fee
- $1,500
- Fee frequency
- Annually
- Water
- Public
- Sewer
- Cesspool
Listing courtesy of Daniel Gale Sothebys Intl Rlty · 516-626-7600
MLS #KEY1061123 · Active

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