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MLS ID KEY1061123Last updated Oct 27, 2026

Single Family

31 Chestnut Hill Drive

Active · Oyster Bay · Nassau County, NY 11771

Bedrooms
6 Beds
Bathrooms
10 Baths
Year built
1989
Est. monthly taxes
$4,455.33
Property gallery0 / 49
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About this home

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.

Listing snapshot

Days on site
13 days
Listed on MLS
Oct 15, 2026
Full baths
6
Half baths
4
Annual property tax (MLS)
$53,464
Tax year
2026
Association / maintenance fees (MLS)
$1,500 / Annually
Fees include (MLS)
Snow Removal
Area source (MLS)
Measured
Listing brokerage
Daniel Gale Sothebys Intl Rlty
MLS ID
KEY1061123
Last updated
Oct 27, 2026

General features

Property type
Single Family
Property subtype
Single Family Residence
Year built
1989
Garage
Yes
Garage spaces
4
Parking
Attached, Driveway, Garage, Garage Door Opener, Heated Garage
Water source
Public
Sewer
Cesspool
Utilities
Electricity Connected, Propane, Trash Collection Private

Interior features

Basement
Partial, Walk-Out Access
Heating
Electric, Forced Air
Cooling
Central Air
Interior
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
Flooring
Hardwood, Other
Fireplace
Yes
Fireplaces
2

Exterior features

Architectural style
Contemporary, Modern
Construction materials
Frame
Exterior
Balcony, Gas Grill, Lighting, Mailbox
Private pool
Yes

Schools (MLS)

Elementary school
Ann Macarthur Primary School
Elementary school district
Locust Valley
Middle school
Locust Valley Middle School
Middle school district
Locust Valley
High school
Locust Valley High School
High school district
Locust Valley

School information is provided by the MLS. Confirm attendance eligibility with the school district.

Recent activity

  1. Listing updated from MLS
  2. First seen on this site
  3. MLS status changed

Location

Oyster Bay · Nassau County, NY 11771Show interactive map
31 Chestnut Hill Drive

Oyster Bay · Nassau County, NY 11771

Google Maps directions

Estimate monthly payment

Loan detailsFixed-rate, fully amortizing loan. Edit the assumptions below; no market rate is supplied.
Property expenses (USD)
MLS amounts are prefilled when available and can be edited. Confirm what fees include. Unknown fee frequencies cannot be converted automatically.Property expenses: MLS values where available; missing values stay blank.

Estimated monthly principal & interest—

Monthly property taxNot provided

Monthly association / maintenance feesNot provided

Estimated monthly total of entered costs—

Excludes insurance, mortgage insurance, special assessments and lender fees. MLS taxes may reflect abatements or exemptions and can change.

Listing data is supplied by the MLS and may change without notice.