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MLS ID KEY1061600Last updated Oct 13, 2026

Single Family

18 Chestnut Hill Drive

Active · Oyster Bay · Nassau County, NY 11771

Bedrooms
7 Beds
Bathrooms
9 Baths
Year built
1992
Est. monthly taxes
$4,343.39
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About this home

Set on five magnificent acres of sprawling, level grounds along one of Long Island’s most coveted residential streets, this extraordinary contemporary estate, designed by acclaimed architectural firm Mojo Stumer, represents a sophisticated expression of modern luxury, architectural innovation, and resort-inspired living. Distinguished by dramatic proportions, soaring ceilings, expansive walls of glass, and a seamless connection between indoor and outdoor spaces, the residence offers an exceptional combination of architectural significance, privacy, and grand-scale entertaining. A grand entrance foyer introduces interiors defined by remarkable volume and natural light, leading to a breathtaking double-height great room anchored by a striking marble fireplace. Expansive windows frame picturesque views of the surrounding landscape, enhancing the home's connection to its private, park-like setting. The thoughtfully designed main level features an elegant formal dining room, spacious eat-in kitchen, inviting family room, and sophisticated lounge with a wet bar. A powder room and first-floor laundry provide additional convenience. Occupying a private wing of the main level, the luxurious first-floor primary suite offers an exceptional retreat, complete with a generous his and her walk-in closet and a beautifully appointed bathroom featuring a steam shower. An additional first-floor bedroom with a full bathroom provides ideal accommodations for guests or extended family. The second level features four generously proportioned guest bedrooms complemented by two full bathrooms. Additionally an expansive loft with its own balcony and full bathroom offers a versatile space ideally suited for a private office, additional lounge, or secluded retreat. Designed for recreation, wellness, and entertaining, the expansive lower level features a dramatic double-sided fireplace connecting the game room and entertainment spaces. A spacious recreation area with a wet bar provides the perfect setting for gatherings, while a substantial private gym with its own full bathroom creates a dedicated fitness retreat. Additional accommodations include a staff or guest bedroom and another full bathroom. Beyond the residence sits a remarkable private resort featuring a swimming pool, hot tub, and tennis court. A substantial poolside cabana offers a full indoor kitchen, outdoor wet bar, comfortable lounge, full bathroom, and dedicated laundry facilities. A built-in outdoor grill completes the exceptional entertaining amenities, providing an effortless transition between indoor luxury and outdoor leisure. A four-car garage further complements the estate, providing generous space for automobiles and storage. The property presents a remarkable opportunity to experience architectural distinction, privacy, and an uncompromising lifestyle.

Listing snapshot

Days on site
16 days
Listed on MLS
Oct 12, 2026
Full baths
8
Half baths
1
Annual property tax (MLS)
$52,120.72
Tax year
2025
Association / maintenance fees (MLS)
$1,500 / Annually
Fees include (MLS)
Other
Area source (MLS)
Public Records
Listing brokerage
Daniel Gale Sothebys Intl Rlty
MLS ID
KEY1061600
Last updated
Oct 13, 2026

General features

Property type
Single Family
Property subtype
Single Family Residence
Year built
1992
Garage
Yes
Garage spaces
4
Parking
Attached, Garage
Water source
Public
Sewer
Cesspool
Utilities
Cable Connected, Electricity Connected, Water Connected

Interior features

Basement
Finished, Full
Heating
Forced Air
Cooling
Central Air
Interior
First Floor Bedroom, First Floor Full Bath, Cathedral Ceiling(s), Chefs Kitchen, Eat-in Kitchen, Entrance Foyer, Formal Dining, Granite Counters, High Ceilings, His and Hers Closets, Kitchen Island, Marble Counters, Open Floorplan, Pantry, Primary Bathroom, Master Downstairs, Sauna, Sound System, Stone Counters, Storage, Walk-In Closet(s), Wet Bar
Appliances
Convection Oven, Cooktop, Dishwasher, Dryer, Electric Cooktop, Electric Range, Exhaust Fan, Freezer, Microwave, Oven, Range, Refrigerator, Stainless Steel Appliance(s), Washer
Fireplace
Yes

Exterior features

Architectural style
Contemporary
Construction materials
Wood Siding
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
18 Chestnut Hill Drive

Oyster Bay · Nassau County, NY 11771

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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.