18 Chestnut Hill Drive , Upper Brookville, NY 11771

$4,980,000
  • 18 Chestnut Hill Drive , Upper Brookville, NY 11771 Main Photo

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New to the Market
BEDS7 BATHS8 full 1 partial SQUARE FEET8,925 MLS#1061600
STATUSActive PROPERTY TYPEResidential - Single Family SCHOOLLocust Valley

Property Description

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 ef

18 Chestnut Hill Drive | MLS# 1061600

This single family home located at 18 Chestnut Hill Drive , Upper Brookville, NY 11771 is currently listed for sale with an asking price of $4,980,000. This property was built in 1992 and has 7 bedrooms and 8 full and 1 partial baths with 8925 sq. ft. Chestnut Hill Drive is located within the Locust Valley school district. Search Upper Brookville real estate on www.laffey.com today.

Property Features

Property Type: Residential - Single Family
Basement: Yes
Basement: Finished, Full
Cooling: Central Air
Garage: 4
Heating: Forced Air
Home Style: Contemporary
Lot Size: 5.00 Acres
Taxes: $52,120
Year Built: 1992

Amenities

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

Feature Descriptions

Appliances: Convection Oven, Cooktop, Dishwasher, Dryer, Electric Cooktop, Electric Range, Exhaust Fan, Freezer, Microwave, Oven, Range, Refrigerator, Stainless Steel Appliance(s), Washer
Association Fee: $1500/Annually
Association Fee Includes: Other
Attic: Unfinished
Building Area Total: 8925
Exterior: Wood Siding
Fireplace Y/N: Yes
Formal Dining: Yes
GarageY/N: Yes
On Market Date: 2026-10-12
Parcel Number: 2427-24-E-00-1052-0
Parking Features: Attached, Garage
Rental Term: Monthly
Rooms Total: 13
Sauna: Yes
Sewer: Cesspool
Swimming Pool: Yes
Utilities: Cable Connected, Electricity Connected, Water Connected
Water: Public

Local Schools

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

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Estimated Payment

$ 16,879.15 per month $11,083.32 Principal & Interest $4,343.33 Property Tax $1,452.50 Homeowner's Insurance

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Listed By / Shown By

Listing By

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

Shown By

Agency Title: Laffey Real Estate
Agency Phone: 1-888-289-6902

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