39 Chestnut Hill DR Upper Brookville, NY 11771
UPDATED:
Key Details
Property Type Single Family Home
Sub Type Single Family Residence
Listing Status Active
Purchase Type For Sale
Square Footage 12,708 sqft
Price per Sqft $1,003
MLS Listing ID 1056809
Style Estate
Bedrooms 8
Full Baths 8
Half Baths 2
HOA Fees $2,000/ann
HOA Y/N Yes
Rental Info No
Year Built 2001
Annual Tax Amount $68,805
Lot Size 5.000 Acres
Acres 5.0
Property Sub-Type Single Family Residence
Source onekey2
Property Description
The home makes an immediate impression with a distinguished foyer featuring classic checkered flooring, where graceful archways establish a sense of symmetry and sophistication. Beyond, the formal living room is beautifully appointed with intricate hardwood floors, a marble fireplace and mantel, and French doors opening directly to the terrace, creating an effortless connection between the interiors and gardens.
A formal office boasts distinguished rich hardwood paneling, an intricately finished plaster ceiling, and its own wood-burning fireplace. The formal dining room is equally refined, framed by substantial moldings and anchored by another fireplace—an elegant setting for both intimate dinners and grand-scale entertaining. One of the home's most memorable architectural moments is a discreet curved staircase leading to the dramatic family room. Here, soaring vaulted ceilings, exposed wood beams, and a monumental stone fireplace create a remarkable sense of scale. A concealed door reveals a private wet bar, adding an unexpected and sophisticated element for entertaining.
The kitchen and service areas have been conceived with both beauty and function in mind. A handsome butler's pantry features a hand-painted tile backsplash, marble countertops, and abundant preparation space. The expansive farmhouse-inspired eat-in kitchen is finished with warm terracotta floors, two porcelain farmhouse sinks, oversized chef's appliances, a substantial center island, and a sun-filled breakfast area overlooking the grounds. A pantry and discreetly positioned powder room are located just off the kitchen, while a circular rear staircase provides convenient access between levels. A separate side entrance opens to a practical mudroom with an additional service pantry, complete with sink and refrigerator.
Ascending to the second floor, an oval wood architectural ceiling crowns a gracious landing overlooking the level below, creating a striking transition to the private bedroom quarters. The secondary accommodations include four generously proportioned bedrooms, one with its own loft space, each appointed with a marble en-suite bath. Near the rear-stair landing, a convenient preparation or household station with sink adds functionality, while a private office provides a dedicated workspace.
The primary suite is an extraordinary private retreat. Generous in scale and beautifully secluded, it offers separate dressing rooms and walk-in closets, along with a spa-inspired bath featuring a jetted soaking tub and oversized walk-in shower. An adjoining sitting room creates a quiet sanctuary, with access to a walk-up attic offering additional possibilities.
The lower level rivals the principal entertaining spaces in both scale and amenities. Remarkably high ceilings enhance an expansive den and recreation area, complemented by a powder room, full bar, billiards and game room, wine cellar, professionally matted gym, and an impressive 15-seat private theater. Two additional staff or guest rooms, supported by two full baths, complete this exceptionally versatile level.
Across the estate's five pristine acres, the grounds unfold as a private resort. Expansive slate and brick terraces provide multiple settings for dining and entertaining, while covered patios framed by graceful archways offer shaded retreats overlooking the property. Beyond, a swimming pool and spa form the centerpiece of the property's recreational amenities, accompanied by a substantial, one-of-a-kind pool house that further elevates the estate's resort-like appeal.
Location
State NY
County Nassau County
Rooms
Basement Finished, Full
Interior
Interior Features Beamed Ceilings, Cathedral Ceiling(s), Chefs Kitchen, Double Vanity, Eat-in Kitchen, Entrance Foyer, Formal Dining, Granite Counters, High Ceilings, His and Hers Closets, Kitchen Island, Marble Counters, Natural Woodwork, Pantry, Primary Bathroom, Quartz/Quartzite Counters, Sauna, Sound System, Speakers, Stone Counters, Walk-In Closet(s), Wet Bar
Heating Forced Air, Hot Air, Radiant, Radiant Floor
Cooling Central Air
Fireplace No
Appliance Cooktop, Dishwasher, Dryer, Freezer, Gas Cooktop, Gas Oven, Gas Range, Microwave, Oven, Range, Refrigerator, Stainless Steel Appliance(s), Washer, Wine Refrigerator
Exterior
Parking Features Attached
Garage Spaces 3.0
Utilities Available Electricity Connected
Garage true
Private Pool Yes
Building
Sewer Cesspool
Water Public
Structure Type Brick
Schools
Elementary Schools Bayville Elementary School
Middle Schools Locust Valley Middle School
High Schools Locust Valley
School District Locust Valley
Others
Senior Community No
Special Listing Condition None
Nearby Locations
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