39 Chestnut Hill Drive, Upper Brookville, NY

$12,750,000

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8

Beds

10

Baths

12,708

Square feet

5.00

Acres

About 39 Chestnut Hill Drive

Built in 2001 and privately set on five pristine acres, this extraordinary estate is a residence of rare character and enduring elegance, blending old-world craftsmanship, architectural drama, and gracious modern living. From richly detailed formal rooms to expansive spaces designed for entertaining, every level reveals another layer of thoughtful design. 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.

Features of 39 Chestnut Hill Drive

MLS® # 1056809
Price $12,750,000
Bedrooms 8
Bathrooms 10.00
Full Baths 8
Half Baths 2
Square Footage 12,708
Acres 5.00
Year Built 2001
Type Residential
Sub-Type Single Family Residence
Style Estate
Status Active

Community Information

Address 39 Chestnut Hill Drive
City Upper Brookville
County Nassau County
State NY
Zip Code 11771

Additional Information

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Amenities

Utilities Electricity Connected
Parking Attached
# of Garages 3
Is Waterfront No
Has Pool Yes

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
Appliances Cooktop, Dishwasher, Dryer, Freezer, Gas Cooktop, Gas Oven, Gas Range, Microwave, Oven, Range, Refrigerator, Stainless Steel Appliance(s), Washer, Wine Refrigerator
Heating Forced Air, Hot Air, Radiant, Radiant Floor
Cooling Central Air
Fireplace Yes

Exterior

Construction Brick

School Information

District Locust Valley
Elementary Bayville Elementary School
Middle Locust Valley Middle School
High Locust Valley High School

Additional Information

Short Sale No
RE / Bank Owned No
Taxes (total) $68,805

Listing Details

OfficeDaniel Gale Sothebys Intl Rlty
Office Contact516-626-7600

Listing Map

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