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39 Chestnut Hill Drive, 
Upper Brookville, NY 11771

$12,750,000


8

Beds


12

Baths


12,708

Sq Ft


Single Family

Active

Listed by

Jason P. Friedman

, 

Sarah R. Friedman

Daniel Gale Sothebys Intl Rlty

Last updated:

November 14, 2026, 12:32 PM

MLS#

1056809

Source:

OneKey MLS

About This Home

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.

Home Facts

Single Family

12 Baths

8 Bedrooms

Built in 2001

Price Summary

12,750,000

$1,003 per Sq. Ft.

MLS #:

1056809

Last Updated:

November 14, 2026, 12:32 PM

Added:

1 month(s) ago


Rooms & Interior

Bedrooms

Total Bedrooms:

8

Bathrooms

Total Bathrooms:

12

Full Bathrooms:

8

Interior

Living Area:

12,708 Sq. Ft.


Structure

Structure

Architectural Style:

Estate

Building Area:

13,620 Sq. Ft.

Year Built:

2001


Lot

Lot Size (Sq. Ft):

217,800


Finances & Disclosures

Finances

Price:

$12,750,000

Price per Sq. Ft:

$1,003 per Sq. Ft.

Source:OneKey MLS
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Contact an Agent

Yes, I would like more information. Please use and/or share my information with a Coldwell Banker ® affiliated agent to contact me about my real estate needs. By clicking Contact, I request to be contacted by phone or text message and consent to being contacted by automated means. I understand that my consent to receive calls or texts is not a condition of purchasing any property, goods, or services. Alternatively, I understand that I can access real estate services by email or I can contact the agent myself.

If a Coldwell Banker affiliated agent is not available in the area where I need assistance, I agree to be contacted by a real estate agent affiliated with another brand owned or licensed by Anywhere Real Estate (BHGRE®, CENTURY 21®, Corcoran®, ERA®, or Sotheby's International Realty®). I acknowledge that I have read and agree to the terms of use and privacy notice.