97 A Pound Hollow RoadOld Brookville, NY 11545
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$62,049Steeped in the grandeur of Long Island's celebrated Gold Coast, this extraordinary 15+ acre equestrian estate formally named 'Westward' presents a rare opportunity to acquire a significant piece of North Shore history. Privately nestled amid rolling pastures, mature woodlands, and formal gardens, the estate seamlessly blends timeless architectural elegance with an unparalleled country lifestyle just moments from New York City. Originally commissioned in 1924 for noted industrialist and financier Benjamin Brewster Jennings - President and Chairman of Socony-Mobil and a prominent figure in New York's financial and corporate circles - this Georgian Revival brick residence with a cascading slate roof was masterfully designed by renowned architect Walter B. Chambers. The estate's distinguished landscape plan was created by legendary landscape architect Ellen Biddle Shipman, whose formal gardens and thoughtfully designed grounds continue to define the property's enduring beauty. Approached by a long, tree-lined drive framed by classic stone walls, the stately residence commands a setting of exceptional privacy and serenity. Encompassing three full levels of living space, the home is distinguished by grand entertaining rooms, soaring proportions, multiple wood-burning fireplaces, graceful arched windows, leaded-glass details, and an abundance of natural light. A gracious entrance vestibule opens to a sweeping curved staircase, while expansive formal living and dining rooms provide an elegant backdrop for entertaining on any scale. The 10 bedroom, 9.5 bathroom primary residence also features a spacious eat-in kitchen, indoor spa pool, vast slate patios and an outdoor swimming pool with cabana set against picturesque grounds, providing an idyllic backdrop for outdoor enjoyment. For equestrian enthusiasts, the property offers a turnkey horse facility. The grounds include a well-maintained main barn, run-in sheds (equipped with stalls, water, and electricity), a hot walker, extensive paddocks, and open acreage ideal for riding and grazing. Additionally, this unmatched property includes charming gatehouse cottages, staff apartments, and multiple ancillary structures, most of which have been recently renovated, creating flexibility for guests, caretakers, or income-producing opportunities. Located within one of the North Shore's most prestigious and historically significant communities, the estate enjoys close proximity to Long Island Sound beaches, renowned equestrian facilities, and some of the region's finest private clubs and golf courses. Zoned within the esteemed North Shore Central School District. Rarely does a property of this caliber come to market - offering a remarkable combination of provenance, architectural distinction, equestrian amenities, acreage, and development potential. A legacy estate of exceptional character and enduring significance, representing the very essence of North Shore country living.
| a month ago | Listing first seen on site | |
| a month ago | Listing updated with changes from the MLS® |
Based on information submitted to the MLS GRID as of 2026-09-18 07:56 PM EDT. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.
Azure Vue Realty Group LLC – New York Location
Real Estate Corp Lic# 10991241538
231 McNamara Rd, Spring Valley NY 10977
914-522-0232
Broker of Record
John Scardino Jr: Lic#10491213691
New York Real Estate Sales
Simon Zarour: Lic#10401396686
Azure Vue Realty Group LLC – Florida Location
Real Estate Corp Lic# CQ1073236
20200 West Dixie Highway Suite 902 Aventura, FL, 33180
786-535-8574
Broker of Record
John Scardino Jr: Lic#BK3639696
Florida Real Estate Sales
Simon Zarour: Lic#SL3626957
John Scardino Jr – NMLS# 261624-MLO
Simon Zarour – NMLS# 2684220-MLO
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