97 Pound Hollow Road, Old Brookville, NY 11545

$21,500,000

Steeped in the grandeur of Long Island's celebrated Gold Coast, this extraordinary 33+ 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… Read More 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, four 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. Read Less

Listing Courtesy of Daniel Gale Sothebys Intl Rlty, 516-759-6822.

Listing Snapshot

Days Online

Last Updated

Jun 17, 2026

Property Type

Single Family Residence

Beds

Full Baths

Partial Baths

Square Ft.

14,761

Year Built

1924

Property Tax

$230,018

MLS Number

1010319

30 Days Snapshot Of 11545

$2.11M

(avg) sold price

homes sold

168

-29%

(avg) days on market

Snapshot

Area Map

Additional Details

Appliances & Equipment

Description: "Dishwasher", "Dryer", "Freezer", "Microwave", "Oven", "Range", "Refrigerator", "Washer"

Basement

Description: "Partial", "Storage Space"

Building

Area: 14761, Architecture: "Estate", Construction Materials: "Brick", Levels: "Three Or More", Year Built: 1924

Cooling

Details: "Central Air", "Ductless"

Exterior Features

Features: "Courtyard", "Garden", "Mailbox", "Rain Gutters", Patio Features: "Patio", "Porch", "Terrace"

Fence

Description: "Fenced"

Fireplaces

Total Fireplaces: 9

Floors

Flooring: "Carpet", "Tile"

Garage

Garage Spaces: 10

Heating

Heating: "Oil", "Propane"

Laundry

Description: "In Basement"

Lot

Features: "Back Yard", "Cleared", "Front Yard", "Garden", "Landscaped", "Level", "Part Wooded", "Private", "Secluded", "Stone/Brick Wall", Acres: 33.09

Pool

Features: "In Ground", "Indoor", "Outdoor Pool", Private Pool

Utilities

Sewer: "Cesspool", Water Source: "Public", Utilities: "Electricity Connected", "Sewer Connected", "Trash Collection Public", "Water Connected"

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Debra A Chiappetta, Real Estate Broker

Debra A Chiappetta, Real Estate Broker