Published In: Stroll Magazine Old Westbury - May 2025
By Dalia Elison
It all started with a phone call.
Sometimes, a listing is more than just a home—it’s a gateway into history. That’s exactly what I discovered when I brought another beautiful Old Westbury property to the market. I expected the usual calls from potential buyers and curious neighbors, but one call caught me entirely off guard—it was from the great grandson of the original owner. He wasn’t calling to inquire about the price or square footage. Instead, he said, “You know, my mother used to play down in the tunnels when she was a kid.”
Tunnels? My curiosity was instantly piqued.
He went on to describe how his mother would take the train from Manhattan to her grandfather’s estate. She and her cousins would sneak away during family gatherings and explore the hidden underground passageways that once ran beneath the estate. Today, those tunnels have been transformed into a stunning wine cellar—but back then, they were part of a mysterious and magical world, serving a very different purpose. I learned these underground passageways, tall enough for horse and buggy, winding discreetly through the estate grounds, were designed to connect various parts of the property, providing a hidden network for staff to move unseen, or perhaps even to allow for the discreet comings and goings of the estate’s more prominent residents. He also reminisced upon stories about the "big playroom"—a grand, open space where his great-grandfather and family hosted everything from elegant weddings to lively theatrical performances and charitable events. It was a place of joy, community, and celebration, woven into the very fabric of their family history.
His great grandmother gifted the family with a book, written by his great grandfather, “Recollections For My Family” – full of the interesting and beautiful memories of the past. In it he shared how when he was searching for land, his initial plan was to buy in Port Jefferson. But the moment he visited Old Westbury, he was captivated by two magnificent cherry blossom trees in full bloom, yards away on top of a hill, the only sight for miles — and just like that, his decision was made. Their beauty was absolutely captivating, especially in the spring. I couldn’t help but relate — each year, my own backyard in Old Westbury transforms into a sea of cherry blossoms, their delicate blooms blanketing the property in a breathtaking display.
His mother would often reminisce about the estate’s unique features, especially the intricately patterned tiles around the fireplace, which were imported from Mexico — a place her grandfather frequently visited for business. She also shared the sweet memory of two grand, unclothed marble statues that once stood at the estate’s entrance. As little girls, she and her cousin would cover parts of the statues with mud, hoping to “protect their modesty,” leaving faint stains – and a lot of trouble for them, which eventually became part of the home’s story.
When the time finally came for the family to part ways with the property, the original plan was to sell the estate to an all-girls boarding school — but the deal unexpectedly fell through.
It’s these kinds of stories — full of charm, history, and heart — that make life in Old Westbury so special.
Hearing this history, I began to dig deeper—literally and figuratively—into Old Westbury’s past. I learned that these tunnels weren’t unique to this one property. Many of Old Westbury’s grand estates, built at the turn of the 20th century, included subterranean networks. Some were used for practical purposes—moving coal, food, or laundry between buildings—while others may have served more secretive roles. It’s even rumored that during Prohibition, certain tunnels offered a way to enjoy a quiet drink without attracting the wrong kind of attention.
Old Westbury’s history stretches far beyond its estates and architectural marvels. The area was originally known by its Native American name, "Wallage," loosely translating to “ditch” or “hole.” It later became known as Wood Edge, then “the Plains edge,” and finally Westbury—named in 1683 by one of the first English settlers, Henry Willis, after his hometown in Wiltshire, England.
The village truly began to transform in the 19th century, as the arrival of the railroad in 1836 turned this quiet Quaker farming community into a desirable location for New York’s elite. Wealthy families, drawn to the expansive, wooded Hempstead Plains, came here to build lavish estates, raise horses, and play polo at the nearby Meadow Brook Club.
In 1924, Old Westbury officially incorporated as a village, distinguishing itself from the growing population centers nearby. It was a haven of refinement, discretion, and quiet prestige. The “Old” in the name wasn’t just a nod to history—it was a declaration of identity.
The name “Phipps” has become nearly synonymous with Old Westbury. Industrialist Henry Phipps, Andrew Carnegie’s business partner and one of the wealthiest men of his time, gifted his son John Shaffer Phipps the land that would become the iconic Westbury House. In keeping with a promise to his fiancée, John built an English-style country estate reminiscent of the homes she knew from abroad. Today, Westbury House and its spectacular gardens are open to the public as Old Westbury Gardens — a living monument to elegance and legacy.
Another towering figure in Old Westbury’s history was Edwin Denison Morgan III, born Alfred Waterman Morgan, grandson of New York Governor Edwin D. Morgan and distant cousin of J.P. Morgan. A Harvard graduate and accomplished businessman, Morgan commissioned the grand estate “Wheatly,” designed by the famed firm McKim, Mead & White — a masterpiece of Gilded Age architecture.
Old Westbury’s streets are lined with stories: from the Italianate splendor of “Old Acres,” built by Congressman Robert Low Bacon, to Gertrude Vanderbilt Whitney’s "Apple Green" estate, which today lives on as the Old Westbury Country Club.
Some chapters are more hidden, but no less profound. During World War II, the village played a quiet but essential role when the 187-foot water tower — now part of the Old Westbury Golf & Country Club — served as an aircraft lookout post. And even earlier, during one of the darkest periods of American history, Old Westbury was a station on the Underground Railroad. Quaker families in the area risked everything to shelter those seeking freedom, using hidden staircases and secret passageways that led to waiting boats in Roslyn Harbor.
Old Westbury is a place where history lives on in the most unexpected corners — in the tunnels beneath a wine cellar, the bricks of an old watchtower, or the whispers of ancient oaks lining winding country roads.
For me, representing homes here has become more than just a career — it’s become a passion for uncovering and sharing these stories, one listing at a time.
Because in Old Westbury, every home is part of history. And every story, no matter how small, adds to the legacy of our extraordinary village. What other wonders are there left to uncover?
