The Fairytale in the City: Discovering Pomander Walk

In a city renowned for its endless reinvention, the greatest surprises are often the ones that have quietly endured. Nestled within the Upper West Side, just off the hum of Broadway and West End Avenue between 94th and 95th Streets, lies one of New York’s most beguiling architectural secrets: Pomander Walk. A place that seems more imagined than real, this tiny gated community is a living fairytale—a quaint and colorful crescent of English Tudor-style cottages that transports visitors not just out of Manhattan, but out of time.

I was first introduced to Pomander Walk two decades ago by a friend lucky enough to call it home. The moment I stepped through its discreet wrought-iron gates, the world shifted. The roar of the city faded, replaced by the gentle clink of garden tools and birdsong. Time slowed. My fascination quickly turned to reverence. So when a resident recently called SIMPLIFYnyc for help preparing one of these storied homes for market, I didn’t hesitate. And just a few days ago, I had the honor of bringing that very listing to life.

A Storybook Lane, Hidden in Plain Sight 
Pomander Walk is more than a residential enclave—it’s an architectural love letter. Designed in 1921 by Thomas J.Healy, a nightclub impresario known more for bright lights than brickwork, the development was originally conceived as temporary housing while Healy awaited approval for a grand hotel. That hotel never materialized. But the houses, delightfully, did—and they’ve endured for over a century.

Twenty-seven buildings, painted in cheerful pastels and trimmed with half-timbered detailing, sit on a narrow pedestrian-only path shaded by cherry blossoms and framed by climbing ivy. Each home has its own miniature garden. Some boast antique lanterns. Others are fronted by wrought-iron fences draped in wisteria. It’s hard to believe this village-within-a-city could be real—until you walk it.

The name, Pomander Walk, comes from a 1910 Edwardian play by Louis N. Parker that envisioned an idealized block of English row homes. Though New York’s Pomander is thousands of miles from London, the whimsical spirit remains intact. It’s no wonder the enclave has long attracted creatives and legends: Lillian Gish, Rosalind Russell, and even a young Humphrey Bogart once called the Walk home.

Over the years, its cinematic charm has been featured in films like Hannah and Her Sisters and novels like Emma Straub’s This Time Tomorrow. But its true magic lies in the present—in the people who live there now.

A Conversation With a Resident: Robin Skye 
To better understand the soul of Pomander Walk, I spoke with longtime resident Robin Skye, a Broadway actress and artist who has lived on the Walk for nearly 28 years. Her insights reveal a deeper kind of beauty—one rooted not only in design, but in community.

“There are several reasons why I love the Walk,” she told me. “The beauty, the feeling of community, the gardens, the location. To be able to plant my garden, in the middle of a city no less, brings me a sense of peace, hope, and a lot of joy. It’s a privilege I don’t take for granted.”

What makes Pomander truly unique, Robin explained, is the way neighbors support one another —not just in times of joy, but especially during hardship.

“During COVID, those of us still here checked in with our neighbors. We supported each other through those dark times. We all know how very lucky we are to be a part of each other’s lives here. It’s an oasis steeped in history. I live in what was once Humphrey Bogart’s home. We all share the same level of respect for where we live.”

When asked what she’d tell a potential buyer, she smiled and said, “Welcome to Pomander Walk. Dive into a truly unique community that will be very happy to have you. I hope you enjoy gardening—or, like me, the journey to becoming someone who fell in love with it. The location, the subway on the corner, Symphony Space up the street, Riverside Park, restaurants, quick access to the highway, not to mention the shops in our immediate area, make Pomander Walk a sweet spot on the Upper West Side.”

In a metropolis that prides itself on forward momentum, Pomander Walk offers a pause—a breath—a step sideways into a world where neighbors chat over fences, where blossoms mark the seasons, and where history feels tangible.

For those who crave both charm and connection, who seek heritage without sacrificing convenience, this might just be the city’s most enchanting address. And as fate would have it, one of these rare homes is now available. I would be delighted to offer you a private tour of Pomander Walk. Because some places, like some stories, are best experienced in person.