Love at First Sight and a 200-Year-Old House: Becoming Stewards of Robins Hollow
Listing photo of Robins Hollow in the summer of 2020
Is there such a thing as love at first sight?
The older I get, the more I believe that the things meant to be yours somehow find their way to you when the moment is right. That doesn’t mean life is easy, or without trials, but the law of attraction is real. Experiences, places, and people that resonate on the same wavelength seem to turn up exactly when you need them.
September is always an important month for us — it’s when Sean and I first met, it marks one of our anniversaries as a couple, and it is also the milestone month when we became the stewards of Robins Hollow. That’s why we’re writing this post now, as September has us reflecting on beginnings, connection, and the places that feel meant to be.
Lately, I’ve found myself reflecting as I navigate the twists and turns of a career transition. After architecting a thoughtful exit from a company I helped build a part of over five years, I took a pause — a rare stretch of time to reflect, refresh, and gain inspiration.
Across both career and life, I’ve seen the same pattern: no matter how many times you hear “no,” the right opportunity always arrives.
I’ve had a number of chapters in my career so far — each one beginning and ending when the moment is truly right. Each builds on the past while layering in new challenges and adventures. Sometimes it has felt like I’ve heard “no” a hundred times before finding what’s next. Other times, things click on the very first conversation. Either way, it’s unmistakable when an opportunity is right; it just fits.
And the same has proven true in love. We often joke that neither Sean nor I would have described the other as our “ideal” partner on paper. I lean on the Billboard 100, Sean curates his own weekly playlists. I’m an avid planner, and Sean tends toward spontaneity.
But when we found one another, we just clicked.
Finding Robins Hollow
It’s in this context that I want to tell the story of Robins Hollow — how we became its stewards. People often ask how many houses we saw before we found the one. The funny truth: we weren’t even seriously looking.
I don’t know too many people who stumble upon an (almost) 200-year-old, 20+ room farmhouse with barns, a tennis court in ruins and 2.5 acres in need of a good brush hog during a pandemic and decide to buy it.
The prior year, we had casually looked at a few New York City apartments. Then the pandemic hit, and Sean, like so many, began exploring real estate with the intensity others reserved for sourdough bread.
He even found a castle just outside the city upstate in Tuxedo Park — twice the size of Robins Hollow and needing far more work — and we fantasized about buying it. It felt like a harmless daydream, a distraction during one of the strangest periods of our lives.
We had always dreamed of a house with some land, maybe a barn, a place to make our own over time. That summer, while renting on the North Fork, we kept an eye on local listings.
One day early in the month, a listing appeared: an old house with a name, a barn, and enough land to feel spacious. Initially, there were no interior photos — just a description. Because of pandemic-era restrictions, you needed pre-approval for financing just to see the property. It made every viewing feel like a small victory before you even stepped inside.
We hopped on bicycles and rode twenty minutes from our rental to view Robins Hollow. From across the street, I remember thinking the house didn’t match the description. I almost didn’t want to see it. I could barely make it out through the overgrown trees, shrubs, and bushes that clearly needed some care.
But we had pre-approval in motion, and Sean said, “Why not?”
The Viewing
On the day of the viewing, we put on our masks and walked through the house. I was stunned. What had been listed as a six-bedroom, two-floor house included a third floor, an attic, and several additional rooms that could be used as bedrooms.
The house had enough bedrooms to host friends and family — and sometimes forget they’re there. It felt immediately alive — as if it had been waiting for us to become its caretakers.
From the moment we stepped inside, the house began to reveal itself. It seemed to wander at points — hallways, nooks, and wings almost daring you to get lost, with light shifting across wavy glass and floorboards creaking beneath each step.
Sean’s favorite spot quickly became the second-floor guest wing hallway, with six doorways that would inevitably confuse any visitor. It remains one of his favorite stops on the house tour. It’s a labyrinth of charm, history, and quiet magic.
There were endless details to discover: built-in window benches complete with cubbies and stacks of old books hidden within, a butler’s pantry pass-through to the dining room, a wine cellar stocked with 1970’s french wines, a second floor in the barn complete with a Santa’s sleigh, tennis court (in ruins, waiting patiently for restoration), and even an ice house dating back to the late 1700s where we imagine ice once stored for summer gin rickeys — a small joy connecting the house’s past to our present rituals.
At that moment, during a frenzied North Fork pandemic real estate market, we knew the timing and offer mattered. Offers in New York City were flying — cash offers, immediate purchases — as people fled the city for the bucolic nature of the North Fork. But Robins Hollow felt like it had waited for us.
We debated our offer carefully. The house needed substantial love and repair. Three inspections later, an inspector chuckled,
“You know it’s an old house, right?”
“Yes,” we said.
“Well,” he said, “it’s as solid as it can be.”
That line has become a kind of mantra — not perfection, but persistence.
We submitted an offer below asking and asked the sellers to address a few key items from the inspection. We waited anxiously. We were told there was another competing offer — two families hoping to buy it as a shared vacation home. Somehow, that offer never materialized.
By early September, we got the call: the house had chosen us as its next stewards. Sean’s daughter, then six and deep in her “stuffie” era, was away visiting her mother. We presented her a Robin stuffed animal upon her return to celebrate and mark the occasion.
We got the house — Robins Hollow was ours! The moment felt both unreal and inevitable, as if the house had been waiting for us all along.
A Sense of Home
In so many ways, Robins Hollow felt like it had always been ours. From the moment we stepped inside, it resonated on a frequency we couldn’t ignore. It was meant to be.
Our devotion to the house has grown over the past five years. Like any long-term relationship, it has deepened through patience, care, and shared effort. From peeling back carpets to restoring wood windows. From uncovering hidden nooks to celebrating small victories, persistence has been the real craft. This house has become more than a home. It’s a living story — a blend of past and present, filled with room for friends, family, neighbors, and memories yet to come.
Robins Hollow was love at first sight. But as with any great relationship, the devotion deepened with time — peeling back carpets, restoring windows, discovering hidden nooks. That ongoing care is what makes a house a home and builds a lasting legacy.
Do you believe in love at first sight? Tell us in the comments — and subscribe to our newsletter for more stories from life at Robins Hollow.
