The Reimagining of A Landmark

What Shall Henceforth Be Known As

The Roa Estate…

There’s a house in Pound Ridge that for years was known as ‘that house’. Longtime locals will recall wild pool parties and epic tennis matches, thrown by the late, legendary real estate maven Doris Seidletz. And by the time John Roa and Candice Milano arrived at this once-beloved residence, it was barely standing. Sagging into the earth with no foundation to speak of, it had become more ruin than retreat. Most prospective buyers didn’t make it past the front door…

Built in the mid-1800s, the home was once part of the historic Hunt Farm, originally tied to the Purdy family, who were among the area’s earliest and most prominent settlers. Over the next century and a half, the house passed through only two families.

“Where others saw a teardown, we saw potential. We knew within minutes that we were going to buy this place,” John says. “It just had a presence.”

And so began a multi-year restoration and expansion, orchestrated by architect Ira Grandberg, who’s known for his reverent touch with historic homes. “The house was literally sitting on rocks,” Ira says. “We had to jack it up and build a foundation underneath. But that opened up endless possibilities, and John and Candice had an imagination and openness that allowed us to do some really amazing things here.”

“The house actually almost fell over during the construction process,” John laughs. “Nobody could believe that the structure was still intact given that it was resting on loose boulders. Thankfully, Ira made sure it didn’t fall over, and we can laugh about it now!”

Sightlines were crucial to Ira’s plan.

“I design homes around what you see,” he explains. “Every corridor leads to a painting, a window, or a vista. That’s what makes a house feel alive.”

Rather than overwrite its history, John and Candice chose to embrace it. Candice explains, “We wanted to preserve the soul, but make it ours, and make it really comfortable for our family.”

John and Candice approached the renovation like an archaeological dig crossed with a mood board masterclass. “We probably looked at hundreds of images,” Candice says. “But it wasn’t about copying. It was about decoding what we loved.”

“Take the flooring, for example,” John recounts, “We found centuries-old planks in the attic and reclaimed and reinstalled them throughout the main living spaces. We sourced delicate plaster crown molding for the parlor from Europe and had it shipped in sections, then hand-blended them on-site until the seams disappeared. The shipment came on pallets that weighed 5,000 pounds! And then there’s the banister in the front hall that’s still adorned with the original mortgage button - a forgotten tradition where homeowners would ceremonially place the button signifying that their deed was paid-off onto the post.”

The couple created a basement that fulfilled some of the more modern amenities that they still wanted to enjoy, adding an ultra-cozy mini movie theater, a gym, an oversized laundry room, and two guest suites.

The outdoor spaces are just as much a part of the home and living space as the inside. A gorgeous covered back porch with picturesque rocking chairs boasts reservoir views; a completely windowed room with a hanging swing porch chair serves as an indoor-outdoor living room; and; the yard was turned into a sublime recreation space with a Har-Tru tennis court and pool connected by a patio.

Though the home grew in size, nearly tripling from its original 1,700 square feet, it remains intimate by design. The couple linked the main house to a neglected outbuilding, once suspected to be a schoolhouse or caretaker’s quarters, via a light-filled breezeway.”The breezeway was Ira’s idea... and it makes the house feel so much more expansive, and it allowed us to make the facade a bit more interesting as well… we added a trellis to the inlet, and the two oval windows became defining features,” Candice shares.

The guesthouse, with its own sitting room, bathroom, bedroom, and kitchen, was gutted and re-envisioned. The absolute showstopper of the space is a mint green kitchen by Bilotta. Though it looks like something that might have been restored from the original estate, each piece was fabricated to have that historic aesthetic, and appliances were carefully selected so that they could be hidden. It serves as a private haven for visiting friends and family - a love letter to rustic elegance.

The main kitchen is a delightful space that feels like a retreat in the English countryside, with a slightly more formal dining room off to one side, and a quaint windowed breakfast nook on the other. John, who took up woodworking during the renovation, hand-crafted both the dining room and breakfast room tables himself.

The pantry is absolutely adorable.

“I found these quirky maple slabs from a lumberyard in Ridgefield that really give the space some character. From there, the rest was all Candice’s vision! Obviously the oval window adds an interesting touch to the space, and we hunted down the antique doors from a warehouse in Pennsylvania and then had custom brass hardware fabricated to fit perfectly,” John beams.

The couple even installed a pot-filler faucet over Prada’s (the couple’s White Cream Retriever) water bowl. Prada being a nod to Candice’s last name - Milano.

“We reveled in the details. No kidding, our vision board to get started was a 500-page powerpoint! …And then we spent about a year shopping, antiquing, and sourcing all of the finishing accents and furniture that make the place feel like a home,” John says.

Candice’s obsessive eye for lighting led her to obscure European artisans, sourcing sculptural pendants and sconces with the fervor of a curator. And you wouldn’t know it by looking, but the house is one of the most technologically advanced in the area. Facial recognition security, custom Lutron automation, smart climate systems… the kind of invisible infrastructure that operates without interrupting the old-world charm. “There are no iPads on the walls,” John, who’s a tech entrepreneur, insists. “We wanted it to feel like a 19th-century country house, not a Silicon Valley command center.”

…And that juxtaposition—of antique soul and modern function—is where the home finds its rhythm.

“All throughout the renovation, neighbors and strangers alike have been stopping by, eager to see what’s become of that house. It was like the town was rooting for us,” Candice says. “And we felt that. It’s part of why we wanted to open the house up to B&NC Mag…”

The result of John and Candice’s vision is a home that feels layered with time, thoughtful in function, and utterly original.

“This was never a flip,” John says. “This is where we plan to live forever. I mean it. Take me out of here in a box!”