Appleberry Farm in Sandy Hook is no stranger to Kate Osborne. She grew up just a quarter mile down the road on the same property that once belonged to her grandparents and, before that, her great-grandparents.
At its center is a modest three-bedroom 18th-century saltbox farmhouse believed to date back to around 1770. For Osborne’s family, it was a constant gathering place, shaped by four generations with “hundreds of animals, laughs, swims, parties, adventures, and multitudes of shenanigans.”
“It always had this open-door policy,” says Osborne. “No invitation was needed. Everybody was welcome, all the time. There was always enough food.”
Her great-grandfather, Robert Young (R.Y.) Brown, purchased what was then the Keane dairy farm in 1939, and he and his wife, Dorothy, raised their two children, Betty Lou (Osborne’s grandmother) and Bob, here. They named the property Appleberry Farm for its apple orchard and wild blackberry fields.
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“My grandmother and her brother were raised here. And then my grandmother and grandfather raised their four children here,” says Osborne. “With my grandmother's four children, their spouses, and all their children, we'd all get together, and there'd be 35 people in the house for Sunday dinner. It was so much fun, but there was no room to move and no place for people to stay the night.”
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After her grandmother’s passing, the family weighed the options of how to proceed. In 2019, they decided it was time to consider selling it, and Osborne raised her hand and purchased it in 2020. The 2,000-square-foot house was in serious disrepair, she says, with extensive rot, failing windows, and no insulation. But Osborne had a vision of bringing the house back to its essence, unlocking its full potential, and expanding it into something that could support generations to come.
Living elsewhere in Fairfield County, Osborne and her husband began looking for architects specializing in historic home restoration and renovation. They immediately liked the style and previous work of Haver and Skolnick Architects, based in Southbury and Fishers Island, N.Y.
When Charles Haver and Stewart Skolnick first arrived at the property, the original form of the house was almost unrecognizable, buried beneath decades of what they describe as “unsympathetic additions.” It wasn’t until they began measuring and examining the post-and-beam structure that the original saltbox shape revealed itself.
“No one in the family had ever seen it in that form even though they had owned it for generations,” Skolnick explains.
They decided to strip the previous additions and porches from the house to return it to its original structure, preserve what could be saved, and let its historic core guide the design of an additional 7,800 square feet.
Osborne says that the large addition would allow not only their two adult children to come and stay with their future families, but also their entire extended family. She wanted to continue her family’s legacy, recreating the “gathering place vibe,” but with a lot more space.
“The challenge was scale,” says Haver. “How do you create something this large without dwarfing what you’re trying to celebrate?”
So rather than overwhelm the restored saltbox, they allowed it to remain the visual and emotional centerpiece. Instead of adding to the right and left of it, they approached the addition as a backdrop. Portions step down along the natural slope of the land, ensuring the new construction does not rise above the original structure. Detailing was kept simple and straightforward, responding to the saltbox form.
Inside, the great room with cathedral ceilings is at the epicenter. Bedrooms are intentionally grouped into separate wings, each with its own staircase, creating a sense of privacy within the larger whole.
“We wanted people to be together and gather, but also wanted places where you could retreat and have a quiet moment,” says Osborne.
The original saltbox retains its lower ceilings and cozy proportions, while the new spaces are open with light-filled rooms and views of the surrounding landscape.
Throughout, materials create a sense of continuity with reclaimed wood floors, exposed beams, and plaster walls that echo the textures of the antique structure.
“We wanted it to feel like one house. Even though the scale changes, the materials tie everything together,” says Skolnick, who notes that Chris Spiller of CDS Contracting LLC was the contractor for this project, which won a 2026 AIA Connecticut Alice Washburn Award in the Additions/Renovations category and a national Palladio Award, honoring outstanding achievement in traditional architecture. The design and build process took roughly two years.
Preserving the original home required meticulous effort. Floors were carefully removed, labeled, and reinstalled. Custom windows, crafted to replicate antique glass, replaced those lost to decay. Fireplace mantels and paneling were recreated to match their historic counterparts.
“It was important to me emotionally,” Osborne says. “That part of the house holds so many memories.”
The now six-bedroom, five-bathroom home is furnished with some family pieces from Osbourne’s parents and some items they found in the and restored. The rest is a mix of antiques and modern furniture.
Beyond the walls of the home, Appleberry Farm is still a working landscape. It’s now home to a growing cut flower business and design studio run by Osborne and her sister. What began as a pandemic-era project has evolved into a full-fledged operation. They work with locally grown, seasonal flowers from their farm and other local flower farms to create floral pieces for weddings, corporate, and private events.
“There’s always been a connection to the land here,” Osborne says. “We just found a new way to carry that forward.”
Like the interior, the outdoor spaces were also designed to gather, to linger, and to connect. A series of terraces, gardens, and seating areas extend the living space beyond the house, from a pergola overlooking the orchard to a sunken pool framed by an ipe wood deck. In the warmer months, the family spends as much time outdoors as indoors.
Even the lower level, outfitted with a golf simulator, media room, and pub-style gathering space, speaks to what the house has always embodied: bringing everyone together.
“Charles and Stewart worked with us to bring our vision to life,” says Osborne. “I had ideas, and they made them a reality in a tasteful, thoughtful, and respectful way. They brought the vibe I relayed to them to reality and are the artists behind this renovation and rebirth.”