Breezy Hill: A 20-Acre Compound Reinvisioned by Joshua Leonard

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Joshua Leonard’s decision to leave Hollywood for the Hudson Valley home renovation scene may seem like a surprising turn for the actor, director, writer, and producer known for such envelope-pushing projects as The Blair Witch Project, Humpday, and HBO’s “True Detective.” As is the case with most creatives, however, there’s usually always another passion quietly simmering away on the backburner.

“I’ve spent almost 25 years in the film industry, and I’ve probably been renovating houses since the start,” Leonard says. “For many years, I would do film jobs in order to be able to come back and renovate and build.” His first big project was his Los Angeles loft in 1999, followed by the succession of homes he bought and sold as he and his wife, actor Alison Pill, moved through the phases of their life.

In 2018, while working on projects in New York—Leonard on a film in the Hudson Valley and Pill on Broadway—they began spending weekends upstate. “The more we came up, the more we fell in love with the area, both the natural side and the sense of community here,” he says. “I think as soon as my daughter was born in 2016, it became really important for me to find some kind of consistent nature refuge for her because it had been such a big part of my childhood in central Pennsylvania.”

Soon after, the two purchased a home in Ulster County, and Leonard spent the next year fixing up their cabin in the woods. Then the pandemic hit, and instead of heading back to the West Coast the family planted their roots firmly in the Hudson Valley. Weary of traveling and spending time away from their daughter, Leonard decided there was no better time or place to go all-in on his other creative passion. “I had a deeply skilled crew from working on our house, and I had fallen in love with building up here,” he says. “And, because of my gung-ho nature, I ended up taking on a five-building, 20-acre compound that essentially had to be rebuilt from absolute scratch.”

Restoring Breezy Hill’s Historic Legacy

When Leonard first laid eyes on 45 Breezy Hill Road in 2021, its 20 acres were overgrown and marshy in spots, with an eclectic collection of semi-abandoned structures dotting one corner of the property. There was a two-story stone house dating to the early 1800s, a Civil War-era barn, and two 1950s boarding houses. Where many others likely saw chaos, Leonard could already envision the property’s future as a creative family refuge that could be passed down for generations.

Working closely with Carlos Hernandez of Ulster County-based HER Construction, Leonard completely reimagined the Breezy Hill Compound—imbuing it with the same spirit of craftsmanship belonging to a historic property that has been tenderly shepherded through its years. “That property, even in its most derelict, raw, scary form, held the same kind of energetic magic and potential for me that my own early property did,” he says. “I knew it could be extraordinary.”

To rehabilitate the 19th Century stone house, they completely repointed the stonework on the exterior and opened up its cramped rooms by adding five feet of bluestone to raise the ceilings on the second story. The entry to the home now soars skyward, with an open staircase made from reclaimed wood and a cupola that diffuses light onto the white oak floors below.

They also built a three-story addition that expanded the total square footage to just over 3,000 square feet. It houses a brand new chef’s kitchen and dining area with two-story-tall windows that offer breathtaking views of the property and spotlights a rugged 100,000-plus-pound bluestone boulder excavated during the building process. A reading nook on the second floor looks out over the property, and, tucked behind a reclaimed barn door, are the primary bedroom and ensuite bathroom complete with a private deck.


Primary Bedroom

The boarding houses were transformed into sweet two-bedroom guest cottages that offer a blend of modern conveniences and charming historic details, including reclaimed stained glass windows and copper staircase handrails.

The Civil War-era barn was lovingly refurbished with an eye toward preserving its character and rich history. “You can tell that Breezy Hill was built with love by people who probably had humble means, and we kept a lot of that wabi-sabi imperfection in the work,” says Leonard.

Primary bath

Faced with a crooked roof and walls, they built an exoskeleton around the barn’s exterior to straighten the structure and make it watertight, and made alterations to the interior using only period work. “The chestnut staircase to the hayloft was carved with just a chisel and a saw by one of the guys who loved working with reclaimed wood,” he says. “There were so many of the team who got to spend a year-and-a-half on the project honing the things that they were great at.”

Not one to be content with simply directing operations, Leonard himself would often meet with the crew in the mornings, then spend the rest of the day on the excavator or skid-steer—terraforming the property’s landscape, building swales, and channeling water in ways that enhanced the beauty and functionality of the gently rolling terrain.

“I have worked collaboratively for all of my career, and in my later film years, had moved into a leadership role as director or producer, so I love working with people,” he says. “In terms of running a crew, that’s really part of what I think I’m pretty good at—recognizing people’s value and then really fostering that, while also keeping my eye on that end goal.”


The Breezy Hill Compound Team

Project Management: Carlos Hernandez of HER Construction
In Architectural Collaboration with: William Brinnier
Custom Woodwork: Hudson Valley Hardwood
Staging and Design: Spruce Design + Decor; Milne Antiques & Design
Custom Cabinetry: Little Deep Studio
Landscape and Garden Advisor: Courtney Wilder
Electrical Contracting and Lighting Consultation: Sean Correa of AC/DC Electrical Services

For more information on 45 Breezy Hill Road in Accord, NY, contact Robert Airhart with the Clement, Brooks & Safier Team of Berkshire Hathaway HomeServices Hudson Valley Properties at (917) 304-3864 or email [email protected].

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