See How This Woodside Home Follows The Contours Of The Landscape

Looking back at the homes his firm has created, architect Timothy Chappelle says this new Woodside abode “has one of the most unusual shapes.” The residence, situated at the top of a hill, follows the serpentine contours of the landscape as it cascades down the slope, creating a sense of connection and timelessness as it goes.

Chappelle spread the home along the ridgeline, keeping it to one story (though there is a basement) to be sympathetic to the valley below. “We didn’t want to be a bright white box on the hill,” he explains. And by cleverly positioning the building, the architect was also able to protect the property’s oak trees, one of which, just off a patio, acts as “the guardian of the house,” he says.

To establish a sense of history, Chappelle and the owners—a couple with three children— focused on an agrarian architectural style and a natural material palette: cedar for depth and texture, St. Helena stone as a tie to wine country and a corrugated metal roof. “Tim and his team are masterful at creating beautiful, high impact spaces that still feel comfortable,” the husband says. “We gravitated to a design that felt like it had always been there,” the wife adds. “We love the old-world style because it reminds us of a Tuscan villa we stayed in many years ago.”

Brought on to realize Chappelle’s design, general contractor Mike Smith refers to the new abode as “one of my most gratifying builds,” he says, noting the pool house and fitness barn that round out the site. “Tim’s approach to compound architecture, with all its different massing, just blends beautifully with nature. It’s a combination of rustic and modern.”

The interiors speak the same language, with designer Jennifer Robin taking an equally considered approach. “My goal was to create interiors conducive to entertaining while maintaining comfort for more intimate family connections, as well as durability for everyday life,” she explains. “Every room has a distinct personality and function, yet we also wanted to ensure cohesion as one transitions from space to space.” To that end, she blended mountain and wine country aesthetics with the homeowners’ more traditional tastes for a unique experience. “It was amazing how quickly Jen got our style,” the wife says. “The whole house reflects our family and how we live. It’s more beautiful than we could ever have imagined but still so comfortable and warm.”

“Working with a team of detail-oriented craftsmen was instrumental in bringing the design vision to life,” adds Robin’s project manager, Dani Souza. That vision resulted in an airy wire-brushed cedar dining room ceiling as well as a living room with a large cocktail bar and doors that open to the patio and fire pit. The kitchen, with its curved built-in banquette, is specially designed for more casual family gatherings. “It’s my dream kitchen that I’ve been waiting 20 years to cook in,” the wife says.

Other key spaces include a media and games room that connects to an exterior dining pavilion and barbecue area, and a primary bedroom suite designed to “nurture and promote rest and revival,” Robin describes. “The richly saturated upholstered wall is unexpected but perfectly harmonizes with the emerald tones of the landscape.” There are “smaller moments that we treasure, too,” explains the wife, like a nook for the Bösendorfer piano (“Our very first purchase for the home,” she recalls) and a daybed that overlooks that majestic guardian oak.

Landscape architects Ben Langford and Johnson Bullard assisted the homeowners in further tailoring the site to their interests. “Our work is about connecting people to place and crafting everyday experiences they can delight in,” says Langford, noting the sports lawn, olive grove near the pool, fruit trees by the tennis court, vegetable garden, and new vineyard created by David Page of Post & Trellis, which had its first harvest last fall. There are also climbing roses in a nod to the wife’s mother’s rose garden, and flowering trees that recall places the couple have been together. “It helps clients connect more to a site by adding plants that mean something to them,” Bullard says.

“The way this house flows encourages everyone to be present in each place—it’s a testament to Tim’s architecture,” Bullard continues. “This house, inside and outside, is a collection of experiences.”