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The three attached structures house an office, guest suite, and game room, used by the family to watch football games.

The 5,200-square-foot retreat is designed to look like a cluster of old barns upon first glance.

The Portola Valley Barn blends into its rustic setting.

The simple finishes provide a backdrop for the homeowners’ collection of carefully curated furnishings, many of which are vintage (and, yes, cozy). One partner is a graphic designer, and she brought her own strong design sensibilities to the project. “She likes contrast, black and white, and bold color,” says Cuppett.

The guest house and main house are connected between the buildings—the kids are constantly running barefoot from space to space.

The freestanding garage also houses an art studio and meditation space.

The siting here is critical to the property’s sense of timelessness. “The whole compound is rotated 45 degrees relative to the street, so you’re not actually looking at the front face when you drive up—you’re looking at the courtyard of the compound,” explains Kilpatrick.

The dining table, a custom design by Formwork, and red Non chairs by Komplot complement the addition’s cypress cladding.

Birdsall and Atticus are seated on an ipe bench designed by Anna Boeschenstein; the stucco exterior cladding was matched to Cast Iron 6202 paint by Sherwin-Williams.

The perennial plants on the green wall were plotted out as a piece of verdant abstract art. Edibles, like strawberry, thyme, and rosemary, are planted within children’s reach.

This casual eating area in the kitchen features a built-in bench and shelf.

The roof's overhang also employs paneled Siberian larch.

Sliding glass doors allow the kitchen and living room to be fully opened to the deck, creating a seamless integration between the interior and exterior space.

A breezeway complete with swings connects the front and back decks. “We knew we wanted a covered entry, but we left it open to create a larger outdoor space,” says Scott, who admits to occasionally using the swings himself. Mud guards are built into the Kebony decking to keep dirt from being tracked inside. The teak chairs are by Skagerak.