Nearly 15 years ago, a young family moved into a traditional shingle-style house on a meandering Winnetka lane. They decorated its newly constructed interiors as young homeowners often do—with not quite enough furnishings and an assist from a friend of a friend whose residence they admired and hoped to emulate.

As the years passed, the couple became known for entertaining on a grand scale, their children grew into talented athletes, and that stylish acquaintance and decorator—Andrea Goldman— became a good friend and designer renowned for creating interiors with a subtle, quiet beauty. The dwelling, however, hadn’t quite kept up with any of them and needed to evolve to accommodate the family’s social proclivities, active lifestyle and more contemporary taste.

When the neighboring property came up for sale, the owners and Goldman saw an opportunity to update the home’s functionality and aesthetic without tearing down walls. In collaboration with architect Mark Weber and his team, as well as general contractor Mike Wujcik, they created a contemporary guest house and sports pavilion with party-ready terraces that, when positioned alongside the main residence and around a new outdoor pool, transformed the two adjacent properties into one dynamic compound.

The simple new structures nod to the existing abode with their matching cedar shingle roofs, copper gutters and stacked-stone walls, but their modern steel windows introduce “a different sensibility,” Weber says. “These outbuildings are gracious, but they’re not trying to be the same as the house.” That said, Weber and his team did borrow some of the accessory buildings’ contemporary flavor by inserting the same steel windows into the primary dwelling’s façade—a move made to maximize views from the kitchen and adjacent hallway along with the primary bathroom. “We were taking old pieces out and putting new ones in, celebrating the contrast between the typical sensibilities of a traditional residence and our modern injections,” Weber explains.

To strengthen the new outbuildings’ feeling of belonging, landscape architects Sara Furlan and Dennis Murphy painstakingly preserved the property’s mature trees, including a massive old oak that shades the pool. “Those old-soul trees do so much in terms of setting a sense of place, scale and proportion,” Furlan says. “Seeing branches behind a roofline settles the space, making it feel like it has always been there.”

Goldman aimed for a similar effect when orchestrating dramatic transformations inside the main residence. “Everything got lighter and more clean-lined, from millwork to furniture,” she says. A new barrel-vaulted ceiling finished in glossy Venetian plaster bounces light from the entry hall into the adjacent living and dining rooms while floor-to-ceiling windows allow sunlight to fill the kitchen, which was further brightened with white cabinetry.

From iconic midcentury modern chairs to an antique Indian charpai daybed, the home’s new furnishings are upholstered in fabrics that beg to be touched. “In our sample library, I have bins that are simply labeled ‘fuzzy.’ We love fabrics that you want to pet,” Goldman says, pointing to the Army-green boiled-wool felt on the family room ottomans and the lavender brushed linen on the living room’s custom banquette—a piece that plays to the clients’ desire for a lounge-like atmosphere. Even the dining room walls invite touch with a handmade fringed wallcovering created by artist Anna Wolfson from burlap strips.

Adding further layers of texture are wood, stone and ceramic vessels that Goldman sourced from all over the world, then, as she says, “hoarded for a couple of years” in anticipation of filling this abode’s many display shelves. “To me, the composition of accessories is as important, if not more important, than the bigger pieces that you place,” the designer explains. “That’s when a space starts to get truly finessed and feel more like a home.”

Bringing color to the serene palette are contemporary artworks that range from a text-based Mel Bochner painting in the family room to the foyer’s aerial photograph by David Burdeny, which provides a graphic backdrop for African headdresses that once decorated the original residence. Such connections to what came before were just as crucial to this renovation’s success as the design team’s updates. “The owners didn’t want it to feel totally new,” Goldman says. “They wanted something familiar yet exciting; a reflection of them at this stage in their lives. And I knew we had succeeded when, after the big reveal, they said, ‘We feel like we’re back home again—but in a better version of it.’”

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