More than a decade ago, musician and vintage furniture purveyor Greg Wooten began looking for a quiet place where he could escape from New York City. He found a five-acre parcel upstate in the town of Milan and called upon architect William Massie to create something unique. Massie—who was head of the architecture department and an artist-in-residence at Cranbrook Academy of Art in Bloomfield Hills, Michigan at the time—answered with what he calls a "site-driven, 90-percent-prefab social environment, built with Greg’s collection of eccentric, beautiful modernist furniture in mind." As such, the 2,300-square-foot layout is open (with plenty of floor space for guests who wish to crash there) and enveloped in warm wood panels that embrace Wooten’s well-edited furnishings. "Every piece had to really matter," says Wooten. "Most of those pieces have a story, and often that story relates to a friend or an experience. If it wasn’t something created by an artist or designer friend, it’s the one thing I brought home with me on the plane from Italy or the flea market in Tokyo." Though Wooten has since relocated to Los Angeles, where he recently opened the Window—a shop special-izing in 20th-century furniture and objects he gets back to the house as often as he can.