When the New York design gallerist Greg Wooten asked Bill Massie to design an upstate retreat in Dutchess County, the 45-year-old architect agreed, but insisted the house conform to his own ideas about country life. For Massie, the head of the architecture department at the Cranbrook Academy of Art in Bloomfield Hills, Michigan, an exalted post once held by Charles Eames, this meant "having cocktails, staying up late laughing and drinking, and finally everyone going their separate ways to sleep."

These are words worth remembering when approaching the house, because at first it appears as if a minimalist sculptor, not a committed bon vivant, designed it. Tucked behind oak trees on a remote road, the traditional modernist form—a crisp, white box—has been pinched and given nonconformist rounded corners: The side walls curve inward, a front deck slopes off into the woods, and the house soars out from a rocky ledge. Thanks to a radical building technology, it all ends up feeling wonderfully fluid and playful. Massie, you realize, has pulled off an unlikely triumph: Modernism, so often earnest and utopian, has succumbed to the pleasure principle.

Inside, the architect's subtly orchestrated intent is more immediately apparent. The house opens up to a magnificent view of the surrounding woods. Its modest but comfortable proportions (only 2,000 square feet) are reminiscent of the works of such pioneering modernists as Neutra and Schindler. "To strike a delicate balance of overall size, scale, and transparency in a house is so tough," Massie said. "But those architects got very, very good at it."

Massie is now very good at it, too. The irrepressible architect has become famous—some might say infamous—for continually exploring and inventing new design technology. Having emerged from Columbia during the early 1990s, when computer drawing was held to be the savior of the profession, Massie proved exceptionally adept at it. He soon learned how to transfer his intricately generated plans—for everything from walls to bathroom sinks—to something called a Computer Numerically Controlled machine, which cut into solid materials with an accuracy that matched within a thousandth of an inch the measurements on his drawings. Massie began using his CNC device to hollow out Styrofoam molds. Pouring concrete into them enabled him to make improbably undulating walls, but with a structural toughness that surpassed conventional equivalents. Once, when I questioned this claim, Massie jumped behind the wheel of a large pickup and drove over a curving section of concrete roof that lay on the ground awaiting assembly. It remained totally intact.

Now speeding around Cranbrook in a Mini Cooper, Massie, who lives nearby with his wife and two children, offered a rapid-fire tour of the campus. He lavished praise on the superbly elegant school buildings designed by the academy's first president, Eliel Saarinen, father of Eero Saarinen; sounded off about the current dire state of residential architecture ("McMansions big enough to give birth to other McMansions!"); and even squeezed in references to John McEnroe's opinion of the newest high-tech tennis racquets ("a huge advance for the game"). Massie, whose long blond hair is cut evenly just above the neck, is an avowed tennis nut.