Set on over five private acres along New Canaan's coveted Oenoke Ridge, this extraordinary estate is a reimagined 1890s cow barn masterfully transformed by the Hobbs family with architects Joeb Moore and Louise Brooks. Blending agrarian charm with refined modern design, the residence honors its heritage while offering sophisticated comfort. A tree-lined drive and landscape lighting set a gracious tone on arrival. Inside, the dramatic two-story great room features a soaring stone fireplace, post-and-beam framing, and antique pine floors. A storybook catwalk leads to a second-floor library, while the sunlit gourmet kitchen flows into a breakfast room and formal entertaining spaces. The six-bedroom layout includes a first-floor primary suite with a sitting room ideal for a nursery or office. The walk-out lower level offers a wine cellar, playroom, bedroom, and full bath. A detached three-car garage includes a guest apartment with its own entrance, living room, bedroom, and bath-perfect for in-laws or extended stays. Outdoor living is elevated with a heated gunite pool overlooking the reservoir, a fireplace, meditation pool, and secret garden path. Designed by Kathryn Herman Design, the award-winning landscape features terraced gardens, meadows, specimen trees, and a producing apple orchard. Just minutes from town, this is a rare opportunity to own a timeless piece of New Canaan's history.