Tucked along the coveted crest of Oenoke Ridge in New Canaan, this extraordinary country estate unfolds across five secluded acres, a masterful transformation of an 1890's cow barn that bridges agrarian heritage with refined architectural vision. Thoughtfully reimagined by the Hobbs family in collaboration with acclaimed architects Joeb Moore and Louise Brooks, the residence honors its pastoral roots while embracing a timeless, contemporary elegance. A stately approach, lined with linden trees and subtly lit by bespoke landscape lighting, sets the stage for what lies within. At the heart of the home, a soaring two-story great room stuns with a dramatic floor-to-ceiling stone fireplace, framed by original post-and-beam construction and antique pine floors. A charming catwalk leads to a second-level library, while below, light pours into formal and informal spaces designed for effortless living and entertaining. The gourmet kitchen opens into a sun-filled breakfast room, and the 6-bedroom layout includes a serene first-floor primary suite with its own sitting room, ideal for a home office or nursery. The finished walkout lower level offers a wine cellar, playroom, bedroom, and full bath. A detached three-car garage is topped by a guest house with its own entrance, complete with living room, bedroom, and bath, perfect for extended stays, in-laws, or an au pair. Outside, the landscape is nothing short of a living canvas. Designed by Kathryn Herman Design, the grounds feature terraced gardens, rolling meadows, a producing apple orchard, specimen trees such as umbrella pine and magnolia, and stone walls that shape the land with natural rhythm. A newly built, heated gunite pool overlooks the reservoir and is paired with an outdoor fireplace, meditation pool, and hidden garden path, spaces designed as much for reflection as for gathering. A rare fusion of history, artistry, and privacy...this is a singular opportunity to own an iconic piece of New Canaan, just minutes from the town's world-class amenities, public and private schools, and Metro North with express trains to NYC.