Welcome to Hollow Farm, a spectacular and ultra-private Connecticut estate set on approximately 77± acres of pristine land. Secluded yet accessible, this remarkable property offers a rare combination of historic charm, modern convenience, and natural beauty. Designed for refined living and seamless entertaining, the main residence is impeccably maintained and features timeless elements such as original wood floors and a mid-century stone sink, a pebble mosaic floor, and storage for up to 600 bottles. This temperature and humidity-controlled space offers an ideal setting for curated wine experiences, complete with inventory labeling and seating for four. Outdoor living at Hollow Farm is equally exceptional. A saltwater pool, heated by solar panels located across the driveway from the barn, is complemented by a covered cabana with a full kitchen and comfortable lounge area. A stone fire pit and patio overlook the pool and lush surroundings. The estate boasts over 20 acres of professionally landscaped grounds, complete with walking paths, night lighting, and extraordinary stonework throughout. Two scenic ponds grace the property, one of which can be stocked with carp and is bordered by ancient boulders placed decades ago. A charming gazebo overlooks the pond, and a wide, pristine stream flows through the land, culminating in a seasonal waterfall near the remains of an old grist mill. The orchard boasts mature apple, pear, and peach trees, along with raspberry and blueberry bushes—perfect for enjoying fresh, homegrown fruit. Additional structures include a one-bedroom guest house with a full kitchen, living room, and fireplace; and a caretaker's apartment above the barn. The barn itself houses a large playroom, extensive storage space, and ample room for a car collection. Three wells serve the property—one each for the main house, guest house, and caretaker's apartment. On-site electric, diesel, and gas pumps provide fuel for both vehicles and farm equipment, supported by a large propane-fueled generator and an underground electric fence for added security. Fitness enthusiasts will appreciate the fully equipped home gym with top-tier machines and amenities. The estate's multiple lots are deeded as three, with the potential for a fourth, and include a separate road to the back parcels. A portion of land is zoned under the 490 Forestry program, offering potential tax advantages and long-term flexibility. The owners also once considered adding a tennis court and a three-hole golf course on the pasture above the barn—options still well within reach. Hollow Farm is more than just a home; it is an extraordinary estate that brings together luxury, privacy, and natural splendor. Whether you're seeking a peaceful retreat, a generational compound, or a turnkey property with exceptional amenities, this one-of-a-kind offering delivers a lifestyle beyond compare. Owner licensed Realtor in NY.