A rare historic estate in New York’s Southern Tier, offering the character of the past with the flexibility buyers are looking for today. Set behind a solar-powered gated entrance on approximately 3.5 beautifully landscaped acres, this exceptional circa 1840 property combines timeless architecture, thoughtful updates, resort-style amenities and an incredibly versatile layout. Formerly operated as a bed and breakfast, the estate offers 5+ spacious bedrooms, 6.5 bathrooms, multiple gathering spaces and a separate one-bedroom guest house. Just as importantly, the home offers the option for first-floor living, with a bedroom, full bath, laundry and everyday living spaces on the main level, an appealing setup for multigenerational living, guests or those looking for greater flexibility now and in the future. Inside, the home's history is part of its charm. Beautiful hardwood floors, an impressive grand staircase and multiple living rooms create spaces that feel both elegant and comfortable. A screened porch and private sunporch off the primary suite offer quiet places to unwind, while individual Mitsubishi split heating and cooling systems in each bedroom provide personalized year-round comfort. The separate guest house adds another dimension to the property, with exposed wood beams, a gas fireplace, quartz countertops, updated appliances and views overlooking the heated in-ground pool and patio. Whether used for extended family, guests, a private retreat or additional living space, it's a feature that makes this property especially unique. Outside, the grounds feel like a private park. A circular driveway, gazebo, cedar fencing and mature landscaping surround an established apple orchard and vineyard, along with blueberry bushes, a peach tree, rhubarb, flowering dogwoods and crabapple trees. A detached two-bay garage with independent power provides additional space for vehicles, storage or hobbies. Dual solar-powered automatic gates with smartphone controls, a professionally monitored security system with cameras, and extensive perimeter lighting add another level of convenience and peace of mind.