Once a tavern for travelers and a stagecoach stop in the early 1800s, 1607 Massey Road stands as a testament to Vermont’s enduring spirit, now paired with compelling income potential. This distinguished 1810 Federal style home rests gracefully on over 48 acres of rolling meadow, woodland, and quiet pasture, offering a rare blend of seclusion, scale, history, and short-term rental opportunity. With more than 4,100 square feet of living space, the home features generous rooms, wide fireplaces in the living room and bedrooms, and the kind of character and authenticity that today’s guests actively seek in high performing Vermont vacation rentals. A classic kitchen with a center island opens to a breakfast nook bathed in morning light, ideal for hosting guests seeking a warm, authentic farmhouse experience. Upstairs, a vast attic space invites conversion into additional bedrooms, a studio, or a private owner’s retreat, further enhancing rental flexibility and revenue potential. Outside, a wide entertaining deck overlooks a tranquil pond and dock, creating a setting perfectly suited for memorable stays, seasonal bookings, and premium nightly rates. Beyond the main home, an old sugar house and barn wait patiently for revival, offering exciting possibilities as event spaces, creative studios, or future income producing amenities. At the summit of the property, a separate off-grid cabin delivers a standout revenue opportunity, with breathtaking hilltop views, ideal for guests seeking privacy, adventure, and panoramic Vermont scenery. This dual rental setup allows for diversified income streams while preserving owner flexibility. Zoned to support short-term rentals, private, and steeped in history, this is a property that offers land and legacy and multiple paths to meaningful income, whether as a full time investment, a part time retreat with revenue support, or a long term generational holding.