An exceptional opportunity to acquire the historic South Shire Inn, a meticulously restored Victorian property in the heart of Bennington. Originally built in 1887 by renowned architect William C. Bull, this landmark property offers exceptional flexibility for its next owner. Currently operating as a successful turnkey boutique inn, it features beautifully appointed guest rooms, many with fireplaces, inviting common areas, owner's quarters, a detached carriage house with additional guest accommodations, and an established restaurant leased to a thriving Thai restaurant serving lunch and dinner. The property is newly zoned for additional uses, including a restaurant, bar/lounge, and catering services on the grounds, creating opportunities to expand the existing business or explore other permitted uses. Whether you're looking to continue operating a boutique inn, create a private estate, pursue residential or commercial redevelopment, or explore other investment opportunities, the property's layout, location, and flexibility make it well suited for a variety of future possibilities, subject to applicable approvals. The South Shire Inn has an established reputation, loyal clientele, well-maintained operational systems, and a rich history, providing a strong foundation for continued success. Ideally located in Bennington between the shopping and dining of Manchester and the cultural attractions of Williamstown and the Berkshires, the property offers convenient access to year-round recreation, arts, and tourism, making it an exceptional opportunity for owner-operators, investors, or buyers seeking a distinctive Southern Vermont property.