Live, work and invest in the heart of Picton. This remarkable historic property offers a rare opportunity to own an approximately 9,000 sq. ft. landmark on Main Street, combining an impressive private residence with established commercial income and additional residential income potential. Originally built in 1905 for the Order of the Oddfellows and later home to various bank tenants, the property was extensively renovated in 2008 into a one-of-a-kind executive residence while retaining many of its original architectural details and character. The expansive 4-bedroom, 3.5-bathroom home offers generous living and entertaining spaces throughout, blending historic charm with modern comfort. Notable features include the original oak staircase, a gas fireplace, the original bank safe repurposed as a wine cellar, formal and casual living spaces, an entertainment room, home gym, art studio and a spacious primary suite with a luxurious 7-piece ensuite. A rooftop deck overlooking downtown Picton provides an incredible outdoor space with panoramic views of the town - a truly unique offering. Adding to the versatility of the property is a separate 1-bedroom secondary suite with its own kitchenette, bathroom and living area, offering excellent potential for guests, extended family or additional rental income. Accessibility has also been considered, with an existing chair lift and a framed shaft designed to accommodate a future elevator. The main-floor commercial space is occupied by a long-term government tenant, providing established rental income and creating an attractive opportunity to offset the costs of ownership. Set in the centre of downtown Picton, steps from shops, restaurants, cafs and amenities, 229 Main Street offers an exceptional combination of history, lifestyle, location and income potential. Whether envisioned as an extraordinary private residence, a live-work opportunity or an investment, this is a truly unique offering in the heart of Prince Edward County.