Live, work and invest! This stunning historic property, located on Main Street in the heart of Picton offers a unique opportunity to live and work in the center of it all. Built in 1905 for the Order of the Oddfellows and home to various bank tenants, the property was beautifully renovated in 2008 as a private executive residence. Offering 9,000 sq.ft. of living space, this property includes a 4-bedroom, 3.5-bathroom family home with additional income from an STA/long-term rental and a long term commercial Government tenant. A grand foyer welcomes you with an original oak staircase that leads to the main living areas including an open-concept kitchen, living room with a gas fireplace and eat-in dining area. The kitchen also houses a unique historical element - the original bank safe, now cleverly repurposed as a wine cellar. This level also includes a cozy den and powder room. Through glass doors, continue to a formal dining room and a large entertainment space, with custom pool table and movie screen - perfect for hosting gatherings. A full bedroom and bathroom complete this floor. Upstairs, the third floor is dedicated to guest comfort and relaxation - two guest rooms, 4pc bathroom, in-home gym, functional laundry room, and bright art room. The spacious primary suite includes a sitting area, large walk-in closet, and a luxurious, spa-like 7-piece ensuite bath including double tub and steam shower. A secondary suite with 1 bedroom, a bathroom, kitchenette, and living room offers privacy and rental income potential. A rooftop deck boasts panoramic town views, perfect for entertaining. The home is designed with accessibility in mind, featuring a chair lift and a framed shaft for an elevator. The main floor commercial space is leased by a government office, providing stable rental income and lowering property costs. Don't miss this rare opportunity to own a piece of Picton's history with modern amenities and income potential.