Set on one of the most picturesque neighbourhoods of Hamilton, this lovingly maintained historic home of Durand has been owned and cared for by the same owner for more than 20 years. 314 Hess St S blends timeless craftsmanship with the flexibility today's buyers are searching for - main floor bedroom & bathroom, and ADU potential. Original oak floors, soaring ceilings, exposed brick, stained glass details, oversized wood trim, and two marble fireplaces create spaces that feel both elegant and deeply inviting. Sunlight pours through the original windows, casting warmth across gracious living spaces designed for gathering, quiet mornings, and everyday living. The thoughtful layout offers exceptional versatility with 3 bedrooms, including a main floor bedroom and full bathroom ideal for guests, multigenerational living, or aging in place. Two additional den spaces provide endless options for home offices, playrooms, studios, or storage, while two separate family/living rooms allow everyone room to spread out and unwind. Main floor laundry adds convenience rarely found in homes of this era. Outside, the property is extraordinary for the neighbourhood. A long private driveway with parking for at least 5 vehicles and leads to a rare 3-bay brick garage with additional workshop space - seldom found in the old neighbourhoods of Hamilton. Whether you are a hobbyist, car enthusiast, entrepreneur needing workspace and storage, or an Accessory Dwelling Unit - the possibilities are endless. Combined with the generous yard space for entertaining & relaxing, nearby schools, parks, hospitals, transit (bus routes and GO Train), and walkable access to downtown Hamilton and Locke Street shops/cafes; this is a home that offers not only charm and history, but a lifestyle with room to grow, create, and settle in for years to come. Many updates over the years, with 2026 updates being new AC, furnace, electrical wiring and panel, water line, exterior paint, and front landscaping.