A rare opportunity in Windsor, this beautifully maintained century-old side-by-side duplex combines historic character with thoughtful updates and exceptional care. Both spacious units feature new kitchens, updated bathrooms, new flooring, improved heating, an additional half bath and numerous other upgrades, all completed without sacrificing the warmth and charm of the home. Unlike many duplexes, each side truly lives like a full-sized single-family home, offering four bedrooms plus a den and loads of living space. Outside, mature landscaping creates a beautiful backyard setting, while each unit enjoys its own attractive storage shed and separate driveway, adding to the privacy and independence of each side. The condition of this property is truly impressive, making it ideal for an owner-occupier looking to live comfortably on one side while renting the other to significantly offset their mortgage. With estimated rental potential of approximately $2,400-$2,700 per month per side, it also offers excellent flexibility for investors or multi-generational living. Properties of this age, size and character are rarely found in such remarkably well-kept condition. This is one you truly need to see in person to fully appreciate.