This extraordinary estate offers the rare opportunity to experience luxury living on a grand scale in the heart of Picton. Originally dating back to 1862, the Uplands house has been fully reimagined to deliver the elegance of a heritage property with the comfort and sophistication of modern design. Soaring 11' ceilings, refined architectural details and expansive principal rooms create an atmosphere of effortless grandeur from the moment you step inside. Designed for both intimate living and large-scale entertaining, the home flows beautifully from the chef-style kitchen to the stunning great room, where vaulted ceilings and a dramatic fireplace set the stage for memorable gatherings. The primary suite evokes a boutique hotel retreat, while 3 additional bedrooms, including a custom bunk room, offer versatility for family or guests. Entertainment spaces such as the theatre room and bar lounge enhance the home's appeal, complemented by built-in speakers and thoughtful storage throughout. The lower level extends the premium experience with a spacious recreation room, private gym and relaxing infrared sauna and cold plunge. Outside, the property unfolds like a private resort, featuring an inground heated pool, hot tub, pergola with built-in kitchen and multiple seating areas surrounded by professionally landscaped grounds - perfect for summer evenings and weekend celebrations. Remarkably, the lot spans nearly half a town block, providing the space and privacy of a country estate with the convenience of walkable in-town living. A 3-car garage with 12' lift-ready ceilings completes this exemplary offering. A truly unparalleled home for the discerning buyer seeking luxury, character and lifestyle without compromise.