346 Picton Main Street

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.

Welcome to this beloved county gem, a century old red brick home located just on the edge of Bloomfield, elegantly set back from Loyalist Parkway in a grove of conifers. This home is historically significant, as seen in The Settlers Dream as the Simpson Mallory house, with similarities to its neighbours The West Lake Boarding School and Fair Lea but with the added benefit of 29+ acres including prime agriculture land under cultivation. The classical symmetry is compared with grand homes like Macaulay House and the Striker Walmsley House in Picton. When Benjamin Simpson, a wagon maker came to this town in 1837 it is likely that the present kitchen tail of the house was a wooden frame farmhouse facing Mallory Crossroad. This outstanding home showcases fascinating architectural features and enduring touches that reflect its Quaker influence. Bloomfield was established in1799 and remains a village with many historical homes and charming shops on Main Street. The house boasts 5 bedrooms and 4 bathrooms, an elegant living room and dining room, perfect for entertaining and family gatherings. The kitchen has been renovated to reflect the character of the home. This property has a fabulous old barn perfect for animals or converting to an elegant event space, a workshop and a woodshed, and a lane way access to the Millennium Trail to complete the perfect picture. Only six minutes from Picton home to the Prince Edward County Memorial Hospital, The Regent Theatre, The Royal Hotel, The Waring House, many unique shops, as well as numerous fine dining restaurants, and the PEC Yacht Club. The County is one of the premier destinations for those seeking unforgettable experiences whether its exploring nature, enjoying watersports, savouring food and wine, or relaxing at the beaches. There truly is something for everyone! Conde Nast Traveler Magazine has voted Prince Edward County as one of the top places in the world to visit in 2026!