This iconic Bermuda residence on Pitt’s Bay Road invites you through a grand foyer that immediately sets the tone for a home rich in history, character, and refined charm. Designed for entertaining, Chelmsford offers a formal sitting room for intimate gatherings and a spacious dining room with an adjoining bar room that has hosted countless memorable dinner parties. A dedicated office provides the ideal setting for working from home, while the gourmet kitchen (featuring indoor-outdoor flow to the pool patio) caters beautifully to both chefs and entertainers alike. For outdoor dining, plenty of space is available for gatherings of any size, as well as a fire pit lounge and a large flat yard, ideal for kids or pets at play. Upstairs, five generous bedrooms each include their own en-suite bathrooms, offering privacy, comfort, and understated luxury for family and guests. Additional amenities include a full bathroom on the lower level and two powder rooms. Tucked away on the property is a separate one-bedroom apartment, ideal for guests, staff, or extended family. An oversized garage, gym, and even a wellness retreat within the lower level of the estate create a private sanctuary designed for both convenience and rejuvenation. This is more than just a home. It’s a piece of Bermuda’s heritage, thoughtfully reimagined for contemporary living. Please contact co-listing agents Ben Rego and Christina Georgopoulos for a tour at your earliest convenience.