Step into the enchanting world of a charming Nantucket-style 1900's converted barn colonial, complete with a separate, legal 1-bedroom, 650 sq ft rental cottage, all located within the Chappaqua school district. This home captivates with an updated kitchen adorned with white cabinetry, granite countertops, stainless steel appliances, and a distinctive Elmira Works Range, seamlessly flowing into a family room highlighted by hand-hewn beams and a wood (pellet) burning stove. The living area, designed for both elegance and comfort, features a gracious living room with a cozy fireplace and built-ins, a dining room with a charming alcove and second fireplace, a sun-filled, multi-windowed breakfast room, and a convenient adjacent mudroom with external access and a walk-in pantry. Further enhancing the ground floor is a powder room (PR) and dual staircases leading to the second floor. The upper level divides into two distinct bedroom wings, offering a primary bedroom with an ensuite bath and three additional bedrooms alongside a hall bath and a den/office space. Throughout this captivating home, custom stained glass windows, meticulously handcrafted stencil work, and quaint nooks and crannies add layers of character and history. The property is enveloped by majestic old-growth trees and lush, mature floral gardens, creating an atmosphere of artistic inspiration and whimsical charm. Its location is ideally situated for convenience to schools, shops, a bike path, and a gourmet market, making it a truly unique and inspired offering. This updated antique colonial farmhouse has been lovingly maintained by the same owner for over 40 years, featuring countless special details. The driveway accommodates six vehicles, enhancing this property's appeal as a distinctive and treasured home.