Built in 1911, this two-story structure, often called the Copland Building, was the fourth building to appear along Main Street. Except for the removal of a separate side entrance on First Street near the rear and the addition of brick facing to the first floor in the mid-1970's, it stands as originally built. A drug store and notions counter occupied the corner space at 397 Main, with a fountain and candy store in front, and visitors passed through them to reach the post office in the rear. Mr. and Mrs. H.G. Copeland ran the entire operation, and for a time Mr. Copeland reactivated and published the Los Altos Star, the news organ of the Altos Land Company. In 1923 the drugstore was sold to Jack Gregory, who operated it for more than a decade, and Jack Shoup, Paul's son, owned the store when Samuel Kahn bought it in 1939. The 395 Main side housed a bakery for many years and then a theatre in 1926, where Charlotte Gregory played piano for movies and live talent also performed, making it a popular Saturday night gathering place. Upstairs, the building served first as living quarters for the Copelands and later the Gregorys, and eventually as the first office space available in town.