Initially Warren and Sadie Gregory turned to their neighbor and close friend John Galen Howard to design their summer home. In January and February of 1926 Howard’s office drew up initial plans, which included the repurposing of the original house on the property. By April 1926, Howard’s office drew up plan’s for a new house on the property. Several of the elements that William Wurster would later distill and redefine are in those drawings- the courtyard plan, water tower, and sleeping porches. By June, John Galen Howard’s architect son, Henry Howard, had produced a set of working drawings for a substantially altered design. The Gregory’s believe the design to be too formal and too elaborate. By the fall of 1926 they had passed the commission on to Wurster.In 1927, six months after Warren Gregory’s death, Sadie Gregory asked Wurster to resume his analysis. Wurster’s design, after what he maintained was only a day’s work, embodied everything Sadie and Warren had been looking for. It was a deeply original conception, but one that benefited from the close analysis of Henry Howard’s earlier planning. Wurster’s solution was to keep only the bare outline of Henry Howard’s L-shaped plan. He pared it to the bone, removing as much stylistic elaboration as possible. Out went the stucco walls, wrought iron grille-work and tile roofs. Wurster concentrated on the idea that this house would be used primarily during the warmest months of the year and made sure every major room opened directly to the out-of-doors. His design contains only one short hallway, from the living room to the two bedrooms, and even that opens onto a courtyard.