One Whitney Avenue was originally the site of Hillhouse Place, James Abraham Hillhouse's mansion, built in 1762. The property originally included ten acres of land reaching from where the house stood on the comer of Whitney and Grove to Prospect and Orange Streets. It was passed down to the younger James Hillhouse, well known for serving the state of Connecticut in Congress and later working for Yale University as treasurer. The Hillhouse property was sold and became Grove Hall, a boarding school for girls, in 1840. In the hands of the school directors, Mrs. Hutton and later Professor Hubbard , the building was doubled in size by traditional hand-build additions. The New Haven register lovingly refers to these historic methods, "the additions to the original house can be traced easily; and the hand wrought nails; the hewn stone foundations, curving stone steps ... belong to the real colonial type"'



In 1925 Grove Hall was demolished as New Haven began to transition from a town of mansions and lawns to a city designed for the automobile and the influx of consumers that came with it. Some saw this change as the demolition of history. In the "Now and Then" series, the New Haven Register reminded its readers of the monumentality of historic buildings like Grove Hall. Describing its history as the home of a political figure and then an academic institution, the Register mournfully explains, " it must follow that almost every person of note in political, intellectual and social life who was in New Haven, from Nathan Hale, Aaron Burr, and Noah Webster to Huxley and Dana, must have entered that door"'. In 1931 the Whitney-Grove building was built in the Tudor Revival style by the Whitney-Grove Association'. It was, and continues to be, a mixed use building, with commercial space on the ground floor and office space above. The first tenant of the Whitney-Grove building was Mesrick C.S. and Co, a plumbing and hardware emporium. A billboard on the roof of the building, much like the one there today, advertised their name and the slogan "Modernize your bathroom"·. The building and its billboard were like the sign post for urbanization at the foot of the newly commercial Whitney Avenue.