The Sanborn map from 1937⁶ shows that the entire square was filled and there were no longer empty spaces within the blocks just fifty years after the beginning of its construction.  The most notable addition to the site was the Myles Standish Apartments which constituted a “boat” shaped form between Beacon Street and Bay State Road.  Along the lower level of the building was a block full of storefronts, and the Lumber Mutual Fire Insurance Company stood sandwiched between Myles Standish and Raleigh Street.  Several of the single family brownstone dwellings across the street were converted to doctors’ offices and three undergraduate fraternity houses.  The triangular edifice jutting out between Beacon Street and Commonwealth Avenue housed an undertaker, most likely the Waterman Funeral home which still occupies the site today.  More medical offices were established along the south side of Commonwealth Avenue along with the distinctive Hotel Kenmore and the Hotel Braemore.  The Peerless Auto Sales and Services building and garage were located along Beacon Street.  The Kenmore Square building on Deerfield Street housed two stores.  Finally, the remainder of Bay State Road was populated by mostly single family dwellings with the exception of the distinctive Hotel Sheraton that faced the Charles River.

            The large presence of medical practices, the prominent “undertaker” at the center of the square, and the emergence of storefronts along Beacon Street and Commonwealth Avenue were the direct consequences of the prevalence of residential land use and overall population growth of Kenmore Square in the 1930s.  The intersection of major railways that was present before the Back Bay was filled and the junction of major roadways in the square most likely contributed to the transportation-themed commercial land use at the center of the square, which included the Peerless Auto Sales and Services building.  Moreover, the numerous hotels on the site at the time suggest that the railroads continued to bring travelers from Worcester, Providence, and Albany to Boston via Kenmore Square.  Finally, the few fraternities with houses in the region mark the beginning of institutional land use and mark the prelude to the expansion of various educational institutions into the formerly residential portions of the square.