After a trolley line was extended along E. Jefferson Avenue in 1880 and the road was paved in the early 1900s, the vacation retreats built along Lake Shore Drive from the mid-nineteenth century were adapted or replaced with new houses for year-round use. The advent of the automobile soon thereafter and the economic prosperity of the 1920s hastened this transformation. The splendid houses that still line this road are particularly expressive of the economic and social status of some of Michigan's wealthiest residents. Some of the finest mansions erected in the road's early decades regrettably were demolished; many of the large estates have been subdivided for resale and the mansions razed because of taxes and development pressures.

Ellen Shipman created the plan for Lake Shore Drive, screening the noise and traffic while allowing views across the boulevard to the lake. She kept plantings principally to evergreens, willows, flowering trees, and shrubs. The drive culminates at the Mediterranean-inspired Grosse Pointe Yacht Club (1927–1929, Guy Lowell; 788 Lake Shore Road). The stucco-walled and red tile–roofed building is on a man-made island in Lake St. Clair surrounded by boat slips. A campanile soars 187 feet to serve as a navigational aid.