W. Herbert Reed built the core of the Oake Grove Hotel in 1894, starting with just five guest rooms. By 1915, it was renowned as the area's leading hotel, and had grown to a 150 room facility. Boothbay histories and archival documents spell the hotel's name in various ways, as either Oak or Oake.

Grand hotels lost their stature by the mid 20th century, with tourists favoring more contemporary accommodations like motels. The Reed family sold the Oake Grove Hotel in 1960, and the new owners tore down the structure in 1965. The region's first condominiums were built on the hotel site in 1971.