[3] In 1838, Domingo Sais received a land grant from General Mariano Vallejo known as Cañada de Herrera, which consisted of 6,659 acres (2,695 ha) covering what is now Sleepy Hollow, Fairfax and segments of San Anselmo.

The next person to acquire the land was a man named Peter Austin who was responsible for planting the multitude of poplar and eucalyptus trees that now line the road.

[7] Due to foreclosure, Austin was forced to sell the land to the Hotalings, a wealthy family from San Francisco.

The Hotalings threw many elaborate parties for hundreds of guests, but soon left the mansion and returned to San Francisco.

Later a Chicago syndicate bought the land and attempted to create a luxury hotel complete with golf course, pool, and private man-made lake, but this idea quickly fell through due to the stock market crash prior to the Great Depression.

[8] Sleepy Hollow became a residential area due to the opening of Lang Realty shortly after World War II.

In 1966 the Dominican Order of the Catholic Church bought the "Sleepy Hollow" mansion and opened the San Domenico School for Girls.

[8] Sleepy Hollow is in east-central Marin County and is bordered to the south by the town of San Anselmo.

Lucas Valley-Marinwood lies to the north of Sleepy Hollow, but there are no roads directly connecting the two unincorporated communities.