If you’re looking for a great place to take your young kids to do some level bike riding in a charming neighborhood with very low traffic, you can’t do better than Sleepy Hollow in San Anselmo. Well, technically, Sleepy Hollow is not actually within the city limits of San Anselmo. It sits in Marin County, and feels a little like stepping back into “Leave It to Beaver” time warp. The streets are meandering, the lots wide and spacious, and the houses spread out and graced by beautiful shade trees and expansive lawns. Set well down Butterfield Drive, Sleepy Hollow started life as part of the original land grant in 1838 from General Vallejo to Domingo Sais. Then it became a dairy farm owned by Harvey Butterfield. Eventually it was purchased by the Hotalings, a wealthy San Francisco family who built a country mansion and named it Sleepy Hollow but deserted it after a few years to return to San Francisco. In the 20th century the land served several varied purposes including a golf course, WWII secret munitions storage facility and again a country mansion. After being deserted again in the late ’40’s, it burned and the land was bought by a land development company for residential development.
The Dominican Order bought the mansion grounds in 1966 and started San Domenico School for Girls, which is now a K-8 coed day school and a 9-12 girls day and boarding school.
Many of the homes in Sleepy Hollow have been significantly altered since their original construction in the ’50’s an ’60’s, some down to the studs and completely re-built. An excellent example of that is 114 Van Winkle Drive, which started life as a modest ranch styled home (brick and stucco exterior according to an original neighbor) with 3 bedrooms and 2 bathrooms. It was completely remodeled and expanded so that it is now a handsome home combining elements of the original configuration with more current and higher-end finishes, carpentry and building components.
Home prices in Sleepy Hollow now regularly exceed $2,000,000, as the demand for large level lots, an intimate and exclusive neighborhood feeling, and the sought-after San Domenico private and San Anselmo public schools continues to grow.