On its age, its old homes and the National Register, Sleepy Hollow is more historic than 20% of U.S. towns, #470 of 847 in California. Its share of homes from before 1940 holds the grade up; its National Register listings pull it down.
C−
HistoryA character grade: shown, never part of Sleepy Hollow’s overall grade.
Few California towns list much on the Register (a typical California town has 0.0 per 10,000 residents, the U.S. 2.4), so Sleepy Hollow’s 0.0 sits below most of its state (31% of California towns have fewer) while its 0 listings outnumber those of 23% of U.S. towns.
How sure. Graded on two of the three inputs, so a change in either one moves the letter more than it would with three. The pre-1940 share is a Census survey estimate (±5.1 points).
Founding year: our sources. Homes: Census ACS 2020–24. National Register: National Park Service, May 2026 list; each listing counted once (boundary changes and added documentation belong to their listing), and a historic district counts its contributing buildings. How TownRatings grades history →
What stands out about Sleepy Hollow’s past
Read from the archive, the National Register and the record. The page puts what stands out first.
Every edition of the U.S. Geological Survey’s map of Sleepy Hollow. Tap a year, or press play to watch the town change.
1914Petaluma sheet · 1:62,500
U.S. Geological Survey historical topographic maps (public domain), via Esri’s collection of the scans. The red ring marks the center of Sleepy Hollow.
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. In the 1850s, Sais leased the majority of the land that is now Sleepy Hollow to Harvey Butterfield. Butterfield started a dairy farm on the land, and the long, winding 2-mile trail that is still to this day the only way in and out of the community became known as "Butterfield's Road". 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.
Sleepy Hollow is more historic than 20% of U.S. towns, #470 of 847 in California. The History grade combines the town’s founding era, the share of homes built before 1940 and its National Register listings. It’s a character grade, so it isn’t part of the overall grade. How it works.
How old are the homes in Sleepy Hollow?
5% of Sleepy Hollow’s homes were built before 1940 (Census estimate, ±5.1 points), against a typical 3.4% for a California town; the median home was built in 1956.
Founding dates: Wikidata, Wikipedia, the U.S. post office records of Blevins & Helbock (CC0) and the Census. Homes by year built: Census ACS 2020–24. National Register of Historic Places: National Park Service (list of May 22, 2026). Old photos, postcards and papers: Wikimedia Commons, the Library of Congress and other public archives, credited on each item’s page. Maps: U.S. Geological Survey historical topographic maps (via Esri) and Sanborn fire-insurance maps (Library of Congress). History text and census tables: Wikipedia (CC BY-SA 4.0). Places that used to be: USGS Geographic Names Information System (2021).
From Wikimedia Commons (3), Wikipedia, U.S. Geological Survey historical maps and the USGS Geographic Names Information System. Archive images are copied here with their credits and licenses, shown on each photo’s page. Refreshed monthly.
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