Rollingwood

Homes are distinctly mid-century in style. Many are raised ranch homes, with garages and basements at street level and finished living space above and three or four bedrooms. A full 50 percent were built between 1950 and 1959. Another 12 percent were completed during the 1960s. Recent sales of Rollingwood real estate show homes trading for a median price of $1.1 million, with recent listings ranging in asking price from $900,000 to $1.2 million and sales coming in between $950,000 and $1.45 million. With the “average” Rollingwood home clocking in at somewhere between 1,100 and 1,500 square feet of living space, that gives the neighborhood a median value of upwards of $900 per square foot.

In 1950, the population of San Bruno was 12,487, almost all of whom lived within a mile or two of downtown. The hills to the west were sparsely settled, a series of small vegetable farms, dairies and cattle ranches carved out of the 3,000-plus acres once owned by Richard George Sneath. The Sneath Dairy once covered all of the land from El Camino to Sweeney Ridge; the family began selling off or renting out parcels in the 1920s.

Rollingwood, known at various times as Golden Gate Estates and Rosswood, was built on land that was once part of Sneath’s Dairy, a segment known as “Jersey Dairy #1.” Prior to that it had been the site of loosely organized gatherings of Ohlone tribe members, drawn by the creek that flowed from present-day Rollingwood to the modern site of the Golden Gate Military Cemetery. By 1950, cattle roamed the hills of soon-to-be Rollingwood, which began subdividing for development in 1953. By 1957, the new neighborhood had enough of a foothold that it needed its own school. Rollingwood Elementary was opened that year.