Some Representative Streets

Crystal Springs Road (such as 891 Crystal Springs, the De Guigne/Musk Estate), Glenbrook, Melrose Court, Parrott Drive, Salmark 

Parrott Drive Area MLS Listings

Neighborhood Overview

The Parrott Drive Area holds an illustrious past with roots dating back to the 1870's of Parrott and De Guigne Family ownership. This small sub-district is accessed through different junctions with San Mateo: where San Mateo’s Parrott Drive turns into Hillsborough; westward towards the College of San Mateo where San Mateo residences begin, and at the base of the flats along Crystal Springs Road. Here, entered from Crystal Springs Road, and extending 47 acres into the hills, you will find Hillsborough's #2 Sale of all time, long known as the De Guigne Estate, but sold by its second owner Elon Musk in December 2021 for $30,000,000. (For the curious, the #1 highest sale in Hillsborough history is found on Chiltern Road selling for $37,500,000 at the heights of the Dot-Com Era, year 2000).

The Parrott Drive Area is known for its high elevations and soaring Bay views. It can also represent an entry level price point into Hillsborough’s South School, as it will be more approachable on price than Lower South or Mid South. Architecturally, there are many ranch homes along Parrott Drive from the 1950s-1960s, as well as some new executive homes from the 1980s - 2000s that resemble the larger estates of the adjacent Tobin Clark area. The feeling of hilltop privacy highlights this area, often framed by glorious Bay vistas. Although not a “heart of Hillsborough” location, the Parrott Drive Area shines with its convenience to downtown San Mateo, Highway 92, and primarily South School assignment. Consider it a “best-kept secret,” especially for the view aficionado.

All of the lands, including San Mateo's adjacent Baywood, once comprised the Parrott Family estate going back to the 1870s. Patriarch John Parrott (d.1884) had six daughters, one of whom married French aristocrat Christian De Guigne in 1879. Hence, the De Guigne era at these lands. De Guigne commissioned architects Bliss and Faville to design the hilltop Italian-inspired mansion at the base of the Parrott Drive area in 1912 (first picture above). Bliss and Faville were also heralded for designing San Francisco's Bank of California building in 1908 and the St. Francis Hotel. The original estate known as Guignecourt, was sited on 47 forested acres and stayed in the same family for decades. Finally in 2017, the estate changed hands for the first time after being quietly consummated with buyer Elon Musk at a sale price of $23,364,000. Musk was only the second owner to possess the land in nearly 150 years. He sold the estate in December 2021 for $30,000,000. 

The Parrott Family has a grand mausoleum in the historic St. John’s cemetery at the border of San Mateo and Hillsborough. 

The Parrott Drive Area is assigned primarily to South School, Crocker Middle, and Aragon High.

For Hillsborough School District School Boundaries, North, South, West, click here. 

Explore All Hillsborough Neighborhoods at Geoffrey Nelson’s Hillsborough Google Map.

Appeal for Residents and Homeseekers

• Thrilling "Top of the World" Bay views
• Convenience to Aragon High School, Downtown San Mateo, and Highway 280
• Approachable price points, including many entry-level Hillsborough prices
• Assigned primarily to South School 

Potentially Adverse for Residents and Homeseekers

• Not a "heart of Hillsborough" location, meaning there is an annexed feeling and largely requires passing through neighboring San Mateo for access. 
• Far southwest location creates longer drive to Crocker Middle.