Some Representative Streets

Bridge Road, Chelmsford, De Sabla, El Cerrito, Fallen Leaf, Poett, Ravenscourt, Richmond, Rockridge, Roehampton, Roblar, Sierra, Uplands, West Santa Inez (lower), Woodstock

Neighborhood Overview:

Lower South is regarded as one of the most prestigious and in-demand areas in all of Hillsborough. Lower North and Lower South together comprise what you will hear locally referred to as “Lower Hillsborough.” The word Lower indicates the location in the flats west of El Camino, and lower “down the hill” as opposed to Upper, near Highway 280. Lower South usually ranks #2 in Hillsborough based on median sales price and price per sq. ft. achieved, with Lower North typically ranking in the #1 position. 

Lower South is one of Hillsborough’s most history-laden corridors, extending westward from the circa-1890s A.P. Gianinni estate in current San Mateo near the junction of El Cerrito and El Camino. Lower South boasts many of Hillsborough’s premier streets such as West Santa Inez, Roblar, Roehampton, and Bridge Road. An abundance of large lot sizes, usable flat property, and surrounding grand estates create high land value as a foundation of this real estate desirability.

Lower South’s proximity to South School (K-5), downtown San Mateo, as well as downtown Burlingame, are highly sought-after. Flat usable land, impressive trees, and an established prestige are immediately felt driving down roads such as Stonehedge, Roblar, and Roehampton. Streets such as Chelmsford, Ravenscourt, and Woodstock are known for storybook architecture, neighborly spirit, and walking distance into downtown Burlingame. Those seeking an "East Coast" ambiance of established traditional homes will find a treasure trove in Lower South. South School is the smallest of Hillsborough’s three elementary schools, and parents and students alike find a close-knit community and walkability. For those choosing private schools, Lower South is also very convenient to St. Matthew’s Episcopal (in San Mateo K-8), St. Matthew’s Catholic (in San Mateo K-8), Carey School (in San Mateo K-5), and Crystal Springs Uplands (in Lower South Hillsborough 6-12). Lower South is adjacent to the Peninsula's other vintage jewel neighborhood of San Mateo Park.

In Lower South, you will find some of Hillsborough's finest homes on the most desirable streets. Lower South Hillsborough encompasses the sub-districts of Brewer Subdivision and Hillsborough Heights. Lower South is assigned primarily to South School. I have represented the #1 sale in Hillsborough for 2020 at $16,225,000 in Lower South. I look forward to discussing your goals in this premier neighborhood. 

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

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

Appeal for Residents and Homeseekers:

• Along with Lower North, Lower South is one of Hillsborough's most valuable and in-demand locations
• Proximity to South School, downtown San Mateo, as well as downtown Burlingame (many streets within walking distance of either) 
• Very convenient location for those parents choosing private schools in San Mateo or Hillsborough
• Undeniable prestige with Old World character and mostly flat streets

Historic Notes:

Lower South Hillsborough is one of the Town’s most history-laden corridors, as it was here around current El Cerrito Ave. and De Sabla Road, that William Davis Merry Howard and wife Agnes Poett settled the first Hillsborough estate in the 1850s. At the time, it was a mere sliver of Howard's 6,500 acre holding known as Rancho San Mateo.Titled El Cerrito, the Carpenter Gothic mansion likely built by Agnes Poett and second husband George Howard (William Davis Merry Howard's younger brother after William's passing in 1856) was the benchmark that initiated the great promise of these lands: a country refuge where wealthy San Franciscans could reflect success in their architecture, sporting life, family, and bucolic tranquility. Those foundations continue to ring true. William Davis Merry Howard's prescience had him well-positioned in San Francisco merchant and trade lines just before the explosion of the 1849 Gold Rush. Although the East Coast native passed in 1856 at age 36, Howard's vision and family lineage was to define future Hillsborough. 

At the heart of Lower South Hillsborough, at 252 El Cerrito, you will notice the back of what appears to be a non-descript vintage building and small parking lot. This was originally the clubhouse of the illustrious San Mateo Polo Club. Architect George Howard designed the clubhouse in 1907, and it backed up to the polo field, complete with viewing terrace. Today the building is still functional for private events and known as the Hillsborough Racquet Club. But turn back the clock to 1910, and imagine that vast polo field of 300 yards long by 160 yards wide, just behind today's Racquet Club! The Tobin property at 360 Poett Road would have backed up to the polo field, as well as other properties on emerging Roblar Avenue. The San Mateo Polo Club field would also have occupied today's Town baseball diamond adjacent to the school district headquarters. 

Another architectural landmark of Lower South Hillsborough is the Western White House, which is the c.1930 Julia Morgan-designed home of George Hearst, son of William Randolph Hearst. The home can be seen from the intersection of El Cerrito and Poett. The Western White House at 401 El Cerrito Avenue was listed for sale on MLS at $25,000,000 on October 13, 2021 and later closed escrow for $15,000,000 on September 2, 2022. Interestingly, before being rebuilt to resemble the White House, this home was originally Uplands I, and was moved on skids from the site of the current Uplands II, now Crystal Springs Uplands School (at today's 400 Uplands Drive). Uplands II is one of the finest masterpieces in all of Hillsborough, built for Charles Templeton Crocker in Beaux Arts style with design by Willis Polk 1914 - 1917. The Western White House can be seen at the bottom of the second aerial photo above. Note the "Oval Office" protruding on the facade. 

Guignecourt, the c.1914 Bliss and Faville-designed Italian mansion on 47 acres, straddles the borders of Parrott Drive Area and Lower South at 891 Crystal Springs Road. The lands were in the De Guigne/Parrott family since the 1870s, and finally changed hands for the first time in 2017 with Elon Musk purchasing at $23,364,000. In May 2020, it became public that Musk was offering the estate for sale on Zillow at $35,000,000. The listing later went public on MLS for $31,990,000 and was marked pending on November 23, 2021, closing escrow at $30,000,000 on December 1, 2021. The Italian Renaissance mansion built in 1914-1916 is approx. 16,000 feet.