What makes a place iconic? How do some cities lose their core identity amidst shifts in culture, commerce, and the passage of decades? And how do others retain a character so immune to outside pressure that they evolve while remaining timeless? The essence of an icon. 

Deep roots. Bold statements. Uncompromising vision. Commitment to a cause. 

Hillsborough's Founding Fathers, and indeed, Founding Mothers, embedded deep roots from the beginning. They made bold statements in how they lived. They acted with uncompromising vision from Day 1. And they remained committed to a cause with unwavering passion and verve. In 1910, after resisting annexation pressures from neighboring San Mateo and Burlingame, they officially incorporated as the Town of Hillsborough. The result is one iconic community representing Then, Here, and Now: layered with its share of mystique, but still a beacon for those ready to make their mark on a revered heritage. 

No other suburban town matches Hillsborough's direct link with the colorful and affluent history of early San Francisco tracing back to the Gold Rush. Hillsborough's very existence emerged with prestige as the country estate and sporting destination of early San Francisco's monumental wealth. Pioneering figures included Comstock Lode and Banking millionaire William Ralston, his business partner William Sharon, renaissance man Francis Newlands (attorney, land developer, U.S. Senator, married to William Sharon's daughter) and the landed families of William H. Crocker (youngest son of "Big Four" transcontinental railroad builder Charles Crocker), early pioneers the Howards, Poetts and Redingtons, and Harriett Pullman Carolan (daughter of Pullman Rail Car magnate George Mortimer Pullman) and her sportsman husband Frank Carolan. The formation of the Burlingame Country Club in 1893 parallels the growth of early Hillsborough. 

From the beginning, it was railroads, ballrooms and polo grounds. Newly established railroad stations in San Mateo and Burlingame were the catalyst for quick transits down from San Francisco in the formative years of 1893 - 1910. And in fact, it was the Transcontinental Railroad that brought immense wealth to the Hillsborough heirs of Big Four Associate Charles Crocker (1822 - 1888). Burlingame Club founding members made sure Burlingame had the "prettiest station on the line" when a young George H. Howard designed the c.1894 depot that would serve the new Country Club and early "Cottages" model homes. Howard (1864-1935), who went on to a prolific architectural career, was the son of Agnes Poett Howard, who could hold the indisputable title of Founding Mother of Hillsborough. Agnes was the teen bride of William Davis Merry Howard. W.D.M, as he was known, had perhaps more prescience than anyone in California history, as he established his land holdings and merchant business opportunely just before the 1849 Gold Rush. In 1846 he purchased Rancho San Mateo, a 6,439 acre Mexican land grant that encompassed much of today's San Mateo, Hillsborough, and Burlingame. After W.D.M.'s passing in 1856, widowed Agnes married W.D.M.'s younger brother George. Architect George H. Howard was their son. In addition to the Burlingame Train Station of 1894, George went on to design c. 1914 Kohl Mansion, any many private residences such as the c.1916 355 Hillsborough Blvd and 2155 Parkside Avenue from 1913. Per the Town of Hillsborough's Historic Building Survey, other George Howard-designed homes still standing include 245 El Cerrito c. 1890, 120 W. Santa Inez c. 1903, 1 Homs Court c. 1905, 124 Stonehedge c.1906, 108 Stonehedge c. 1908, and c. 1927 "Treehaven" at 816 Hayne Road.

Shortly before developing early Hillsborough and the Burlingame Country Club, Francis Newlands created a similar 1890s country club community in Chevy Chase, Maryland. Golf, Tennis, and Polo became de rigueur in Chevy Chase and also translated to the new Hillsborough. Polo grounds in Hillsborough were first championed by Frank Carolan and other founding members of the Burlingame Club. Frank and Harriet Pullman Carolan's Crossways Farm in Burlingame was the pre-eminent destination for polo and the sporting crowd. Later Hillsborough polo grounds could be found near House on Hill, also known as the Tobin Clark Estate designed by architect David Adler in the southwest quadrant of Hillsborough bordering San Mateo. Celia Tobin's (1874-1965) first husband was copper king heir Charles Clark, thus the "Tobin Clark" surname. Celia's father Richard Tobin was president of Hibernia Bank. The Tobins maintained a c.1906 French Normandy home by Lewis Hobart, still standing on Lower South's Poett Road. Later generations of Tobins owned one of Hillsborough's ultimate parcels at 888 Irwin Drive. The flat 2-acre lot presides at one of Lower North's very best streets and featured a c.1955 Joseph Esherick home that was torn down when the property changed hands in 2013. Driving by, it's now a momentous new composition by San Francisco architect Richard Beard. 

"Newport of the West" Reaches Architectural Heights

Early Hillsborough architects such as George H. Howard, Willis Polk, Lewis Hobart, and Arthur Brown Jr. were creating nothing less than a "Newport of the West," a passionate punctuation to the West Coast's Gilded Age. If Newport, Rhode Island had its Vanderbilts and Astors, Hillsborough, CA was to have its Crockers and Pullmans. And architecture was the preferred expression. Inspired by New York Fifth Avenue society by way of Nob Hill, Hillsborough mansions were designed with grand receiving and entertaining in mind. And that meant porte cocheres, ballrooms, grand salons, and banquet-scale dining rooms. As the Victorian era yielded to the 20th century, the architecture of choice became the Beaux Arts. Willis Polk-designed Uplands, a Crocker property from 1917, embodies the epoch perhaps best of all. Of note, the inspiration for Uplands was none other than Newport's c.1900 Rosecliff, itself a classically marvelous echo of Versailles' Grand Trianon. 

Carolands became the boldest of all statements, its construction foreshadowing World War I in 1914. With 65,000 sq. ft. and entire rooms imported from France, this authentic French Chateau could not have been more continental in its opulence. The drafting boards of architect Willis Polk must have been quite the visual between 1910 and 1920! In addition to Uplands and dozens of San Francisco projects, He was also the stateside supervising architect responsible for the construction of the Carolands. Harriett Pullman's French architect Ernest Sanson never visited the Hillsborough site. Carolands is considered one of Sanson's later works, the architect having passed away at age 82 in 1918.

Architect Lewis Hobart (1873-1954) earns a class of his own, as many of his great Hillsborough mansions still exist as thriving icons of an era. Villa Rose (later renamed Strawberry Hill by second owner Charles Blyth in 1936) from 1912 commands the end of the Forest View Avenue historic corridor (main entrance at the end of Redington) still on nearly 50 intact acres. Villa Rose was commissioned by Joseph D. Grant, who like many wealthy San Franciscans, was intent on dividing his time between City and country at the advent of Hillsborough. Grant was a charter member of the Burlingame Country Club. Hobart's c.1910 New Place built for William H. Crocker today serves as the Burlingame Country Club clubhouse. Like Villa Rose, New Place leaned on Italian Villa inspiration, both in dwelling and garden. The original gateposts still stand at the intersection near North School, New Place Road, and the golf course. In 1914, Hobart designed the Beaux Arts French masterpiece Newmar (later renamed La Dolphine under Spreckels ownership) originally on 30 acres at Lower North's 1761 Manor Drive. San Francisco businessman George A. Newhall (1862-1929) was an influential early property holder as he first owned the c.1892 A. Page Brown Cottage at 1615 Floribunda, and later made his mark building the classically magnificent La Dolphine. Also of note in Lower North, Hobart's elegant 12,000 foot villa, c.1913 Rosecourt, was originally accessed at 815 Eucalyptus. Complete with towering music room, the home was built for George T. Cameron, who was married to Helen de Young, of the San Francisco Chronicle family. Later re-configuration of the cul-de-sac now places the home at 10 Stacey Court (below)

One can only imagine the excitement in Hillsborough's air around 1912-1914. The bucolic pace of life was being interrupted with the construction of no less than Villa Rose, Carolands, Uplands II, La Dolphine, Guignecourt, Kohl Mansion, and Rosecourt! It was the age of the Titanic, the brink of World War I, and for wealthy San Franciscans, it was a brilliant phase of "carpe diem" real estate after the 1906 earthquake. From the basis of land holdings and architectural magnificence, we will never again see such a moment in time. 

Bliss and Faville, masters of the Beaux Arts vernacular, designed Guignecourt in 1914 on 47 acres with inflections of Italian Renaissance. Bliss and Faville were also heralded for designing San Francisco's Bank of California in 1908 and the St. Francis Hotel on Union Square. All of the lands around Guignecourt (entered at 891 Crystal Springs Road) 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 Hillsborough's Parrott Drive Area. After generations of De Guigne ownership, the estate finally changed hands in 2017 after being listed at $29,850,000. The transaction was quietly consummated with buyer Elon Musk for $23,364,000. In May 2020, it became public through Zillow that Musk was offering the estate for sale at $35,000,000 following a Twitter proclamation to purge his real estate holdings. Musk is only the second owner to possess the land in nearly 150 years. On October 11, 2021 the De Guigne/Musk Estate at 891 Crystal Springs Road was listed on MLS for $31,990,000. 

Subdivisions and Modernism Advance the Century

The early subdivision of Carolands in the 1930s and beyond would introduce a wave of original estates breaking into smaller parcels. Now beyond the Beaux Arts period, and into the 1930s-1950s, smaller scale Revival and Modernism were infused by notable architects Angus McSweeney, William Wurster, Gardner Dailey, and Joseph Esherick. McSweeney examples include the 1936 Colonial at 863 Chiltern, the Spanish Revival from 1931 on 2.8 acres at 862 Chiltern, c.1931 869 Culebra, c. 1933 1830 Brookvale, the 1941 traditional at 270 Bridge Road, and the English storybook gems, both from 1933, at 2900 Ralston and 1210 Kenilworth. Many of the homes were designed while McSweeney was employed at Willis Polk & Co. 

U.C. Berkeley-trained William Wurster credits include 711 Bromfield c.1931, 735 Bromfield from 1936, 761 Chiltern c.1937, 1800 Floribunda c.1939, and 301 Ascot from 1940. Many of Wurster's designs were complemented by the landscape architecture of Thomas Church throughout the 1930s-1960s. 

San Francisco architect Gardner Dailey (1895-1967) was significant in his contributions to the Bay Area Modern style, articulating with clean lines and indoor/outdoor dynamics. Dailey should be considered the Godfather of Peninsula modern architecture as we know it, as his concepts were ahead of their time in the 1930s. Unusually tall windows and doors, integration of home and garden, and unadorned sleek lines were all signature precursors of modern design. Hillsborough examples by Gardner Dailey include the c.1938 711 Hayne Road, c.1949 170 Bridge Road, the quintessential 875 Vista Road from 1935 (Lloyd Liebes House), and 405 Chapin Lane (Littlefield House) dating to 1938. I have been fortunate to represent the sales of Wurster's 711 Bromfield, as well as Dailey's 875 Vista, 405 Chapin, and 1802 Floribunda. 

Present Day into Perpetuity

Today's new constructions proliferate with eight-figure price tags often in the transitional and modern architectural genres. Recent examples abound by both owner-users, and those built on spec by local developers. Current practitioners seen around town include architects Randy Grange of TRG, Charlie Barnett, the aforementioned Richard Beard, neoclassicist Andrew Skurman, builders Wilkinson Construction, Peninsula Custom Homes, RG Development, All Wood Construction, Landscape architects Terra Ferma and Michael Callan. Recent showcases accent the Lower North corridors of Sharon Avenue, Irwin Drive, Forest View, and New Place Road. John Stewart and Farro Essalat are other well known architects with long Hillsborough track records dating to the 1980s. Essalat became known for a Neo-classical style of grand scale spaces mixing formality with garden living and modern family flow. I have represented one of his 2013 masterpieces at 2125 Ralston in Lower North. I have also sold a Farro Essalat design at 510 Laurent Road in the Carolands with Bay views, guesthouse, and tennis court. Another Essalat example is near the "top of the world" view summit at 225 Tobin Clark Drive. 

On the national stage, no other town in the United States matches Hillsborough's enviable milieu of historic prestige, topographic beauty, and proximity to both San Francisco and Silicon Valley. Hillsborough continues to thrive on its core foundations of undisturbed estate living, commitment to architecture, and a phenomenal school system. The wisdom of generations will pass this lifestyle down for perpetuity. 

By Geoffrey C. Nelson, C. 2020

Lower North Hillsborough Area

Beginning with the formation of the Burlingame Country Club in 1893, Hillsborough society flourished around the Lower North Hillsborough area, with many of San Francisco’s most influential citizens commuting to country leisure via the newly minted Burlingame Train Depot. An early collection of weekend country homes known as "The Cottages," was designed pre-1900 by San Francisco architect A. Page Brown. Visionary Francis Newlands (son-in-law and heir to William Sharon) spearheaded these “model” homes as symbols of the new country affluence, developing the former Sharon Estate lands to rally the right prospective members around the new Burlingame Country Club. All located in Lower North, Cottages still in existence include c.1892 Newhall Manor at 1615 Floribunda, which sold for $5,200,000 in June 2012; the c.1889 50 Kammerer Court, which has had the same owner since 1993, and 141 Pepper Avenue (moved to today's Burlingame Park on Pepper Ave). George Newhall purchased one of the first cottages at 1615 Floribunda, christening it "Newhall Manor." With architect Lewis Hobart at the helm, Newhall later went on to build the spectacular Beaux Arts estate “Newmar” in 1913 at 1761 Manor Drive, later renamed La Dolphine when subsequently owned by the sugar titan Spreckels family. Although no longer on its 30 acres, the French masterpiece is still majestically preserved as a private residence. La Dolphine (pictured above) was opened to public for the 2010 Hillsborough Historic Homes Tour. Just prior to its 2012 sale, 1615 Floribunda was also featured on the 2010 Historic Homes Tour, which was held in commemoration of Hillsborough's centennial. The Floribunda mansion was also once owned and remodeled by Reagan-era Secretary of Defense Caspar Weinberger. The famous politician’s library is still a highlight of the home. 

Another intact Lewis Hobart-designed legacy estate is the approx. 50-acre Strawberry Hill, originally known as Villa Rose, and built for financial titan Joseph D. Grant in 1912. William H. Crocker’s circa-1910 New Place mansion now comprises the Burlingame Country Club clubhouse with its iconic gateposts still near the entrance of New Place Road near North School. Lower North’s Fagan Estates area hosts the Paul Fagan mansion (85 Fagan Drive) and the Bing Crosby Estate (1200 Armsby Drive) The c.1917 Paul Fagan mansion occupies the end of the cul-de-sac on 3 acres.The Fagans were the second owners of this English Manor originally known as "Danvers House" for the Van Antwerp family designed by Bakewell & Brown (Arthur Brown Jr.). In June 2020, the Hillsborough ADRB posted news of a planned subdivision of the 3.08 acre lot into a Parcel A of 2.18 acres that would host the existing mansion and a Parcel B of .90 acre. The lots would be accessed via two separate driveways off Fagan Drive. In July 2021, the Fagan Estate was listed on MLS for $11,500,000 inclusive of the house on Parcel A, with the option to purchase Parcel B. Interestingly, the listing does not have a garage, as the house next door at 55 Fagan was originally the carriage house! In 2012, I represented the sellers at 55 Fagan Drive, which had been converted into an eclectic family home by famed designer John Wheatman. Arthur Brown Jr. is also immortalized for designing San Francisco City Hall, War Memorial Opera House, Stanford's Hoover Tower, and Woodside's Folger Estate. Perhaps the most romantic expression of Arthur Brown Jr.'s lasting legacy is Le Verger (The Grove), the magnificent French chateau that can be seen at 808 Irwin Court, today on 1.6 acres. The home was built for Brown and his family as a personal residence in 1925. 

Lower South Hillsborough Area

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 elements 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. 

Architectural landmarks in Lower South Hillsborough include the Western White House, the circa-1930 Julia Morgan-designed home of George Hearst, son of William Randolph Hearst, this home was listed on MLS for $25,000,000 on October 13, 2021; Charles Templeton Crocker’s circa-1917 Willis Polk-designed Uplands mansion (pictured above, now the private Crystal Springs Uplands School, grades 6-12), and Guignecourt, the circa-1914 Bliss and Faville-designed Italian mansion on 47 acres at 891 Crystal Springs Road. By way of De Guigne's marriage to a Parrott daughter, these lands were in the same family since the 1870s. The property and mansion at 891 Crystal Springs Road were finally sold in 2017 to Elon Musk for $23,364,000. 891 Crystal Springs Road was listed on MLS for $31,990,000 on October 11, 2021, indicating a 16,000 sq. ft. home on 47 Acres. On a smaller scale, but no less wondrous is the c.1906 Shingle Style home of Hibernia Bank founder Richard Tobin, still intact in Lower South Hillsborough at 360 Poett Road between Roblar and El Cerrito.