"An icon is not chosen by fashion, it is confirmed by history."

Hillsborough began less about a place, and more about an ideal...

By the 1870s, Hillsborough's Founding Families were uniquely positioned to manifest their success from the East Coast, to harness their pathways as entrepreneurs and heirs, to leverage business acumen of the Industrial Revolution and Gold Rush, and to channel the Gilded Age inspiration of Europe into something new, just fifteen miles south of wildly prosperous San Francisco. 

No other suburb matches Hillsborough's lineage with the colorful affluence of early San Francisco tracing back to the Gold Rush. Hillsborough began less about a place, and more about an ideal. The vision was of a sunny country refuge, far enough outside of the big city to take in more pastoral air, yet intrinsically tied to the best of San Francisco. This would evolve into the first private country club west of the Mississippi, and a way of life completely suited to the scenic lands and temperate climate. Hillsborough was to become the vehicle for San Francisco gentry to express their wealth through architecture, entertaining, the arts, acreage, gardens, and sporting life. With this came the vastness of estate parcels and a sense of park-like privacy they never experienced even in the finest locations of San Francisco. This became an enduring theme essential to Hillsborough as we know it. 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), the landed heirs of Big Four railroad icon Charles Crocker (youngest son being William H. Crocker), the earliest pioneers of 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, with the efforts of many others notwithstanding, 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 pre-automobile years of 1893 - 1910. San Franciscans had already been using the train to reach weekend picnics and park grounds in Belmont as early as the 1860s, and William Ralston had set up court hosting Senators and Presidents in his Belmont Victorian mansion, Ralston Hall, from about 1867 when the house was rebuilt and until his death in 1875. But the lands that would become Hillsborough were to be something completely different. The Country Club as nexus of social, political, and sporting life was the crucible for community growth, and became a natural foil to develop surrounding ”summer houses.” The acreage was originally called Burlingame, namesake to U.S. Congressman Anson Burlingame who had purchased the lands, yet never really enjoyed or developed it before his death at 49 in 1870. William Ralston was the next steward of the acreage, and was intent on developing it as Ralstonville before his untimely passing in 1875: "planned after the English country style, which allowed for the building of substantial cottages in an exclusively residential setting, with winding roads and much space between homes for recreational pursuits." Ralston's business partner William Sharon, together with his son-in-law Francis Newlands, would develop the private country club concept that gave birth to Hillsborough. By 1910, the vision of this new community became so crystallized that it was essential to resist annexation from San Mateo and Burlingame, and officially incorporate as the Town of Hillsborough. 

The ideal of the private country club moves west: founded at Chevy Chase MD, evolved with the Burlingame Club as Crown Jewel of the West

Shortly before developing early Hillsborough and the Burlingame Country Club, Francis Newlands created a similar 1890s country club community in Chevy Chase, Maryland, the first of its kind in America. 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 such as Walter Hobart and the Tobin family. Frank and Harriet Pullman Carolan's Crossways Farm in Burlingame was the pre-eminent destination for polo and the sporting crowd. Other polo grounds were found on El Cerrito Avenue for the San Mateo Polo Club, with today’s Hillsborough Racquet Club once the clubhouse and viewing pavilion for the now-demolished polo field. Walter Hobart’s field was at his El Palomar estate later purchased by copper heir Charles Clark (husband of Celia Tobin, later to divorce) that now comprises St. Matthew’s Catholic Church and School. House on Hill, also known as the Tobin Clark Estate, was built by Celia Tobin after her divorce from Charles Clark. Famous for its stone-clad English Cotswold mansion still standing at 40 Verbalee Lane, this compound purveyed significant equestrian facilities In the southwest quadrant of Hillsborough dating to the late 1920s. Celia Tobin Clark (1874-1965) is interred in nearby St. John’s Cemetery. Celia's father Richard Tobin (1829-1887) co-founded Hibernia Bank, while her brother Richard Tobin (Jr. - 1866-1952) maintained a c. 1906 whimsical Craftsman cottage by George Howard still standing at 360 Poett Road, which would have backed up to the El Cerrito polo field in those days: "Richard Tobin's new home at Burlingame is rapidly nearing completion. Mr. Tobin is so devoted to the game of polo that he chose the site for his home that adjoined the polo field. While the house is being furnished Mr. Tobin will be the guest of his sister Mrs. Charles W. Clark."  -San Francisco Examiner Feb. 24, 1907.  San Francisco jeweler George Shreve was just across the street at the circa-1884 245 El Cerrito by architect Howard (the 1880s Shreve estate surely included acreage of what is now 295 El Cerrito). George Howard had meanwhile built "Versailles Park" for himself atop Roehampton Road that was a French classical indulgence like a page out of Newport.  Later generations of Tobins owned one of Hillsborough's ultimate modern-day parcels at 888 Irwin Drive. This flat 2-acre lot (at the corner of Forest View) presides at one of Lower North's very best streets and featured a c.1955 Joseph Esherick home that was demolished after the property changed hands in 2013. Driving by, it's now a stunning new modern/transitional composition by San Francisco architect Richard Beard. 

The Transcontinental Railroad brought immense wealth to the Hillsborough heirs of Big Four Associate Charles Crocker (1822 - 1888). Accordingly, Burlingame Club founding members were intent on a train depot of sophistication, and with a sense of arrival. A young George H. Howard designed the c.1894 depot that would serve the new Country Club and early "Cottages" model homes. The depot was as innovative as it was native, capturing the essence of the Mission style with tiled rooflines and arcades that pre-dated 1920s popularity of Spanish Colonial in California and Palm Beach, Florida. Howard (1864-1935) went on to a prolific architectural career, and 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, and many other 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 360 Poett (Richard Tobin house) 245 El Cerrito (Shreve), c. 1890, 120 W. Santa Inez c. 1903, 1 Homs Court c. 1905, 124 Stonehedge c.1906, 108 Stonehedge c. 1908, 2305 Forest View (Stetson c.1909) and c. 1927 "Treehaven" at 816 Hayne Road.

"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 began as summer homes, and were always designed with grand receiving and entertaining in mind. And that meant porte cocheres, ballrooms, grand salons, banquet-scale dining rooms, and on-site lodging (often attic levels) for extensive staff. As the Victorian era yielded to the 20th century, the architecture of choice became the Beaux Arts. Perhaps the most pure example is the Willis Polk-designed Uplands II, Charles Templeton Crocker's gift to his new bride Helene Irwin, built 1914-1917 amidst World War I. Of note, the inspiration for Uplands was none other than Newport's c.1900 Rosecliff, itself a classically marvelous echo of Versailles' Grand Trianon. The 35,000 foot Uplands mansion today houses the private Crystal Springs Uplands School, grades 6-12. The Crocker family were no strangers to architectural patronage, hiring only the most illustrious designers of the era including Lewis Hobart, Willis Polk, and Arthur Brown Jr. primarily. As uncle to Charles Templeton Crocker, William H. Crocker surely was an inspiration, having just completed his New Place (today‘s Burlingame Country Club) in 1910 with architect Lewis Hobart. 

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 II and dozens of San Francisco projects, Polk was also the supervising architect responsible for the construction of the Carolands and the designer of Woodside's Filoli. Harriett Pullman's French architect Ernest Sanson never visited the Hillsborough site. But his signature could not have been more profound, echoing the symmetry of the legendary Vaux Le Vicomte, and the Parisian elegance of Sanson's 1892 hotel particulier of Hotel Porges. Carolands is considered one of Sanson's later works, the architect having passed away at age 82 in 1918. Harriet's choice of Sanson as architect was not surprising, considering her Francophile passions and Beaux Arts still being the king of Newport and New York architecture.

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. Hobart made his own home at 124 W. Santa Inez Avenue, built 1905 in Lower South Hillsborough. Hobart's 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, and as of 2026, only on its third owner. 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, and his City home was at 2200 Broadway, currently the Convent & Stuart Hall Private Schools. San Francisco society pages chattered away with news of Grant's new construction in 1912. Grant was committed to building no less than the finest estate on the Peninsula, with Lewis Hobart as his muse, and plenty of acreage where his previous home was lost to fire: "Joseph D. Grant is planning to build the finest home in Hillsborough, or, to be more explicit, he has Lewis P. Hobart, the architect, planning for him the most handsome and commodious mansion in that city of expensive domiciles."  The third owner of Strawberry Hill, the Regan Family, cherished the home from 1975 until Mrs. Regan's passing in 2026: "Strawberry Hill, one of the last great Peninsula estates, has been sold. The purchasers are Ada and Barrie Regan of Hillsborough and the price is $1.15 million. Originally built by the late Joseph D. Grant at the turn of the century, it was sold to the late Charles Blyths in 1936. The home has remained in the Blyth family since that time. The palatial residence in Hillsborough was designed in an Italian-rococo style by Lewis Hobart. The name originated from the fact that wild strawberries grew where the garden is now located. The estate originally adjoined the William H. Crocker residence, which is now the Burlingame Country Club. Mr. Regan, who is in electronics, said they plan to live on the estate and have no plans to subdivide it." -San Francisco Chronicle, Tuesday August 19, 1975.

Lewis Hobart's c.1910 New Place built for William H. Crocker was an early benchmark for the newly incorporated Town. Like Strawberry Hill, New Place originally had a Redington Road entrance (2141 Redington for New Place, which was later changed to 80 New Place Road). Expanded and modified, New Place has served as the Burlingame Country Club clubhouse since 1955. Like Villa Rose, New Place leaned on Italian Villa inspiration, both in dwelling and a magnificent garden by Bruce Porter. What would have been the rear gateposts still stand at the intersection near North School, and the original front gates are still at 2141 Redington near Skyfarm Drive. At the time of installation a couple years after the home was completed, Hobart's New Place gates were an extravagant $8,000 finishing touch! Crocker Lake was the man-made reservoir designed to service the New Place estate. 

In 1913, Hobart designed the Beaux Arts French masterpiece Newmar for the George Newhall Family, later renamed La Dolphine under Dorothy Spreckels ownership in 1940. Originally on 20 acres at Lower North's 1761 Manor Drive, this classical masterpiece was a Francophile dream and a true statement of home and garden, reflecting the Beaux Arts summer homes of the East Coast: "Mr. and Mrs. George Newhall's home at Burlingame so attracted Mrs. William Kissam Vanderbilt Jr. that she promptly asked Lewis Hobart to design her new country place on Long Island. The Newhall estate, which is one of Hobart's chef d'oeuvres, was completed last year. It suggests a French chateau, surrounded as it is with sunken gardens of a quaintly formal nature." San Francisco businessman George A. Newhall (1862-1929) was an influential early Hillsborough property holder as he first owned the c.1892 A. Page Brown Cottage at 1615 Floribunda, and later made his mark building the tour de force Newmar. Newhall's Floribunda Cottage, today with a plaque stating "Newhall Manor, c. 1892," was also owned by Caspar Weinberger from 1975 until 1981, at which point he sold it for $995,000 upon moving to the Pentagon to serve as Ronald Reagan's Secretary of Defense. 

Also of note in Lower North, Hobart's elegant 12,000 foot villa, c.1913 Rosecourt, was originally accessed at 815 Eucalyptus. Mirroring the symmetrical rectangular lines of Villa Rose, 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, Newmar, 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, having mentored on the East Coast with legendary McKim Mead and White, designed Guignecourt in 1912-1913 on 47 acres with Italian Renaissance symmetry.. 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, and closed escrow for $30,000,000 in December 2021. As of 2026, this sale ranks #3 in Hillsborough history, with #2 at 835 Chiltern for $37,500,000, and #1 in 2026 at 3000 Ralston Avenue for $70,000,000. 

Subdivisions and Modernism Advance the Century

The first subdivision of Carolands beginning in 1929 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. Twenty miles north in San Francisco's Pacific Heights McSweeney was designing the celebrated circa-1933 Tudor Revival at 2500 Divisadero. The c. 1936 Tudor gem at 901 Baileyana is a quintessential McSweeney overflowing with architectural charisma, and originally sited on larger acreage. 810 Lombardi Lane from 1930 is an authentic and emphatic culmination of the popular Spanish Colonial Revival era of the 1920s. Several of the homes were designed while McSweeney, upon Willis Polk's death in 1924, carried on at the firm as Willis Polk & Company from 1924-1934. 

Educated at UC Berkeley, mentored by Bernard Maybeck, and ultimately dean of the UC Berkeley Architecture School in 1950, William Wurster was influential in the Bay Region style. Private Hillsborough commissions include 711 Bromfield c.1931, 735 Bromfield from 1936, 761 Chiltern c.1937, 1800 Floribunda c.1939, and 301 Ascot (Dinkelspiel House) from 1940. Many of Wurster's designs were complemented by the landscape architecture of Thomas Church throughout the 1930s-1960s. Wurster's epoch (born 1895, d. 1973) kept him in the wheelhouse of important architectural movements in Hillsborough including European Revival, Mid Century, and early modern. 

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. One of the associates in his boutique San Francisco office was notable Joseph Esherick. Hillsborough examples by Gardner Dailey include the c. 1936 510 N. San Raymundo Road, 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 and 1802 Floribunda, as well as Dailey's 875 Vista and 405 Chapin Lane. Perhaps Gardner Dailey's most innovative composition is the circa 1954 123 Bella Vista Drive (photo below). Overlooking the Bay and Skyfarm ridge lines, the 1.53 acre estate showcases esoteric themes of Mid Century, Far East, and Bauhaus. 

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, Michael Kao of MAK Studio, Leonard Ng of LNAI, Eric Nyhus, Charlie Barnett, the aforementioned Richard Beard, classicist 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 prolific architects with long Hillsborough track records dating to the 1980s. Stewart European-themed private estates include the early 2000's 125 Robin Road and 150 Bridge Road. 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 a French style near the "top of the world" view summit at 225 Tobin Clark Drive, last sold in July 2026 for $10,500,000. 

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. 2020-2026 (a work in progress!) 

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 Ralston and 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 last 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 in the 1940s by the sugar heiress Dorothy Spreckels family. Although no longer on its 20 acres, the French masterpiece is still majestically preserved as a private residence. La Dolphine (pictured above) was opened to the 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 in 1912 for Joseph D. Grant, Burlingame Club charter member, influential industrialist, and nature lover. 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, and what were the original front gates at Redington and Skyfarm. Lower North’s Fagan Estates area hosts the Paul Fagan mansion (85 Fagan Drive) and the Bing Crosby Estate (1200 Jackling Drive at Armsby, sold for $25,000,000 July 2025) 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. The Fagan Estate was listed on MLS as 85 and 90 Fagan and sold all together for $14,850,000 in October 2021. 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 Avenue 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 (W.D.M. Howard's younger brother George married Agnes, his brother's widow after 1856 death of W.D.M. Their son was architect George Howard Jr.) 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, San Mateo, and Burlingame. 

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. Fashioned by Morgan in Greek Revival and Georgian Colonial themes, it sold for $15,000,000 in September 2022, far below its $25,000,000 asking, and was subsequently flipped in October 2024 for $23,000,000. Of historic note, the White House at 401 El Cerrito was the original Uplands I before it was moved across the creek to El Cerrito to make way for Charles Templeton Crocker’s c. 1914 Willis Polk-designed Uplands II mansion (pictured above, now the private Crystal Springs Uplands School, grades 6-12).  Guignecourt, the c. 1914 Bliss and Faville-designed Italian mansion on 47 acres at 891 Crystal Springs Road, is now associated with Elon Musk, who owned it briefly in 2017-2021 as only the second owner in some 150 years.  By way of De Guigne's marriage to a Parrott daughter, these lands were in the same family since the 1870s. . On a smaller scale, but no less wondrous is the c. 1906 Shingle Style home of Hibernia Bank President Richard Tobin Jr., still intact in Lower South Hillsborough at 360 Poett Road, by architect George Howard. This home backed up to the San Mateo Polo Field (now school district office and baseball diamond) and other estates of the era including the 1880s home of jeweler George Shreve (intact, 245 El Cerrito) and the architect George Howard (atop the Roehmapton Road cul-de-sac, since demolished).