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History of Hillsborough, California

The fabled residential enclave founded by California's most illustrious 19th Century business icons, Hillsborough presents a unique heritage of distinguished living. No other suburban town matches Hillsborough's direct link with the illustrious, colorful, and affluent history of early San Francisco tracing back to the Gold Rush. The Town'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, financier William Sharon, attorney Francis Newlands, and the famous gentry families of William H. Crocker (youngest son of "Big Four" transcontinental railroad builder Charles Crocker) and Harriett Pullman Carolan (daughter of Pullman Rail Car magnate George Mortimer Pullman).

Grand mansions of the early 20th century designed by renowned architects such as Willis Polk, Arthur Brown Jr., Willis Polk, Angus McSweeney, Gardner Dailey, and William Wurster, stand amidst today's handsome mix of traditionals, moderns, and new constructions...most properties boasting over half-acre parcels in private country seclusion. No other Town in the Unites States boasts this enviable milieu of understated prestige, security, bucolic environs, and proximity to San Francisco and Silicon Valley. Despite its worldly heritage, Hillsborough continues to thrive on its core foundations as a beautiful place for both sophisticated leisure living and family and educational desirability.

Incorporated in 1910, the town of Hillsborough is a purely residential hamlet, noteworthy among the most affluent towns in the United States. Distinguishing characteristics for homebuyers include the ambiance of rustic serenity, the phenomenal school system, and the quality and diversity of architecture on large parcels.  These are the qualities that have formed the character of the Town and have remained stable for over 100 years. Visit the official Town of Hillsborough Web site Here


Villa Rose


Beginning with the formation of the Burlingame Country Club in 1893, Hillsborough society flourished around the Lower North area, with many of San Francisco’s most influential citizens commuting to country leisure via the newly minted Burlingame Train Depot. Along with the circa-1897 Newhall Manor at 1615 Floribunda, which sold for $5,200,000 in June 2012, and circa-1889 50 Kammerer Court, which has had the same owner since 1993, 141 Pepper Avenue (in today's Burlingame Park) is part of a group of historic weekend country homes often referred to as “The Cottages.” These rare jewels were designed pre-1900 by famous San Francisco architect A. Page Brown. Landowner Francis Newlands (administrator of the vast Sharon Estate) used these new “model” homes as symbols of the affluent country comfort, developing the former Sharon Estate lands while rallying the right prospective members around the new Burlingame Country Club. George Newhall purchased one of the first cottages at 1615 Floribunda in 1897, 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 known as La Dolphine, originally on 20 acres. The home is still majestically preserved and was opened for the 2010 Hillsborough Historic Homes Tour. Just prior to its recent sale, 1615 Floribunda was also featured on this 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.

Another intact Lewis Hobart-designed legacy estate is the approx. 50-acre Strawberry Hill, originally known as Villa Rose (pictured above), 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. Also in Lower North’s Fagan area is the Bing Crosby Estate.


The Lower South area is one 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. Architectural landmarks in the area include the Western White House, the circa-1930 Julia Morgan-designed home of George Hearst, son of William Randolph Hearst; 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 approx. 50 acres off of Crystal Springs Road in the de Guigne family since the 1870s. On a smaller scale, but no less wondrous is the circa-1906 Normandy-style shingled home (pictured below) of Hibernia Bank founder Richard Tobin, still intact on Lower South's Poett Road.





For more history on Hillsborough's Founding Families, follow here



UPPER HILLSBOROUGH: Exploring Hillsborough's History and Residential Diversity

By Geoffrey Nelson (unabridged from Gentry Magazine October 2011)

Carolands, Skyfarm, Tobin Clark: the very names evoke Hillsborough’s legendary early estates. Once the land holdings and palatial domains of 19th and early 20th century Hillsborough, these areas today represent sought-after subdivisions with a diversity of topography, vistas, architecture, and commute ease. Breathtaking views above San Francisco Bay are a defining hallmark of Upper Hillsborough. Hillsborough’s most dramatic multi-county views are showcased from the elevations of neighborhoods such as Carolands, Skyfarm, and Tobin Clark. Often in unobstructed glory, Upper Hillsborough plateaus showcase vistas above the waters of the Bay, twinkling city lights, the San Francisco skyline, multiple bridges, Mt. Diablo, and beyond. Another distinguishing aspect of Upper Hillsborough locations is the sheer commute ease connecting directly onto Highway 280. Preceded by the recently restored Carolands gatehouse, Chateau Drive is a reliable artery linking 280 to the west, and downtown Burlingame to the East.  Travel times into San Francisco and Palo Alto are minimized via this 280 proximity. Upper Hillsborough neighborhoods such as Carolands, Skyfarm, and Woodgate Hills (along Summit Drive), embody this rare balance of “alpine scenic retreat” feeling with easy navigability and commute optimization. Prestige and real estate desirability are also in evidence, as the #1 MLS sales of year 2009 and 2011 were both in the Carolands area, each selling at over $10,000,000. This corridor also claims the rarity of many consecutive 2-acre parcels.

Centrally located West Elementary School on Carolands’ Barbara Way provides a sense of community synergy. This public school is consistently ranked at the very height of all Bay Area schools for both API results and parental support. At the time of this writing the Academic Performance Index was an impressive 987. Acclaimed Crocker Middle is easily accessed at the base of Chateau Drive. Nearby private schools include The Nueva School at the summit of Skyfarm, and Crystal Springs Uplands (6-12) in the Lower South neighborhood.

Historic presence, although typically more associated with Lower Hillsborough, is the backbone of Upper Hillsborough lore. The Carolands neighborhood is home to one of the most magnificent private residences ever built in the United States: the circa-1914 Carolands mansion (west facade pictured below), National Register of Historic Places # 75000478.  Originally conceived by Harriett Pullman Carolan, Pullman railcar heiress, this French Mansard Chateau of elite standards spans approx. 65,000 sq. ft.  It remains a private residence, now masterfully restored and complete with its own coffee table book and film documentary “Three Women and a Chateau.” Also of historic and architectural significance is the Tobin Clark Estate, first known as “House on Hill.” Wonderfully preserved and renovated in all its elegance, this circa-1931 mansion is a genuine handcrafted Cotswold Tudor by famed architect David Adler. “Skyfarm,” originally attributed to William H. Crocker circa 1890s, is now part of The Nueva School atop Skyline Boulevard. Lesser known, but intriguing in its own right, the Crocker Lake Open Space is tucked below streets such as Jacaranda and Skyfarm. Man-made Crocker Lake was first created to provide irrigation to William H. Crocker’s New Place estate gardens. It is now a hidden greenbelt ecosystem owned and protected by the Town of Hillsborough.




As with all Hillsborough neighborhoods, pleasant micro-distinctions emerge along every unique twist and turn of the rustic streetscape. The new Web site presents a wealth of this nuanced information, organized into the 10 areas of town. From the most lavish view terrace, to the most quaint garden gazebo, Upper Hillsborough endures as a treasured lifestyle across the generations.

Senior Partner, Luxury Real Estate Group
Agent No. 01313666
1427 Chapin Avenue , Burlingame , CA 94010
Phone: (650) 455-3735
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