Featured Hillsborough Listings

In Hillsborough, California

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Estate-Sized Building Site

Estate-Sized Building Site

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210 Uplands is the last of the estate sized building sites in the famous Uplands Estates. The merging of two .9 acre lots, the parcel totals 1.8 acres, is entirely flat and located just inside of the historic Uplands Estate stone wall and pillars. The parcel faces south to west and is sheltered by many of the original heritage trees. With 200 feet of frontage along Stonehedge Road, the Parcel faces some of Hillsborough’s most beautiful estates. 210 Uplands is a once in a lifetime opportunity to build the estate home on one’s dreams.

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Building site in Hillsborough

Building site in Hillsborough

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If spectacular views of the SF Skyline and Bay, a prime Skyfarm location, plus total privacy are what you are seeking this could be the perfect building site. Don’t settle for anything that does not exactly meet your desires. Create your exact dream home on this rare parcel. Atop one of Hillsborough’s highest hills where hawks soar above the towering peaks and plunging canyons, this spectacular building site has vistas beyond the wooded Skyfarm reserve, San Francisco Bay, all the way to the skyline of San Francisco. Nestled among mature Oaks, this is the perfect building site for those wanting an absolutely natural and unspoiled setting and the perfect place to build an architecturally significant home. With .66 acres, there is room for a home of grand proportions, plus an Accessory dwelling unit. Moderately down sloping, there is also the perfect place for an infinity pool.

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Home in Hillsborough

Home in Hillsborough

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SOLD

2/3 acres in prime North Hillsborough

2/3 acres in prime North Hillsborough

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2/3 acre, substantially level lot in prime upper North Hillsborough. 
Magnificent bay views. Existing mid-century home.

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Spectacular Country Inspired Retreat

Spectacular Country Inspired Retreat

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Completely rebuilt and expanded for the current and second owners, no expense was spared, no detail overlooked in the creation of this special home. Custom built in 1951 by one of Hillsborough’s most prominent families and one of the founders of the original Crystal Springs Girls’ school, this architecturally significant Cliff May home was gutted to the studs and meticulously rebuilt while preserving the classic country Ranch style of the 40’s and early 50’s.

Welcome to

Hillsborough, California

Twenty miles south of San Francisco, on the beautiful San Francisco Peninsula, is one of the world’s most desirable residential communities where magnificent scenery, breathtaking architecture, and a cosmopolitan sophistication combine with the world’s most dynamic economy to create a place unique in all the world.

The extraordinary destiny of an untamed area of the foothills that overlook San Francisco Bay began with the financial boom that followed the discovery of gold in California in 1849, and the transformation of San Francisco from an obscure and wild frontier town into a world famous destination for those with dreams of wealth, adventure, and new beginnings. From all over the world they came, defying great odds, those with unyielding determination, great ambition, and unwavering belief that in the golden land of California, anything was possible. A select few of these pioneers achieved a level of wealth beyond anything experienced in history. They built huge ornate mansions atop San Francisco’s Nob Hill and Pacific Heights. Their lives were glamorous, and the newspapers of the day documented their lives as celebrities are followed today. 

In the 1880’s, these barons of real estate, banking, commerce and industry, whose ruthless approach to acquiring wealth, and larger than life personalities, had made them world famous, began to follow in the tradition of the East Coast super wealthy, and seek out the ideal location for their summer estates, one where the weather was perfect, the scenery magnificent, and the lifestyle idyllic. Many of these individuals chose an area 20 miles south of the San Francisco Peninsula that would become Hillsborough. Not unlike the newly wealthy of today, those who founded Hillsborough wanted the world’s ultimate symbol of wealth and power, a magnificent country estate. Determined to outdo their peers, and inspired by visions of how the European Aristocracy lived, they constructed Beaux-arts Palaces, French Chateaux, Italian Palazzos, English Manors.

Designed by the most talented architects of the day, Willis Polk, Arthur Brown Jr, Bernard Maybeck, Julia Morgan, among others, these great estates were constructed of the finest materials, without regard to cost or restraint, and included enormous Ballrooms, baronial scaled Dining Rooms, outdoor Pools, Ponds, fountains, Colonnade, Loggias, and much more. With names like The Carolands, The Uplands, House-On-Hill, Skyfarm, these monuments to wealth and power stood majestically amid huge acreage that had been transformed from an Oak and chaparral wilderness into manicured and enchanting gardens of exotic plantings, waterfalls, and pools, Roman and Greek statuary and temples, Stables and kennels.

Secured behind imposing gates, walls, and dense vegetations, these Estates were reached by long winding Driveways, lined by alleys of trees, often reaching a mile or more into the hills and sometimes up to the highest peaks. With thousands of acres of woodland and meadows, outdoor activities included Polo, equestrian riding, steeple chasing, fox and wild boar hunting, skeet shooting, breeding thoroughbred horses and show dogs. During “The Season” there was a constant schedule of balls, pageants, dinners and teas. In the late 19th Century, and early 20th century Hillsborough had reached its’ pinnacle of sumptuous wealth and privilege with its’ own private Country Club, Polo Field, and Bridle trails. A few miles away on San Francisco Bay there was sailing and partying aboard opulent Yachts. There was now a social register, and a code of where one ranked within the social order, of who could join, and who could only look in.

There were now names with great cachet like Spreckels, Crocker, Pope, and many others that appeared in the papers that covered their every move. Vying for recognition were titles of every kind including Ambassadors and Consuls, Colonels and Senators, plus a few Counts and countesses. There were also pretenders and swindlers, a couple of famous murders, and more than a few scandals. As these Estates were mostly used in the summer, and their occupants spent the rest of the year in their Mansions in San Francisco, there was, and still is, a strong social connection between Hillsborough and San Francisco, and the famous organizations such as the Bohemian and Pacific Union clubs. Today, for one to have roots in this Golden era of San Francisco is an attribute of great distinction.

As the 1920’s approached, Hillsborough, with its’ proximity to the business centers of San Francisco, attracted a new, more conservative, and genteel generation of leaders of business, culture, and Society. Now living in Hillsborough were the elite of their professions, bankers, doctors, lawyers, and other professionals. From this generation of residents originated the enduring Hillsborough tradition of civic mindedness, and community betterment that continues to this day. One of country’s best school districts was founded. Private Schools of great distinction were built. A first rate police and fire department was organized, and in 1917 Hillsborough became an incorporated city. At the same time Hillsborough expanded upon its’ architectural legacy and distinction with romantic historical period homes being designed by such famous architects as David Adler, Angus McSweeny, Gardner Dailey, William Wurster, and others. Along Hillsborough’s leafy lanes were now a proliferation of Spanish Colonials, French and English County homes, New England Colonials, English Tudors, and a few Art Decos and Modernes. 

After World War 2 came another building boom that saw a further breakup of the old estates. Celebrating Hillsborough’s mild, sunny climate came sprawling California ranch and modern homes that opened to the outdoors, swimming pools, patios, and most importantly spectacular bay views. Architects and designers such as Sandy Walker, Robert Steiner, and Robert Onorato oriented these homes to the sun, the setting, the Views, and incorporated such features as skylights, walls of glass and family rooms.With these homes came an influx of families, new schools, athletic fields and parks. Just outside of Hillsborough the charming village of Burlingame blossomed with new supermarkets, beautiques, art gallaries, plus dining institutions such as the Black Horse, Bit of England, the Alpine Inn, and Nathans. New Banks and office buildings were built, the historic train depot renovated,, and trees planted along Burlingame Avenue.

Still several of the grand old estates remain, some now Private Schools, Country Club Clubhouses, a few still private residences, living reminders of Hillsborough gilded past, layered with history, and mystery. Even where great estates have been lost, there are reminders of past glories, ornate gates, Stone walls and bridges, balustrades and urns, that while not much more than a hundred years seem as ancient as a Roman ruin.The millions of trees that were planted during the time of the great estates mostly remain, now towering majestically over such streets as Eucalyptus Ave, Manor Drive, Geri Lane, and along Roblar Avenue.

Today, Hillsborough is attracting a new generation on residents who come from all over the world to enjoy Hillsborough’s award winning schools, perfect location, great climate, and excellent city services such as police and fire protection. Also, attracted to Hillsborough are a new generation of entrepreneurs, the titans of technology, venture capital, and private equity. As bold and brash as Hillsborough’s founding fathers, they are now replacing many of the older homes with new mansions of world class quality and design.

Strategically located halfway between San Francisco and Silicon Valley, and close to San Francisco Airport, major universities, and esteemed medical centers, Hillsborough offers amazing value and opportunity to home purchasers. To Those buyers’ from abroad, America, California, and Hillsborough offer a refuge from uncertain economies and politics. There still is an American Dream, and California, and especially Hillsborough, are still golden.

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