Hillsborough was built on a question of taste. Its founding generation, drawn from the Crockers, the Pullmans, the Newhalls, and a small circle of San Francisco's Gilded Age families, asked what a country residence on the Peninsula could be when scale and craft were unconstrained. The architects they hired — Ernest Sanson, Willis Polk, Lewis Hobart, Arthur Brown Jr. — answered with a generation of estates that still set the standard for the town today.
The five properties below are not a complete catalog. They are, in chronological order, the houses most often cited when long-tenured residents describe Hillsborough's architectural identity. Each remains intact in some form: as a private residence, as a school, as a club, as a museum. Together they form an unusually continuous record of a single town's commitment to a single idea.
The 1868 Floribunda Estate
The 1868 Floribunda Estate occupies what many consider the most coveted 2.5-acre parcel in Hillsborough's historic landscape, with the fairways of Burlingame Country Club bordering it to the north and south. Bound by century-old trees and serenely abutting golf greens, the estate offers the rare combination of unrivaled exclusivity, genuine privacy, and a sense of agricultural history that the rest of the town has largely lost.
Reconstructed over seven years under the discerning eye of a former owner, the property's present form is an extraordinary synthesis of California ease and Asian elegance. The interiors, spanning approximately 15,000 square feet, comprise five bedrooms, six full bathrooms, and two half-baths, organized around eight fireplaces and four laundry facilities. An elevator connects all three levels. The architecture flows effortlessly between interior and exterior spaces, each room positioned to capture an interplay of light, air, and garden views.
The grounds are a feat of landscaping prowess. A rose garden, a koi pond, an arboretum, and a cast bronze statue from sculptor Ju Ming's Taichi series anchor the gardens. A newly designed pool and spa, a pool house with two full baths, and a caterer's pavilion with an outdoor pizza and bread oven extend the estate's hospitality outward. A separate guest house and office, a two-bedroom caretaker's home, four garage spaces, and seven carports complete the program. The estate is the third-oldest in Hillsborough and remains a private residence.
New Place
Commissioned in 1910 by William H. Crocker, son of Central Pacific Railroad founder Charles Crocker, New Place is an Italian Renaissance mansion designed by the San Francisco architect Lewis Hobart. The estate was conceived as a country house for one of the most powerful families in California finance and remains, in its scale and detailing, one of the most refined examples of the form on the Peninsula.
The house was sold by the Crocker family in 1955 to the Burlingame Country Club, which has used it as its clubhouse ever since — its fifth and current. New Place is therefore one of the very few Hillsborough estates with a continuous public function, and it has been preserved with an unusually high level of care. Generations of members and guests have moved through its formal rooms, terraces, and gardens without altering the underlying architectural intent.
For students of Hillsborough's history, New Place serves as a kind of working museum. It demonstrates what the early 20th-century estates of the town aspired to be, and it answers, in stone and stucco, why the surrounding fairways and adjacent residences command the prices they do. Its presence is the reason large parcels along the Burlingame Country Club border carry a distinct premium in the Hillsborough market.
La Dolphine
Set on Manor Drive in Lower North Hillsborough, La Dolphine was originally built in 1913 for George Newhall on a 30-acre estate then known as Newmar. The architect, again, was Lewis Hobart — a figure whose hand on the town is as visible as Polk's, though less often credited outside Bay Area architectural circles. Hobart's work on Newmar and a handful of neighboring properties shaped the streetscape that defines Lower North Hillsborough today.
The house has passed through several owners and has been adapted, expanded, and restored multiple times across its first century, but the core gesture remains. La Dolphine is an example of the Hillsborough estate at its most quietly confident: a long, low silhouette settled into its landscape rather than imposed on it, with formal gardens that defer to the topography rather than flatten it. The original 30-acre parcel has been subdivided over the decades; what remains is still among the most sought-after addresses in town.
La Dolphine is referenced in nearly every serious account of Hillsborough's architectural history. For buyers seeking a property with documented provenance, the estates within walking distance of La Dolphine — and the surviving fragments of the original Newmar landscape — represent the deepest record of the town's pre-WWI period.
The Uplands
The Uplands was built between 1913 and 1917 for Charles Templeton Crocker, grandson of railroad baron Charles Crocker and a notable San Francisco patron of the arts. The architect was Willis Polk, by then perhaps the most important architect working in California, and the resulting house is among Polk's most fully realized residential commissions. The Uplands is unambiguously Beaux-Arts, but its proportions are restrained and its detailing precise rather than ornamental.
Today the property serves as the campus of the Crystal Springs Uplands School, an independent grades 6–12 academy that ranks among the most selective private schools in the Bay Area. The conversion has preserved the principal structure and the landscaped grounds while adapting outbuildings and courtyards for academic use. The house, in other words, has remained a working building rather than a frozen one — a rarity among American estates of its caliber.
The Uplands is also a useful reference point for any buyer evaluating Hillsborough properties at scale. Polk's other residential work in the town — and the small group of houses built by his draftsmen and successors — defines a recognizable architectural lineage. Properties documented to that lineage carry both stronger market positioning and stronger long-term holding value than otherwise comparable homes.
Carolands Chateau
Carolands is the house most outsiders associate with Hillsborough, and rightly so. Completed in 1916 for Harriett Pullman Carolan — daughter of George Pullman, the railroad-car magnate, and wife of San Francisco's Francis Carolan — the chateau is a 98-room, approximately 46,050-square-foot, four-and-a-half-story residence modeled faithfully on the royal French chateaux of the Loire Valley, in particular Vaux-le-Vicomte. The French architect Ernest Sanson produced the design; Willis Polk supervised construction in California.
The original parcel ran to 554 acres. Today, after generations of subdivision and donation, Carolands sits on roughly 5.83 acres, but its physical mass remains essentially undiminished. The house is a California Historical Landmark and is listed on the National Register of Historic Places. The Carolands Foundation operates the property as a museum, with restricted public access and a continuing program of architectural conservation.
For Hillsborough specifically, Carolands functions as both an aspirational anchor and a market reference. It is the reason buyers from outside California arrive with an idea of the town that exceeds the typical Peninsula expectation. It is the reason serious estate-scale parcels — anything above an acre with mature canopy and views — are evaluated against a standard most other West Coast cities do not even attempt to set.
Looking for a property in Hillsborough?
Lisa M. Lum has spent years studying the architectural and market history of Hillsborough's historic estate landscape. If you are evaluating a purchase or sale at this level, she can help you understand both the documented record and the current market position of any given parcel.
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