Hillsborough Historic Estates
Carolands, La Dolphine, The Uplands, New Place, Floribunda — the estates that built the town.
Hillsborough Historic Estates Real Estate Market Snapshot
Living in Hillsborough Historic Estates
Hillsborough's identity as one of America's most exclusive residential towns was built estate by estate, beginning in the 1860s when Bay Area lumber, railroad, and mining fortunes purchased large parcels of the rolling hillside south of Burlingame and commissioned country houses on a scale that rivaled the great estates of the East Coast and Europe. Today many of those original parcels have been subdivided into still-substantial one- and three-acre lots that comprise the Hillsborough Country Club, Lower North Hillsborough, and Tobin Clark sub-neighborhoods. A small number of the original Gilded Age and Beaux Arts estates survive intact, and they continue to anchor both the town's architectural character and its zoning ethos: privacy, mature landscape, and architectural review that takes its cues from a century of precedent.
This page is an editorial survey of those notable historic estates rather than a marketing page for active listings. The properties profiled below are landmarks — most are privately held and rarely trade on the open market. When they do, they often trade off-market or through invitation-only marketing. If you're interested in the broader Hillsborough market, see Hillsborough overview; for the country club neighborhood specifically, see Hillsborough Country Club.
Carolands Chateau
A 65,000-square-foot Beaux Arts mansion completed in 1916, designed by Ernest Sanson with grounds laid out by Achille Duchêne for Harriett Pullman Carolan, daughter of railroad-car magnate George Pullman. Carolands sits on a 5.83-acre parcel and is one of the largest private residences ever built in the United States. The chateau is now operated as a non-profit and offers limited public tours through the Carolands Foundation.
La Dolphine
Built in 1912 for sugar heiress Mrs. George Newhall, La Dolphine is a French Neoclassical estate modeled after the Petit Trianon at Versailles, designed by Lewis P. Hobart. The estate features formal gardens, a grand entry court, and remains one of the most photographed historic homes on the Peninsula.
The Uplands
Originally the C. Templeton Crocker estate, The Uplands was designed by Willis Polk in 1912 in the Italian Renaissance style on a hilltop site with panoramic Bay views. The 47-acre original parcel was later subdivided into the Crocker Hillsborough Estates neighborhood, with the main house preserved.
New Place
An English Tudor estate originally built by William H. Crocker (Charles Crocker's son) in 1907, New Place is among the earliest of the surviving great Hillsborough estates. The property has had several stewardship periods over its century-plus history and remains an architectural touchstone for the town's reverence for English country house style.
Floribunda Estate
Dating to 1868, Floribunda is among the oldest surviving estates in Hillsborough — predating the town's incorporation. The property's name reflects its historic rose plantings, and it remains a private residence.
Frequently Asked Questions about Hillsborough Historic Estates
What is the transfer tax in Hillsborough Historic Estates, San Mateo County?
Does Hillsborough Historic Estates require a sewer lateral inspection at sale?
What disclosures are required when selling a home in Hillsborough Historic Estates?
What is the difference between median and average home price in Hillsborough Historic Estates?
Search Hillsborough Historic Estates Homes
Browse current listings in Hillsborough Historic Estates with Lisa M. Lum.
Search Listings