Hillsborough's Carolands Neighborhood rich in history, views, and Hillsborough's #1 Sale of all time

Carolands is a sprawling and scenic area of upper Hillsborough with a broad housing diversity. Carolands grabbed all the headlines in 2026 with the #1 sale of all time in Hillsborough history at 3000 Ralston Avenue for $70,000,000. The Carolands area was originally the 554 acre hilltop kingdom of Harriett Pullman Carolan, who built one of America’s greatest estates at 565 Remillard Road in 1914. Painstakingly restored, the authentically French Carolands Chateau is now held in a Foundation and proudly hosts occasional events and private tours. The Chateau currently holds 5.37 acres with gates visible on both Remillard and Craig Road. Tours are by lottery on Wednesdays. But every Halloween the motor court is decked out in full regalia for the public to enjoy the front grounds. 

Hillsborough Architectural Diversity from Ranch Homes to 2-Acre Bay-View Mansions

The Carolands neighborhood offers a bit of everything: from 1950s classic ranchers on half-acre lots, to new luxury constructions from the 2000s, to glamorous Bay-view estates on 2 acre minimums. Streets around West School such as Darrell, Barbara, Craig, and Remillard originated as the 1950s California suburban dream: a ranch-style  house opening to swimming pool. The 600 block of Pullman and Craig Road present good examples of early 2000s two-story luxury homes built-out to maximize their mostly half-acre lot coverages. The first subdivision of the Carolands Chateau starting in 1929 comprised a unique sub-district that I call the 2-acre corridor. Today, these streets such as Robin Road, Upper Ralston (2900-3300 blocks), Pullman, and Pinehill showcase epic Bay-view estates in the exclusive 2-acre minimum location. High-end estates in this pocket will rival Lower Hillsborough for some of the top prices in town. The #1 Hillsborough sale of all time at 3000 Ralston in August 2026 is a unique highlight of the 2-acre corridor as it features compounded parcels totaling over 12 acres, and anchored by an Italian Renaissance mansion by architect Andrew Skurman. All of Carolands enjoys easy proximity to Highway 280, and is served by the main artery of Chateau Drive (a straight shot up and down the hill) linking downtown Burlingame and commute highways. Many of the subdivision street names (Denise, Barbara, Darrell, Moseley) were dubbed after friends and family members of 1940s landholder the Moseley family.

Explore the Google Map for Carolands, Hillsborough, and also Carolands real estate sales data