Some Representative Streets

Alberta, Barbara, Craig, Darrell, Denise, Laurent, Moseley, Mosswood, Pinehill, Pullman, Ralston (upper), Remillard. Robin Road. Warmwood

Neighborhood Overview

Carolands is a sprawling and scenic area of upper Hillsborough with a broad housing diversity. The lands were originally the 554 acre hilltop kingdom of Harriet Pullman Carolan, who built one of America’s greatest estates at 565 Remillard Road in 1914. Painstakingly restored, the authentic French Chateau "Carolands" is now held in a Foundation and proudly hosts occasional events and private tours. The 65,000 sq. ft. Chateau currently holds 5.37 acres with gates visible on both Remillard and Craig Road.

The Carolands neighborhood offers a bit of everything: from 1950s classic ranchers on half-acre lots, to new luxury constructions from the 2000s, and 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 500 block of Craig Road present good examples of newer 2-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), 400 block of Pullman, and all of 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. 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.

The Carolands neighborhood is assigned primarily to West School, Crocker Middle, and Burlingame High. 

For Hillsborough School District School Boundaries, North, South, West, By-Street click here. 

Explore All Hillsborough Neighborhoods at Geoffrey Nelson’s Hillsborough Google Map.

Appeal to Residents and Homeseekers

• Strong housing diversity from classic 1950s ranchers, to glamorous eight-figure new estates
• Neighborhood feeling with nearby West School, Nueva School, and easy 280 connection 
• Incredible views of Bay, SF skyline, and Valley
• Along with Lower North and Lower South, Carolands will have opportunities for those seeking $10M+ estates with 1-2 acre lots and resort-like amenities

Potentially Adverse to Residents and Homeseekers

• Proximity to Highway 280 creates varying degrees of freeway noise
• Upper location makes "walking to downtown" mostly prohibitive. Requires a car to reach downtown amenities of Burlingame or San Mateo. 

Historic Notes

Original hilltop site of one of the most storied private residences ever built in the United States: the circa-1914 Carolands Chateau, National Register of Historic Places # 75000478. Now a masterfully restored private residence complete with its own coffee table book and DVD feature “Three Women and a Chateau.” Many of the subdivision street names (Denise, Barbara, Darrell, Moseley, etc) were dubbed after friends and family members of 1940s landholder the Moseley family.

Geoffrey's Recent Track Record in Carolands Area of Hillsborough

• 465 Barbara Way, Listed at $5,788,000 SOLD $6,350,000 with 3 offers (2022 Buyer Representation) 
• 480 Pullman Road, Listed at $7,388,000 SOLD $7,400,000 (2021 Seller Representation) 
• 30 Mosswood Road, SOLD at $6,866,000 (2021 Buyer Representation) 
• 1415 San Raymundo Road, Listed at $5,298,000, SOLD $5,407,000 (2021 Buyer Representation)