Homes for sale in Hillsborough, CA are scattered across a town with no center, so the first question is what you want from the land around you. A flat yard, a long view and a short drive to the airport tend to be found in different places. Here is where to look for each.

You want a flat, usable yard

Hillsborough is hilly, so level ground is worth noticing. The Brewer subdivision and the streets around the old Uplands mansion have some of the most even half-acre lots in town, the kind of yard that suits a lawn, a pool or children’s games.

Sales there show the range. In the past year a Brewer Drive home of 6,835 sq ft sold for $8.6 million, and a 3,800 sq ft house on Uplands Drive sold for about $7.17 million after being listed at $6.75 million. A six-bedroom on Uplands Drive was pending at $10.88 million in early November.

You want a classic family street

Picture big oaks, narrow lanes and half-acre lots. That is Hillsborough Park, in the lanes off Hayne Road, and Hillsborough Oaks on the oak-covered north slope. Homeplace, in the high middle of town, was carved from one of the original estates.

These areas are near the heart of the market, which Highnote360’s neighborhood notes put at about $5 million to $8 million for much of the town. Remodeled homes can go well past that. A seven-bedroom on Hayne Road sold for $10.75 million in June, above its $9.998 million list price.

All of Hillsborough feeds the same public K-8 school district, with North, South and West elementary schools and Crocker Middle School. High school is assigned by address through the San Mateo Union High School District, so run any home you like through the district’s school locator.

You want land and real privacy

Go up. Hillsborough Knolls, around San Raymundo Road and Jewell Place, has larger lots. A 5,923 sq ft home on Jewell Place sold for $7.3 million in June. The Parrott Drive area climbs to two-acre lots at the top, Skyfarm has some of the largest typical lots in town on the old Crocker estate, and Hillsborough Hills takes in the highest ground of all.

Two things to check at this altitude. Land this size takes real upkeep, and slopes bring drainage questions. Parts of the western edge and south of town also fall in Moderate and High fire hazard zones on state maps dated February 2025, so look up the address before you get attached.

You want a house that makes a statement

The Tobin Clark Estate and Polo Terrace area, around the 1931 Adler house, is known for the town’s largest homes. Four Tobin Clark Drive homes sold in the past year, from $6.89 million to $11 million, and each was at least 6,498 sq ft.

Carolands, on a wooded plateau around the chateau completed in 1916, has two-acre lots on Robin Road and a real sense of history. At this level the market works differently: none of the 10 top sales asking $12 million or more closed above asking, so a patient buyer has room to negotiate.

You want an older home with character

Country Club Manor holds the town’s oldest streets, around Burlingame Country Club. Across town you will find mid-century ranches beside 1930s Tudor revivals, and it is worth asking what the lot allows before you plan changes. The town reviews nearly all exterior work and protects trees 18 inches or wider.

You want the quickest way out of town

If you fly often or commute, stay low. Hillsborough Heights has the lowest, closest-in streets, and the Ryan Tract runs along the northern edge on evenly sized lots. San Francisco International Airport is only about three miles from town.

If your work is to the south, look at Lakeview instead, on the high southern end above Crystal Springs and handy for I-280. A four-bedroom on Lakeview Drive was pending at just under $4 million in early November, around the point where the town’s market starts.

You just want a way in

With 14 homes listed in early November and a median asking price of about $10.4 million, the listings can look out of reach. The homes that actually sell tend to cost less, with the typical sale around $6 million and entry homes near $4 million.

Those lower-priced homes are spread around town, and some need updating. A 3,150 sq ft house on Bluebell Lane was asking $4.087 million, and a four-bedroom on Kingswood Drive was pending at about $4.1 million. Competition is keen at this end: of the top sales asking less than $8 million, 12 of 22 closed above asking.

Making the shortlist

Choose two or three areas now, since waiting for a perfect match in one could take a very long time. Drive them at the hour you would really be coming and going. Then spend ten minutes on foot, because with no sidewalks on most streets, how a road feels to walk tells you a lot about living on it.

By Mark Choey, a broker with Christie’s International Real Estate San Francisco. Sale and listing details are from MLSListings as of November 9, 2026.