Homes for sale in Hillsborough rarely number more than a couple of dozen at once. In early November 2026 there were 16, with a median asking price of about $10.3 million and an average of 130 days on market. Below $8 million, homes often sell at or above asking. Above $12 million, buyers negotiate.

A town with almost nothing for sale

Hillsborough sits about 20 miles south of San Francisco, between the city and Silicon Valley. It is entirely residential. There are no shops, no condos and no apartment buildings, just single-family homes, most of them on lots of half an acre or more.

That shapes the market in two ways. First, supply is tiny. With 16 homes listed and 8 pending in early November 2026, the town had about 2.0 months of inventory, and roughly 3 homes were in contract for every 10 on the market. Second, the homes that do come up vary enormously, from a 2,320 sq ft house pending at just under $4 million to estates asking $39 million and $48.9 million.

When the range is that wide, averages mislead. The page-level median asking price of $10.3 million is pulled up by a handful of estates that take months to sell. Highnote360’s market notes put the typical sale closer to $6 million.

Three markets inside one town

To see how buyers actually behave, Highnote360 looked at the 50 highest-priced Hillsborough sales from November 2025 to October 2026 and grouped them by asking price. Because these are the top 50 of 120 sales, the lowest band here starts at an asking price of about $6.75 million.

Asking price	Sales	Sold above asking	Sold at asking	Sold below asking	Typical result
Under $8M	21	11	4	6	Competitive: just over half went above asking
$8M to $12M	19	7	5	7	Balanced: an even split above and below
$12M and up	10	0	6	4	Negotiated: none sold above asking

Below $8 million, well-presented family homes still draw several buyers. The middle band can surprise too: a Chiltern Road home listed at $11.995 million sold for $14.5 million. At the very top, the buyer pool is small enough that price is a conversation. The largest sale of the year, on Ralston Avenue, listed at $78.8 million and closed at $70 million.

Why price per square foot tells you so little

In most markets, price per square foot is a useful shortcut. In Hillsborough it barely works. Among the 50 top sales, it ran from about $795 to more than $5,600 per square foot, with a midpoint near $1,740.

The spread is clearest among similar-sized homes. Eighteen of those sales were houses of 4,000 to 5,500 sq ft. They sold for anywhere between $7.1 million and $12.5 million, or roughly $1,600 to $2,900 per square foot.

What explains the gap is mostly the land: lot size, slope, views, privacy and the street. A 4,500 sq ft house on a flat, gated acre near the top of the hill and a house of the same size on a smaller lot near the Burlingame border are, for buyers, different products.

How serious buyers approach an estate purchase

• Proof of funds comes first. Many purchases are cash or private-bank loans. Listing agents expect to see financing or funds before they schedule a second showing.
• Ask about off-market homes. With so few listings, some homes trade quietly between agents. A local agent can tell you what is available beyond the public sites.
• Check what you can change. New homes, additions and visible changes such as gates and front fences go through the town’s Architecture and Design Review Board in public hearings. If you plan to remodel, ask the planning department what the specific lot allows before you make an offer.
• Add hillside inspections. Beyond the standard home inspection, budget for a drainage review, a sewer lateral inspection and, on sloping lots, a geotechnical report.
• Plan for property tax. California’s base rate is 1% of the purchase price plus local bonds and assessments, so most owners pay about 1.1% to 1.25% a year.

How Hillsborough compares with other luxury markets

For buyers used to luxury markets elsewhere, a few things stand out. There is no condo or townhouse option inside the town, so buyers who want a lock-and-leave home usually look in neighboring Burlingame or San Mateo. The town runs its own K-8 school district, which is a big draw for families. And with San Francisco International Airport about 15 minutes away, it suits owners who travel often.

What it does not offer is a resort-style lifestyle. Hillsborough is quiet, wooded and private by design, and most buyers choose it for exactly that reason.

What estate buyers often ask

Why do some Hillsborough homes sit on the market for years?

Very large estates have a small buyer pool, and some are priced ambitiously. One Ralston Avenue listing had been on the market for more than 1,300 days in November 2026. Homes priced in line with recent sales usually move much faster.

Is it better to buy in spring or fall?

Inventory is too small for strong seasonal rules. It is more useful to watch the specific streets and lot sizes you want and be ready when the right home appears.

Do Hillsborough homes ever sell well above asking?

Yes, mostly under $12 million. In the past year, several sold 5% to 21% above their list price.

Browse current Hillsborough listings

Inventory changes week to week, so live data is the best guide. You can browse current homes for sale in Hillsborough, along with pending and recently sold homes and a guide to each neighborhood.

Market figures are from Highnote360’s listing data (MLSListings), as of November 3, 2026.

About the author: Mark Choey is a real estate broker with Christie’s International Real Estate San Francisco and the founder of Highnote360.