Hillsborough just recorded a $70 million home sale. Median prices have risen sharply over the past year, inventory has tightened, and more than half of homes in one recent reporting period sold above asking. If you're a homeowner, that might sound like the perfect time to sell. If you're a buyer, it might sound like the worst time to start looking.Having lived in both Hillsborough and Burlingame, and spent more than 25 years working with buyers and sellers throughout the San Francisco Peninsula, I've seen firsthand how much location, lifestyle, and the details of a property matter here. A home near the Burlingame border and a secluded hillside estate may be only minutes apart, yet attract entirely different buyers. That's why a citywide statistic is a starting point, not an answer to what your home is worth or what you should offer on the next one.
Are Hillsborough Home Prices Still Rising in 2026?
According to Redfin's rolling three-month figures ending September 2026, Hillsborough's median sale price reached approximately $6.55 million, an increase of 27.7% compared with the same period in 2025. In a community where homes already sell for millions, that is an attention-grabbing number.But here's where I would caution homeowners: it doesn't mean your particular home appreciated 27.7%. Hillsborough has relatively few sales, and the mix of properties closing in any given month can vary enormously. A handful of exceptional estates can lift the median even if prices for otherwise comparable homes haven't moved nearly as much.Consider October. The reported median sale price was approximately $6.075 million, compared with $6.807 million in October 2025. Yet over the 12 months ending in early November 2026, the median increased approximately 15%, from $5.564 million to $6.4 million. Those figures tell different stories because they measure different windows and different homes.Is Hillsborough a Buyer's or Seller's Market Right Now?
The supply numbers suggest sellers have had an advantage in many parts of the market. [real estate agent.com](http://real estate agent.com) reported 26 active listings in September 2026, about 16% fewer than a year earlier. An MLS-based report estimated 1.5 months of supply, down from 3.8 months in September 2025. Redfin's rolling three-month figures also showed approximately 53% of sales closing above asking price, with an average sale-to-list ratio around 103%.That sounds like a seller's market, and in some price ranges it is. But I don't believe in telling every seller that low inventory gives them permission to price however they please. Buyers at this level are sophisticated. They compare options, understand renovation costs, and recognize when a listing is priced for the owner's expectations rather than the market.The question I ask isn't simply, "Is Hillsborough hot?" It's, "How many homes compete directly with yours, and how many qualified buyers are looking for that specific kind of property?" That's the market that matters.What Do Active, Pending, and Sold Homes Reveal?
A November 2 MLS-based snapshot identified 16 publicly listed houses and three vacant lots, along with eight houses and one lot under contract. That is a point-in-time snapshot, not a live count for November 8. Listing sites can report different totals depending on whether they include contingent homes, land, or properties outside the city limits, so it's important not to mix them casually.Closed sales add another layer. October 2026 recorded 10 sales, versus 15 in October 2025, a decline of one-third. On its own, that might look alarming. But over the 12 months ending in early November, Hillsborough recorded 137 sales, compared with 118 during the preceding 12 months—roughly 16% more.For sellers, I pay close attention to the homes that are pending, not just the ones that have closed. Pending activity can reveal what buyers are responding to right now, although final prices remain unknown until closing. For buyers, I study listings that have been sitting, price reductions, and properties that returned to market. Sometimes those are signs of an issue. Sometimes they reveal an opportunity to negotiate without a crowd.What Does Hillsborough's $70 Million Record Sale Really Mean?
In August 2026, Villa de Verano at 3000 Ralston Avenue reportedly sold for $70 million, doubling Hillsborough's previous reported residential sale record of $35 million. The approximately 12-acre property is not an ordinary comparable sale. Its scale, setting, and amenities put it in a category of its own.It wasn't the only notable transaction. Publicly reported 2026 closings included $28.5 million at 100 New Place Road, $18.77 million at 600 Eucalyptus Avenue, and $12.5 million at 1545 Bellevue Avenue. At least nine identified transactions closed at $10 million or more, together exceeding $182 million. That's a selected group of reported sales, not a verified complete count of every $10 million-plus transaction this year, and it shouldn't be mistaken for a year-over-year total.What interests me isn't simply the size of those checks. It's what buyers are paying a premium to obtain. At this level, another bedroom or a slightly larger kitchen rarely explains the difference. Meaningful acreage, architectural distinction, established landscaping, privacy, usable outdoor spaces, and a location convenient to Silicon Valley and San Francisco are difficult to reproduce.There's also an important marketing lesson for owners of exceptional properties. The right buyer for a Hillsborough estate may live in Atherton, Palo Alto, San Francisco, New York, or abroad. They may not be searching local listing sites every morning. Selling that kind of property requires more than excellent photography and an MLS entry. It requires identifying who would value it most and putting the opportunity in front of that audience.Why Do Some Hillsborough Homes Sell Quickly While Others Don't?
Imagine two homes with similar interior square footage and similar asking prices. One is near Floribunda Avenue, with relatively convenient access to Burlingame Avenue, restaurants, and everyday errands. The other sits on a larger hillside parcel, surrounded by mature trees, with privacy and views. Which is the better buy?Neither, without knowing the buyer.Having lived in Hillsborough, I appreciate the ability to spend time in lively Burlingame or downtown San Mateo and then come home to a quieter, predominantly residential setting. But I also know that what feels wonderfully secluded to one person can feel inconvenient to someone who wants to walk out for coffee or minimize time in the car.Then there are differences that don't photograph well. Is the lot actually usable? How steep is the driveway? How much of the home needs updating? Are there insurance challenges, drainage considerations, or substantial maintenance obligations? How does the floor plan work for the way people live today?Is Now a Good Time to Sell a Hillsborough Home?
For some homeowners, yes. Tight inventory and meaningful buyer demand can create an attractive window, especially when a property offers something scarce and has little direct competition. But I wouldn't advise selling solely because a record was broken across town.I start with a different set of questions. What would your property likely command today? What competing homes are coming to market? What would you need to spend preparing the home? And, perhaps most importantly, what would you actually keep after selling?That last question matters in Hillsborough, where many owners have held their properties for years or generations. Capital gains taxes, property tax implications, and the cost of a replacement home can change the economics substantially. Those decisions deserve coordination with qualified tax and legal advisers, not assumptions based on a neighbor's sale.Is It a Good Time to Buy a Home in Hillsborough?
I wouldn't tell buyers to rush simply because inventory is limited. I also wouldn't tell them to wait for a broad price correction that may or may not arrive. I would encourage them to look closely at the individual opportunities in front of them.A property that's been listed for months may be overpriced, poorly presented, or misunderstood. It may also have a genuine problem that needs careful investigation. A home requiring renovation can offer a path to creating value, but only when the purchase price, construction budget, timeline, and likely finished value make sense together.For buyers considering Hillsborough for the first time, I also encourage spending time in the neighborhoods before choosing a house. Drive the routes you'll use every day. Visit nearby Burlingame and San Mateo. Think about school logistics, privacy, outdoor space, and whether you want a more connected or secluded lifestyle.Which Hillsborough Neighborhoods Offer the Best Value?
I get this question often, and my answer usually begins with another question: value for whom?Lower Hillsborough, particularly near the Burlingame border, can appeal to buyers who want access to Burlingame Avenue and neighboring amenities. Carolands and Skyfarm can offer a very different experience, often emphasizing hillside settings, views, and a greater sense of separation. Other established areas offer their own combinations of traditional homes, generous parcels, mature landscaping, and convenient routes around the Peninsula.One of the best ways to avoid an expensive mistake is to decide how you want to live before falling in love with the architecture. That extra 500 square feet may matter less than the commute, the driveway, or whether the backyard actually works for your family.What Should Hillsborough Buyers and Sellers Watch in 2027?
No one can reliably predict next year's prices, especially in a market with so few comparable transactions. Interest rates, equity markets, technology-sector wealth, buyer confidence, and the number of owners choosing to list will all influence activity.I'll be watching new inventory, the pace of pending sales, days on market, and sale-to-list-price ratios. I'll also be watching whether the market above $10 million continues to produce significant transactions. But I won't assume that strength at the very top automatically carries through to a $5 million or $7 million property.My Perspective: The Most Important Number Isn't the Record
I love Hillsborough for reasons that have very little to do with a price chart. The winding residential streets, mature landscaping, privacy, and proximity to the restaurants and energy of Burlingame and San Mateo offer a balance that's hard to replicate. You can feel removed from the activity around you without being far from it.That lifestyle helps explain the town's enduring appeal. But when you're making a multimillion-dollar decision, affection for a place has to be paired with clear-eyed analysis. The $70 million sale is extraordinary. The rise in the longer-term median is meaningful. Neither tells you, by itself, what to offer or what your home should sell for.If you're thinking about buying or selling in Hillsborough, I'd welcome a conversation about your particular property, neighborhood, and goals. The best real estate advice isn't a prediction designed to sound impressive. It's a strategy grounded in what buyers are doing, what the alternatives look like, and what makes sense for you.**Milana Ostroy**Founder, SERHANT. CaliforniaMilana Real Estate Group25+ Years of Bay Area Real Estate ExperienceOver $700 Million in Real Estate SalesHillsborough | Burlingame | San Mateo | San Francisco | Silicon ValleyMilana Ostroy
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