Why San Mateo's Mayor Keeps Bringing Up Bay Meadows When Talking About the Hillsdale Mall

"Two city blocks that are vacant almost 20 years on." That's how San Mateo Mayor Rob Newsom described the Bay Meadows development to his own City Council last December, in a meeting called specifically to discuss the Hillsdale Shopping Center redevelopment. Newsom represents the district that includes Bay Meadows. He wasn't offering a cautionary tale about someone else's project. He was talking about the neighborhood he watches every week, and he was doing it in a meeting meant to build excitement for the mall's replacement.

That's worth sitting with, because the renderings for what's now called Hillsdale Reimagined are the kind that make a neighborhood feel inevitable: a walkable town center, up to 1,670 new homes, ground-floor retail, a Caltrain station at the edge of it all. The city's own planning file describes demolishing 1.49 million square feet of the existing mall and replacing it with as much as 2.06 million square feet of new commercial space and 2.39 million square feet of new housing. It reads like San Mateo's next great neighborhood, fully formed. The mayor's comment is a reminder that San Mateo has built this kind of project before, on a site less than two miles away, and the result took closer to two decades than two years.

The Reference Point Nobody Asked For

Bay Meadows is the obvious comparison because it is, structurally, the same bet. An aging single-use property, in this case a horse racetrack instead of a mall, gets entitled for a mixed-use neighborhood with housing, retail, and a direct line to Caltrain. City Council approved the Bay Meadows Phase II plan roughly 20 years ago, with an entitlement agreement meant to govern build-out over about 18 years. That agreement expired at the end of 2023. Parts of the site are still not finished. The mayor's comment about vacant blocks wasn't a slip. It was him naming the gap between an approval date and a completion date, using a project he drives past regularly as the evidence.

Sares Regis vice president Andrew Turco, who is part of the development team on the Hillsdale project, pushed back on the comparison at that same meeting. His argument was that leaving half a site undeveloped doesn't make financial sense once housing entitlements are in hand, so the market itself would push residential construction forward faster than Bay Meadows saw. That's a reasonable argument. It's also the same argument every large mixed-use project makes at the entitlement stage, and Bay Meadows made it too.

What Twenty Years Actually Looked Like

The two projects line up closely enough that the comparison holds up under its own numbers.

The pattern in that table is the point. Bay Meadows didn't get the height it was originally pitched at either. Developers proposed nine stories to match the grandstand that used to stand there, and after years of negotiation with residents, the city capped everything at five. The 8-10 story figure attached to Hillsdale right now, and the 160-foot towers shown in early site plans along El Camino Real, are opening numbers in a negotiation that hasn't finished. Nobody should treat them as the building that will actually stand there in 2035.

What the Long Timeline Actually Bought

None of this means the bet failed. Bay Meadows today has condos priced from roughly $1.1 million, townhomes in the $1.5 million to $2 million range, and newer single-family homes from about $1.5 million up past $2.5 million, based on current listings. The Nueva School chose the neighborhood for its upper campus. The Hillsdale Caltrain station sits at the development's edge. On paper, the smart-growth pitch delivered.

It just took the better part of two decades to deliver it, through a recession, a lawsuit from a group called Friends of Bay Meadows, and years where the site was mostly a construction zone bordered by a handful of finished blocks. Anyone who bought early because they believed in the vision waited a long time to see it match the renderings. Anyone who bought a home in one of the older neighborhoods next door, in San Mateo's west side or in Beresford, lived next to that construction the entire time.

The Same Objections, a New Address

The Beresford Hillsdale Neighborhood Association is already raising the concerns that Bay Meadows opponents raised a decade earlier: traffic strain on El Camino Real and Hillsdale Boulevard, and whether city services can keep pace with thousands of new residents. Board member Dana Sahae has specifically flagged the neighborhood's Trader Joe's, noting that residents currently walk to it and don't want it replaced with a higher-end grocery concept. The project's own FAQ page confirms a grocery-sized retail space is part of the plan but stops short of guaranteeing which grocer fills it, since Trader Joe's is a private company and no deal is public.

That's not a criticism of the project. It's the same negotiation Bay Meadows went through, playing out again with a different cast and a different mile marker.

Where the Timeline Actually Stands Right Now

Strip away the renderings and the process looks like this, based on the public record so far:

• 2021: community engagement begins under the name "Reimagine Hillsdale"
• February 2025: a preliminary SB330 application is submitted to the city
• Early December 2025: the formal Planned Development application is submitted
• June 1, 2026: the city deems the planning application complete
• Mid-to-late 2026: CEQA environmental review and the first Planning Commission and City Council hearings are expected
• Roughly four more years after approval before permits clear for the first phase
• A stated city goal of full build-out around 2040

That's a realistic decade before ground actually breaks on a meaningful share of new housing, and closer to two before the full vision resembles the site plan. If you're weighing a purchase near Hillsdale on the assumption that a finished neighborhood is a few years out, the Bay Meadows timeline says otherwise.

What This Means If You're Buying or Selling Near Hillsdale Today

The current market isn't waiting on any of this. San Mateo homes sold for a median of roughly $1.8 million over the three months ending in May 2026, up about 13 percent from the same period a year earlier, with homes typically going pending in around 13 days. Beresford Park specifically posted a median sale price near $2.26 million as of May 2026, up more than 16 percent year over year. Buyers are pricing the neighborhood as it exists right now, next to a working mall, not as it might exist in 2040.

That's actually the useful takeaway. If you're comparing Beresford against other San Mateo neighborhoods, or weighing whether to buy now versus waiting to see what Hillsdale becomes, the Bay Meadows precedent argues against waiting. The neighborhood you'd be waiting for is a decade or more away, and the disruption that comes before it, the demolition, the years of active construction, the traffic studies playing out in real time, is the more immediate thing to plan around. If you already own here and are thinking about timing a sale, factor in that a construction-adjacent stretch is likely at some point in the next several years, the same way it was for anyone who owned near the racetrack site starting in the mid-2000s.

If you're weighing a move-up purchase on San Mateo's west side more broadly, our guide to San Mateo neighborhoods for move-up buyers looks at how the westside pockets compare on their own terms, independent of what happens at Hillsdale.

A Few Direct Questions

Will construction near Hillsdale start soon? Not by most reasonable definitions of soon. Hearings aren't expected until late 2026, and the development team itself has cited roughly four more years for permitting before the first phase can begin.

Is Trader Joe's confirmed to stay? No. The project guarantees retail space sized for a grocery tenant, but the developer can't commit to a specific store since Trader Joe's is a private company that hasn't made a public decision.

Does any of this affect what my Beresford home is worth today? Not based on current sales. Prices in the immediate area were still climbing as of the most recent reporting period, with no visible drag from the pending redevelopment.

If you're trying to figure out what a Peninsula redevelopment like this actually means for your specific street, or you want a clear read on where your home stands in today's market before any of these long-term plans move forward, the Laugesen Team can walk through the numbers with you directly. Request a complimentary market and home valuation, and let's talk about timing that fits your actual plans, not a rendering's.