For years, the two blocks near the Hillsdale Caltrain platform sat behind chain-link, a stubborn gap in a neighborhood that otherwise looked finished. You could walk from Town Square to Bay Meadows Community Park and back and forget those blocks existed. Then you'd pass them again and remember: this place still isn't done.
In February, that changed. Developers Stockbridge and Wilson Meany announced they had signed leases for the final two commercial parcels at the 83-acre site, closing out a redevelopment plan that started when Stockbridge acquired the old Bay Meadows horse-racing track in 1997. The tenant is described only as "a major technology tenant." The buildings themselves may take a while longer to go up. But the question that has followed this neighborhood for two decades, whether it would actually get finished, now has an answer.
A Deadline That Kept Moving
The original development agreement was supposed to run its course by the end of 2023. Pandemic-era delays to the office market pushed that timeline back, and the City of San Mateo approved a three-year extension that stretches the legal window to December 20, 2026. That's the deadline Bay Meadows was racing against. The February lease signing beat it by ten months.
Wilson Meany managing partner Chris Meany put it plainly when the deal closed:
"Bay Meadows has fulfilled the vision we had some 20-plus years ago."
That's not a small claim for a neighborhood built on a former racetrack. According to the developers, the finished project totals more than 1 million square feet of office space, nearly 1,000 homes, 18 acres of parks, a private high school, and over 40,000 square feet of retail. Those numbers only matter if you know what they replaced: a horse track that closed as the racing industry declined, and a Peninsula stretch that had no residential density, no park network, and no reason for anyone to get off the train there.
None of this means the neighborhood is free of friction. At an August 2025 Planning Commission review, commissioners found the developers compliant with the ongoing agreement, but some residents raised concerns about a recent change to off-street parking that affected day-to-day life in the finished blocks. A neighborhood can hit its twenty-year finish line and still have residents annoyed about where they're supposed to park. Both things are true here.
What Was Already Finished While You Weren't Looking
Here's the part that gets lost in a headline about office leases: the parts of Bay Meadows that residents actually use every day have been complete for years. The office blocks were the last domino, not the first.
The park system alone runs to 18 acres, and it's not one big lawn. It's a string of small, specific spaces:
- Bay Meadows Community Park, which the city describes as home to a full-size soccer field, a walking path that loops the perimeter, and a landscaped pond that hosts local wildlife
- Persimmon Park Community Garden, where residents can rent a plot rather than just admire someone else's tomatoes
- Paddock Park, the smaller kids' space tucked closer to the housing blocks
- Landing Green Park, built for bocce rather than soccer
That's a park system built for four different ways of spending a Saturday, not one generic green rectangle. And it connects directly to the San Francisco Bay Trail, so a short walk from your front door turns into as long a ride as you want.
Where Town Square Actually Lives Now
Town Square is the part of Bay Meadows that never waited on a construction deadline. It's anchored by a sculpture from artist Jeppe Hein, and on any given evening you'll find the beer garden at Fieldwork Brewing Company doing steady business alongside Blue Bottle Coffee, the Mediterranean small plates at Bahche Mezzehouse & Wine Bar, and smoothie bowls at Sidewalk Juice. The Breakfast Club at Midtown San Mateo handles the weekend brunch rush. Whole Foods anchors the grocery run. None of that required the office towers next door to be finished first.
That's worth sitting with for a second. The neighborhood's identity, the reason someone already living here would recommend a coffee spot to a new arrival, was never contingent on those last two parcels. What the February lease signing actually closes is a different kind of uncertainty: whether the promises made in the original master plan would ever fully materialize, or whether Bay Meadows would be permanently "almost done" the way some big Bay Area developments seem to stay for a decade past their announced completion date.
The Two Habits Worth Adopting This Month
If you already live here and haven't built these into your week, this is the excuse to start.
- The Basecamp Run Club meets twice a week, Wednesday evenings at 6pm and Saturday mornings at 8am, starting at 3050 S. Delaware. There's no membership fee and no signup required. Routes run 2, 3, 4, or 6 miles depending on how the week has gone, and the group tends to end up back in Town Square for coffee or a beer after.
- The Sunday farmers market, held year-round at 222 East 4th Avenue in downtown San Mateo, is close enough to reach by bike from Bay Meadows without much effort. Residents describe leaving with fresh flowers and produce more often than a specific shopping list, which is probably the correct way to use a farmers market.
Neither of these routines needed the office parcels to lease. They existed because enough of Bay Meadows was already built to support them: enough housing to fill a run club, enough foot traffic to keep Town Square's restaurants open on a Tuesday, enough of a critical mass that a neighborhood built on a racetrack started to function like one that had been there for generations.
What Changes Now That the Deal Is Signed
The practical answer, for someone who already has a key to a place here, is less about a new amenity opening and more about a kind of closure. The fencing around those last two blocks will come down eventually. The question of whether this development would actually reach its finish line, a question that's been open since before some current residents moved in, has been settled. Whatever gets built on those final parcels, the shape of the neighborhood around it is locked in now.
That's a strange thing to feel relief about if you didn't grow up watching a horse track get torn apart and rebuilt in phases. But if you've lived through even the last few years of "final two blocks" headlines, there's something satisfying about a press release that finally says the word "final" and means it.
If you're curious what any of this means for property values in Bay Meadows or the surrounding Hillsdale Caltrain corridor, or you're weighing a move within San Mateo now that this chapter has closed, The Canlas Brothers know this stretch of the Peninsula block by block. Schedule your free Home Strategy Consultation and we'll walk you through what a twenty-year build-out actually means for what you'd be buying into today.
