
Mathew Humphrey has a problem most landlords in Healdsburg must envy—almost 120 parking spots just steps from downtown, with a steady stream of traffic that slows down for the Roundabout.
The lot is surrounded by aged but functional buildings that already house some of Healdsburg’s most recognizable businesses, including the Parish Café, the Elephant in the Room and Coyote Sonoma.
But for much of the day, Humphrey said, it’s not full. “The busiest our parking lot gets is probably like a Friday, Saturday night when Elephant in the Room has a band and Coyote has a band,” he said.
It’s with an eye toward making the most of that most valuable of assets—parking in Healdsburg—that Humphrey is filling up the available leases on the property one by one, and staggering their prime hours so the lot is productively filled as much as possible. The highest and best use, one might say, to echo the realtor’s mantra.

Take the Parish Café, at 60 Mill St. There’s the morning trade, with breakfast beignets and chicory coffee. It’s in an older building on one of the three parcels that the Humphreys own—including 177 Healdsburg Ave., current home of the Elephant in the Room, and 44 Mill St., formerly known for Mill Street Antiques.
The Elephant and Coyote both have evening-oriented businesses, with beer, wine and frequent live music. Then there’s JANE Dispensary, which opened in early May, and while it rarely does a huge trade at any given time it is open 9am to 9pm every day and is already profitable, according to Humphrey (a part owner).
The main 44 Mill St. building, where the 15,000-square-foot antiques mall used to be, is in the midst of a significant upgrade and partitioning, with new electrical boards, plumbing, sewer hookups and grease traps. Two of the projected tenants will bring the variety that Humphrey seeks: the celebrated Quail & Condor bakery will move in before the end of the year, as will Acre Pizza, adding Healdsburg to its other Sonoma County locations in Petaluma, Cotati and Sebastopol.
The Quail & Condor is a real “get,” as it were. The popular bakery started during the pandemic, as Melissa Yanc and Sean McGaughey, both alumni of SingleThread, began selling baked goods at farmers’ markets. When they opened their storefront on Healdsburg Avenue their popularity exploded; a dinner service was started (Troubadour) and the bakery began looking for a larger space.
“We do have a lot of parking, but we are still very conscious and working with the city, planning to make sure that we’re not overwhelming the system,” Humphrey said. “That’s why Quail is such a good fit, being a morning business.”

He shifted in his seat. “I’m looking out the window at the property now and the parking lot’s empty … . We feel like we can absorb the roughly 200 customers that Quail will get from 8am to noon every day without a problem. It’ll help bring some vibrancy to the parking lot.”
That leaves one significant space of 1,500 square feet, said Humphrey, that would be perfect for a tasting room. The remodel he’s doing will be plumbed for such a use, and while a conditional use permit would be necessary for a tasting room, no other tasting room exists south of the Roundabout. So 44 Mill St. is as good a location as any and better than most.
The Humphrey family—grandfather Wayne recently passed away (though his wife Lorraine is still engaged), 70-year-old father Steve and Mat, 42—have owned the properties since 1977. A dairy was here at one point, as was a plywood factory and a True Value hardware. The Humphreys tried various small businesses over the years, always focusing on maximizing the property but doing so “synergistically,” said Mat Humphrey.
“We’re really trying to keep it simple, more of a warehouse-type atmosphere,” he said. “Our main inspiration was when Oxbow in Napa opened up. My dad and I went over there, walked around and said, ‘This is exactly like our building. We could do the same thing on a different budget, different scale; do it slowly over time.’”
Developer Steve Carlin opened Oxbow in Napa in 2007. He has also been involved in other significant projects, such as the San Francisco Ferry Building and Oakland’s Jack London Square, and operates at a financial level somewhat above what an old lumber yard on Mill Street can deliver.
“We’re trying to do things in accordance with cash flow, you know—keep it all in-house,” the youngest Humphrey said. “Getting to know everyone at the city and just kind of figuring out not just how to do this one job, but letting them know we have a plan down the line to do more … and making sure that we’re not shooting ourselves in the foot for bigger projects down the line.”

That means one can find local charm at the newly branded The Row, at 44 Mill St. As well as the two music venues, other tenants include Yoga on Center. It finally re-opened a Healdsburg studio last year at 44C Mill St., after more than two years of searching for a replacement to the original 401 Center St. location.
Top Cheer Elite gym and dance studio moved from 44C to 44B, around the corner, with its door now facing south toward the parking lot and Coyote Sonoma.
Speed of Sound Live, a music school that bounced around a couple of Healdsburg Avenue locations over the past several years, finally landed at 44A Mill St. It’s the corner spot next to the Mill Street entrance, where a new yellow, red and white Mill Street Row sign appeared a few months ago.
When Quail & Condor and Acre Pizza move in, The Row will have an enviable list of consumer-friendly, local businesses on one three-acre lot, with 119 parking spaces, at the Roundabout in Healdsburg.