Historic Healdsburg evolves into a wine and dining hotspot
At the junction of three gorgeous wine valleys – Russian River, Dry Creek, and Alexander – rural-suburban Healdsburg might as well be listed under “wine country" in the dictionary. Named for its mid-19th-century founder, Harmon Heald, Healdsburg has long been home to historic houses, a lively central plaza, and small-town vibe that welcomes families and retirees. Today, though, this is a popular tourist destination with some of the most celebrated wineries and restaurants in California, much less Sonoma County. “Looking at it now, it’s amazing to think this used to be a simple redneck town, as anyone who grew up here would tell you,” says Julia Lander, who’s lived and worked in Healdsburg since 1996. “There are still farmers and families who’ve lived here for generations, but the nature of the town, from who lives here to what you can spend your money on, has changed a whole darn lot since I arrived.”
Luxury homes and hobby vineyards shape Healdsburg’s market
Overall, Healdsburg real estate prices average $1.7 million, while a well-preserved Craftsman or Victorian within walking distance of charming Healdsburg Plaza averages $2.8 million. Elsewhere in town, there are modest midcentury ranch-style houses; contemporary model homes from the 1980s; Craftsman-style homes from the 1990s through right about now; and the occasional jaw-dropping villa. Subdivision developments have generally gotten smaller, while individual estates have gotten larger, often topping 4,000 square feet. Along winery byways like Dry Creek Road, there are plenty of hobby vineyards, high-end custom kitchens, wine cellars and infinity pools, as recent transplants create their own wine-country resorts at home. To the rural north, housing includes attached townhouses, suburban subdivisions and brand new mansions; some of the latter dot the 258-acre sprawl of the Montage Healdsburg resort, which includes super-modern homes (and homesites) rimmed by low-water plantings and long-mature trees.
Condo developments like Foss Creek enable living near downtown at a relative bargain, while construction is ongoing at downtown’s Mill District, a 10-acre mixed-use development set just east of the Plaza. "Mill District is coming together fast,” says Lander [in May 2023], “and is already driving up area real estate prices. The Canopy building is already up, with luxury apartment condos that are almost $2 million for a one-bedroom, one-bath,” continues Lander. “The low-income apartment building is almost done, too, which is much needed.”
Michelin-starred meals and casual eats share the spotlight
Downtown Healdsburg has been a desirable address since the railroad arrived in 1872, but today it’s full of lauded restaurants and top-notch winery tasting rooms and upscale galleries and boutiques — almost all of them locally owned. “Long ago, the Healdsburg City Council decided that almost no big box stores or chains would be allowed here,” says Lander, “which gave small, locally owned businesses a fighting chance. That decision has paid off, because we're now famous for some of those businesses.”
Big-ticket restaurants include Michelin-starred Single Thread, acclaimed for its multi-course menus using produce harvested from their own Dry Creek farm, and The Matheson, a gleaming, multi-level California-cuisine and sushi hotspot from local chef/restaurateur Dustin Valette. Slightly more budget-friendly fare is at weeknight favorites like Bravas Bar de Tapas, with its cava sangria and light-strung, tree-shaded patio; and Oaxacan-style El Farolito, part of a local dynasty of Mexican restaurants. Lander asserts that “Flying Goat Coffee makes the best espresso in town — period,” while watering holes range from casually upscale Duke’s Spirited Cocktails to rough-and-tumble dive bar John & Zeke’s. “Just know that if you don’t drink or aren’t up for a $200 dinner, the sidewalks here roll up at 6 p.m.," says Brooke Wright, who vacationed in Healdsburg for years before moving here in 2016. “Fortunately, though, the parklets that popped up during Covid are staying, which makes it feel even more friendly and social during daylight hours.”
Downtown winery tasting rooms are part of that charm offensive, from exclusive respites to de facto living rooms. “Portalupi is my favorite,” says Wright, “because it’s distinctly non-snooty. The staff is so friendly, and they always remember their customers’ names; it’s fun to see people light up and feel special there.” Local wines are ubiquitous on the Healdsburg Plaza during summertime Tuesday nights, when locals gather for live music on the bandstand and picnics on the lawns. As for day-to-day shopping, Safeway is in Vineyard Plaza.
Veterans Beach and Parkland Farms offer active escapes
Aside from wine, there’s plenty to do. Head to Healdsburg Veterans Memorial Beach for a kayak, SUP or float session on the river (followed by a frozen treat from Amy’s Wicked Slush) or tee off at the Healdsburg Golf Club. In the Parkland Farms subdivision, the peaceful, 150-acre Healdsburg Open Space Preserve offers challenging, dirt-packed hiking trails up grove-shaded hills and across grassy fields.
Healdsburg High supports both AP and vocational students
Local public schools include Healdsburg Elementary, highly rated for its students’ strong academic progress and test scores; and Healdsburg High, which earns average marks for its test scores but a whopping 9/10 from GreatSchools for students’ college readiness. About the high school, Wright cautions, “Having sent two of my kids there, I’d say it’s great for AP students who are driven to succeed, and kids who plan on pursuing culinary, vineyard or construction jobs; the work-training programs are really strong.” Private local options include The Healdsburg School, where focused K-8 classes are no larger than 10 students.
Photography Contributed By
Luke George
