Healdsburg

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.”

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 you’ll see 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, you’ll see plenty of hobby vineyards, high-end custom kitchens, wine cellars and infinity pools, as recent transplants create their own wine-country resorts at home. The coolest temperatures are found in the rustic, redwood-shaded Del Rio Woods, which traces the Russian River. To the open, rural north, housing includes attached town houses, 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.”

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. You’ll find (slightly) more budget-friendly fare 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 customer’s names; it’s fun to see people light up and feel special there.” Beyond downtown, you’ll find family-owned spots like Davis Family Vineyards, with picnic tables beside the Russian River; modern-chic Comstock, surrounded by Dry Creek vineyards; and the elegant Alexander Valley sprawl of Jordan, renowned for their French-style chateau. Local wines are ubiquitous on the Healdsburg Plaza during summertime Tuesday nights, when locals gather live music on the bandstand and picnics on the lawns.

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. The biggest playground is at Giorgi Park, your dog will love the gated run by Villa Chanticleer, and you’ll see your neighbors out walking the Foss Creek Pathway along the former railroad tracks.

You can stop and get to know those neighbors at the glorious, seasonal downtown Healdsburg Farmers Market, held Tuesdays around the Plaza and Saturdays in a nearby parking lot; you’ll be able to buy some of the most colorful produce on Earth here, mid-April through December. You can get all your staples at the Safeway in Vineyard Plaza; pick up organic, sustainable and homeopathic everything at Shelton's Natural Food Market; or delight in the gourmet prepared foods and adorable homewares at Big John’s.

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. If your kids are just average students, though, they run the risk of being left behind. Consider Windsor High School, which is just five minutes down the 101.” Private local options include The Healdsburg School, where focused K-8 classes are no larger than 10 students.

Blending a friendly small-town feel with the prestige of world-class California wine country, living in Healdsburg could make you feel like you’re on vacation every day.

Written By

Tina Davis

Photography Contributed By

Luke George