Healdsburg had good bones, and today homes in the city are highly sought after.


It wasn’t all that long ago that Healdsburg was a rather rundown vacation town for those seeking affordable relaxation on the Russian River. In fact, it was the second sister to the more popular Russian River resort towns of Guerneville, Monto Rio and Rio Nido.

Not anymore.

Healdsburg has left those towns in the dust and has become what some call “the Hamptons” of Northern California’s wine country. And the homes for sale in Healdsburg are the furthest thing from the dogeared holiday cabins of old.

Healdsburg: Hip, Sophisticated Yet Retaining its Small Town Charm

Making your home in Healdsburg will mean you have landed in one of America’s favorite small towns. Healdsburg had good bones, and today homes in Healdsburg are much sought after because quite a lot of people want to buy a home in the wine country. 

With about 12,000 residents, Healdsburg's popular town square – known as The Plaza – is a block of green space with Redwood trees and featuring a central gazebo that hosts summertime concerts. It also serves as the community's central gathering place with kids, dogs, retirees and young couples sitting on its many park benches. 

Today it is ringed by blocks of upscale hotels, boutiques, tasting rooms and eateries that draw foodies from around the world. Visitors come for the farm sourced food, the wine, bicycling events and the shopping. 

So, Healdsburg has been discovered, but it’s not overrun. Besides the laid-back atmosphere, the central shopping district, world class wineries on Dry Creek Road and throughout Alexander Valley are frequented by both locals and visitors alike.

Michelin Stars & Stars of the Stage

Living the good life in Healdsburg isn't a difficult goal and it continues to get better. Great restaurants abound. There are too many to mention - include Madrona Manor, which boasts a Michelin star, the adventurous Barndiva, the tony Single Thread and Valette, to name just a few.

Nightlife is centered on the Raven Performing Arts Theater, which hosts jazz, rock, and Broadway musicals.

The Russian River shares its banks with Healdsburg as it meanders around this city. Each summer season sees hundreds laying on Memorial Beach - near the newly restored Healdsburg Bridge.

But before Healdsburg became a mecca for the upscale good life, it, like other western towns in the 1800’s and early 1900’s, experienced its own version of the wild, wild west.

Western Justice: Hang’em High

In the 1800’s, Healdsburg and the surrounding area was not as lawless as other western towns of that era like Tombstone or Dodge City. There were some rough and tumble pioneers, adventurers and, of course, outlaws, but many of the residents were transplanted Missouri farmers who lived prosperous but routine lives.  

In those days, the  criminal justice system was often spotty if it worked at all. Vigilante groups would often fill the vacuum had occurred a number of times during San Francisco’s wild and lawless Gold Rush period. In northern

  A little over a hundred years ago, one of the last and most noted acts of “citizen” vigilantism took place in Healdsburg and Santa Rosa . A local sheriff and two deputies were shot down by three outlaws. Locals were outraged and wanted justice – now. When the murderers were brought to jail, over 3,000 local residents tried to storm the jailhouse, but they failed.

A  group of men called the Healdsburg Vigilantes gathered at the Standard Machine Works on Healdsburg Ave. to plan a break-in of the jail.

On the night of the of the attack , dozens of local citizens made their way to the Santa Rosa jailhouse. They brought with them acetylene torches to breach the iron bars.  Each man had an assigned roll and like clockwork they quickly broke into the jailhouse, removed the three outlaws and hung them from a tree at a nearby cemetery.

 No one was ever caught, and the event was hush-hushed for decades. Despite Healdsburg’s current image of sophistication and refinement, it clearly wasn’t always that way.

Buckle of the Prune Belt

When Prohibition was enacted, most of the area’s wineries shut down. Vines were replaced by fruit trees. Some not-too-good copywriter came up with a new advertising tagline for Healdsburg; “The Buckle of the Prune Belt”. Unfortunately. The term stuck but thankfully by the 1970’s, most of the prunes trees were removed with vineyards replacing them. Yet another industry was born.

Buying a Home in Healdsburg

Healdsburg is hot and so is its real estate market. There’s no better symbol of this than new condo complex that is currently being built in downtown Healdsburg were studio apartments start at $1 million and go up to a whopping $8.5 million.

Fortunately, not everything home for sale in Healdsburg is that expensive. However, if you’re looking to buy a winery in Sonoma County, properties in Dry Creek & Alexander Valley where, depending on vineyards and acreage size, can be for sale in the $3 – 25+million range.

Real estate in Healdsburg takes many shapes and styles, ranging from Victorians in the Plaza District to one of a kind architectural masterpieces set in the rolling hills that surround the town. Cute late 19th century houses – cottages, bungalows, etc. - are for sale and can be found throughout Healdsburg.

Currently (March ’23), there are thirty-four homes for sale in Healdsburg*. Of these, the least expensive is a nice 1,200 sq ft California ranch style home with two bedrooms and two bathrooms. The most expensive home is a beautiful four bedroom, six bathroom house on 16-acres selling for $8,750,000. It’s 5,700 sq ft and even has a lake.

In fact, there are four homes on the market for over $6 million. However, the median price of a home is $1 million as compared to the national median home price of $363,000. Finally, homes sell pretty fast in Healdsburg taking just over a month to sell.

From a modest vacation spot in the seldom visited wine country, to an upscale, international vacation destination, Healdsburg has come quite a way.

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