Healdsburg has just eleven thousand or so residents but in spite of that small package it offers an amazing historic downtown area with a world class foodie scene, beautiful suburban neighborhoods, and finally some of the most stunning rural vineyards and farms you can live amidst if that’s your preference. If you choose to live in a small town but want that town to deliver an amazing lifestyle you could hardly do better than Healdsburg. 

Three-for-One

The Best Thing About Healdsburg?

So this is a tricky one. What’s it like to live in a town so beautiful and iconic that everyone flocks there to visit? If you live in Healdsburg, at least in the Downtown, expect to see lots of tourists enjoying the art, food and wine at the local spots. Is this a bad thing? Since many locals earn their living from the hospitality industry most would argue its a good thing. We’ll suspend judgment and simply note that plenty of locals will moan about tourists (and SF tech types) ruining the humble town they remember. 

Tourism

The Worst Thing About Healdsburg?

Healdsburg is often described as a haven for wine lovers and a theme park for grown-ups with world class restaurants and wineries. It is though a tale of two cities as you have second-home owners and airbnb renters mixing with long-time local families and agricultural workers. If you want a suburban family lifestyle – kids in public schools, little league and girl scouts, dogs and playing in parks on weekends, then Healdsburg has that available. If on the other hand you’re looking for a second or retirement home with lots of great wine, meals a short walk from home, and tons of downtown events and boutique experiences (and you have the money to pay for it) then Healdsburg offers that as well. 

A Tale of Two Cities

Lifestyle of Healdsburg 

Pretty much no one moves to Healdsburg to find a job. Unless you’re in the wine or farming biz. And if that’s the case then you’re probably going to live well outside the expensive city confines. Healdsburg is primarily a tourist town and so most people work in the hospitality industry or they’re wealthy tech types working remotely, or they’re empty nesters/retirees looking to enjoy the warm weather and entertaining downtown. If you’re looking for work and aren’t planning to work in wine/farming or hospitality then check out Santa Rosa, about 15 miles south. 

Worklife of Healdsburg

The prices of homes in Healdsburg are mind-boggling for those unfamiliar with Bay Area realty. A median price for homes of $1.8mm makes it out of reach for most. If you do have the bucks though and are empty nesting or retiring then Healdsburg is pretty wonderful. It checks off a lot of boxes for most: year-round warm weather, good walkscore to downtown culture and entertainment, and a population looking to enjoy the fruits of their labor. 

Fruits of Your Labor

Why You Should Move Here Now? 

Downtown Healdsburg is a wonderful area of the town to live if you can find an apartment to rent or a home to buy. It’s the center of the cultural and social experiences available, all within a short walk. If you’re a young professional in the hospitality biz or otherwise then this is really your only choice. There are several apartment building options, both standalone and above the downtown retail. The most notable area of downtown is on the south side, which is where the largest, most historic homes are and where those who want to live just a few minutes from the city center and can afford the prices. 

Young Professionals/Empty Nesters/Retirees/2nd Homers

Downtown/Healdsburg Plaza

A great neighborhood close to downtown on the northeast side of town that has homes closer to $1.2mm or less. Your walk to the downtown plaza is a mile or so and while the are itself is largely residential you are surrounded by parks and open spaces like the Healdsburg Ridge Preserve to the northwest, which has tons of hiking and panoramic views of the Russian River Valley. You also have Riverfront Park, along the banks of the Russian River, just south of the area. Finally just east of The Lanes is Fitch Mountain Park and Preserve, another amazing hiking trail option that winds through the redwood trees and also has stunning views of the area. 


Families

The Lanes

If you’re looking for a 55+ community in the area then check out **[River’s Bend](https://www.myriversbend.org/home/)**. You get beautiful homes at significantly lower prices than other neighborhoods and you’re just a mile from Healdsburg Plaza. River’s Bend sits at the base of Fitch Mountain and the Russian River so if you’re a hiker, walker or paddler, you could hardly pick a better location. The neighborhood is primarily two bedroom, single story homes and you get wonderful common green spaces for daily walks or community events, and a beautiful pool, tennis court, and clubhouse for parties and dining. 

55+ Empty Nesters/Retirees

River's Bend

Healdsburg

**Moving to Healdsburg or Windsor**

Hey there fellow upper right-er!

Moved to Sonoma County from Connecticut just over three years ago, and I've lived in Sonoma, Kenwood and now Sebastopol.

You're moving to a pretty killer spot if you end up in Healdsburg or Windsor. You'll be about 30 minutes from the coast and surrounded by more places to hike and be outside than you can possibly count. I can't get enough of the hiking trails in the Sonoma Valley. Places like Sugarloaf and Annadel are incredible.

The beer here isn't too bad either. You have Russian River in Windsor and Santa Rosa, Lagunitas in Petaluma (about 15-20 minutes down the road) and tons of different little craft spots to satisfy your need for a brew. Personally, I'm a huge fan of Moonlight and Henhouse.

I've never had too much trouble meeting folks out here (pre-COVID). There are tons of meetup groups that are active, the bar scene is pretty diverse and there's quite a few younger people working in the wine industry. Just keep your eye out for the tourists... there'll be a ton of them once we open back up.

Now for the downsides: the fires can be very prevalent during the summer. Get that go-bag ready.

Housing is expensive too. If you're looking for a one bedroom, you should plan a modest chunk of income for rent. Especially if you wanted to live in a trendy area like down by the square in Healdsburg. You might have a little more luck in Windsor for something affordable and Santa Rosa is the cheapest by far.

Cool brotha', if you're ever down to grab a beer and listen to some Phish when this whole thing is over, you've got a kindred spirit in the county.

**Relocating to Healdsburg area**

I used to work for a company based there but I never lived there. Healdsburg basically rolls up their sidewalks at night (even pre-COVID). It's a small town dominated by old money that likes to keep things the same. From what I was told, 4 or 5 old money families own about 90% of downtown Healdsburg so what they say, goes. That might be a good thing or a bad thing depending on your perspective, I'll leave that up to you, but if you are expecting a vital night life and more access to people your age, go further south to Santa Rosa.

**What I Wish I Knew BEFORE Moving to Healdsburg California... (PROS AND CONS)**

Healdsburg, California

The Prune Packers

Looklyloo Score: 86

We're on it!