Windsor offers the stunning beauty of the wine country but with fewer tourists and a more relaxed vibe than the wine country cities of Napa or Sonoma. The town is most notable for its utterly charming Old Downtown which is filled with excellent restaurants, cafes and local boutiques that surround the Windsor Town Green public park - where year-round music, farmers’ markets and festivals are held.  It also has plenty of local breweries and vineyards where locals and visitors hang together. You also get a wonderful farm-to-table foodie scene owning to the region’s rich agricultural output. 

Charm

The Best Thing About Windsor?

We could put costs down for virtually any northern California city but it’s worth noting for Windsor since you’re getting pretty far north of the tech scene for the prices for homes to be ~$850k. Windsor is less of a second home city for the wealthy, like Healdsburg or Guerneville, so the locals tend to be genuine locals and that housing price can be a tough pill to swallow. Cost of living in general is also pricey in the area but given you’re likely considering among different Marin or Sonoma county cities this will likely be no shock. 

Costs

The Worst Thing About Windsor?

The Town Green, in the center of Old Downtown, is a big driver of the community lifestyle in Windsor. It serves as the year round center of city activities with farmers’ markets, festivals, city celebrations and most notably the Annual Summer Night on the Green Concerts. While families go about their business, going to parks and good schools, and enjoying the amazing Sonoma County outdoors, it is really the Green where the lifestyle of Windsor is most exemplified. 


Lifestyle of Windsor

Plenty of people live in Windsor and commute to Santa Rosa or other Sonoma county jobs but if you want to live and work here then you’ll probably working in the wine production or general agricultural/farming industries. You could also find a gig in the growing hospitality and tourism industry. Much to the chagrin of some locals Windsor has been growing its tourism biz and so job opportunities in service are on the rise. 

Worklife of Windsor

While other Sonoma cities have exploded in popularity and tourism Windsor remains a bit off the radar. There is some desire among more growth-minded locals to spike the size of the local and tourist community and so if you want to get in on an amazing city before it is untouchable then make your move now. 

Before The Rise

Why You Should Move Here Now?

While Windsor is a small town, the energy of Downtown/Town Green Village draws young professionals that choose to live north of Santa Rosa as well as empty nesters and retirees who want to live in a beautiful, albeit small downtown with lots happening to keep them entertained. There are single family homes in the area but also plenty of condos and apartments for those looking to rent or downsize. As was noted there is a never-ending series of events happening in the Town Green and plenty of good restaurants, bars and boutique shopping to keep you occupied. 


Young Professionals/Empty Nesters/Retirees

Downtown/Town Green Village

If you’re craving a family-focused gated community kind of experience then check out Lakewood Hills. You get beautiful single-family homes, tree-lined streets with big yards, walking paths, tennis courts, a swim center and fishing and water sports on two private lakes. It’s also located on the western side of the city so you have easy access to towns like Guerneville and even better, the Pacific Ocean. 

Families

Lakewood Hills

East Windsor is a mix of families, professionals and retirees. Single-family homes at slightly better prices than other Windsor neighborhoods, townhomes and condo/apartment options means families, and SINKs/DINKs can all find a place to live here. You get a break from the energy of Old Downtown here if you want a bit quieter of a pace but there's plenty of parks like Lakewood Meadows, Pleasant Oak, and Robbins means there is tons of room for the kiddos to run, bike and play. East Windsor also has its own commercial options for dining and shopping and excellent public schools so families love the neighborhood.

Families/DINKs/SINKs

East Windsor

Windsor

**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.

**Moving to Healdsburg or Windsor**

Wal-mart/Home Depot are in Windsor, and the other sort of businesses you might expect based on that. Basically Windsor is the outskirts of Santa Rosa and there is the highway and convenient shopping. Also if the last couple years are any indication, wildfires. So from summer through early winter might keep a bag prepped as there is a good chance you will be evacuated at some point. (we were evacuated twice in 2020). I'm lucky in that I rent from a friend and haven't tried anywhere else, so not sure what others are paying, so not much help there. Might try google maps and zoom in and have a look around.

**Living In Windsor Ca - Everything You Need To Know (VLOG TOUR)**

**Moving to Healdsburg or Windsor**

Born and raised in the area and down in LA now myself. Given the above, I think you'd be in a good position. It does at times feel remote from other people our age, but thankfully San Francisco/Oakland is only a short drive away. There are healthy bar scenes in Santa Rosa, Petaluma and Cotati (when SSU is in session) but even if that's not your thing there are definitely other social things to do (20/30 club, wine tasting groups, etc. Wednesday Night Markets in SR). In terms of location, I think stick close to Santa Rosa, Windsor, or Petaluma for the younger crowds. Otherwise you're mostly going to find families and older couples. Petaluma is a bit of a commute though. The nature though is truthfully the selling point for me. Living in LA, I never take it for granted whenever i'm home. I could go on and on... happy to answer any questions!

Windsor, California

Pony Express

Looklyloo Score: 84

We're on it!