Windsor is a community that has close ties to its agricultural roots.


Windsor is a community that has close ties to its agricultural roots. Rolling hills dotted with live oaks and acres of vineyards surround the town’s core properties. Windsor has done an incredible job of preserving its  heritage while looking to the future.

The downtown area offers a mix of shopping and housing centered on the four-acre “Town Green.” In an echo of times past, some of the owners of the restaurants, bookstores, and boutiques proprietors live above their stores here as well. It is one of the most popular places to buy a home in Windsor.

​​​​​​​Today, the Town Green Plaza serves as a vibrant meeting place and a focal point for local activities, including a farmers' market held Thursdays and Sundays, where you'll find top chefs from Bay Area restaurants sourcing the ingredients for that night's menu. Each June, Windsor hosts the Sonoma County Hot Air Balloon Classic, an event that draws dozens of balloonists and thousands of spectators.

And of course, wineries and acres of vineyards surround Windsor. It’s the home of many well known wineries including Le Crema, Martinelli, Windsor Oaks and Sonoma Cutrer Vineyards.

Windsor is 3-miles north of Santa Rosa and a few miles south of touristy Healdsburg which attracts visitors from throughout the world. It is the epicenter of Sonoma’s wine country with many  $600 a night hotel rooms and Michelin-starred restaurants.

Named After a Castle

The first European to settle in Windsor was an English Pony Express rider Hiram Lewis. He named the town after Windsor Castle because he thought the area looked very much like the area surrounding the British monarch’s home.

Once the train arrived in Windsor in 1872 many people settled in the area from San Francisco which is just 63-miles away. Today, 28,600 people call Windsor home.

Many of the surrounding vineyards used to be dotted with fruit trees – apples, prunes, etc. – but as Sonoma wine became world renowned, these were pulled out and replaced by grape vines. In fact, there is hardly a patch of empty pastureland that isn’t now planted with rows of vineyards.

Hogan’s Heroes: German POWs in WWII

For those of a certain age, the 1960’s TV  comedy show Hogan’s Heroes depicted Allied prisoners of war during WWII hoodwinking fumbling German guards. Though it may be hard to believe, in real life, something similar occurred in Windsor. From 1944 to the end of the war, Windsor held over 1,000 German POWs at a prisoner of war camp just outside of town.

These prisoners were bought to Winsor to help local farmers harvest their fruit crops. Apparently, by this stage of the war, the confined Germans were quite happy to pick prunes and apples instead of dodging Allied bullets. In fact, there were a number of occasions where guards left their rifles in the fields only to have them retrieved by German prisoners.  

There were also a number of escapes, but these usually entailed Germans who snuck into town to watch a movie or who hitchhiked to the coast to see the Pacific Ocean. None, as the records show, ever attempted to escape so they could return to the Fatherland. In fact, a number returned after the war to call Windsor home.

Buying a Home in Windsor

Windsor has only nineteen homes on the market (3/23*) today. They range in price from $2,850,000 for a three bedroom, three bathroom ranch style home that is 3,800 sq ft. It also has 13-acres of vineyards. On the other side of the market, you can buy  a 1,500 sq ft two bedroom, three bathroom home for just $660,000.Median prices in Windsor are, as of early 2023, $814,000.

Whether you are buying a home in this Wine Country paradise, or selling a home in Windsor, you’re likely to complete the transaction fast because it takes only a little over two months once they are put on the market.

You’re also likely to become a bit of a wine snob because after tasting the regions fine wines, you are unlikely to drink anything else, German beer included.

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