Rural and affluent, Woodside is the perfect place to be one with nature…if you can afford it.
Woodside has a below average violent crime rate and a below average property crime rate compared to other cities in the United States.
Woodside is a small town of about 5,000 residents incorporated into San Mateo County. True to its name and population size, Woodside has a distinctly rural feel to it and is completely different culturally from the rest of Silicon Valley — it's much more cowboyish than techie. Though it has an idyllic setting it's actually one of the wealthiest cities in the country.
Woodside’s business district is extremely small. There are very few restaurants, a post office, and a supermarket, but other amenities are fairly limited. However, Woodside offers easy access to surrounding Silicon Valley cities with more shopping and dining options.
As you might expect of a little town in the woods, there is great hiking and mountain biking here. Nature lovers will fall in love with the natural beauty in the area.
Housing options for all but the wealthiest are nonexistent – real estate prices are some of the highest in the already high region, with median prices well into the millions of dollars. The tech and business elite have chosen to make this home to their luxurious mansions, hidden away in the woods.
The older ranch style homes from humbler days are disappearing in favor of homes with huge lot sizes and gates, hiddne among the trees. There are no apartments or affordable housing options to speak of, so mere mortals will find it difficult to afford to live here.
Those who can afford to live here will find themselves falling in love with this charming town in the woods. Almost nonexistent crime and a friendly community make it a great place to settle down and raise a family.
Woodside is bordered on the north by Emerald Hills and Redwood City, on the east by Atherton and Portola Valley, and on the south and west by the Santa Cruz Mountains.
Woodside LOCAL schools 
Woodside Local Flavor 
This 16 acre country estate from the 20th century is a beautiful park and art museum and hosts different eventsand exhibits throughout the year. This estate captures the essence of Woodside, with sprawling gardens and a charming tour of the classic home.
The centerpiece of this 4,711-acre preserve is Purisima Creek Canyon, which features redwoods, rushing creek, and wildflowers. Offers magnificent views of the coast and Half Moon Bay from the northern part of the preserve.
What affluent neighborhood would be complete without its own winery? This spot has a lmited wine selection, opting for quality over quantity. There are beautiful views of the Bay on offer while sipping your wine here.
This classic Western saloon has been the only local spot to come to grab a drink for residents of Woodside for over 100 years. It's a great place to come socialize, have a drink, and listen to live music.
Photo Credits: Thanks to @kylerobertpeter, @scottdunlap, @sarafoster, @guiding99, @eqhuntjump, @runneragogo, @duck_muscle, @slipsill, @nicohughes, @archstudioinc, @ripvanwaffle, @emilykrausmd, @solkava, @cjagich, @jillerst, @jrpandit, @itshollyhaines, @nocontingencies, @nicolasjay, @tapperg, @joshuatheodoreclark for your great photos of this neighborhood!
