Nestled alongside the open space preserves of the Santa Cruz Mountains, Woodside is a town that prioritizes nature. Those lucky enough to live here have immediate access to stunning views, challenging trails, and giant redwoods while without feeling too cut off from the rest of the peninsula.

Like several neighboring towns, Woodside has a history of lumber and sawmills. The redwoods that grew here in the 1800s were used in some of the first homes of San Francisco and again in rebuilding after the 1906 earthquake. Now the sawmills are gone, the redwoods grow tall, and Woodside basks in the quiet nature that surrounds it.

With sprawling estates and beautiful single-family homes, most listings here run in the multi-millions. The price tag is well worth it for the beauty and tranquility that Woodside has to offer.


What to Love 

  • Art and nature intertwine at Filoli Historic House and Garden
  • Numerous parks and horse riding trails throughout town
  • Michelin-star restaurants and cozy neighborhood cafes

People & Lifestyle 

A leisurely pace of life welcomes the residents of Woodside. The focus here is on the outdoors, and most who live here take advantage of it consistently. From hiking and biking to horseback riding or simply enjoying the stunning views that surround the town, residents enjoy living so close to nature.

Woodside is home to many retirees and those with generational wealth, and it’s an amazing place for families who want to live in a rural setting close to some of the most vibrant neighborhoods in the world.


Dining, Shopping & Entertainment 

Woodside is mostly residential, but it’s close enough to the other peninsula towns that residents have access to anything they are in the mood for. There are also a handful of gems that put Woodside on the map as a destination.

Robert’s Market is a market and deli full of old-world charm that caters to the needs of the community. The customer service here is impeccable, as are the specialty goods they carry. Shopping for your home is a breeze in Woodside, thanks to the high-quality, fashionable goods at Emily Joubert Home & Garden.

Buck’s Restaurant is an eclectic diner that offers delicious breakfast, lunch, and dinner options. If you’re in the mood for an amazing pub burger in an elegant atmosphere, The Village Pub is a Michelin-starred restaurant in this woodsy town. Woodside is also home to Thomas Fogarty Winery, a gorgeous vineyard surrounded by an open space preserve.


Things to Do in Woodside

The rural landscape and small-town atmosphere of Woodside lend themselves to peaceful outings in nature. There are plenty of trendy things to do nearby, but here you will find undiluted access to the outdoors for all levels of activity.

Filoli Historic House and Garden enchant its visitors with beautiful gardens, walking trails, and an art gallery inside the Georgian revival country estate. Canyon Ranch is a retreat space among the redwoods that offers residents and visitors alike the opportunity to reconnect with themselves.

The true gems of Woodside are its nature and horses. There are numerous parks and open space preserves, such as Huddart Park, Wunderlich Park, and Thornewood Preserve. There is also an extensive network of equestrian trails throughout town, as well as Woodside Horse Park, which has an arena for dressage and jumping.



Woodside is home to an excellent elementary school and is served by the award-winning public high schools in neighboring towns. Top educational opportunities include:


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