Live Oak Real Estate

“Live Oak” refers to an unincorporated community whose borders run from the beach to the Santa Cruz Mountains and from the northern edge of Capitola to the southern end of Santa Cruz. Though sometimes wrapped into the umbrella of the “Eastside,” Live Oak is a unique place all its own, offering diverse housing, shopping and lifestyle choices for those who live within its boundaries. Once an area dominated by small and large chicken farms, Live Oak has evolved over the past sixty years into an eclectic alternative to Santa Cruz’s east and west sides.

Live Oak’s public profile is dominated by Pleasure Point, the surfing beach made famous by surf industry titan, Jack O’Neill, whose East Cliff Drive home is a point of pilgrimage for modern enthusiasts. O’Neill allows public use of part of his property known as “The Dirt Farm,” giving visitors easy access to “O’Neill’s,” the surf break outside his door.

Despite the eternal presence of Jack O’Neill, Pleasure Point has changed plenty during its early days. Once a ragtag neighborhood of drifters and surfers, Pleasure Point is now Live Oak’s most affluent address, where ocean view homes sell for the mid-millions and the last of the remaining beach shacks command almost seven figures.

Further inland, Live Oak is even more eclectic than it is on the coast. Orderly post-war neighborhoods adjoin rustic, rural ones; gleaming new condos share space with the last of the 2-acre lots sold 100 years ago to would-be chicken ranchers as “kit houses.” East of Highway 1, most homes date only to Live Oaks period of 1960s and 70s growth, but mixed in among them are a few surviving mountain cabins and a growing number of impressive newer abodes built to escape the buzz of the city.

Despite, or perhaps because of, Live Oak’s eclecticism, the community’s varied population seems to have no problem finding common interests. Many locals, possibly inspired by Live Oak’s agricultural roots and the still-functioning Live Oak Grange Hall, spend their spare time gardening, growing organic food or purchasing their eats at the year-round Live Oak Farmer’s Market. Live Oak residents capitalize on their proximity to Santa Cruz and Capitola for nightlife and entertainment, but also enjoy their own small, surfer-friendly commercial center at 41st Avenue and Portola Drive in Pleasure Point. The Capitola Mall is also an easy drive, bike ride or stroll away.

Homebuyers choose Live Oak not for high-end restaurants and boutiques, but for the quiet serenity of its mostly-residential streets. Live Oak is a place where blocks often have no sidewalks, where sailing and boating enthusiasts haunt nearby Santa Cruz Boat Harbor, where “the beach” can mean Pleasure Point, Twin Lakes, Sunny Cove, Black’s, Santa Maria’s and others, and where outdoor pursuits rules the day.

The “Live Oak lifestyle,” if there could be such a thing in such a diverse place, revolves around making the most of the natural beauty of the region, connecting with neighbors, caring about local schools and protecting the laid-back nature of the community. Everyone who lives in Live Oak, be they a grandfathered-in beach shack-dwelling surfer, a tycoon on Opal Cliffs, a suburbanite living inland, a secret chicken farmer or someone living in an aged mountain cabin surrounded by redwood trees far from the ocean, chose to live here instead of Santa Cruz or Capitola. Live Oak isn’t the hub of the Santa Cruz area, everyone’s favorite vacation spot or the “in” place for nightlife-loving Millennials. To the locals, it’s something more than that: Live Oak is home.

Neighborhood Price Point

$300,000-$4,000,000+

Favorable Attributes
  • Diverse neighborhoods and price points
  • Beaches and mountains
  • Rural and urban neighborhoods
  • Strong community awareness
  • Quiet, mostly away from tourist attractions
  • Outdoor recreation opportunities

History of Live Oak

In late 2008, a century-old local landmark was razed after a long period of back and forth between preservationists and opposition comprised of property rights activists, local history buffs and old time locals. Located on East Cliff Drive between 38th and 41st Avenues, the Pleasure Point Roadhouse was an early Arts & Crafts-era building whose historic significance was arguable. What was not up for debate, however, was that along with its demolition went a wealth of Pleasure Point history.

Though the Roadhouse served many uses during its 106 years, including a gas station, a beach resort, and a saloon and brothel, it began as a private home, built by former San Francisco saloonkeeper, John Henchy. Shortly after the turn of the 20th century, Henchy purchased a large piece of a coastal wheat farm in Live Oak. He began construction a residence but quickly adapted it to what would now be called “mixed-use.” Before the home was even completed, Henchy was running a saloon out of its basement.

During Prohibition, Henchy, now living in Capitola, continued to operate the Roadhouse as a speakeasy. It became a very popular destination whose notoriety played a major role in the surrounding area earning the name “Pleasure Point.” Post-prohibition, as the giddiness of the Roaring 20s subsided and landowners began to subdivide, the Roadhouse adapted, becoming a gas station and store, and later the Cosy Cottage Resort.

Over the years, the Pleasure Point Roadhouse donned different hats, watching silently as G.I.s returning from World War II duty in Hawaii brought their enthusiasm for surfing to the point, transforming it from a local secret to a world-class destination. After years of barely scraping by first as a hippie commune then a boardinghouse and collection of privately rented cabins, the Pleasure Point Roadhouse fell into disrepair. It eventually became a victim of the great contrast between its colorful historic shabbiness and the rising value of its prime oceanfront location. Finally, in 2007, longtime owners began the process of razing the property. Despite a spirited campaign to save the Roadhouse, it lost its battle to history on a sunny Friday morning in late September 2008.