Castlewood: Pleasanton's Storied Country-Club Enclave

There may be no Pleasanton neighborhood with a richer story than Castlewood. Set in the oak-studded hills surrounding the Castlewood Country Club, this prestigious enclave traces its roots to Phoebe Apperson Hearst's legendary estate — and today it offers a blend of historic character, stunning golf-course-and-ridge views, and a resort-style lifestyle just minutes from downtown Pleasanton. Here's the full picture.

Where it sits

Castlewood is nestled in the hills on the southwest side of Pleasanton, along Foothill Road, surrounding the private Castlewood Country Club. One important and often-overlooked detail: Castlewood is actually located in unincorporated Alameda County rather than within the city limits, and it has its own water supply — practical points worth understanding for any buyer. Despite the secluded, hillside feel, you're only minutes from I-680, I-580, and downtown Pleasanton.

A storied history

Castlewood's story begins with Phoebe Apperson Hearst — philanthropist, education advocate, and the first female Regent of the University of California — who built her grand estate, the Hacienda del Pozo de Verona, on this hillside. Designed in part by trailblazing architect Julia Morgan, the Mediterranean and Moorish-style mansion is often considered a precursor to the more famous Hearst Castle at San Simeon. After Phoebe's death in 1919, the property was sold in 1924 to a group of businessmen who established the Castlewood Country Club. The original Hacienda served as the clubhouse until it was destroyed by fire in 1969; a new clubhouse was rebuilt on the same spot in the style of the original, preserving some of its features. The club is now celebrating roughly a century of history. Many of the earliest homes here were built as summer retreats for the San Francisco and Oakland elite — a legacy you can still feel in the neighborhood today.

The homes

Castlewood is a blend of older and newer single-family homes in a wooded, golf-course setting. Many of the original homes date to the late 1960s and early 1970s, with newer homes sprinkled throughout. They range widely in size — generally from around 2,000 square feet to well over 5,000 — on generous lots that run from a quarter-acre to more than an acre. Mature oaks, rolling hills, and views of the valley and the Pleasanton ridge give the area a setting that newer developments simply can't replicate, and the homes on "The Hill" are considered some of the prime real estate in the area.

The country club and amenities

At the heart of it all is the private Castlewood Country Club, with two golf courses: the Hill course, which winds through the scenic hills and home sites adjacent to the clubhouse, and the Valley course below, on the east side of Foothill Road. The club also offers racquet sports (tennis and pickleball), a resort-style pool, dining, and a full calendar of events. One important note: club membership is separate from home ownership, so it's not automatic with a home purchase. There's also a Castlewood property owners association. As always, I'll help you understand the membership options, association details, and what's included for any specific home.

Schools

Castlewood is served by the Pleasanton Unified School District, including the fittingly named Phoebe Hearst Elementary. Because Castlewood sits in an unincorporated area and assignments can come down to the specific address, I always confirm the current designated elementary, middle, and high schools parcel by parcel before a client counts on an assignment.

Getting around

For all its secluded, hillside character, Castlewood is genuinely convenient. You're along Foothill Road with quick access to I-680 and I-580, and downtown Pleasanton's shops, restaurants, and weekly farmers' market are just minutes away. It's a rare combination of privacy, history, and accessibility.

Thinking about Castlewood?

Castlewood is one of the Tri-Valley's most storied and sought-after neighborhoods, and its homes are tightly held — so when one comes available, it's worth being ready. Whether you're seriously searching or simply want to understand values in this one-of-a-kind market (including how the country club and county location factor in), I'd be glad to give you a clear, honest read.

I know Pleasanton's neighborhoods and the wider Tri-Valley market inside and out, and I'd love to help you find the right fit. Reach out anytime — let's find your home in Castlewood.

— Rebecca Rook, Living Tri-Valley | Compass