Perched in Pleasanton’s rolling hills, the Castlewood neighborhood blends historic charm with a level of privacy and luxury few communities can match. Behind its gated entrances, winding streets lead to custom estates, panoramic Tri-Valley views, and a country club lifestyle that’s as social as it is exclusive. For homebuyers seeking a place where heritage meets high-end living, Castlewood offers a rare opportunity to be part of one of Pleasanton’s most distinguished addresses.
A Community with a Storied Past
The Castlewood neighborhood has roots that stretch back more than a century. In the late 1800s, philanthropist Phoebe Apperson Hearst chose this scenic hillside to build her 53-room estate, the Hacienda del Pozo de Verona. Designed by architect A.C. Schweinfurth and later expanded by Julia Morgan, the Hacienda became both a local landmark and a gathering place for prominent guests.
When a group of investors purchased the property in 1924, they reimagined it as the Castlewood Country Club, with the Hacienda serving as its clubhouse. Members enjoyed fine dining, social events, and the newly constructed Hill Course, a championship layout framed by sweeping valley views. Though a fire in 1969 claimed the original Hacienda, a new clubhouse rose in its place, carrying forward the community’s spirit of hospitality and elegance.
Today, Castlewood blends that rich history with modern luxury. The country club remains its social centerpiece, offering two renowned courses, tennis courts, a resort-style pool, and an active calendar of events, all within minutes of Downtown Pleasanton.
A Country Club Lifestyle
Life in the Castlewood neighborhood centers around the Castlewood Country Club, one of the most respected private clubs in the Bay Area. Here, residents enjoy:
- Two Championship Golf Courses: The Hill and Valley courses offer distinct challenges and stunning vistas.
- Racquet Sports: Tennis and pickleball courts for both competitive and casual play.
- Aquatics: A resort-style pool complex perfect for summer afternoons or swim lessons.
- Bocce Leagues and Social Events: From wine tastings to holiday celebrations, the club’s calendar is full year-round.
- Dining Options: Private dining at The Veranda and The Grille offers elevated experiences with scenic views, while Castlewood Grill provides casual American fare, and Morgan’s Restaurant serves classic club cuisine.
The country club isn’t just about recreation; it’s a social hub. Trivia nights, movie nights, themed dinners, and community galas create opportunities for neighbors to connect, making Castlewood feel as close-knit as it is high-end.
Architecture and Home Styles
The Castlewood neighborhood features a wide range of architecture, reflecting decades of growth and refinement. Original mid-century ranches remain alongside expansive Mediterranean estates and contemporary luxury builds. Many homes have been remodeled to include gourmet kitchens, spa-inspired bathrooms, and seamless indoor-outdoor living spaces.
Generous lot sizes, often half an acre or more, allow for creative landscaping and amenities like putting greens, outdoor kitchens, and multi-tiered decks. Meanwhile, the mature oak trees and rolling terrain give each property a sense of individuality while contributing to the neighborhood’s cohesive, upscale aesthetic.
Lifestyle and Recreation
Beyond its golf courses and country club amenities, Castlewood places residents close to some of the area’s best outdoor experiences. Just minutes away, Pleasanton Ridge Regional Park offers miles of hiking and biking trails, where panoramic views of the Tri-Valley reward every climb. A short drive in the other direction leads to the Livermore Valley Wine Country, where acclaimed wineries and tasting rooms provide a perfect weekend escape, no long trip required.
Evenings in Castlewood are often spent enjoying sunset views from hilltop patios, hosting friends for al fresco dinners, or walking the quiet, winding streets under a canopy of mature trees. The elevated location keeps the neighborhood peaceful while still keeping all of Pleasanton’s shopping, dining, and cultural events within easy reach.
Real Estate Market Overview
The Castlewood neighborhood consistently ranks among Pleasanton’s most desirable markets. Limited inventory, combined with the community’s exclusivity, drives steady demand. As of 2025, home prices often range from $1.8 million to over $3.5 million, with larger estates or recently updated properties commanding premium prices.
Homes here are sought after not just for their features, but for the lifestyle they represent. Buyers often value the privacy, security, and sense of community as much as the architecture or amenities. Sellers benefit from the neighborhood’s reputation, often attracting competitive offers when homes are presented well.
Buying in Castlewood
With limited inventory and steady demand, homes in Castlewood often sell quickly, sometimes before they even hit the open market. Buyers who are serious about securing a property here should be pre-approved, clear on their priorities, and ready to move fast when an opportunity arises. Because the neighborhood features a wide range of home styles, lot sizes, and settings, having a local agent with strong connections can make all the difference.
Some properties back directly onto the golf course, offering fairway views and easy club access, while others sit on ridge-top parcels with sweeping panoramas of the Tri-Valley. There are also homes tucked into more wooded, private corners of the community. The team at Armario Homes knows the nuances, like how sun exposure affects outdoor living spaces or how HOA guidelines shape property improvements, and can help buyers choose a home that matches both their lifestyle and long-term goals.
Selling in Castlewood
Castlewood’s prestige gives sellers a natural advantage, but achieving top value still requires preparation and a thoughtful marketing plan. Buyers in this market expect a home to reflect the community’s high standard, which means polished landscaping, a well-maintained exterior, and interiors that feel fresh and move-in ready. Features such as golf course frontage, panoramic views, or distinctive architectural details should be front and center in the presentation.
Rather than relying on standard listing photos alone, effective marketing often includes aerial drone footage to capture the neighborhood’s rolling hills and oak trees, as well as twilight photography to highlight outdoor entertaining areas. Combining this visual storytelling with targeted outreach, particularly to Bay Area buyers looking for a country club lifestyle, helps ensure the property reaches a highly qualified audience ready to appreciate what Castlewood has to offer.
Living in Castlewood: A Rare Blend of Heritage and Luxury
Castlewood offers something rare in the Bay Area: a gated, luxury community with deep historical roots and a vibrant social scene. From championship golf to sunset dinners on the Veranda, life here is about savoring both the scenery and the connections that come with it. For Pleasanton homebuyers who value privacy, recreation, and a strong sense of place, the Castlewood neighborhood remains one of the area’s most exceptional choices.
Make Your Move to Castlewood with Armario Homes
From its panoramic valley views to its championship golf courses and private club amenities, the Castlewood neighborhood offers a rare blend of elegance, recreation, and community. Homes here are as distinctive as the setting, and opportunities to buy or sell require a strategic, locally informed approach.
The team at Armario Homes knows Castlewood inside and out, its history, its market trends, and the details that make each property stand out. If you’re ready to experience the best of Pleasanton living, let Armario Homes guide you toward your next move in this remarkable neighborhood. Reach out today to get started.
