Hiller Highlands Oakland Homes for Sale
Hiller Highlands is a unique community in the Oakland Hills — a modern hillside development of shared-wall townhomes with some of the most dramatic panoramic Bay views in the entire East Bay. Situated above Hiller Drive off Highway 13, the community was entirely rebuilt after the 1991 Oakland Hills firestorm and offers buyers a turnkey hillside lifestyle with HOA-maintained amenities, contemporary construction, and unobstructed 180-degree views of San Francisco Bay, the Golden Gate Bridge, and Marin County.
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The Views
The defining feature of Hiller Highlands is its views. The development occupies a raised canyon on the western face of the Oakland Hills, and the steep incline of Hiller Drive means nearly every home faces west across the Bay without obstruction from neighboring properties. Views from most units encompass San Francisco Bay, the Golden Gate Bridge, the Bay Bridge, the San Francisco and Marin skylines, and on clear days extend south to the Peninsula and north toward Mount Tamalpais. Evening and nighttime views across the Bay are among the most compelling in any Oakland Hills neighborhood.
The canyon setting also creates a distinctive microclimate. A cooling afternoon breeze channels through the canyon on days when the flatlands below are warm, giving Hiller Highlands a more temperate feel than many surrounding hill neighborhoods during summer months.
The Homes
All homes in Hiller Highlands were built in 1994 following the complete destruction of the original development in the 1991 firestorm. The rebuilt townhomes are modern in design — open floor plans, large windows oriented toward the Bay views, updated kitchens and baths, and construction that meets current fire-resistant building standards. As shared-wall townhomes, they combine the low-maintenance benefits of a homeowners association with the equity-building advantages of ownership.
HOA coverage at Hiller Highlands includes exterior maintenance, landscaping, and access to community amenities: a swimming pool and Jacuzzi, sauna, tennis courts, and a putting green. All amenities share the development’s signature hillside setting and Bay views. For buyers who want Oakland Hills living without the maintenance demands of a detached single-family home, Hiller Highlands is one of the few options in the area that delivers that combination.
Location and Access
Hiller Highlands sits at the convergence of Highway 13, Tunnel Road, and Caldecott Lane — one of the Oakland Hills’ most strategically connected locations. The Caldecott Tunnel is approximately 2 minutes east, providing direct access to Orinda, Lafayette, Walnut Creek, and the broader Contra Costa County via Highway 24. Westbound, Highway 24 leads to Rockridge BART (less than 3 miles) and onward to the Bay Bridge and San Francisco.
Highway 13 southbound connects to I-580, I-880, and the broader East Bay freeway network, and northbound reaches Montclair Village in approximately 5 minutes. The Claremont Hotel and Spa is a short drive down Tunnel Road via Ashby Avenue, connecting residents to Berkeley, Emeryville, and westbound I-80. Downtown Oakland is approximately 9 miles; San Francisco approximately 18 miles by freeway.
Nearby Amenities
Montclair Village is the nearest neighborhood commercial district — independent restaurants, cafes, bookstores, wine shops, a Sunday farmers market, and practical retail are all within a 5-minute drive via Highway 13. Lake Temescal, directly below the neighborhood off Highway 13, offers swimming, picnicking, and walking trails around the lake. Grizzly Peak Boulevard above Hiller Drive connects to Tilden Regional Park for hiking, the Berkeley Botanical Garden, and Lake Anza.
The Bentley School — a well-regarded private K–12 academy — occupies the original Stanley Hiller mansion at the foot of Hiller Drive. College Preparatory School, another highly regarded private secondary institution, is nearby. Kaiser Elementary is the nearest public elementary school, with Chabot Elementary and Claremont Middle School also within reach.
The History of Hiller Highlands
The original Hiller Highlands development traces its origins to Stanley Hiller Sr., an inventor who owned a large hillside parcel in the Oakland Hills and subdivided it into 27 lots with underground utilities. The underground utility installation was intended as a demonstration project to convince PG&E to adopt the technology — a pitch that failed, leaving the lots without power connections and therefore unsold until 1963. Hiller’s mansion on the property survived and today serves as the main building of the Bentley School campus at the base of Hiller Drive.
The original homes built on the development were destroyed in the 1991 Oakland Hills firestorm, which swept through the area with devastating speed. The rebuilt community that stands today was completed by 1994, transforming the site into the modern townhome development it remains.
Frequently Asked Questions: Hiller Highlands
Where is Hiller Highlands in Oakland?
Hiller Highlands sits above Hiller Drive, a loop road at the convergence of Highway 13, Tunnel Road, and Caldecott Lane in the Oakland Hills. It is approximately 2 minutes west of the Caldecott Tunnel, with Highway 24 providing direct access eastbound to Orinda and Lafayette and westbound toward Oakland and San Francisco.
What happened to Hiller Highlands in the 1991 firestorm?
The entire original Hiller Highlands development was destroyed in the 1991 Oakland Hills firestorm. The community was completely rebuilt by 1994 as modern shared-wall townhomes with fire-resistant construction. The rebuilt homes reflect current building standards and are designed to take full advantage of the hillside views the site provides.
What are Hiller Highlands homes like?
Modern shared-wall townhomes built in 1994, with open floor plans, large windows oriented toward Bay views, and contemporary finishes. HOA amenities include a pool, Jacuzzi, sauna, tennis courts, and putting green. The HOA covers exterior maintenance and landscaping, reducing individual ownership maintenance demands.
What are the views like from Hiller Highlands?
Panoramic 180-degree views of San Francisco Bay, the Golden Gate Bridge, the Bay Bridge, and Marin County. The steep incline of Hiller Drive allows nearly every home to face west across the Bay without obstruction. Evening and nighttime views of the illuminated Bay and San Francisco skyline are a defining feature of the development.
What is the history of Hiller Highlands?
The development was created by inventor Stanley Hiller Sr. as a demonstration of underground utility technology. The original lots went unsold until 1963 after PG&E declined to connect to the system. Hiller’s original mansion now serves as the Bentley School’s main building. The original homes were destroyed in the 1991 firestorm and rebuilt by 1994.
What schools are near Hiller Highlands?
The Bentley School and College Preparatory School — two of the Bay Area’s most regarded private institutions — are immediately adjacent. Kaiser Elementary is the nearest public elementary school. Chabot Elementary, Claremont Middle School, and Maybeck High School are also within reach.
Work With a Local Oakland Real Estate Expert
Hiller Highlands is a small and specialized market — a specific type of property with a specific buyer profile. Understanding the HOA structure, what drives pricing variation between units, and how to compete effectively when a home comes available requires familiarity with this particular development. Bruce Wagg works throughout the Oakland Hills and can help you evaluate Hiller Highlands alongside the broader hillside market. Learn more about Bruce Wagg.
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