Pleasanton's Highland Oaks: 1965–1969 homes & subdivision history
Pleasanton's Highland Oaks: a suburban ideal, 1965–1969
Tucked against the rolling, oak-studded hills of what is now the Pleasanton Ridge Regional Park, Highland Oaks emerged in the mid-1960s as one of west Pleasanton's first large-scale residential developments. Built in four phases between 1965 and 1969, the subdivision brought 363 homes to the edge of what was then still a small, agrarian town on the brink of suburban transformation.
The homes were constructed by Schulte-Blackwell, a builder known for creating family-oriented neighborhoods with modern comforts. Though sales quietly began in October 1965, the official grand opening wasn't until January 1966—by which time more than 100 homes had already been sold, a testament to the area’s appeal and the shifting demand for suburban living among Bay Area families.
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| Map of Highland Oaks subdivision (1965–1969): This map outlines the full buildout of Pleasanton’s Highland Oaks neighborhood, developed by Schulte-Blackwell across four phases. It highlights original street layouts and the central recreation area, reflecting the master-planned vision behind one of west Pleasanton’s earliest suburban communities. |
A new lifestyle on Foothill Road
Situated off Foothill Road, before the construction of the West Las Positas Boulevard overpass, Highland Oaks was a neighborhood defined by both its geographic beauty and a sense of promise. Commuters reached it via the Foothill exit off the new Interstate 580, or the Bernal exit from 680, which wouldn’t officially open until 1967—a major event that would shorten commutes to Fremont and San Jose, helping solidify Pleasanton's role as a bedroom community for the South Bay tech industry.
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| Highland Oaks grand opening advertisement, January 1966: This vintage ad heralded the official grand opening of Highland Oaks, complete with a stylized logo evoking rolling hills crowned by a single house—symbolizing the promise of elevated suburban living. Featured are the first five model homes and the proposed recreation center, underscoring Schulte-Blackwell’s vision of a self-contained, community-focused neighborhood nestled against Pleasanton’s scenic west hills. |
In those early years, before Pleasanton’s own west side schools were built, children from Highland Oaks were bused to Dublin schools. The subdivision would later include Lydiksen Elementary School and Muirwood Community Park, shaping a self-contained community where education and recreation were central values.
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| "Fields give way to houses and schools" – Highland Oaks aerial, October 1967: This 1967 aerial photo captures Highland Oaks in mid-construction, looking east toward Pleasanton. Rows of newly built homes trace the contours of the hills, while open agricultural land still dominates the horizon. The image marks a pivotal moment in Pleasanton’s transformation from rural valley farmland to a modern suburban community, with Highland Oaks as one of its earliest and most visible developments on the west side. |
Homes that reflected a new era
With prices starting at $20,950 and down payments as low as $650, buyers were promised more than just square footage—they were sold on a lifestyle. Marketing materials invited families to “move up to the good life” at Highland Oaks, where homes came complete with:
Front lawns and rear yard fencing
Tappan kitchen ranges and dishwashers
Handcrafted oak staircases (in 2-story models)
Shake roofs
Pre-wired master antenna systems that offered reception from up to 11 television stations
These weren’t just homes—they were gateways to postwar prosperity and the suburban ideal that was rapidly transforming the Tri-Valley region.
A community built around recreation
At the heart of Highland Oaks was its defining feature: a private recreation center and swim club reserved exclusively for residents. Unlike the typical neighborhood pool-and-cabana model, the Highland Oaks Swim Club spanned two acres and featured:
A 13,000 sq. ft. deck area
A large swimming pool for family recreation
A multi-purpose clubhouse with kitchen and 26’ x 10’ meeting room
Most uniquely, two Viking sauna baths, a rare amenity in Pleasanton’s housing developments at the time
This investment in recreation highlighted the developers’ commitment to fostering not just houses, but a strong sense of community and wellness, reflective of broader suburban planning trends of the 1960s.
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| "Move up to the good life" – Highland Oaks advertisement, May 1967: This playful 1967 ad promoted the leisure lifestyle of Highland Oaks with the tagline “Move up to the good life.” Set at the community pool, it featured two women in bathing suits modeling by the water while a man, perched on the diving board, looks on—an image steeped in the era’s aspirational suburban ideal. Beyond selling homes, the ad sold a vision of status, sunshine, and social life in one of Pleasanton’s most modern developments. |
The homes of Highland Oaks
The model home complex opened on Capewood Place in January 1966. Over the next two years, six models were showcased to prospective buyers, though the neighborhood included twelve total floor plans, offering a variety of sizes and layouts to accommodate different family needs.
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| Map of Highland Oaks model home complex: This map shows the layout of the Highland Oaks model home complex on Capewood Place, just off Highland Oaks Drive. It highlights the locations of the six model homes showcased between 1966 and 1968, which gave prospective buyers a firsthand look at Schulte-Blackwell’s diverse floor plans and interior features. The model court became a key destination for families considering a move to Pleasanton's growing west side. |
Pricing history
- 1965: $20,950 - $24,950
- 1966: $21,500 - $26,950
- 1967: $22,950 - $28,500
- 1968: $23,950 - $29,500
- 1969: $26,950 +
Model homes
1. The Southwood (Plan H-142X) - 4 bedrooms, 2 bathrooms; 1,593 sq. ft.
2. The Redwood (Plan H-142Y) - 4 bedrooms, 2 bathrooms; 1,680 sq. ft. Introduced 1967; featured the "Four Seasons" kitchen.
3. The Highland (Plan H-343) - 4 bedrooms, 2.5 bathrooms; 1,868 sq. ft. Split-level with a formal dining room.
4. The Westwood (Plan H-132) - 3 bedrooms, 2 bathrooms, 1,255 sq. ft.
5. The Hillcrest (Plan H-253) - 5 bedrooms, 2.5 bathrooms; 1,810 sq. ft. Most popular model.
6. The Castlemont (Plan H-342) - 4 bedrooms, 2 bathrooms; 1,911 sq. ft. Introduced in Unit 2, April 1966, included a formal dining room.
Models not shown in the complex
The Oakwood (Plan H-132X) - 3 bedrooms, 2 bathrooms; 1,355 sq. ft. The twin of The Southwood, but one less bedroom.
The Sequoia (Plan H-132Y) - 3 bedrooms, 2 bathrooms; 1,555 sq. ft. The twin of The Redwood, but one less bedroom.
The Northwood (Plan H-333) - 3 bedrooms, 2.5 bathrooms; 1,707 sq. ft. The twin of The Highland, but one less bedroom.
The Hillview (Plan H-142) - 4 bedrooms, 2 bathrooms. The twin of The Westwood, but one more bedroom.
The Cliffwood (Plan H-263) - 6 bedrooms, 2.5 bathrooms; 2,098 sq. ft. The twin of The Hillcrest, but one more bedroom.
The Havenwood (Plan H-242) - 4 bedrooms, 2 bathrooms; 1,682 sq. ft. With 2 bedrooms on the first level, and 2 on the second, perhaps it had the most character. However, it was only built in Unit 1, then discontinued.
Highland Oaks today
Here are the former model homes as they appear today.
The Southwood today
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| The Southwood today – a similar home stands in While the original Southwood model home remains camera shy, this similar example elsewhere in the neighborhood showcases the characteristic features: low-pitched rooflines, modest ornamentation, and functional single-story layout—hallmarks of the practical, family-centered mid-1960s ranch style. |
The Redwood today
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| The Redwood today – mid-century comfort endures This home still reflects the charm of the Redwood plan, introduced in 1967. Designed for comfort and space, it retains its broad front facade and large windows, once used to showcase the innovative “Four Seasons” kitchen. |
The Highland today
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| The Highland today – split-level suburban style With its signature split-level design, the Highland model emphasized separation of space and formal living. This home continues to show off that architectural tiering, once considered cutting-edge for suburban families. |
The Westwood today
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| The Westwood today – modest footprint, enduring style The smallest of the original model homes, the Westwood remains a charming example of efficient mid-century planning, ideal for smaller families. Its simplicity is a lasting testament to form meeting function. |
The Hillcrest today
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| The Hillcrest today – the neighborhood favorite lives on Often cited as the most popular plan in Highland Oaks, the Hillcrest model continues to impress with its larger footprint, five-bedroom layout, and classic California ranch design. |
The Castlemont today
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| The Castlemont today – quiet prestige in the heart of Highland Oaks Originally added in the second phase of development, the Castlemont offered spacious living with refined touches like a formal dining room. Its well-preserved exterior today hints at the upscale aspirations of the neighborhood’s later offerings. |
Legacy and buildout
By late 1968, the model complex was retired, and final sales were handled out of Schulte-Blackwell’s nearby Foothill Farms development. The final homes sold by mid-1969, completing a neighborhood that would become a quiet cornerstone of Pleasanton’s west side.
Today, Highland Oaks stands as a living example of mid-century suburban planning, representing the optimism and aspirations of a generation seeking space, stability, and community just beyond the reach of the rapidly urbanizing Bay Area.
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