Cavaleros marks 100 years with Cape Town expansion
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Cavaleros marks 100 years with Cape Town expansion. The Cavaleros Group has celebrated its centenary, tracing its roots back to 1926. The family enterprise has grown over four generations into a diversified property investment group, with interests in South Africa and the United Kingdom. The celebration was held on 5 November 2026 at Portside Tower, in Cape Town's central business district. The Group launched Portside under its ownership structure about one year after buying its interest. The building is jointly owned with FirstRand Bank. Since then, the Group has focused on strengthening the tenant mix and improving asset management. It has also acquired the ABSA building on Lower Long Street, its second significant commercial investment in the city. Alexi Cavaleros, Director and Head of International Acquisitions, says the Group is exploring further investments in the Western Cape and across the African continent. Chief Executive Penny Cavaleros said: "Our family remains committed to South Africa, and we continue to put our capital, expertise and energy behind that confidence." Read the full story by Neale Petersen on rei.co.za.
From humble beginnings in 1926 to a diversified international property investment group, the Cavaleros family celebrates a century of entrepreneurship with the repositioning of Cape Town’s iconic Portside Tower and another major CBD acquisition.
- 100 years of enterprise: The Cavaleros Group celebrates its centenary, marking a remarkable journey from its 1926 origins to international property investment.
- Cape Town investment: Portside Tower anchors the Group’s growing commercial property portfolio, complemented by its acquisition of the ABSA building.
- Confidence in South Africa: CEO Penny Cavaleros outlines the family’s commitment to unlocking property value and expanding its investment footprint.
A century of vision, resilience and property investment
One hundred years after its entrepreneurial beginnings in 1926, The Cavaleros Group has marked a remarkable milestone in South African business history, celebrating its centenary at one of Cape Town’s most recognisable commercial landmarks – Portside Tower.
The celebration, held on 5 November 2026, brought together the Group’s century-long entrepreneurial legacy and its ambitious plans for the future, with the landmark Portside building providing a powerful symbol of its growing confidence in Cape Town’s commercial property market.
What began as a family enterprise has evolved over four generations into a diversified property investment group with interests spanning commercial, retail, industrial and hospitality assets across South Africa and the United Kingdom.
For the Cavaleros family, the centenary was more than a celebration of longevity. It was an opportunity to reflect on the entrepreneurial principles that have sustained the business through changing economic cycles, while reaffirming its commitment to investing in South Africa.
The Group’s growing Cape Town portfolio reflects that philosophy: identify opportunities, invest with conviction, improve asset performance and build long-term value.
Portside Tower: A landmark investment in Cape Town
The centenary celebration coincided with the official launch of Portside under the Group’s ownership structure, approximately one year after its acquisition.
Located in Cape Town’s central business district, Portside is one of the city’s most prominent commercial towers and a defining feature of its skyline. The building is jointly owned by The Cavaleros Group and FirstRand Bank.
For Cavaleros, the investment represents far more than acquiring a landmark property. It reflects a deliberate strategy to identify established commercial assets with opportunities for improved leasing, tenant experience and long-term capital appreciation.
Since acquiring its interest in Portside, the Group has focused on strengthening the tenant mix, enhancing asset management and positioning the building to attract businesses seeking premium commercial accommodation.
These initiatives have contributed to the Group’s strategy of unlocking additional value from existing assets rather than relying solely on new developments.
Portside’s strategic importance
- A landmark commercial property in Cape Town’s CBD.
- A platform for expanding the Group’s Western Cape investment footprint.
- Opportunities to improve leasing performance and tenant composition.
- Exposure to demand from local and international businesses.
- Long-term potential through active asset management and repositioning.
The Portside investment also reflects the Group’s confidence in Cape Town as an increasingly attractive destination for international companies and investors.
Penny Cavaleros: Building on 100 years of entrepreneurial ambition
For Penny Cavaleros, Chief Executive Officer of The Cavaleros Group, the centenary represents both a celebration of the family’s achievements and a renewed commitment to its future.
“Celebrating our centenary at Portside brings together our heritage and our ambitions for the future. We have built our reputation on identifying gaps in the market, recognising potential where others may overlook it and pursuing opportunities with conviction.”
That entrepreneurial mindset has remained central to the Group’s investment philosophy across generations. Rather than simply acquiring properties and holding them, the Cavaleros approach places emphasis on actively improving assets, identifying opportunities and continuously pursuing stronger performance.
Penny reinforces that philosophy: “We never stand still. Once we invest, we keep pushing to realise that potential. That determination and ambition to achieve excellence are what set us apart.”
Her message also reflects the family’s continuing belief in South Africa’s investment potential. “Our family remains committed to South Africa, and we continue to put our capital, expertise and energy behind that confidence.”
At a time when many investors remain cautious about domestic economic conditions, that commitment provides a strong statement about the Group’s long-term outlook.
Cape Town expansion gathers momentum
The acquisition of the ABSA property on Lower Long Street represents another important step in the Group’s Cape Town investment strategy.
Following Portside, the transaction strengthens its presence in the CBD and provides a second significant commercial property investment in the city. Together, the acquisitions signal a focused approach to building a portfolio of established commercial assets with opportunities for active management, repositioning and long-term growth.
The strategy also aligns with the Group’s broader experience in identifying properties whose commercial potential can be enhanced through improved leasing and asset management.
For investors, the expansion illustrates the importance of looking beyond current property performance to identify opportunities for value creation.
Alexi Cavaleros: Confidence in Cape Town’s commercial future
Alexi Cavaleros, Director and Head of International Acquisitions at The Cavaleros Group, says Portside marked an important milestone in the Group’s entry into Cape Town’s commercial property market.
“Portside marked our entry into Cape Town’s commercial property market, reflecting our confidence in this world-class city and its long-term prospects.”
He explains that the Group recognised an opportunity to align the building’s commercial offering and tenant experience with its prominent position on Cape Town’s skyline.
“A year into our ownership, we have made meaningful progress in strengthening the tenant mix and unlocking its potential.”
The Group also sees opportunities emerging as more international businesses consider Cape Town as a base for operations and expansion.
“As global companies increasingly recognise Cape Town’s appeal, we see growing opportunity to provide premium commercial space for local and international businesses.”
According to Alexi, the acquisition of the ABSA building on Lower Long Street builds on that strategy, with the Group actively exploring further investments in the Western Cape and across the African continent.
The investment philosophy behind a century of success
The Cavaleros Group’s centenary offers valuable lessons for property investors and entrepreneurs.
Its evolution demonstrates how a long-term approach to investment, supported by disciplined asset management and an ability to recognise opportunity, can sustain a business across generations.
Five lessons from the Cavaleros investment journey
- Think beyond the next property cycle. Long-term value creation requires patience, resilience and an investment strategy that can withstand changing market conditions.
- Recognise potential others overlook. Established properties may offer significant opportunities through repositioning, improved leasing and more effective management.
- Invest with conviction. Successful investors need the confidence to act when opportunities align with their expertise and investment objectives.
- Continuously improve assets. Acquisition is only the beginning. Active management and tenant relationships are essential to sustaining property performance.
- Build for future generations. A lasting property business depends on leadership continuity, adaptability and the ability to evolve without losing its entrepreneurial foundations.
These principles have helped shape the Group’s development from its early business origins into an international property investment enterprise.
The next 100 years: A renewed commitment to South Africa
As The Cavaleros Group enters its second century, its growing Cape Town investments signal an ambition to continue expanding its portfolio while strengthening existing assets.
Portside Tower represents the Group’s confidence in the future of premium commercial property in Cape Town, while the acquisition of the ABSA building reinforces its commitment to the city’s CBD. The Group’s wider investment ambitions extend across the Western Cape and the African continent, building on its established interests in South Africa and the United Kingdom.
For Penny Cavaleros and the next generation of family leadership, the centenary is therefore not simply a moment to celebrate past achievements. It marks the beginning of another chapter in a business built on identifying opportunities, pursuing excellence and creating enduring value.
After 100 years, the Cavaleros philosophy remains clear: recognise opportunity, invest with conviction and never stop unlocking potential.
READ THE COVER STORY FEATURE ON THE CAVALEROS GROUP IN NOVEMBER REAL ESTATE INVESTOR MAGAZINE