Rego Sotheby’s International Realty (RSIR) this year celebrates its 75th anniversary. Bermuda’s oldest real estate agency, it was founded in 1949 by Benny Rego, who was just 18 years old at the time.

Benny came from a humble background and was determined to build a better life, after his parents, who instilled a strong work ethic in their son. Ben Rego, the grandson of the founder and son of the firm’s current President, Buddy Rego, is proud to be the third generation to work in the family business. In preparation for this year’s milestone, Ben dug out some ads from 1949. One of them features a cottage with two acres of waterfront property and an asking price of £5,000. Another is a home offered for rent at £11 a month. “It just goes to show that investing in Bermuda real estate is a long game,” Ben says. “We have had 75 years excelling as the market leader in Bermuda and we intend to be here for many years to come. I’m 34 now and plan to be here when we celebrate the 100th anniversary!”

A pivotal moment in the firm’s history came in 2006, when Rego Realtors was invited to become an affiliate of the global Sotheby’s International Realty (SIR) brand. Adding SIR to the business brought the need and expectation for standards to be consistent with what is widely regarded as the world’s top luxury real estate brand. “When it comes to the people who work alongside us, we’re very selective—it’s all about quality and experience in our team,” Ben says. “The affiliation with SIR means we have exceptional partners to serve our clients in Bermuda and overseas. We are the concierge matchmaker for everyone’s real estate needs, no matter where in the world they wish to be.”

Ben was immersed in the real estate business from an early age and, as a child, remembers bombarding his father with questions about properties. He describes his father as “the first person in the office still to this day, and always with a jacket and tie on”. Indeed, Ben says Buddy has continued to set the family example of hard work, determination and professionalism that he strives to emulate. While welcome to join the business, Ben instead wanted to earn his place on merit first. Having graduated from University in 2011, he moved to Boston where he worked for five years with Gibson SIR’s marketing team, while also assisting some of the top agents in the city. This experience of a highly competitive market taught him the importance of superior marketing techniques, excellence in client service and, in particular, being responsive and available 24/7. “My phone is glued to my hip,” Ben says. “Whenever I get a message, I respond immediately, unless I’m at an appointment or with my lovely wife and kids. The real-estate business moves so fast that people need that responsiveness to be able to make decisions and act. Some of the feedback I’ve heard is that people feel they’re my only client. That is my goal!”

Such service is especially important in today’s Bermuda market, with transactions happening rapidly amid more demand than supply. The lack of inventory for sale or rent was extraordinary in 2023 and Ben does not see that changing. As a result, when properties do become available, they are absorbed quickly. “Until someone actually enters the market as a Landlord or Seller, they do not truly appreciate how active the market is,” he adds. “Clients are often shocked when I put something online with first-class marketing exposure that we get multiple offers sometimes in just days. It’s often the case that my clients receive a higher price than they had ever imagined possible.”

Ben says one way of adding inventory would be to remove the requirement for non-Bermudian buyers of Bermudian-owned homes with two or more assessment numbers to amalgamate the assessments, effectively wiping out rentable unit(s). “There are many who could have had the option to rent out these apartments and that’s where the biggest lack of rental inventory is,” Ben says. “Removing habitable units as part of these transactions is putting Bermudian sellers at a disadvantage and continues to add upward pricing pressure on an already diminishing rental inventory. Plain and simple, we should never remove units when we need more places for people to live.”

Now the Agent Manager at the firm, Ben notes that it has been well over a decade since we have seen this same level of interest in Bermuda real estate that we are experiencing today. “It is a welcomed change, as we also look to continue to evolve with this industry to continue to best serve the needs of our clients for the many years and generations to come, just as we have always done, since 1949.”

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