back to archiveRego Sotheby's International Realty Celebrates 75th Anniversary
Press Release By Rego Sotheby's International Realty2024 marks Rego Sotheby’s International Realty’s 75th Anniversary. As Bermuda’s longest serving real estate company, Rego Sotheby’s International Realty leadership looks back at the company’s start, growth and community it serves.
Rego Sotheby’s International Realty was founded by Benjamin “Benny” Rego Sr. in 1949 as Rego Agency with four employees and agents. Originally, Rego Agency’s business spanned residential rentals, sales and property auctions. Benny’s most notable legacies were his strong work ethic and entrepreneurial drive. Benny’s son, Benjamin “Buddy” Rego Jr., admired his father’s tenacity, “He created opportunities for people to own real estate who otherwise thought it impossible”.
Benny was the developer, listing and selling agent behind numerous condominium complexes and residential communities including Forest Hills in Warwick, Beverly Hills in St. David’s and one of Bermuda’s first condominium developments: Cloverdale in Smith’s. The current 100-acre site of Southampton Princess started through Benny’s determination to pull the land together to sell to American tanker billionaire Daniel K. Ludwig in 1959. Ludwig went on to build the original Southampton Princess Hotel in 1972.
In that same enterprising vein, Buddy recalled, “My father asked me if I was ever planning to return home to Bermuda. I said I would if there was an opportunity to be self-employed and if he would sell the company to me.” After nearly 6 years in Hong Kong as a Currency and Precious Metals Trading Manager, Buddy returned home after purchasing then ‘Rego Limited’ in 1983 from his father. Buddy became President of the 10 person company and expanded the business. “It was an exciting time as a young person in Bermuda to make a difference in the competitive real estate industry,” Buddy said, further adding, “In more recent decades, we’ve advanced through providing valuations, commercial real estate and diversification of people and services.”
In 2006, Rego Realtors was invited by Sotheby’s International Realty to join its global network, marking Rego Sotheby’s International Realty as one of the brand’s earliest founding members outside the United States. In 2014, Penny MacIntyre joined as Partner of the business. Now 16 years with the company, Penny continues to lead their Commercial practice including Hotel/Tourism, heads up Human Resources and oversees business operations with Buddy. “Bermuda’s unlike any place in the world to do real estate. Navigating real estate opportunities requires access to information and market conditions not easily visible here. Our team’s commanding direct market share, data-driven analytics and entrepreneurial drive are the key economic resources the private sector, our business community, Government, local and international interests rely upon.”
Buddy acknowledged the key to longevity in the real estate industry as adaptability, “It’s impossible to predict what will happen five years from now with how quickly the industry moves. Our challenge and our responsibility are to keep on the forefront of whatever change is upon us with an emphasis on technology and best practices.”
“Congratulations to the Rego Sotheby’s International Realty on their anniversary of serving the Bermuda community for 75 years. The team continues to define luxury real estate on the island by successfully harnessing the power of the Sotheby’s International Realty brand with its state-of-the-art marketing, global network and connection to the premier Sotheby’s auction house,” said Philip White, President and CEO of Sotheby’s International Realty. “I look forward to continuing to support their success in 2024 and for many years to come.” 
Penny cited, “Within the brand’s 1,100 affiliate offices, the company is a rare find as 1 of 4 affiliates worldwide who can trace their business back three quarters of a century.”
The circumstance that resonates most with Buddy in his 40 years in this business is, “Hearing a client say my father sold them or their parents’ their first house. Then knowing I helped them buy or sell again, and now they or their children are buying through my son who is involved in our business. Three generations of us are serving more than three generations of home buyers and sellers.”
Ben Rego, Buddy’s son joined the company as an agent in 2017 and was promoted to Agency Manager in 2021. He joined the company after working at Boston affiliate, Gibson Sotheby’s International Realty, giving him international experience and a competitive edge. “I always knew I’d be coming back to the island,” Ben says. “After learning from top agents here and in Boston, I now view with a much wider lens to encourage and support our talented agents as they build their book of business for years to come.”
Although Buddy mentions that he inherited his father Benny’s work ethic and entrepreneurial spirit, their management style is what sets them apart. “I like to think I’m more analytical and structured in my approach,” Buddy said. “The industry is much more sophisticated today than it was in 1949. Our ability to retain and attract people is not because we only do things the old-fashioned way. Evolution is an integral part of being a successful business in a collaborative arena.”
Throughout its history and ingrained through the company today are business and charitable collaborations. The company actively volunteers on the Bermuda Chamber of Commerce Real Estate Division Executive Committee, consults with the Bermuda Business Development Agency, Hospitality & Tourism, Banking and Legal sectors and its team members serve on various Boards of developments, businesses and charities. Penny affirmed, “Our 32 all Bermudian/Spouse of Bermudian team are as much about the business of real estate as we are about giving back.” 100% of the company’s charitable giving is spent in Bermuda to help local registered charities serve the island’s neediest in housing, nutrition and education. Penny noted one of the most rewarding programs, “Our coveted annual summer internship program invites serious students to experience Bermuda real estate as they shadow us on site visits, research, marketing and more within each of our departments.”
Buddy hopes our clients recognize the company’s commitment to the community and its investment in the people who have worked here as he emphasized, “Over the course of 75 years, it’s the people who have made this company what it is today, many of whom got their start in real estate with our company and are now running their own businesses. We have a number of veteran employees and agents who have shown their commitment to us because I believe they appreciate the sense of community and the sense of family we’ve established here.”
About Rego Sotheby’s International Realty:
Founded in 1949, Rego Sotheby’s International Realty is Bermuda’s longest established full-service real estate firm and celebrates 75 years of service to its community. We are the leader in luxury, commercial and hotel-tourism real estate and are called upon by Bermudians, Government, Fortune 100 companies and international clients to service their real estate needs. Rego Sotheby’s International Realty is a licensed real estate brokerage and auctioneer providing Residential, Commercial and Hotel/Tourism Sales, Leasing, Development, Property Management, Valuations, Feasibility and Advisory Services. In collaboration with our international brand and Sotheby’s auction house, we continue to deploy intuitive technology to deliver a truly personalized, client-driven experience. With professionals in more than 80 countries and territories worldwide, we are local everywhere, allowing us to walk alongside our clients at every stage of their journey.
For additional information, please email info@regosir.com, call us at 441-292-3921or visit the Rego Sotheby’s International Realty website.
