Our Story
The story of Mile Tree Realty began more than 20 years ago in the hospitality industry, where Trudi and Randy first crossed paths while working at different hotels. Randy worked in general maintenance, specifically within the housekeeping department, while Trudi, who would later become his wife, gained experience across multiple departments as a Management Trainee before moving into the Information Technology Department.
In 2012, while operating their maintenance and landscaping business, Trudi suggested expanding into property management and real estate, highlighting the potential of building a husband-and-wife team. Although Randy found the idea appealing, he felt it did not align with his long-term career plans at the time, and the idea was set aside.
Several years later, in 2018, Trudi decided it was time to pursue a career that was less physically demanding. Believing that property management was her true calling, she began searching for opportunities in the field. Her determination paid off when she was selected to work as a Property Manager with a reputable real estate company, where she gained valuable industry experience.
Meanwhile, Randy continued running the maintenance and landscaping business. During this time, he was given the opportunity to manage a home on behalf of an overseas couple. Through this experience, he discovered a genuine passion for property management and developed a deeper appreciation for the industry.
In 2023, an exciting opportunity presented itself. Drawing on their combined experience, skills, and knowledge, Trudi and Randy decided to establish their own real estate company, with a primary focus on property management, long-term rentals, and holiday rentals. Property sales were later added to their portfolio of services. Their daughter, Naja, subsequently joined the business, bringing her own passion for real estate and fulfilling a long-held dream of working in the industry.
What drives the team at Mile Tree Realty is their genuine passion for what they do. They enjoy building relationships with clients, property owners, tenants, and service providers while delivering professional, friendly, and efficient service at every stage of the process.
The name Mile Tree Realty was inspired by the Mile Tree, also known as the Casuarina Tree, a familiar feature of Barbados’ landscape. Renowned for its deep roots, resilience, and ability to withstand the elements, the Casuarina Tree symbolizes strength, endurance, and stability—qualities that define our approach to serving clients. This symbolism reflects the foundation of Mile Tree Realty: a business deeply rooted in a passion for real estate, a commitment to exceptional service, and values built on trust, dedication, and long-term relationships.
With their combined expertise, knowledge, and hands-on experience, the team at Mile Tree Realty is committed to serving and caring for their clients with excellence.
At Mile Tree Realty, we go the extra mile for you.
MEET THE TEAM

Trudi Sherry-Duncan

Randy Duncan

