Ryan M. Vandegrift
Founder & CEO
“Calisto was born from the belief that owning and enjoying a home — anywhere in the world — should be effortless, beautiful, and deeply personal.”
Roots & Professional Background
Born and raised in West Virginia, Ryan’s foundation is built on hard work, attention to detail, and a love of place. After earning a business degree from West Liberty Unviersity and a law degree from West Virginia University, he began his career at Thomson Reuters. His path took him from Washington, D.C. to Pittsburgh, where he built valuable experience managing complex client needs.
A Passion for Restoration
In Pittsburgh, Ryan fell in love with the city’s historic architecture and began restoring abandoned homes in his free time. He completed seven projects, including a full restoration of a late 1800s home that had been left vacant for over 35 years — a turning point that sparked his passion for real estate and design.
Miami & Global Perspective
Tired of long winters, Ryan moved to Miami Beach to pursue real estate full-time. There, he found success in commercial real estate representing a Danish company expanding into the U.S. market. During this time, he also developed a passion for international travel, eventually visiting 24 countries — a global perspective that continues to shape Calisto’s design sensibility and client experience today.
The Birth of Calisto
In 2015, Ryan began managing vacation rentals in Miami, gaining firsthand experience in hospitality and property care. As his success in commercial real estate grew, he decided to begin investing in vacation homes himself. After exploring opportunities around the world, he chose the Dominican Republic. In 2017, he began acquiring properties there, but quickly became frustrated by the lack of reliable management options. In 2019, he moved to the island to manage his own portfolio — and what began as a personal solution soon evolved into a full-service company. Today, Calisto is trusted by homeowners across the Dominican Republic and Spain.
A Brand That Reflects a Life’s Passion
Calisto is the natural result of Ryan’s journey — combining real estate, design, and travel into a single brand dedicated to trust, transparency, and seamless living. Today, Calisto continues to grow under his leadership, serving clients who value quality, detail, and peace of mind.