Ryan M. Vandegrift
“I built Calisto to remove the friction from owning a home abroad, so what's left is the joy of living beautifully.”
5 Chapters. One Founder.
Founded by Ryan M. Vandegrift, Calisto is the natural result of a journey that brings together real estate, design, and travel in a single brand dedicated to trust, transparency, and connected living. Today, Calisto continues to grow under his leadership, serving clients who value quality, detail, and peace of mind.
Roots & Professional Background
Born and raised in the United States, Ryan brings a strong foundation of hard work, precision, and a deep appreciation for place. Originally from West Virginia, he earned a business degree from West Liberty University and a law degree from West Virginia University before beginning his career at Thomson Reuters. His professional journey led him from Washington, D.C. to Pittsburgh, where he developed valuable expertise managing complex client relationships and navigating high-stakes environments.
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. In 2022, Calisto expanded to Spain. Today, Calisto is trusted by homeowners across the globe.
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 connected living. Today, Calisto continues to grow under his leadership, serving clients who value quality, detail, and peace of mind.