Dylan Leary

Dylan Leary brings an entrepreneurial mindset, a hospitality-driven approach to service, and a thoughtful understanding of property development to John R. Wood Christie’s International Real Estate. Originally from St. Petersburg, Florida, Dylan has lifelong roots in the Sunshine State and now calls Naples home. Before entering real estate, he built his career at the intersection of hospitality, agriculture, and business development. He is a co-founder of Love Farms, a 10-acre [...]

Dylan Leary brings an entrepreneurial mindset, a hospitality-driven approach to service, and a thoughtful understanding of property development to John R. Wood Christie’s International Real Estate. Originally from St. Petersburg, Florida, Dylan has lifelong roots in the Sunshine State and now calls Naples home. Before entering real estate, he built his career at the intersection of hospitality, agriculture, and business development. He is a co-founder of Love Farms, a 10-acre farm-to-table restaurant and agricultural destination on Cape Cod, where he helped guide the property from its early concept through construction and opening. His experience navigating zoning, land-use considerations, site planning, and the development process give him a valuable perspective on how properties can be thoughtfully improved and brought to their full potential. All of this experience taught Dylan how to manage complex projects, communicate clearly, anticipate people’s needs, and remain attentive to the details throughout an important decision. His culinary and hospitality background gives him a natural appreciation for well-designed kitchens, inviting outdoor living spaces, thoughtful landscaping, and the many elements that make a house feel like home.  Dylan earned a Bachelor of Professional Studies in Applied Food Studies with a concentration in Farm-to-Table from the Culinary Institute of America. His approach to real estate is grounded in responsiveness, integrity, thoughtful guidance, and exceptional personal service. Whether assisting a buyer or seller, he believes every client deserves to feel heard, well-informed, and confidently represented. Now based in Naples, Dylan has developed a deep appreciation for the lifestyle, communities, and natural beauty of Southwest Florida. He is actively involved in local agriculture and food initiatives, including volunteering with ECHO Global Farm and supporting the school garden at First Baptist Academy. Above all, Dylan’s wife, Samantha Leigh, and their growing family are his greatest priority. When he is not working, he enjoys cooking for family and friends, exploring local farms and markets, and spending time on the water around Marco Island.