About Anna Richards

Meet Anna

Anna Richards has been a proud resident of the Florida Keys since 1982. A graduate of Coral Shores High School, she offers her clients an unparalleled understanding of the area, combining decades of local knowledge with professional expertise to help buyers and sellers navigate the Keys real estate market with confidence.

In 1994, Anna and her father established Massey-Richards Surveying and Mapping, LLC. Since then, they have completed thousands of surveys throughout the Keys, working on everything from home purchases and elevation certificates to major construction projects. This hands-on experience has given Anna a unique perspective on real estate in the Keys—not just from a local’s point of view, but from someone who understands the details that matter behind every property.

As a committed community leader, Anna currently serves on the Islamorada Village Council and is actively involved with several local organizations. She is a board member and past president of the Upper Keys Rotary Club, a board member of FIRM (Fair Insurance Rates for Monroe), and in Leadership Monroe Class XXXIII. Her dedication to public service reflects her passion for protecting the character of the Keys while fostering a thriving community.

She and her husband, Jason, have been married for 30+ years and raised their four children—Brittany, Cody, Karli, and Kyle—in the Upper Keys. Today, all four are grown, running their own businesses, and continue to be active members of the community.

With her deep roots, technical expertise, and commitment to service, Anna Richards offers her clients more than real estate guidance—she offers the perspective of a trusted neighbor and lifelong Keys resident dedicated to helping others achieve their real estate goals.