About

While originally from Iowa, Anna’s ties to the Keys started when her family began vacationing in the Florida Keys back in the 1950’s well before she was even born. Her great-uncle & aunt, Bob & Erma Stout, opened Stout’s Restaurant located in Marathon in 1963 which they ran for many years until retirement.  Anna’s mother moved her family there to work at the family restaurant in 1982 where Anna started third grade at Stanley Switlik Elementary School.

In 1987 her family relocated to Plantation Key, where she attended 8^th through 12^th grade at Coral Shores High School, graduating in 1992. In November 1994, Anna started her business career, along with her stepfather David Massey, by opening their own land surveying business. Massey-Richards Surveying & Mapping LLC, which strictly serves the Florida Keys area, will proudly celebrate 30 years of  professional services this year. In addition to surveying business she is also a Certified Floodplain Manager & licensed Realtor.

On January 2, 1993 she married Jason Richards at Island Community Church by Pastor Tony Hammon in Islamorada. Jason was born in Homestead, and has worked at Florida Keys Electric Coop for 33 years and is currently the Utility Forster. They have 4 children, Brittany, Cody, Karli and Kyle all of whom were born here and attended Plantation Key School, graduated from Coral Shores High School and continue to live here.

Brittany operates her own business, Bella Vida Hair located at Salon 94 in Tavernier. Her fiancé Julian Garcia also a keys native, graduated from Coral Shores and along with his family owns Boat Depot in Key Largo.

Cody earned his bachelors degree in business management from Florida International University is now a Florida Licensed Surveyor and Mapper. He is working in the family business, with the goal of taking over completely one day. His fiancé Hannah Durham, also raised in the Keys and graduated from Coral Shores, operates her own business Hannah’s Cleaning Co.

Karli also operates her own business, The Beauty Box. She is a licensed nail specialist and aesthetician located in Tavernier.

Kyle is building a career in utility work, he is a graduate of Northeast Lineman School and now works as an apprentice lineman working to become a Journeyman Lineman working for the United States Navy with the Naval Facilities Engineering and Systems Command SE located in Key West.

When not working or volunteering in the community, Anna enjoys spending time with her family, fishing, camping, golfing, traveling and attending sporting events. She has served on Plantation Key School PTA, Coral Shores SAC committee, Upper Keys Little League & Upper Keys Rotary Board of Directors. She is currently President-Elect of Upper Keys Rotary.