Lee County had the same property appraiser for 40 years. On Aug. 20, voters will decide if it will have the same one for eight years.
Matt Caldwell
Matt Caldwell, who succeeded the retired Ken Wilkinson as appraiser in 2020 following a four-decade run, is running for re-election. Steve Cunningham, Caldwell’s opponent in the open primary, has 48 years of experience appraising real estate.
The Caldwell-Cunningham winner would earn a salary, as set by the state, of $189,252. The winner will oversee property valuations of more than half a million pieces of real estate.
Those valuations came into question by the federal government after Hurricane Ian. But Caldwell worked to show FEMA that his property assessments were valid.
Caldwell graduated from FGCU and later earned a master’s degree from the University of Florida in geomatics, which studies the gathering and displaying of interpretive geographic data.
“On the tax roll, development side, it’s a big county,” Caldwell said. “Five-hundred and fifty thousand real estate parcels. One of the biggest parcel counts in the country, really.”
Hurricane Ian struck Sept. 28, 2022, about in the middle of Caldwell’s tenure so far. Communicating with constituents about how their tax values had changed overtook Caldwell’s initial goals for the job. But now, he said, he’s back on track.
“The last three and a half years, I’ve been really blessed,” said Caldwell, a 1999 Evangelical Christian School graduate. “I’ve enjoyed it thoroughly. But there are a lot of things we can work on. Ken Wilkinson was an amazing advocate for the taxpayer—helped pass, I think, seven different constitutional amendments. But I think it’s time to really look at things from top to bottom.
“Day One, I had a whiteboard in the office, where we made out all the goals and objectives for the job. What we need to deliver.”
Caldwell said the office would continue laying eyes on every property in the county, every five years, as mandated by the law. He sees three facets to the job—as CEO, as communications manager and as advocate for property owners, especially during times of crisis, such as after a hurricane.
“We had about 35,000 properties that were either completely destroyed or at least uninhabitable,” Caldwell said. “So, we took them off the roll. About two-thirds of them have come back on. So, we’re right around 12,000 properties now that are in that category.”
Steve Cunningham
Cunningham, who has a finance degree from University of Illinois, said he decided to run because the county needed an experienced and fresh set of eyes at the office.
“I’m running for property appraiser because I love this area,” Cunningham said. “I’ve been here since 1976—actually, December of ’75. I’ve been a real estate appraiser for 48 years.
“Here’s the thought: In 2020, the incumbent came into his office at a time when we were coming out of a global pandemic. Interest rates have been on the rise. It’s been a very volatile market in certain real estate classes. Then Hurricane Ian hit in 2022.
“I’m going to pose a rhetorical question here. Is it unreasonable to have a 48-year seasoned veteran, currently practicing real estate professional take a fresh look at the tax books? We’ve had two appraisers in 48 years.
“I want to get into the office. I want to be there every day. I also want to make sure that the 550,000 people who own real estate in Lee County are aware of all their taxpayer rights.”
