Two familiar names recently filed for a bid to reclaim their seats on the Islamorada Village Council in the November 2026 election.
On March 3, Vice Mayor Sharon Mahoney submitted paperwork for re-election to seat 5. Six days later, councilwoman Anna Richards finalized documents for the seat 1 race.
As of March 11, all three candidates filing for office are incumbents. Mayor Don Horton filed for re-election to seat 4 on Jan. 29.
An Islamorada native, Mahoney entered the village political fray in 2022 when she won the race for seat 5. She secured 43.76% of the vote to beat incumbent David Webb and candidate Tom Raffanello. Two years later, Mahoney returned to the council with no challengers filing for the seat.
“The last two years I’ve gotten a lot of stuff done,” Mahoney told Keys Weekly. “I figure I’m on a roll and have another two years and that’s about it for me.”
Mahoney owns Enchanted Forest and founded the nonprofit Casting for Cats, which holds annual backcountry and sailfish tournaments to raise funds to address the feral cat population.
In February 2025, Richards was selected by the council to fill the remainder of then-councilman Buddy Pinder’s term. She’s a longtime resident of the village who co-owns the land surveying business Massy-Richards Surveying & Mapping. She’s also a certified floodplain manager and licensed real estate agent.
Serving the village a little more than a year, Richards said she wants to continue making “balanced” decisions which benefit the community, from the residents and businesses to the environment.
“We’re making decisions at every meeting and not delaying for another time,” Richards said. “I feel the council is doing really well for the most part. For me, I’m not about entitlement or the bubba system.”
Both Mahoney and Richards say they want to finalize agreements between the village and school district in relation to the $5 million-plus in improvements to the baseball field at Founders Park. The sides are still hashing out differences in a license agreement.
Mahoney said she wants to stay on the path of getting issues resolved in the village, including maintaining a rideshare service through Freebee while taking the financial burden off the village taxpayers.
All five village council seats are up for election this November. To qualify, a candidate must be a registered Florida voter and be a resident of Islamorada. If elected, he or she must maintain residency in Islamorada throughout the two-year term of office.
Candidates can file now through the official qualifying period, which begins at noon on Aug. 4 and ends at noon, Aug. 11.
