Flagler County, Florida

Flagler County Commission District 4

2 candidates are tracked for Flagler County Commission District 4 on the November 3, 2026 ballot: Leann Pennington and Denise "Woody" Calderwood. Candidate information follows official Flagler County election filings; verify with the official election office linked below.

About this race

August 18 primary result: incumbent Leann Pennington won the closed Republican primary with 54.6 percent over Drew Moss and Anna Jones, per FlaglerLive, and faces only the write-in line on the November 3 ballot.

What this office does

County commissioner. The county board is the county's legislative and, in most states, executive body. Commissioners adopt the county budget and property tax rate, oversee roads, the jail, public health, planning and zoning in unincorporated areas, and appoint or confirm department heads. In counties with an elected county executive or judge, the board's role is mainly the budget and ordinances.

This race. The sitting officeholder, Leann Pennington, is on the ballot.

Florida › Flagler County › Flagler County Commission District 4

Leann Pennington

Republican Incumbent

Top priorities

A funded program to pave the county's roughly 125-130 miles of unpaved roads
Permanent funding for beach renourishment and erosion management
Economic development and tax-base diversification via water infrastructure along the U.S. 1 corridor

Per the FlaglerLive Live Interview.

Biography

About 30 years in banking, including due-diligence auditing for Goldman Sachs and Merrill Lynch and internal investigations for JPMorgan Chase; currently a fraud strategist for a large Canadian bank while serving as county commissioner, per her FlaglerLive Live Interview. Described as County Commission chair in FlaglerLive's Tiger Bay forum recap.

Campaign finance

$48,800 raised · county campaign-finance filings

Campaign site (opens in a new tab)

Denise "Woody" Calderwood

Write-In

Biography

No 2026 occupation information verified. FlaglerLive archives show she is a repeat County Commission candidate with prior runs in 2014, 2016, 2020 and 2022; she participated in the 2026 Tiger Bay forum as a write-in, per FlaglerLive's forum recap. No campaign website was found as of September 6, 2026.

Next on your ballotFlagler County School Board District 4

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Voting info and more

Questions about this race

Who is running for Flagler County Commission District 4 in 2026?

When is the Flagler County Commission District 4 election in Florida?

Election Day is Tuesday, November 3, 2026. Registration deadlines, early voting dates and mail ballot rules for Florida are on the Florida election hub at theballotbrief.com.

How do I see my exact Flagler County ballot?

Enter your ZIP code in the lookup at theballotbrief.com for the statewide and congressional races, or a full street address to add the county, city and district contests for that location.

Verify this race

Candidate roster from official Flagler County Supervisor of Elections filings, last verified October 1, 2026. Bios and priorities carry their attribution inline.

Cross-check with the official Florida election office, or see the full Flagler County sample ballot and your exact ballot by address.

The rest of your Flagler County ballot

6 tracked races in Flagler County, Florida. Landed here from another county's search? Look up your own ballot below.

Also on your ballot

Palm Coast City Council District 2 Palm Coast City Council District 4 Florida House District 19 See all 6 Flagler County races

Candidate profiles

Leann Pennington, full profile Denise "Woody" Calderwood, full profile Official Florida election office