[1] In 2018, Kentucky's 6th House district incumbent, Willy Coursey, did not seek reelection and instead chose to run for Judge Executive of Marshall County.

Freeland won the 2018 Republican primary[5] and went on to win the 2018 Kentucky House of Representatives election against Democratic candidate Linda Edwards.

In 2020, Freeland was unopposed in the 2020 Republican primary and won the 2020 Kentucky House of Representatives election against Democratic candidate Al Cunningham.

[7] In 2022, he ran for re-election unopposed in both the 2022 Republican primary and 2022 Kentucky House of Representatives election, winning the latter with 14,928 votes.

[3] In 2024, Freeland was unopposed in the 2024 Republican primary and won the 2024 Kentucky House of Representatives election with 16,558 votes (76.9%) against Democratic candidate Linda Edwards.