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2026 ELECTIONS

Windermere Mayor Jim O’Brien will not seek re-election

Windermere Mayor Jim O’Brien announced Monday afternoon that he will not seek re-election.

O’Brien has served for the past six years as the town’s mayor and for eight years prior as a member of the town council. He was elected to the town council in 2011.

In a statement sent to VoxPopuli via text, O’Brien said that serving as Windermere’s mayor “has been the honor and privilege of a lifetime,” but that “after much reflection and discussion with my family,” he would not run in the March 10 election.

He said he was “excited to return to the role of ‘citizen’ and neighbor and enjoying our Town’s beauty alongside all of you.”

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Windermere Mayor Jim O'Brien (second from left) says he's "excited to return to the role of 'citizen' and neighbor" and just enjoy all that Windermere has to offer. O'Brien is pictured here with District 1 Orange County Commissioner Nicole Wilson (third from left) at Windermere's Veterans Day celebration on Nov. 11, 2025.
Norine Dworkin

Sources tell VoxPopuli that Council Member Loren “Andy” Williams, founder of Lakeside Realty, whose grandfather was once mayor of Windermere, and who has served on the town council himself since 2018, is running for mayor.

Town Clerk Dorothy Burkhalter told VoxPopuli that Williams picked up a candidate packet, but has not yet turned it in.

Williams, in a late afternoon text message, told VoxPopuli that he had “not made any decisions on whether I would run again for my council position or run for Mayor.”

The only candidate to qualify to date is CT Allen. Qualifying ends at noon on Jan. 9.

O’Brien said in his statement that when he was sworn in as mayor, his goal was to “preserve the unique charm and historic character of Windermere while ensuring we built a sustainable and safe future for the generations to follow.”

He said he was “immensely proud” of what’s been accomplished in the town and cited restoring trust and integrity to the town’s police department; building new, modern town facilities; “bringing life to our downtown; “listening carefully to our neighbors”; and celebrating the town’s centennial as major achievements.

O’Brien did not mention the failure of the Healthy West Orange/Rotary Club pavilion project that cost the town a $1 million grant from the Foundation for a Healthier West Orange in 2024. Nor did he address the town’s recent appeal of the Ninth Circuit Court's judgment in favor of the residents in the town's three-year lawsuit over who owns the boathouses in Palmer Park. The circuit judge had ruled that the boathouses belong to the residents and that in attempting to seize the structures and evict the residents, “there is nothing equitable or fair about the goal Plaintiff [the Town of Windermere] is trying to achieve or the manner in which it is trying to achieve it.”

Under O’Brien’s watch, the town spent upwards of $637,000 pursuing the boathouses. The case has been referred for mediation by the Sixth District Court of Appeal.  

Asked by a boathouse owner/defendant at the Dec. 9 town council meeting who approved the appeal, O’Brien refused to say.

O’Brien concluded his statement, saying he wanted to spend the remainder of his term “focusing on the completion of town projects, supporting our staff and Town Council while ensuring a smooth transition process.”

He said he looked forward to “watching Windermere rise to meet the challenges faced by local governments today and am fully confident in the leadership of those who answer the call to serve in the future.”

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