For a few years now, Rachel Hildebrand, an east Orange County mom of twins, has been a feisty advocate for her rural community in a never-ending legal fight against urban sprawl and mega developments.
She said she never expected to be a leading voice.
It all started when she naively attended a community meeting in a middle school media center to learn about a proposed development across the street from her home. Hildebrand lives on two acres along Chuluota Road with her husband, Jessup, their kids and a small menagerie of animals, including an African spurred tortoise, a miniature donkey and Lily, her lifelong pet horse.
“That meeting,” she recalled, “was the moment I realized I hadn’t just moved into my dream home, I had stepped onto the front lines of a much bigger, long-standing issue.”
Now, following a judge’s pivotal ruling in February, Hildebrand has assumed an even larger role as the last plaintiff standing in a statewide legal battle against a 2025 Florida law that curtails local communities’ ability to control growth.
“When you say it that way, it honestly makes it feel even more like a David and Goliath situation. It’s a little nerve-racking, to be honest,” she said.
“I care deeply about protecting the peace and rural character out here. I don’t want communities like mine to have their voices overlooked or be pushed into changes that are unsustainable or detrimental to their quality of life, especially when those changes are driven at the state level, where many people don’t have the time or awareness to follow what’s happening in Tallahassee,” she added.
Rachel Hildebrand, standing in front of her family home on Chuluota Road, wears a red “STOP Urban Sprawl” t-shirt identifying east Orange County residents opposed to urban-style development in their rural community. (Joe Burbank/Orlando Sentinel)
The lawsuit was filed in October by South Florida lawyer Richard Grosso on behalf of the not-for-profit, smart-growth group 1000 Friends of Florida. The goal was to blunt impacts of the law (SB 180) passed last year by the Florida Legislature, which installed sweeping limits on land-use regulation under an innocuous guise.
The bill was cast as a relief measure intended to help property owners rebuild quickly in the wake of recent hurricanes by clearing away local building restrictions, but its language is far broader, and the DeSantis administration is pushing an unfettered interpretation of its impact. Already, local land use plans around the state have been sidelined, including Orange County’s long-studied Vision 2050.
When Grosso put together the lawsuit, he was worried it could get tossed without a plaintiff who could be harmed by the law.
So he recruited Hildebrand, who lives in a log cabin in a rural settlement across from a cattle ranch where landowners and developers have sought repeatedly — but so far unsuccessfully — for two decades to build an 1,800-home community on the pastures.
“She has every right to bring a challenge to defend her property, her lifestyle, her way of life,” Grosso said.
Leon County Circuit Judge Angela Dempsey, presiding over the case filed in Tallahassee, decided only Hildebrand had a legitimate interest to fight SB 180’s wide reach, which could nix land regulations protecting Hildebrand’s homestead from “encroachment by incompatible urban and suburban development.”
Rachel Hildebrand at her rural home on Chuluota Road in east Orange County, Wednesday, April 8, 2026. Hildebrand is fighting plans for an 1,800-home development proposed for the cattle pastureland across from her home. (Joe Burbank/Orlando Sentinel)
Dempsey booted 1000 Friends of Florida from the suit. She also sharply limited the scope of companion litigation brought by local governments around the state, including Orange County and Windermere, saying they also lacked “legal standing” for most of their claims.
That left only Hildebrand to challenge the extensive interpretation of SB 180.
“In many ways, she represents thousands of people around the state,” Grosso said. “She knows that.”
Hildebrand, 37, who works from home as an internet consultant, often showed up at public meetings in Orange County to oppose Sustanee, the latest name for the proposed mega-development across the road, or to speak up at county meetings in favor of a protective rural boundary charter amendment, which won 73% of the vote in 2024.
“I’m a regular person with no background in law, politics or public speaking,” she said. “I just want people to play by the rules.”
Hildebrand didn’t expect to be leading the charge, even locally, let alone in a statewide showdown.
That was supposed to be a former neighbor, Debbie Parrish, 68, who sold her family’s home in 2024 and moved out-of-state with husband, Tom, to help him recover from unexpected health challenges. Parrish had chaired a neighborhood committee for the better part of two decades.
She rallied the rural community to show up at public meetings, write emails to county leaders and fight sprawl in other ways.
Parrish said Hildebrand was a logical successor.
“She, like me, is very passionate and a believer about what should and should not happen,” Parrish said in a phone interview. “I was happy she took the lead with our group. You need someone polite and willing to listen to everybody and then discern what’s really fair.”
In group chats in their community near Lake Pickett, neighbors share cute Easter photos of their kids while Hildebrand reminds followers of upcoming meetings. She said neighbors recognize her and often thank her for staying involved in the community’s fight.
“Sometimes it makes me a little nervous, but it’s nice to know people appreciate it and I’m not being the annoying neighbor…”
shudak@orlandosentinel.com