Feature | By Jocklyn Mundy | Photos by Michael Kleinfelt • Windermere Photography
Some people drift into a community. Stephen and Amanda Lewis drove right into the heart of one, quite literally, on a pandemic-era car date through the quiet, oak-lined streets of Windermere. What began as a Sunday drive with two toddlers in car seats and a world on pause became something neither of them could have scripted: the beginning of a life they had been building toward for years.
Both raised in Apopka, Stephen and Amanda were shaped by the same Central Florida landscape, their lives overlapping through family friendships long before Amanda realized she had a crush on her best friend’s older brother. “I still do,” she says with a sparkle in her eye.
When the world went quiet during COVID, and they found themselves home with two small children and nowhere to be, they started asking a question they hadn't slowed down long enough to ask before: where do we actually want to raise our family? The answer came on one of their car date drives through the oak-lined streets of Windermere. It was immediate.
"We just really felt like — this is where we start putting our energy. This is where our kids are going to grow up." — Amanda Lewis
AMANDA — TEACHER, CAREGIVER
Amanda is a born educator. After high school, she moved to Tallahassee, not to attend FSU, but to find her niche enrolling in Flagler College's satellite campus elementary education program, an intimate, immersive experience with just 35 students and 5 dedicated professors that felt less like a university and more like a calling. She emerged as a teacher parents and students fondly remember years later, and went on to pour herself into classrooms at Keene’s Crossing and Dream Lake Elementary.
Then life asked something harder of her. She and Stephen walked through years of infertility, a season that required everything and offered no guarantees. When they finally became pregnant with their daughter, Hayden, Amanda stepped away from the classroom to be fully present for the family they had fought so hard to build. Their miracles: Hayden is now in third grade at Windermere Elementary, and their son Lawson is in first grade. And the wait, as Amanda will tell you, was worth every moment.
Getting back into early childhood education came about the way the best things in the Lewis family tend to, through family. Amanda's father had spent years traveling for work, watching from a distance as his grandchildren grew up in Central Florida, too far away to catch the everyday moments. He made a decision: he was done missing it. He approached Amanda about purchasing a preschool together. Now, just a few years later, the family owns a thriving private preschool on the east side of Orlando. It was born not from ambition, but from a family’s shared desire to grow something meaningful together, building a business rooted in learning and a lasting legacy for the next generation.
Amanda runs it alongside her parents, and the place is, in every way, an extension of who she is, warm, intentional, and family-oriented. The kind of place that only someone like Amanda could create.
STEPHEN — SERVANT LEADER, COMMUNITY-CENTERED
As Amanda's gift is nurturing, Stephen's is building the structures that help communities and businesses flourish. A graduate of Florida State University with a bachelor's degree in political science and social science, and a master's degree in political science, Stephen's academic foundation has shaped a career that has been anything but ordinary. In 2018, he earned the Certified Association Executive (CAE) credential, the gold standard of nonprofit management, marking him as someone who not only leads nonprofit organizations but also deeply understands how they are meant to work.
His career with the Associated Builders and Contractors (ABC), a national construction trade association representing more than 24,000 members, took him from executive assistant to lobbyist to the national stage. While finishing his master’s, Stephen served as the director of government affairs for the ABC North Florida Chapter, and after graduation, he was hired as the membership director for the ABC Central Florida Chapter, allowing him to return home while furthering his career in association management. During his tenure as membership director for the ABC Central Florida Chapter, he was presented with an opportunity to join the ABC National team, where he spent 12 years of his career before taking the helm at the West Orange Chamber. With a community-first spirit, Stephen embraces all that life in Windermere has to offer. Whether he’s boating on the Butler Chain, coaching his children’s soccer teams, or enjoying an evening at a theme park or local restaurant, Stephen values the strong sense of community that makes West Orange such a special place for him and his family.
"Strong communities are built by the investments we make today for the future we envision tomorrow."
That philosophy, steady, principled, and oriented toward the long game, is precisely what made Stephen the right person when a call came asking him to step into the top role at the West Orange Chamber of Commerce. He was selected following a months-long nationwide search. He assumed the title of President & CEO in October 2023, and from the moment he arrived, he brought the same intentionality he had honed at the national level to the community right outside his front door.
The West Orange Chamber serves nearly 1200 members and operates several committees, in addition to two affiliated organizations: the West Orange Political Alliance and the West Orange Foundation, a separate 501(c)(3) that serves as the philanthropic arm of the West Orange Chamber. Under Stephen's leadership, the chamber has continued to advance the community by serving as a gathering place for people with different paths but a shared destination. He has leveraged his national network and nonprofit expertise to bridge generations, connect local businesses with world-class partners, and position the chamber as a hub of community, collaboration, and leadership in one of the country's most dynamic economic corridors.
"We have the world's largest theme parks in our backyard that are members of our chamber, we have world-class medical facilities that are members of our chamber, we have businesses, sports franchises, we represent such a large swath of industries," Stephen has said of the chamber's unique reach.
His vision for the chamber is one that the community itself authors. As Stephen describes it: "The visions and goals on those walls? That's not Stephen deciding. That's our community deciding for themselves who we are and what we want to be."
A LEGACY PRESERVED
Perhaps no single moment better illustrates the trust Stephen Lewis has earned than the story of the Windermere Wine & Dine. The beloved annual event was founded in 2008 by a group of seven Windermere families who wanted to raise money for classroom technology after budget cuts. What they thought would be a one-time effort grew into one of the most anticipated community events in the region, drawing more than 1,000 attendees, selling out within minutes, and raising over $2 million in grants for local organizations over eleven years. By 2025, the seven founding volunteers had poured everything they had into the event, and after months of searching for the right organization to carry it forward, they had found no suitable match, and they were facing the very real possibility of closing the chapter entirely. That is when they found Stephen, a community-focused Town resident, and the West Orange Foundation.
"If it wasn't for Stephen at the helm, we probably wouldn't have done it, only because we wanted to make sure the mission stayed on point. We just didn't want to give it to any entity that was just in it for the dollars." — Founding Organizer CT Allen
The beloved annual event has since transitioned to the West Orange Foundation, the philanthropic arm of the chamber Stephen leads, under an agreement that 75% of proceeds benefit the Foundation and 25% flow directly back to the Windermere Legacy Fund, preserving the community roots of the original vision. At the most recent Windermere Town Council meeting, Stephen presented a check for over $51,000 to the Windermere Legacy Fund, a moment that said everything about who he is and what his priorities are. This effort didn’t just help ensure the continuation of a beloved event but also helped honor and preserve a meaningful legacy for our community.
THE NEIGHBORHOOD THAT CLAIMED THEM
The Lewises moved into their Windermere home with two toddlers and the kind of nervous energy that comes with starting over in a new place. Within hours, a neighbor appeared at the door not just to make an introduction but to hold the kids while they unloaded boxes.
Amanda speaks about Windermere the way people speak about a gift they didn't expect to receive. She talks about Windermere’s police officers, who are known by name and greet the kids with a smile. About a town that said yes without hesitation when a group of moms asked for help continuing a beloved Daddy-Daughter Dance tradition. About children who ride bikes to the basketball courts by the Town Hall, while text messages light up from neighbors keeping an eye out and parents looking to join in on the fun. About a community so present, so genuinely watching, that you never once feel alone in it.
"Where else can you just be a group of moms and say, let's go ask if we can do this — and the answer is just yes?"
That quality of life, the smallness of it, the accountability of it, the extraordinary ordinariness of it, is exactly what drew the Lewises in and exactly what they work, every day, to foster and protect. And foster and protect it they do, not through grand gestures, but through consistent presence. Amanda as Communications Director on the PTO board at Windermere Elementary School. Stephen at the Chamber, and at the neighbor's door, and at whatever community event or meeting he is needed at next. Together, they are the kind of couple that makes a community feel like it's worth believing in.
A LOVE THAT SERVES
A precious friend and neighbor, Whitney Henneman, told Amanda within minutes of meeting her that she was a 2 on the Enneagram personality test: “The Helper.” Amanda laughed, not because Whitney was wrong, but because she was so precisely right. “I’ve never felt more seen,” she says.
It becomes clear, watching Stephen and Amanda, that theirs is a partnership shaped not only by love but by orientation: toward people, toward service, toward community.
Stephen and Amanda Lewis arrived in Windermere joyfully, generously, and without reservation. In doing so, they became woven into the very fabric of the community fortunate enough to call them neighbors.
