Feature | By Jocklyn Mundy | Photos Provided by the Family
Photo by Windermere Photography
Some families spend years searching for the perfect neighborhood. The Berrys simply followed the people they loved.
Today, Keegan and Natalie Berry are raising three young daughters in Windermere, balancing two demanding professions with the wonderfully busy rhythm of family life. He is a construction litigation attorney who advocates for homeowners. She is a certified registered nurse anesthetist. Yet neither describes career success as the center of their story.
For them, everything revolves around family.
That philosophy shaped nearly every major decision they have made, including where to call home. They came to be near Natalie's parents, first settling nearby before finding a home on the very same street, just one house away.
Eight years later, that short walk between front doors has become part of everyday life. Grandparents are woven into school pickups, dinners, birthdays, and ordinary afternoons, while three energetic daughters grow up surrounded by the people who love them most.
Ask the Berrys what matters most, and almost every answer eventually circles back to the same thing: family.
Two Gators
Before Windermere, there was Gainesville.
Keegan grew up in Winter Park and attended Lake Highland Preparatory School before heading to the University of Florida. Nearly eight years in Gainesville, as law school followed undergraduate studies.
Natalie was born in Atlanta and lived in Arizona before settling in Fort Lauderdale during her middle and high school years. By the eighth grade, she already knew she wanted a career in healthcare, a goal that ultimately led her to the University of Florida's nursing program.
They met during their final year on campus, his last year of law school and her final year of nursing school. Two students standing on the edge of demanding careers who quickly realized they wanted to build those futures together.
Today, they remain devoted Gator fans. "It doesn't matter the sport," Natalie says. "We're watching."
The University of Florida gave them their education, their careers, and, perhaps most importantly, each other.
Keegan & Natalie while attending the University of Florida
The Family Trade
Keegan became a lawyer because he watched his father be one.
Growing up, he saw firsthand what it meant to help people through difficult situations. He watched his father stand beside clients during some of the most challenging moments of their lives, and somewhere along the way, that example became his own calling.
Like many young attorneys, he began with a broad practice before discovering that construction law was where he truly belonged. He earned board certification in construction law and eventually joined Ball Janik, where he now focuses exclusively on construction litigation. This past January, he was named partner.
His clients are homeowners and homeowners' associations seeking accountability when construction projects fail to meet expectations. The builders on the other side, he says with a grin, are generally not fans of his firm.
Standing beside families whose homes didn't turn out as promised is exactly why he chose this work. In many ways, he's still doing what he watched his father do years ago, helping people when they need someone in their corner.
His father passed away several years ago, but the example he set remains evident in Keegan's life and career. Becoming a partner this past January was a milestone his father would have been immensely proud to see.
Timothy and Keegan Berry
A Steady Heart
Natalie knew what she wanted to do long before most people began thinking about careers.
By the eighth grade, she had already set her sights on healthcare. As she learned more about medicine, one specialty stood out above the rest. She wanted to become a certified registered nurse anesthetist, a CRNA, not simply because it was challenging, but because of the unique opportunity it offered to care for people during one of the most vulnerable moments of their lives.
"I always knew I wanted to do something in the medical field, and I gravitated toward anesthesia," she says, "where I could engage in a challenging but rewarding career caring for people."
Few moments require more trust than the minutes before surgery. Natalie is often the last reassuring face a patient sees before anesthesia takes effect. She describes her work with quiet confidence: ninety percent smooth sailing, punctuated by ten percent that demands complete focus, preparation, and calm under pressure.
Today, she works part-time, a deliberate decision that allows her to continue the career she loves while creating more time for the three little girls waiting for her at home. It is still demanding work, but it provides the balance she and Keegan have worked hard to create.
One House Away
The Berrys' path to Windermere was never really about finding a house.
It was about staying close to the people they love.
After graduating from the University of Florida, the couple moved to Orlando, where Keegan returned to his hometown, and Natalie accepted a position in an intensive care unit. They lived in Winter Garden, then moved to downtown Orlando, where they enjoyed a few years. "We loved it; it was perfect for our lifestyle at the time."
As they began thinking about starting a family, their priorities changed.
Natalie's parents moved north from South Florida, choosing Windermere as their new home. Around the same time, Keegan and Natalie knew downtown no longer fit the life they envisioned as they prepared to start a family.
So they followed.
They first settled in the neighborhood next door before eventually finding a home on the very same street as Natalie's parents, with just one house between them.
Today, that short walk has become part of everyday life. Natalie's parents are woven into the family's routine, helping with school pickups, busy afternoons, and the countless little moments that come with raising three young girls. Keegan's mother, who lives in nearby Clermont, is also a regular presence, spending several days each week with the family.
Between the two grandmothers, the Berry girls are cared for each week by the people who know them best. They know the school routines, the pickup lines, the bedtime rituals, and every favorite snack and stuffed animal.
"It really is the best granny nanny service you could ever ask for," Natalie says with a smile.
With two demanding careers, Keegan and Natalie never have to wonder who is caring for their daughters. They're surrounded by family, and that's exactly how they hoped to raise their children.
Lily — 2019
Abigail — 2021
Amelia — 2024
Summers of Cakes and Candles
These days, if you ask the Berrys about hobbies, the answer is simple: their daughters.
Lillian, the oldest, turns seven this summer. Abigail follows close behind, turning five. Amelia, the youngest, is not quite two. All three girls were born during the summer months, joining both of their parents, in what Natalie laughingly describes as several weeks of nonstop cake, candles, and celebrations, a schedule she jokingly blames on "very poor planning."
This is the season of life they're in, and they embrace every minute of it.
Their calendar revolves around gymnastics, dance, softball, golf clinics, school events, and the tennis lesson they squeeze into an already full week. Even the daily school pickup line has become part of the rhythm they cherish.
"It's busy," Keegan says, "but it's a good busy."
Every stage of parenthood comes with its own pace. For the Berrys, this one is wonderfully full, and they wouldn't trade it for anything.
Where the Memories Live
When they do find a little free time, chances are they're outside.
Living in Windermere has only deepened the family's love for the outdoors. Whether they're boating on the Butler Chain, kayaking at the Florida Springs, or spending a day at the beach, the outdoors has become the backdrop for many of their favorite memories.
Gardening has also become one of Natalie's favorite escapes. Ironically, it's a hobby she inherited from her parents after years of rolling her eyes every time they wanted to stop at another nursery. Today, she's usually the one suggesting they buy more plants, happily spending hours tending flowers and working in the yard.
Keegan enjoys golf and has already begun introducing the game to Lillian, hoping Abigail and Amelia will soon want to join him. Natalie has developed an interest in tennis and hopes all three girls will have opportunities to play both tennis and golf from an early age, something she wishes she had experienced herself.
Keegan also loves to cook, a skill he developed while working as a line cook during his college years in Gainesville. He still enjoys making homemade stocks and experimenting in the kitchen. They both make time for the gym whenever they can, and together they share a love of travel.
Each year, the family tries to fit in at least one ski trip. They've also enjoyed unforgettable adventures farther from home, including Keegan and Natalie's tenth-anniversary trip to Bora Bora, where they swam alongside manta rays and sea turtles, and a memorable vacation through the Greek Islands with Natalie's family, exploring Mykonos, Santorini, and Milos.
As remarkable as those trips have been, they aren't what defines the Berry family.
Their favorite memories are usually much closer to home: Saturday mornings on the lake, afternoons in the backyard, evenings cheering from the sidelines, and the ordinary moments that become extraordinary simply because they're shared together.
The Berrys are also members of Isleworth Country Club, a natural extension of the golf, tennis, and active weekends they already love. For a family that measures everything in time spent together, it is simply one more place those moments happen.
The Windermere Bubble
Ask Keegan and Natalie where they see themselves twenty years from now, and neither hesitates. Right here.
"We're literally never going to leave the Windermere bubble," Natalie says with a laugh.
If they ever move, they say, it would likely be only a few streets away, somewhere else on the Butler Chain.
Windermere is home.
It gave them beautiful lakes and outstanding schools, but it also gave them something far more lasting: a community where friendships deepen over time, neighbors become extended family, and three little girls are growing up known and looked out for.
Family is what brought them home. Windermere is what keeps them here.
L-R Natalie’s parents: Jim and Tarra Curtis, Natalie, Amelia, Keegan, Lily and Abigail Berry, and Keegan’s mother Cheryl DeGroff-Gunter. Photo by Kristina Isgrig with Baby Face Portraits.
