- December 17, 2025
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Bradley Gill walks into the Christmas tree lot tent outside Windermere High School for the first time and is greeted by volunteers from the school’s choir program.
He moseys through the small forest of Christmas trees, each adorned with a different color sequined Santa hat to show the size of the tree and how many years it has been in the ground.
It isn’t long before he finds what he says is the perfect tree: “the greenest, roundest and pointiest” of the 70 or so trees left.
Kyle Flanigan, a manager at the tree lot, picks up the tree, hands the red hat on top to Gill as a keepsake and goes outside, where he removes the stand and uses a chainsaw to cut the tip of the stump. He uses a string to turn the stump into a keepsake ornament and hands it to Gill.
Gill’s purchase benefits the school’s choir. The tree lot serves as the biggest fundraiser of the year for the program, giving students opportunities to expand their musical experiences.
The lot is a magical wonderland created by Kyle’s father, Billy Flanigan — who is in his 44th year as an actor, singer and entertainer for Disney World.
Billy Flanigan, known locally as the Happiest Man on Earth, was approached by a friend who knew how to grow, tend and sell Christmas trees. That friend asked Billy Flanigan to help start a tree lot in downtown Winter Garden. Billy Flanigan was tasked with providing the entertainment.
Santa’s Old Fashioned Christmas Trees was created.
Then in 2017, Linda Boot, the former Windermere High choir director, approached Billy Flanigan to have the tree lot as a fundraiser. The former choir student jumped at the opportunity and opened a second lot at the school. The downtown Winter Garden location eventually closed, but the Wolverine lot is alive and well.
Walking into the lot outside the school, the faint smell of pine lingers.
Christmas music plays on the speakers.
Children can sit at a small wooden table on chairs made of logs and write letters to Mr. Claus before putting them in Santa’s mailbox. They also can talk to St. Nick through the Santa camera.
There are photo opportunities, especially when Santa stops by for a visit.
“Since I work for Disney, I wanted this to be the Disneyland of tree lots,” Billy Flanigan said.
Billy Flanigan recalled how enchanting the tree lot can be for some children. He said by the magic of Christmas, a girl who was questioning her belief in Kris Kringle miraculously received her Christmas wish.
During her visit with Santa at the lot, the little girl told the man in the big red suit that if he were real, the letter she wrote him that day would be in her stocking on Christmas morning.
When she woke up Christmas morning and looked in her stocking, her letter was there.
Billy Flanigan said Boot continues to come each year to purchase a wreath or tree to support her former program.
All the proceeds from the tree lot go to supporting the Windermere High choir program.
All the Flanigans ask is that the choir students volunteer at the tent.
Sophomore Beatriz Bellodi had never stepped into a tree lot before she volunteered at Santa’s Old Fashioned Christmas Trees Friday, Dec. 12. She said it felt cozy.
She and fellow volunteer senior Kemi Agbelusi are pining for real trees in their homes after working at the tree lot, because they feel they are more magical than a fake tree.
For two years, Agbelusi has loved being a part of the magic of a family finding their tree to take home. She cherishes the times the children ask for her input on the tree they should purchase. She said it makes her feel a part of their Christmas, and it also gives her and the other volunteers an opportunity to connect with their community.
But the biggest payoff is financial.
Erin Scully Kolodinsky, the choir director, was thrilled when Billy Flanigan approached her about continuing the fundraiser when she took over the program five years ago.
“Billy is just one-of-a-kind, one of the most amazing people I have ever met, just caring and giving; he has the greatest heart,” Scully Kolodinksy said. “It’s been a great partnership and great relationship.”
She said the money raised at the tree lot is used to pay for transportation to and from field trips and the program’s music performance assessments as well as to pay for the accompanist and music.
“Just being able to have that financial security every year where I’m able to keep our fair share down for the students really does help us,” she said.
The funds have assisted with ensuring students are able to go on trips to Los Angeles, California and New Orleans, Louisiana as well as perform at Carnegie Hall in New York City. Scully Kolodinsky said being able to take the students off campus to experience music and culture directly in a different city is life-changing.
Kyle Flanigan, who coaches high school and Little League baseball, sees the tree lot as an opportunity to teach students hard work ethic and to be grateful.
“It’s kind of a lost art of giving back,” he said. “Now when they come here, they realize how hard their parents work and they kind of have it better than what they thought. They see some of these families that come in that can either barely afford a tree or they’re looking for a (tree) donation.”
Some of the students who volunteered during their years at Windermere High return to their alma mater each holiday season specifically to work at the tree lot but as employees now.
Year after year, Billy and Kyle Flanigan have seen families return to the lot to pick out their tree. They’ve seen children who were carried in their car seats grow up to be running around the lot in search of the perfect tree.
“We have people coming back every year that the whole family walks in, and they all have different hats from past years they’ve been here, so it’s become quite a tradition for local families,” Billy Flanigan said. “There’s just something about going to get your tree as a family and that whole tradition that makes it so much more special than going in your attic and pulling it out and sticking it up. It’s the hunt.”
There are times the Flanigans see couples spending hours to find the perfect tree. Billy Flanigan said there is a couple who comes in every year. The wife is on the hunt, and the husband serves as the marker, standing by the tree the wife is considering purchasing while she hunts to see if she can find a better one.
Normally, the couple comes earlier in the season, when there are 250-plus trees standing, but this year, they came later when there were about 70 left. They left in 30 minutes rather than after two-and-one-half hours.
“(The husband) was like, ‘This is a record; we’ve never been out in 30 minutes. I’m coming late every year,’” Billy Flanigan said with a laugh.
Kyle Flanigan has a family who has been coming to the lot for at least seven years, and he jokes with the family about the University of Florida and Florida State rivalry. He will wear his FSU gear, while they’re in their Gators gear. If UF won the rivalry game, the family buys a big tree, but if Florida State goes home with a win, they get a small tree. More than that, each year, he joins the children on the bench in Santa’s corner and smiles for the family photo. The photo is part of the family’s Christmas card every year.
“We have been in the same pose every year,” he said. “The mom actually sent me a collage this year of everything. It’s really cool having those relationships.”
