Winter Garden Christmas tree stand moves to Windermere High School

Although it isn’t at the corner of Dillard and Plant streets, Santa’s Old Fashioned Christmas Trees is still open.

  • By
  • | 10:26 a.m. November 23, 2021
  • West Orange Times & Observer
  • News
  • Share

Regular visitors to Santa’s Old Fashioned Christmas Trees were concerned not to see the tent go up at the corner of Dillard and Plant streets in Winter Garden like it had been for the last five years. Instead, they got a sign telling them that the stand had moved to Windermere High School this year. 

Owner Billy Flanigan, however, was quick to assure customers there was nothing nefarious about the arrangement. 

“We didn’t get the permit forms in on time to get it,” he said. “The city said that they needed the spot for extra parking, but they helped us out by getting another spot. We’re still up and running, but it just didn’t work out.”

The city of Winter Garden suggested a spot on Dillard Street, but Flanigan turned it down because the spot was not big enough for the tents. Eventually, it was decided he would move the stand to just outside the gates of Windermere High School. 

For those who have never been to Santa’s Old Fashioned Christmas Trees before, this is not the average Christmas tree stand typical for the rest of the country. Flanigan and co-owner Michael Waxler go out of their way to make shopping for a Christmas tree enjoyable for the whole family. 

“We try to be the Disneyland of Christmas trees,” Flanigan said. “Our story is that Santa comes around every year and checks the trees to make sure they are of the highest quality. That’s why we top every tree with a Santa hat.” 

The minute you walk in, there is Christmas music playing to get people into the holiday spirit as they walk around looking for the perfect tree. For the kids, there is a station at which they can write their letters to Santa, complete with a mailbox so their letters can be sent to the big guy himself. There is also a Santa coat for the parents to wear for photos.

Melinda Kane, a resident of Winter Garden, said ever since she moved to the area eight years ago, she always gets her Christmas tree from the stand. 

“The friendly staff and the great trees keep me coming back,” Kane said. “My grandchildren would join me every time, which made it all the more fun.”  

Santa’s Old Fashioned Christmas Trees is very much a family operation. Flanigan and Waxler have several family members who help operate the tent and load trees. Workers also make their own wreaths by hand and sell them on average between $30 and $40. The cost of a tree depends on the size. Smaller trees go for around $100, medium ones for between $200 and $300, and big ones go between $300 and $400. 

All the benefits from the tent go to the Windermere High School Chorus as part of its fundraiser for the year.


Santa’s Old Fashioned Christmas Trees

WHERE: Outside Windermere High School, 5523 Winter Garden Vineland Road, Windermere

HOURS: 9 a.m. to 9 p.m. on weekends; after school to 9 p.m. on weekdays