As of 4/13/2026, we’re at 104 (36.87%) paid members for 2026. King Henry’s Ct and King James Ct lead in membership with 64% each. Winter Woods Blvd is at 60% and Poinciana Rd is at 41%. If you don’t remember if you have paid, click here to see the list of who has paid for 2026.
From the desk of Anthony Riley – May 2026
I like to give a nod to the month at hand, it seems like the thing to do. I think I’ve already burned lamb and lion, so I used some intelligent assistance. From the benefits of AI via Google lifted from The Old Farmers Almanac (such a quaint concept, a book that predicts things), May is: “Known in Anglo-Saxon tradition as Tri-Milchi (cows could be milked three times daily), it is also associated with sheep-shearing festivals.” That could be our next neighborhood event.
Speaking of Neighborhood Events, one more shout out to all the people who attended the Spring Fling. Also, thanks to everyone that made the event possible, it was a roaring success. We managed to get several volunteer families for our Meet Your Neighbor article – none for this issue, but I think you will like the featured group. More stories to come! I also met new neighbors and that is the point, to try to create a sense of community that will help us look out for each other.
I had an interesting conversation with one of the Dads who attended. He had paid his Reasonable $25 Dues and he wanted to know, where does that money go? I tried to clarify. First, where it does not go is to anyone on the HOA Board, we too are volunteers. It also did not go to pay for any of those premium beverages at the Spring Fling.
The HOA has a budget, and we carved out a little for events, and we did pay for the free water, the bounce house (Bouncers gotta Bounce!) and the signs that said, “Neighborhood Event Today”. We also pay for the plants that decorate the entrances. You might think the Reasonable $25 Dues pay for this fabulous newsletter, but with advertising, a lot of the printing costs are covered. The rest of the budget is for the maintenance of the neighborhood and the costs of having an HOA at all. Meaning to justify the Reasonable $25 Dues, you really need to justify having an HOA. And that is easy.
People who share a common goal and are aware that they are not alone have a much greater chance of accomplishing the goal. And what is the goal of Team Winter Woods Residents? To keep the Winter Woods neighborhood the envy of the area. To keep property values up. To show earned respect and honor to our neighbors and the community we create. Enjoy our newsletters, enjoy the scenic flowers, enjoy the working streetlights, enjoy the fellowship of events and contests, enjoy the safety, enjoy your friends, family and neighbors.
Also, it is Mental Health Awareness Month. I’m just saying. Make a trip out to one of our HOA meetings at 7:00 pm on the second Thursday of every month (except June and July) at South Seminole Church of Christ on Lake Howell Rd or online via zoom. Here’s hoping for Showers and Flowers!
From the desk of Anthony Riley – April 2026
March Madness! Am I right? And then there’s that basketball tourney. Don’t even get me started on April Fools. But here we are, almost finished with the rollercoaster weather and can settle into normal hot and sticky like Cinnabon rolls some kid spilled his Kool-Aid on. Oh Yeah!
March saw our Spring Neighborhood Garage Sale and there was good feedback from the sellers. There was even some healthy curb picking afterwards. But the big event was just a few days ago and what a massive turnout we had for the Spring Fling! I know because I just traveled to the future and saw everyone. James maintained an outstanding pour again and the music was bearable but a little eclectic. Tuba? The food trucks were new this time, but the Bounce House must have had extra air – what a bounce! And the booths! Ed masterfully spun yarns at the HOA Booth (Irish Soda Bread!?) and collections for the meager $25 HOA DUES were through the roof. April Fools. Clearly the hit of the street was not Gerty chasing kids – she does that in her sleep – it was the special surprise for the furry pets. People are still talking about it. If you couldn’t make it out, you missed a dandy. We’ll do it again.
Speaking of low, low $25 HOA DUES, we had our drawing for that special prize and the Dave Kuhl family and the Krumm family are winners! They were already winners, but now it’s in print. Thank you to everyone that has paid your $25 HOA DUES and thank you to the people who are planning to pay their $25 HOA DUES and to the rest of you – jump on the fun train. So far, we have about a third of the neighborhood on board and if you are a glass half full person, there’s more than half left to go so try being a glass third full person. Not easy, is it?
The whole neighborhood appreciates the anonymous monetary contributions for replacing the foliage on both entrances after the great freeze of 2026 tried to blast everything out of good dirt. Several people helped, thank you. It has been said that the cleansing of invasive pests because of the freeze is really a good thing. It is especially good if you like brown trees and leaf free shrubs. I admit, I really enjoyed the temporary separation from the mower, a mutual agreement, believe me. The string trimmer hates me. Also, mutual. But the rain is coming (we hope) and a reunion is eminent.
Remember, you are welcome to come to an HOA meeting at 7:30 pm on the second Thursday of every month at South Seminole Church of Christ on Lake Howell Rd or online via zoom. If you come down, you’ll get your name in the minutes – which are now posted on our website. Spring into Summer!
From the Desk of Anthony Riley – March 2026
You can tell Spring is coming because of the clear sky and birds…wait – we’re in for another cold front? Well, if you can’t count on the weather for seasons, you know spring is near because the Star Wars spectacle is almost back in the barn. But then again, on that same stretch of road there are three people-size skeletons hanging out from Halloween. Since ghoul day they have been posed as turkey eaters, Santa, Elf and Rudolf, Superbowl fans, Valentines and Olympians. Besides the obvious Drum and Fife for July Fourth, how about Leprechaun and Gold, Fools for April and a recreation of the “Luke I’m Your Father” moment (a misquote) …but that might step on the neighbor’s toes.
Speaking of skeletons, the foliage around this place took a beating (that may not be over) and the entrance décor was not immune. Luckily, we have money in the Budget for that. Where does that Budget money come from you ask? HOA Dues! And there is still time during this 2026 Annual Membership Drive to be included for the drawing. Get those $25 HOA dues in before March 15th!
What else is in that budget? A little something for an outing to meet your neighbors, have fun, and show your strength at the hotdog-eating contest. If we had a hotdog-eating contest. What we do have is the wildly successful Neighborhood Spring Fling coming to King James Ct. on Saturday March 28 at 5:00pm – so massive we will block the street! Peer, peer, peer! We nixed the Ferris Wheel (invented by George Washington Gale Ferris, Jr – along with Neo Soul) but we will have the requisite Bounce House, beverage station, live music rehearsal, activities for kids, food trucks, and booths of wide variety. If you have a business and want to set up a booth or a table, give us a heads up at WinterWoodsHOA@gmail.com or tell anyone on the HOA Board. Also, for the first time, we will have a Dog Photo Booth so pets are welcome – even Charlie Girl.
Speaking of the board, we will represent at the Neighborhood Spring Fling not just to panhandle for $25 HOA Dues but also ring the bell for any extra contributions to pay for new (and more) flowers for the entrance, the events and any damages directly caused by Charlie Girl. We also want to meet you, encourage you into participating in a Meet Your Neighbor article and listen to any concerns you may have. About the neighborhood. Maybe you are interested in a Spring article about local birds or wildlife or bats. We are open for business.
Lastly, on March 7th we will unleash the Spring Neighborhood Garage Sale. Advertising works and if you will let us know about your sale with an email to winterwoodshoa@gmail.com , we will help.
Our next HOA Meeting is at 7:00 pm on Thursday March 12th at South Seminole Church of Christ on Lake Howell Rd or online via zoom. And now available: The HOA Minutes! You too can read a synopsis of last months meeting, but it is not as good as the live event. Check Winter Woods Homeowners Association – Winter Park, FL or Facebook.
And since I’m Irish enough: “As you slide down the banister of life, may the splinters never point the wrong way”.