As of 5/29/2026, we’re at 115 (41.13%) paid members for 2026. King James Ct leads in membership with 82%. King Henry Ct is at 64%, Winter Woods Blvd is at 60% and Poinciana Rd and King Edwards Ct are at 50%. 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 – June 2026
Summer is upon us. I think I understand this line for the first time:
“Now is the Winter of our discontent made glorious Summer by this
sun of Oviedo. Or Casselbury.” Certainly not Winter Park. Those
three days of freeze brought the discontent of hauling to the curb
enough lawn and garden victims to overshadow a small house. The
debris pick-up guys were so miffed they stopped following me.
We are at the end of school, the end of cool weather and the end of
the crisp paper Winter Woods Newsletter that you might be holding
in your hands right now. For the next two months we will be digital
only. Like your photos and music collection. You will only be able
to read the award-winning Winter Woods Newsletter on the website:
https://winterwoodshoa.com/newsletters/ or the PDF emailed
to you. If you are not getting newsletters via email, send a short poem
to WinterWoodsHOA@gmail.com, doesn’t have to rhyme. The
other thing being suspended is the monthly HOA Board Meeting.
Those will resume in August.
The high school I graduated from is turning 100 years old in 2026.
That country school building housed all 12 grades and I was there 6
thru 12. They are having a combination 50-year reunion (and Centennial),
for classes 76-79 and I got a special invite – thank you Facebook
Internet Detective. This kicked in a remissive nostalgia gear.
Down the street from me is what we would have called a hang-out.
It is a neighbor’s yard. Several kids have made that their playground.
It is wonderful. This reminds me of long hilly bike rides (it
was the country) and meeting up to play Risk or lawn grass football
and the sorts of things that created bonds and community. So be
careful coming around the corner where the outdoor library on Poinciana
is and keep an eye out if they all start wearing matching leather
jackets.
There are a few things for the summer. We are putting together a
how-to guide for getting some support to the local schools, especially
during the tax-free month of August. Looking to the Fall, we will
have our annual Neighborhood Night Out in October. Last year
was a wet one but seeing the Fire Department crew mini golf in two
inches of water was well worth getting soaked. Once it stopped raining,
we had a really good turnout.
We have some new Meet Your Neighbor folks lined up and we’re
going to start a new column about the history of the neighborhood.
There are several neighbors that have lived in Winter Woods for
decades and they can tell us the history. It’s not Housewives of Winter
Woods but they do have stories to tell!
Stay cool in that Summer fun, see you next month on the inner web.
Finally, a column where I don’t mention the incredibly low $25 HOA
Dues. Ooops…
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!