The leading streets are:
And ten families have already paid for 2026.
From the desk of Anthony Riley – October 2025
Did you feel that temperature change? For some – especially early risers – you could pin it to a day. One morning, a crack in the heat. For others, a gradual shift like the proverbial toad in the boiling water – which I recently read is a fallacy – the toad would simply hop out at first signs of discomfort. A more empowering outcome. The ability to hop.
Speaking of hopping – we have it going on! The Neighborhood Night Out on Saturday October 4th, 5:00pm has probably already happened by the time you read this – but maybe not. Let me go into the future and tell you what an extravaganza it was and you can verify – if you made it out.
For the first time, we had Mini Golf! That’s right, 9 holes with treacherous obstacles and impatient Dads waiting to make that putt. And Popcorn! And a Fire Engine without a fire (technically) and Glitter Tattoos! Plus, the Bounce House and Neighborhood Vendors including Food Trucks and the ever-present HOA Booth to remind people to pay their $25 HOA Dues! We did it! Things got started at 5:00pm and for the first time on a Saturday, we still cleared the street by dark. Thank you for coming out to the event. The hope is you met some new people and saw familiar neighbors and gave them a solid What’s Up! Community is built one clown face paint at a time.
In other events, it’s the season of the witch and we are decorating. Gussy the place up (Boo!) for the neighborhood contest judged by all the local ghouls and goblins. There is a prize. All that helpful candy, too. This year’s key-note speech will be by Casper. Who you gonna call?
Don’t forget about the Fall Super Garage Sale Spectacle on Saturday November 15th! Time to clean those closets out. Dare to thin out the clutter!
There is a resident requested Traffic Study happening in the neighborhood. We will post results next month, but experience has taught us we will find 25 mph looks faster from the sidewalk and we have many people visiting on their way through. Just passing by.
And do not forget – the General Membership Meeting is Thursday, October 9th and we will elect new board members. This is the big annual meeting where you can express yourself to a receptive audience. Other than your pets that is. Please come out! This meeting is at 7:00pm at the South Seminole Church of Christ on Lake Howell Rd. See you there! Zoom will also be available for those unable to attend in person – just email winterwoodshoa@gmail.com to get the link.
From the desk of Anthony Riley – September 2025
Welcome back to the printed version of the Newsletter. There is a cold drink ring on this copy already. Special shout-out to our Carriers like James and Sabrina, who delivered this to you for the exercise. For the people who are “digital”, and really like the color pictures, the online version is available at our website: Winter Woods Homeowners Association – Winter Park, FL.
There is so much going on, this column wrote itself (ChatGPT). I don’t even need to mention the Water Main Replacement Project – but I will mention the patient and good neighbors Don and Laura Christie who share their yard with the highly decorative above ground contraption that makes the Water Main – um, the Water Main. Don called me to report – and he had as much hope in his voice as if he had called Google or the Vatican – that there was a kerfuffle with his sprinkler system and could I help. I made a call (left VM) and sent an email to Lynn – Project Supervisor – and within no time at all the crew was back around to make things right. Thank you, Casselberry. If there are any other problems call 407-967-6662 and ask for Larry Stephey, he will sort you out. Actually, that is my number.
And I still have not found a way to take credit for this but how about those new roads? Nice new paths for the cut through people. I had nothing to do with this but when Greg Pfister calls, people pick up the phone. We will see what is next. Ask him about Dollar General next time you see him.
What’s next is our Fall Events! Right around the corner is the Neighborhood Night Out on Saturday October 4th, 5:00pm. Our annual street festivity will feature a bounce house, many kid-friendly fun things (like a big-ole fire truck). Last year, one of the youngsters almost got a free ride in the back seat of a Sherrif’s cruiser. That Sherrif was putting all of us on! There will be food trucks, some neighborhood vendors and a chance to meet some people in our neighborhood. People who know people look out for each other.
Did you say look out? You best look out for all the decorating and tricking and treating that come with Halloween. There Will Be a Contest! All Duespaying houses can win the Contest and prizes!
Did someone say neighborhood HOA $25 Dues? I run the chance of getting rode out on a rail if I don’t mention Dues! It occurred to me that the 53.2% of people who have not paid (Check Here) must think that Dues run from September to August, like school. So here is a special deal. Pay the Dues now, we’ll pro-rate the rest of the year (first 8 months free!) and collect again next Fall. Which we will ask you for in January. Just like this year.
And if that’s not enough, we will have the Fall Super Garage Sale Spectacle on Saturday November 15th! Curbside superlatives!
Finally, the General Membership Meeting is Thursday, October 9th and we will elect new board members. Please come out! This meeting and our next regular meeting Thursday September 11th are at 7:00pm at the South Seminole Church of Christ on Lake Howell Rd. See you there!
And lastly, a special thank you to Gerty Ekdahl for painting the entrance lettering on the sign that reminds us where home is: Winter Woods.