The leading streets are:
And ten families have already paid for 2026.
From the desk of Anthony Riley – November 2025
They came out in droves. Countless, with their costumes and attitudes! Trick or Treat indeed! From my position I see the future, I see the past. I expect that we had another grand turnout of costumed kids running up and down the neighborhood looking for goodies. If you are reading this before All Saints’ then go get some candy or turn that porchlight out. I understand some folks are going to try the popular-other-places table at the end of the cul-de-sac method of distribution.
Thursday, October 30th is when the Ghost Squad comes by to judge all decorations. We have winners of the festive displays, and you will find pictures on our website Winter Woods Homeowners Association – Winter Park, FL. Thank you to all the people who decorated and gave out treats and made Winter Woods a child’s celebration destination!
Speaking of decorations and judging, Santa has confirmed another holiday season as anticipated! Santa’s helpers will be coming around on December 21st at 6:00pm to view your colorful enhancements – light that tree! These part-time judges will be recognizing the best decorations with a prize – must be a good standing member of the HOA to win. We are all good standing, but if you want the prize, you must pay the remarkably low $25 annual HOA dues. Santa says. It’s not too early to think about next year’s dues either. Santa said that too, but Rudolf had to remind him.
We conducted our General Membership Meeting and feedback was positive. We appreciate the consensus that communication access is easy and open. If you have an issue, you can contact the board in many ways and several of our neighbors have brought things to the Boards attention. We will address all concerns and stand by our commitment to help resolve anything we can.
I can report a highly successful Neighborhood Night Out a few Saturdays back. Despite the rain, we had many families come out and enjoy the amenities. Personally, I was soaked from shirt to shorts but that never kept me from a good time. We will be doing it again next year around the same time. Pictures of this event are on the website on the Photo Gallery tab.
Our next event is the Fall Super Garage Sale Spectacle on Saturday November 15th! Send me an email with any special items and your address so that we can include you in adverts on the apps.
We have set some dates for your 2026 calendar that you will not want to miss. First is the Spring Garage Sale on March 7th. The usual parade of bargain hunters. The next event is the Spring Fling on March 28th. That is where the fun meets warmer weather – but not too warm.
And lastly, we had another escaped dog recently and had trouble finding the owner. What do the pet owners think about a private volunteer pet registry maintained and managed by the HOA? We would keep a photo and owner information on file and if a pet is found, we can check the registry. Registry access would be restricted to the board. Send me your thoughts. The number one post on NextDoor is missing dog or cat. Followed by is this poisonous? Followed by can I eat this?
Enjoy the holidays!
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.