SEPTEMBER 2026 EDITION
SEPTEMBER Is For The Locals
September is here, and there's a lot to unpack! Football is back — those relaxing Saturdays and Sundays are now replaced with screaming and yelling as Alma Maters and Fantasy Teams make or break your day.
First, take a look at this month's Naples real estate market trends. Things are heating up — and we're not just talking about the temperature. Pending sales are rebounding, days on market are showing improvement, and inventory continues to tighten, setting the stage for what could be a strong upcoming real estate season.
On the family side, we squeezed every last drop out of summer, spending as much time as possible on the boat with friends in the Keys before school started back up. Jace officially started high school this year — and if you see Michelle out and about looking a little tired, be gentle with her. Turns out 5:30 AM is a real time that actually exists, and she's still adjusting to the unfortunate discovery that it now applies to her too.
Here's to a great September, cooler weather eventually, and hopefully fewer 5:30 AM alarms!
Real Estate News and Updates
SWFL August Market Snapshot
August brought some encouraging signs after a slow-moving July. Pending sales jumped to 640, up from 461 in July — a solid sign that more contracts are working their way toward the closing table this fall. Closed sales came in at 618, a normal seasonal step down from July's 718.
Inventory kept tightening: new listings eased to 784 (down from 903 in July) and total homes for sale dipped to 4,071 from 4,380, pushing Months Supply down to 5.3 — its lowest point of 2026 so far. Perhaps the most notable shift is Days on Market, which improved to 62 days, a meaningful pullback from July's 80-day high.
Bottom line: inventory keeps tightening, buyer activity is picking back up heading into fall, and well-priced homes are moving again. If you've been waiting for the right moment to list, this stretch is worth a conversation.
Data Courtesy of Naples Area Board of Realtors (NABOR)
Local Happenings
If you haven't been to the Vanderbilt Farmers Market on a Saturday morning lately, add it to the list — it's North Naples' longest-running and largest market, with more than 90 vendors set up every Saturday from 8am to noon at the Shoppes at Vanderbilt. Fresh produce, flowers, honey, baked goods, local artisans — bring the dog, bring a tote, and plan to linger.
Courtesy of Vanderbilt Farmers Market
Southwest Florida's restaurant week is going all September long this year to mark its 10th anniversary — 140+ restaurants across Lee, Collier, and Charlotte counties, with $1 from every promotional meal donated to Blessings in a Backpack SWFL. Worth booking a table or two this month.
Courtesy of Sizzle Dining
Local Spotlight: Gulfside Media
Ever wonder why our photos look so good? That's Caleb and Letti of Gulfside Media. They're the husband-and-wife team behind nearly every listing photo we've put in front of a buyer for the last few years, and if you've ever scrolled past one of our listings and stopped because the photos actually made you want to see the house in person — that's them, not luck.
Based right here in Naples, they've shot more than 780 homes across Collier and Lee counties since 2023: magazine-quality stills, cinematic video, FAA-licensed drone and aerial work, 3D tours, floor plans, even virtual staging when a room needs a little help.
They also shot Skip's headshot below — if they can make him look decent, imagine the magic they can work on your property.
Courtesy of Gulfside Media · (239) 326-3862
Landon’s Corner
In a first for Father & Sons Home Watch and Maintenance, our team found that a bee colony had started a hive inside a client's home. Finding and removing it while the owners were away didn't just save them thousands of dollars in damage — it spared them the headache of dealing with an active hive around family and pets.
Special thanks to Hing Family Farm, who safely removed and relocated the bees and educated everyone along the way.
The takeaway: don't leave your home without a professional home watch, and don't leave it in the care of a well-meaning neighbor. We found this hive because we were diligently looking — not by chance.
Courtesy of Father & Sons Home Watch and Maintenance · Bee removal by Hing Family Farm
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Skip Riddle
Real Estate Advisor
Michelle Riddle
Real Estate AdvisorCompass RE is a licensed real estate broker. All material is intended for informational purposes only and is compiled from sources deemed reliable but is subject to errors, omissions, changes in price, condition, sale, or withdrawal without notice. No statement is made as to the accuracy of any description or measurements (including square footage). This is not intended to solicit property already listed. No financial or legal advice provided. Equal Housing Opportunity. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions.
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Call or text any time: 239.776.1726