Author: Katrina Shimer

Naples — Most Expensive homes for September 2026.

Listings (sorted by price):
1. Listing NABOR226008829 — $195,000,000
2. Listing NABOR226005171 — $59,995,000
3. Listing NABOR224019733 — $50,000,000
4. Listing NABOR226019200 — $39,750,000
5. Listing NABOR226003650 — $38,500,000
6. Listing NABOR226028063 — $38,000,000
7. Listing NABOR225072467 — $37,000,000
8. Listing NABOR225072480 — $35,000,000
9. Listing NABOR226016944 — $32,850,000
10. Listing NABOR226016469 — $32,500,000
11. Listing NABOR226015887 — $31,900,000
12. Listing NABOR223077789 — $30,000,000
13. Listing NABOR223085261 — $29,950,000
14. Listing NABOR225072446 — $29,950,000
15. Listing NABOR226020271 — $29,950,000

Lately, I’ve noticed a notable trend in Florida real estate—over 1 in 10 active listings are now priced below what the current owners originally paid. In certain local markets, almost half of homes for sale have already seen price reductions, and seller concessions are becoming more frequent. This shift follows a period of steep price increases, followed by softer demand, higher borrowing costs, and increased inventory—factors that have prompted many sellers to adjust their expectations. As someone who has lived and worked in Southwest Florida for decades, I see firsthand how some sellers who purchased near the market’s peak are accepting smaller returns in order to complete a move, reduce carrying costs, or realign their plans when a community or property no longer fits their needs. For now, more sellers in our area seem willing to accept lower sale prices to move forward with their next chapter, as both buyers and sellers keep a close eye on this cooling market. Navigating these changes requires an understanding not only of numbers, but also of the personal stories and transitions behind every listing—a perspective I bring to every client conversation.

As someone who’s called Southwest Florida home since childhood, I’ve seen how retirement living options in Fort Myers have evolved over the years. For those weighing whether to rent or own in retirement, here’s what stands out: Fort Myers is one of the few destinations where renting comes out ahead financially for seniors. With 23.2% of residents aged 65 and older, and average monthly rents around $1,800, the annual living costs break down to about $48,700 for homeowners versus $45,000 for renters—a difference of roughly $3,600 per year, or an 8% savings for those who rent.

These estimates reflect local home values, rents, living costs, and assume a 10% down payment with a national 30-year fixed mortgage in the mid-6% range. Fort Myers’ large senior population (over 25,000 residents and 20% aged 65+) is a big reason it’s on the radar for retirement comparisons.

As a Senior Transition Specialist and second-generation Realtor with deep local roots, I guide clients through these important financial choices—whether you’re planning to downsize, relocate, or help a loved one navigate a major move. Understanding the real numbers behind rent versus own is just one piece of making your next chapter comfortable and confident.

As someone who’s called Naples home since childhood—and watched it transform over decades—I’ve seen firsthand how HOA dynamics shape our communities. A recent analysis ranked Naples third in the nation for HOA burden in 2025, with median dues coming in at $711 per month. That’s about 20% of the typical mortgage payment here. The study compared HOA fees with monthly principal and interest on a median-priced home (assuming a 30-year loan at roughly a 6% rate with 10% down), and Naples stood out—largely due to our abundance of condos and newer developments, where HOAs are the norm. Plus, recent changes in insurance, inspections, and reserve requirements have nudged association costs higher for many neighborhoods. Out of 300 metro areas, Naples was singled out because so many listings here include HOA dues above the national average. For buyers, sellers, and anyone considering a move, understanding these costs is essential to making a confident decision. As a second-generation real estate professional and lifelong Naples resident, I believe in giving my clients the clarity and local insight they need to navigate our unique real estate landscape.

Indigenous Peoples’ Day celebrates, recognizes, and honors the beautiful traditions and cultures of the Indigenous People
We take a stand for and support the indigenous people on this day.
We should also offer our support to those who invest and uplift the indigenous communities.