So, 2 months ago I made a list of the most expensive single family houses for sale in Naples. Here we are, and most of the listings have changed. Everything is selling, regardless of price. The housing market in Southwest Florida seems to be ignoring the rising interest rates. Florida is the number one state to retire to, and if you’re coming down with deep pockets, I’ve compiled a list of the 10 most expensive houses for sale in Naples right now.

Or maybe you just won the Powerball and want to check out houses for sale in Naples. Or a big raise at the job. No problem, but if you’re looking to finance, better do it quick because interest rates are likely to keep going up. Financing a 30 million dollar house is roughly $150,000 a month for principal and interest. I don’t think they do PMI on loans that big so you better bring something to put down. Don’t forget the taxes, and since many of the homes are on or very near the beach – there’s a lot more upkeep involved. That salt water takes a toll. You live in Naples long enough you’ll see mansions bulldozed and rebuilt.

Many of these homes are pending or even contingent. The Naples market is still hot right now, so if you see something you like best to grab it quick. Shout out to my realtor neighbor Mark, who drives an obnoxious Black Corvette that looks like the Batmobile. He also just got all new furniture in his house, so I know those commission checks are rolling in. I should have been a realtor.

I did a search on Realtor.com for properties in Naples over $900,000 and it came back with 1,412 results. That’s about 400 more than there was in January. Because the prices keep going up.  I’m way too lazy to write an article that long, so just to whittle this down, let’s just look at the ten most expensive properties for sale today.

  • 10. 2060 Gordon Dr - $19,990,000

    I like this one right here. It’s not ‘on’ the beach so you don’t take as much hit from the weather, but it’s got a private walkway to the beach. Also, it’s new construction so you’re not buying a ‘used mansion’.

    2060 Gordon Dr, Naples, FL 34102 | realtor.com®

    See home details and neighborhood info of this 5 bed, 9 bath, 6406 sqft. single family home located at 2060 Gordon Dr, Naples, FL 34102.

  • 9. 3300 Fort Charles Dr - $22,495,000

    Ah, Port Royal. I was at the Port Royal Club once. Once.

    3300 Fort Charles Dr, Naples, FL 34102 | realtor.com®

    View 50 photos for 3300 Fort Charles Dr, Naples, FL 34102, a 5 bed, 8 bath, 6,532 Sq. Ft. single family home built in 2021 that was last sold on 05/08/2023.

     

  • 8. 1857 Galleon Dr - $22,500,000

    The house was built in 1957 and definitely has an ‘Old Florida’ feel to it. Whoever buys it will probably bulldoze it because the location on this one is everything.

    1857 Galleon Dr, Naples, FL 34102 | realtor.com®

    View 29 photos for 1857 Galleon Dr, Naples, FL 34102, a 4 bed, 4 bath, 5,073 Sq. Ft. single family home built in 1957 that was last sold on 04/29/2022.

     

  • 7. 3240 Gin Ln - $23,950,000

    This Port Royal house won’t be finished for another year. So you got time to save up. Maybe those deep OTM Tesla calls will pay off?

    3240 Gin Ln, Naples, FL 34102 | realtor.com®

    See home details and neighborhood info of this 5 bed, 7 bath, 7551 sqft. single family home located at 3240 Gin Ln, Naples, FL 34102.

     

  • 6. 555 Kings Town Dr - $24,900,000

    There’s no picture of a house. What am I buying here?

    555 Kings Town Dr, Naples, FL 34102 | realtor.com®

    View detailed information about property 555 Kings Town Dr, Naples, FL 34102 including listing details, property photos, school and neighborhood data, and much more.

     

  • 5. 300 Capri Blvd - $24,900,000

    Now this one I remember from the last time we did this. Just under 3 acres on the Isle of Capri. 25 million dollars of sand. Yowzers.

    300 Capri Blvd, Naples, FL 34113 | realtor.com®

    View detailed information about property 300 Capri Blvd, Naples, FL 34113 including listing details, property photos, school and neighborhood data, and much more.

     

  • 4. 3131 Gin Ln - $25,950,000

    Port Royal continues to be the place to be.

    3131 Gin Ln, Naples, FL 34102 | realtor.com®

    See home details and neighborhood info of this 5 bed, 7 bath, 7695 sqft. single family home located at 3131 Gin Ln, Naples, FL 34102.

     

  • 3. 3701 Nelsons Walk - $26,000,000

    If you take the sightseeing cruise from Tin City down through Naples bay you’ll see this beauty. And when someone asks “I wonder how much one of these places costs?” You can confidently tell them – 26 million.

    3701 Nelsons Walk, Naples, FL 34102 | realtor.com®

    View 1 photos for 3701 Nelsons Walk, Naples, FL 34102, a 4 bed, 5 bath, 6,200 Sq. Ft. single family home built in 1998 that was last sold on 05/22/2023.

     

  • 2. 4115 Cutlass Ln - $26,900,000

    More new construction.

    4115 Cutlass Ln, Naples, FL 34102 | realtor.com®

    View 1 photos for 4115 Cutlass Ln, Naples, FL 34102, a 6 bed, 8 bath, 6,291 Sq. Ft. single family home built in 2022 that was last sold on 08/31/2022.

     

  • 1. 1330 Galleon Dr - $27,900,000

    Sale pending on this one, but you know how it is, sometimes the financing doesn’t pull through. Who am I kidding, some billionaire will probably buy it as their second house. Maybe one day……..

    1330 Galleon Dr, Naples, FL 34102 | realtor.com®

    View 4 photos for 1330 Galleon Dr, Naples, FL 34102, a 6 bed, 9 bath, 8,430 Sq. Ft. single family home built in 2022 that was last sold on 11/22/2022.

     

  • What About Us Renters?

    I wouldn’t forget you. At a very affordable $135,000 a month you can snag this beauty. Come prepared with first and last months rent. It doesn’t mention a pet deposit.

    960 17th Ave S, Naples, FL 34102 | realtor.com®

    960 17th Ave S, Naples, FL 34102 is for sale. View 49 photos of this 4 bed, 6 bath, 6861 sqft. single family home with a list price of $26500000.

     

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