Most expensive homes for sale in Naples
Written by:
October 6, 2025
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Most expensive homes for sale in Naples
Stacker compiled a list of the most expensive homes in Naples listed for sale on realtor.com. Homes are ranked by price with ties broken by price per square foot.
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#30. 625 21st Ave S, Naples
- Price: $19,995,000
- 5 bedrooms, 5 full bathrooms, 2 half bathrooms
- Square feet: 6,585
- Price per square foot: $3,036
- Lot size: 0.3 acres
- Days on market: 52 days
- View listing on realtor.com
- 5 bedrooms, 5 full bathrooms, 2 half bathrooms
- Square feet: 6,585
- Price per square foot: $3,036
- Lot size: 0.3 acres
- Days on market: 52 days
- View listing on realtor.com
#29. 1935 5th St S, Naples
- Price: $19,995,000
- 5 bedrooms, 5 full bathrooms, 2 half bathrooms
- Square feet: 6,457
- Price per square foot: $3,096
- Lot size: 0.3 acres
- Days on market: 247 days
- View listing on realtor.com
- 5 bedrooms, 5 full bathrooms, 2 half bathrooms
- Square feet: 6,457
- Price per square foot: $3,096
- Lot size: 0.3 acres
- Days on market: 247 days
- View listing on realtor.com
#28. 4021 Gulf Shore Blvd N Ph P11, Naples
- Price: $20,000,000
- 5 bedrooms, 5 full bathrooms, 1 half bathroom
- Square feet: 6,498
- Price per square foot: $3,077
- Days on market: 229 days
- View listing on realtor.com
- 5 bedrooms, 5 full bathrooms, 1 half bathroom
- Square feet: 6,498
- Price per square foot: $3,077
- Days on market: 229 days
- View listing on realtor.com
#27. 4021 Gulf Shore Blvd N Ph 11, Naples
- Price: $20,000,000
- 5 bedrooms, 5 full bathrooms, 1 half bathroom
- Square feet: 6,498
- Price per square foot: $3,077
- Days on market: 224 days
- View listing on realtor.com
- 5 bedrooms, 5 full bathrooms, 1 half bathroom
- Square feet: 6,498
- Price per square foot: $3,077
- Days on market: 224 days
- View listing on realtor.com
#26. 2021 Gordon Dr E, Naples
- Price: $20,995,000
- 5 bedrooms, 5 full bathrooms, 2 half bathrooms
- Square feet: 7,208
- Price per square foot: $2,912
- Lot size: 0.4 acres
- Days on market: 250 days
- View listing on realtor.com
- 5 bedrooms, 5 full bathrooms, 2 half bathrooms
- Square feet: 7,208
- Price per square foot: $2,912
- Lot size: 0.4 acres
- Days on market: 250 days
- View listing on realtor.com
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#25. 10047 Gulf Shore Dr, Naples
- Price: $21,000,000
- nan bedrooms, nan full bathrooms
- Square feet: 9,000
- Price per square foot: $2,333
- Lot size: 0.7 acres
- Days on market: 621 days
- View listing on realtor.com
- nan bedrooms, nan full bathrooms
- Square feet: 9,000
- Price per square foot: $2,333
- Lot size: 0.7 acres
- Days on market: 621 days
- View listing on realtor.com
#24. 970 Aqua Cir, Naples
- Price: $21,000,000
- 6 bedrooms, 6 full bathrooms, 3 half bathrooms
- Square feet: 7,750
- Price per square foot: $2,709
- Lot size: 0.7 acres
- Days on market: 523 days (-$1,500,000 price reduction since listing)
- View listing on realtor.com
- 6 bedrooms, 6 full bathrooms, 3 half bathrooms
- Square feet: 7,750
- Price per square foot: $2,709
- Lot size: 0.7 acres
- Days on market: 523 days (-$1,500,000 price reduction since listing)
- View listing on realtor.com
#23. 55 13th Ave S, Naples
- Price: $22,995,000
- 6 bedrooms, 5 full bathrooms, 2 half bathrooms
- Square feet: 6,143
- Price per square foot: $3,743
- Lot size: 0.5 acres
- Days on market: 25 days
- View listing on realtor.com
- 6 bedrooms, 5 full bathrooms, 2 half bathrooms
- Square feet: 6,143
- Price per square foot: $3,743
- Lot size: 0.5 acres
- Days on market: 25 days
- View listing on realtor.com
#22. 275 Spring Line Dr, Naples
- Price: $23,500,000
- 5 bedrooms, 5 full bathrooms, 4 half bathrooms
- Square feet: 8,591
- Price per square foot: $2,735
- Lot size: 0.9 acres
- Days on market: 138 days
- View listing on realtor.com
- 5 bedrooms, 5 full bathrooms, 4 half bathrooms
- Square feet: 8,591
- Price per square foot: $2,735
- Lot size: 0.9 acres
- Days on market: 138 days
- View listing on realtor.com
#21. 225 4th Ave N, Naples
- Price: $23,500,000
- 6 bedrooms, 7 full bathrooms, 1 half bathroom
- Square feet: 7,504
- Price per square foot: $3,131
- Days on market: 997 days (-$2,495,000 price reduction since listing)
- View listing on realtor.com
- 6 bedrooms, 7 full bathrooms, 1 half bathroom
- Square feet: 7,504
- Price per square foot: $3,131
- Days on market: 997 days (-$2,495,000 price reduction since listing)
- View listing on realtor.com
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#20. 81 Seagate Dr Ph 20, Naples
- Price: $24,990,000
- 5 bedrooms, 6 full bathrooms, 1 half bathroom
- Square feet: 11,698
- Price per square foot: $2,136
- Days on market: 3 days
- View listing on realtor.com
- 5 bedrooms, 6 full bathrooms, 1 half bathroom
- Square feet: 11,698
- Price per square foot: $2,136
- Days on market: 3 days
- View listing on realtor.com
#19. 616 Bougainvillea Rd, Naples
- Price: $25,900,000
- 6 bedrooms, 9 full bathrooms, 3 half bathrooms
- Square feet: 9,447
- Price per square foot: $2,741
- Lot size: 0.5 acres
- Days on market: 138 days
- View listing on realtor.com
- 6 bedrooms, 9 full bathrooms, 3 half bathrooms
- Square feet: 9,447
- Price per square foot: $2,741
- Lot size: 0.5 acres
- Days on market: 138 days
- View listing on realtor.com
#18. 3300 Gin Ln, Naples
- Price: $25,900,000
- 5 bedrooms, 6 full bathrooms, 3 half bathrooms
- Square feet: 8,187
- Price per square foot: $3,163
- Lot size: 0.5 acres
- Days on market: 258 days (-$3,600,000 price reduction since listing)
- View listing on realtor.com
- 5 bedrooms, 6 full bathrooms, 3 half bathrooms
- Square feet: 8,187
- Price per square foot: $3,163
- Lot size: 0.5 acres
- Days on market: 258 days (-$3,600,000 price reduction since listing)
- View listing on realtor.com
#17. 3163 Gin Ln, Naples
- Price: $26,900,000
- 6 bedrooms, 7 full bathrooms, 2 half bathrooms
- Square feet: 7,595
- Price per square foot: $3,541
- Lot size: 0.5 acres
- Days on market: 40 days
- View listing on realtor.com
- 6 bedrooms, 7 full bathrooms, 2 half bathrooms
- Square feet: 7,595
- Price per square foot: $3,541
- Lot size: 0.5 acres
- Days on market: 40 days
- View listing on realtor.com
#16. 4101 Gulf Shore Blvd N Ph 3, Naples
- Price: $27,500,000
- 5 bedrooms, 6 full bathrooms, 2 half bathrooms
- Square feet: 12,135
- Price per square foot: $2,266
- Days on market: 21 days
- View listing on realtor.com
- 5 bedrooms, 6 full bathrooms, 2 half bathrooms
- Square feet: 12,135
- Price per square foot: $2,266
- Days on market: 21 days
- View listing on realtor.com
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#15. 3131 Gin Ln, Naples
- Price: $27,950,000
- 5 bedrooms, 5 full bathrooms, 2 half bathrooms
- Square feet: 7,695
- Price per square foot: $3,632
- Lot size: 0.5 acres
- Days on market: 398 days
- View listing on realtor.com
- 5 bedrooms, 5 full bathrooms, 2 half bathrooms
- Square feet: 7,695
- Price per square foot: $3,632
- Lot size: 0.5 acres
- Days on market: 398 days
- View listing on realtor.com
#14. 3233 Gin Ln, Naples
- Price: $27,995,000
- 5 bedrooms, 5 full bathrooms, 2 half bathrooms
- Square feet: 7,696
- Price per square foot: $3,637
- Lot size: 0.5 acres
- Days on market: 171 days
- View listing on realtor.com
- 5 bedrooms, 5 full bathrooms, 2 half bathrooms
- Square feet: 7,696
- Price per square foot: $3,637
- Lot size: 0.5 acres
- Days on market: 171 days
- View listing on realtor.com
#13. 4115 Cutlass Ln, Naples
- Price: $28,750,000
- 6 bedrooms, 6 full bathrooms, 2 half bathrooms
- Square feet: 6,291
- Price per square foot: $4,570
- Lot size: 0.5 acres
- Days on market: 267 days (-$3,000,000 price reduction since listing)
- View listing on realtor.com
- 6 bedrooms, 6 full bathrooms, 2 half bathrooms
- Square feet: 6,291
- Price per square foot: $4,570
- Lot size: 0.5 acres
- Days on market: 267 days (-$3,000,000 price reduction since listing)
- View listing on realtor.com
#12. 3440 Rum Row, Naples
- Price: $29,500,000
- 5 bedrooms, 6 full bathrooms, 2 half bathrooms
- Square feet: 7,835
- Price per square foot: $3,765
- Lot size: 0.5 acres
- Days on market: 629 days
- View listing on realtor.com
- 5 bedrooms, 6 full bathrooms, 2 half bathrooms
- Square feet: 7,835
- Price per square foot: $3,765
- Lot size: 0.5 acres
- Days on market: 629 days
- View listing on realtor.com
#11. 2999 Rum Row, Naples
- Price: $29,950,000
- 5 bedrooms, 6 full bathrooms, 2 half bathrooms
- Square feet: 7,326
- Price per square foot: $4,088
- Lot size: 0.4 acres
- Days on market: 709 days
- View listing on realtor.com
- 5 bedrooms, 6 full bathrooms, 2 half bathrooms
- Square feet: 7,326
- Price per square foot: $4,088
- Lot size: 0.4 acres
- Days on market: 709 days
- View listing on realtor.com
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#10. 3675 Gordon Dr, Naples
- Price: $29,990,000
- 5 bedrooms, 6 full bathrooms, 1 half bathroom
- Square feet: 7,873
- Price per square foot: $3,809
- Lot size: 0.8 acres
- Days on market: 117 days
- View listing on realtor.com
- 5 bedrooms, 6 full bathrooms, 1 half bathroom
- Square feet: 7,873
- Price per square foot: $3,809
- Lot size: 0.8 acres
- Days on market: 117 days
- View listing on realtor.com
#9. 1601 Gulf Shore Blvd N Apt 2, Naples
- Price: $30,000,000
- 5 bedrooms, 5 full bathrooms, 1 half bathroom
- Square feet: 6,243
- Price per square foot: $4,805
- Days on market: 732 days
- View listing on realtor.com
- 5 bedrooms, 5 full bathrooms, 1 half bathroom
- Square feet: 6,243
- Price per square foot: $4,805
- Days on market: 732 days
- View listing on realtor.com
#8. 30 3rd Ave S, Naples
- Price: $34,500,000
- 6 bedrooms, 5 full bathrooms, 1 half bathroom
- Square feet: 5,699
- Price per square foot: $6,053
- Lot size: 0.7 acres
- Days on market: 228 days (-$1,000,000 price reduction since listing)
- View listing on realtor.com
- 6 bedrooms, 5 full bathrooms, 1 half bathroom
- Square feet: 5,699
- Price per square foot: $6,053
- Lot size: 0.7 acres
- Days on market: 228 days (-$1,000,000 price reduction since listing)
- View listing on realtor.com
#7. 1601 Gulf Shore Blvd N Apt 1, Naples
- Price: $35,000,000
- 5 bedrooms, 5 full bathrooms, 1 half bathroom
- Square feet: 7,010
- Price per square foot: $4,992
- Lot size: 5.2 acres
- Days on market: 740 days
- View listing on realtor.com
- 5 bedrooms, 5 full bathrooms, 1 half bathroom
- Square feet: 7,010
- Price per square foot: $4,992
- Lot size: 5.2 acres
- Days on market: 740 days
- View listing on realtor.com
#6. 4101 Gulf Shore Blvd N Ph 2, Naples
- Price: $37,500,000
- 4 bedrooms, 5 full bathrooms, 2 half bathrooms
- Square feet: 12,050
- Price per square foot: $3,112
- Days on market: 285 days
- View listing on realtor.com
- 4 bedrooms, 5 full bathrooms, 2 half bathrooms
- Square feet: 12,050
- Price per square foot: $3,112
- Days on market: 285 days
- View listing on realtor.com
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#5. 40 32nd Ave S, Naples
- Price: $39,000,000
- 5 bedrooms, 4 full bathrooms, 2 half bathrooms
- Square feet: 5,277
- Price per square foot: $7,390
- Lot size: 0.7 acres
- Days on market: 291 days
- View listing on realtor.com
- 5 bedrooms, 4 full bathrooms, 2 half bathrooms
- Square feet: 5,277
- Price per square foot: $7,390
- Lot size: 0.7 acres
- Days on market: 291 days
- View listing on realtor.com
#4. 71 18th Ave S, Naples
- Price: $44,000,000
- 6 bedrooms, 4 full bathrooms
- Square feet: 5,052
- Price per square foot: $8,709
- Lot size: 0.9 acres
- Days on market: 540 days
- View listing on realtor.com
- 6 bedrooms, 4 full bathrooms
- Square feet: 5,052
- Price per square foot: $8,709
- Lot size: 0.9 acres
- Days on market: 540 days
- View listing on realtor.com
#3. 1611 Gulf Shore Blvd N Ph 5, Naples
- Price: $45,000,000
- 6 bedrooms, 6 full bathrooms, 2 half bathrooms
- Square feet: 9,673
- Price per square foot: $4,652
- Days on market: 601 days
- View listing on realtor.com
- 6 bedrooms, 6 full bathrooms, 2 half bathrooms
- Square feet: 9,673
- Price per square foot: $4,652
- Days on market: 601 days
- View listing on realtor.com
#2. 4296 Cutlass Ln, Naples
- Price: $60,000,000
- 6 bedrooms, 8 full bathrooms, 5 half bathrooms
- Square feet: 15,309
- Price per square foot: $3,919
- Days on market: 6 days
- View listing on realtor.com
- 6 bedrooms, 8 full bathrooms, 5 half bathrooms
- Square feet: 15,309
- Price per square foot: $3,919
- Days on market: 6 days
- View listing on realtor.com
#1. 20 14th Ave S, Naples
- Price: $89,000,000
- nan bedrooms, nan full bathrooms
- Square feet: 4,822
- Price per square foot: $18,457
- Lot size: 2.9 acres
- Days on market: 403 days (-$10,000,000 price reduction since listing)
- View listing on realtor.com
- nan bedrooms, nan full bathrooms
- Square feet: 4,822
- Price per square foot: $18,457
- Lot size: 2.9 acres
- Days on market: 403 days (-$10,000,000 price reduction since listing)
- View listing on realtor.com
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