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Wayside Dr, Naples, FL Property Records

Collier County property records for 23 addresses on Wayside Dr, Naples, FL · Last verified August 2026

Wayside Dr Highlights

Properties 23
Median Sale Price $4,500,000
Deeds and Mortgages on File 39
Median Price per Sqft $942
Owner Occupied 91%
Median Annual Tax Bill $30,235
Median Year Built 2005
Median Ownership Tenure 6 years

Properties on Wayside Dr

Owner names and prior sale amounts shown locked below are available instantly with a free trial.

4418 Wayside Dr

4,057 sqft · Built 2018 · 0.839 acres · Pool

Last Sale Tax Bill Prior Sale Owner Records
—Feb 2022 $40,2332025 Amount on Record Aug 2017 3 Names on Record Owner Occupied Assessor + 3 DocumentsUpdated Dec 2025

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4424 Wayside Dr

5,306 sqft · Built 1998 · 0.8 acres · Pool

Last Sale Tax Bill Prior Sale Owner Records
$3,200,000Jun 2006 $22,7022025 Amount on Record Sep 2000 2 Names on Record Owner Occupied AssessorUpdated Dec 2025

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4427 Wayside Dr

6,155 sqft · Built 2002 · 0.86 acres · Pool

Last Sale Tax Bill Prior Sale Owner Records
$6,350,000Jul 2022 $42,2462025 Amount on Record Feb 2017 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Dec 2025

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4430 Wayside Dr

6,535 sqft · Built 2005 · 0.91 acres · Pool

Last Sale Tax Bill Prior Sale Owner Records
—Sep 2021 $36,9842025 Amount on Record Oct 2013 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Dec 2025

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4431 Wayside Dr

4,938 sqft · Built 2016 · 0.85 acres · Pool

Last Sale Tax Bill Prior Sale Owner Records
$6,105,000Oct 2024 $43,0322025 Amount on Record Aug 2021 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Aug 2026

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4436 Wayside Dr

5,440 sqft · Built 1999 · 0.78 acres · Pool

Last Sale Tax Bill Prior Sale Owner Records
$4,325,000Jul 2025 $29,2172025 Amount on Record Sep 2022 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Dec 2025

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4437 Wayside Dr

5,606 sqft · Built 2007 · 0.839 acres · Pool

Last Sale Tax Bill Prior Sale Owner Records
$2,350,000Aug 2019 $23,6752025 Amount on Record Feb 2005 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Jul 2026

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4442 Wayside Dr

5,771 sqft · Built 2001 · 0.81 acres · Pool

Last Sale Tax Bill Prior Sale Owner Records
$2,850,000May 2021 $30,2352025 Amount on Record Sep 2001 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Aug 2026

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4443 Wayside Dr

7,585 sqft · Built 2015 · 1.7 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$525,000May 2013 $47,4452025 Amount on Record Mar 2013 2 Names on Record Owner Occupied AssessorUpdated Dec 2025

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4448 Wayside Dr

6,543 sqft · Built 1999 · 0.81 acres · Pool

Last Sale Tax Bill Prior Sale Owner Records
$1,900,000Apr 2018 $30,2602025 Amount on Record Jun 1996 2 Names on Record Assessor + 3 DocumentsUpdated Dec 2025

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4454 Wayside Dr

6,739 sqft · Built 2004 · 1.01 acres · Pool

Last Sale Tax Bill Prior Sale Owner Records
—Nov 2001 $39,4622025 2 Names on Record Owner Occupied AssessorUpdated Dec 2025

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4455 Wayside Dr

5,155 sqft · Built 2003 · 0.819 acres · Pool

Last Sale Tax Bill Prior Sale Owner Records
$3,700,000Oct 2021 $40,5982025 Amount on Record Apr 1998 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Dec 2025

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4461 Wayside Dr

6,328 sqft · Built 1996 · 0.819 acres · Pool

Last Sale Tax Bill Prior Sale Owner Records
$200,000Jun 2013 $21,3572024 Amount on Record Dec 1993 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Apr 2026

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4466 Wayside Dr

4,886 sqft · Built 2020 · 0.839 acres · Pool

Last Sale Tax Bill Prior Sale Owner Records
$750,000Jun 2019 $27,2442024 Amount on Record Jun 2005 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Jul 2026

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4467 Wayside Dr

5,926 sqft · Built 2007 · 0.819 acres · Pool

Last Sale Tax Bill Prior Sale Owner Records
$2,795,000Oct 2018 $21,4062025 Amount on Record Jul 2015 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Dec 2025

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4472 Wayside Dr

5,858 sqft · Built 2017 · 0.969 acres · Pool

Last Sale Tax Bill Prior Sale Owner Records
$6,850,000Sep 2022 $49,8462025 Amount on Record Mar 2018 2 Names on Record Owner Occupied Assessor + 3 DocumentsUpdated Dec 2025

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4473 Wayside Dr

5,200 sqft · Built 2006 · 0.819 acres · Pool

Last Sale Tax Bill Prior Sale Owner Records
$6,350,000Jun 2024 $22,3532024 Amount on Record Jan 2004 2 Names on Record AssessorUpdated Apr 2026

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4478 Wayside Dr

4,776 sqft · Built 2019 · 0.919 acres · Pool

Last Sale Tax Bill Prior Sale Owner Records
$4,500,000Mar 2022 $41,5192024 Amount on Record Jan 2021 2 Names on Record Owner Occupied Assessor + 6 DocumentsUpdated Jul 2026

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4481 Wayside Dr

7,083 sqft · Built 2002 · 0.76 acres · Pool

Last Sale Tax Bill Prior Sale Owner Records
$485,000Dec 1998 $33,8512024 Amount on Record Apr 1995 2 Names on Record Owner Occupied AssessorUpdated Apr 2026

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4484 Wayside Dr

4,811 sqft · Built 2004 · 0.769 acres · Pool

Last Sale Tax Bill Prior Sale Owner Records
$1,675,000Aug 2020 $17,1212025 3 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Dec 2025

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4487 Wayside Dr

4,561 sqft · Built 2000 · 0.85 acres · Pool

Last Sale Tax Bill Prior Sale Owner Records
$2,375,000Aug 2011 $19,7062024 Amount on Record Nov 1996 2 Names on Record Owner Occupied AssessorUpdated Apr 2026

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4490 Wayside Dr

4,073 sqft · Built 2020 · 0.76 acres · Pool

Last Sale Tax Bill Prior Sale Owner Records
$2,850,000Oct 2020 $21,3232024 Amount on Record Aug 2017 1 Name on Record Owner Occupied Assessor + 5 DocumentsUpdated Apr 2026

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4493 Wayside Dr

4,639 sqft · Built 2016 · 0.919 acres · Pool

Last Sale Tax Bill Prior Sale Owner Records
—Dec 2019 $22,1072025 Amount on Record Oct 2014 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Dec 2025

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Wildfire Risk on Wayside Dr

Source: USDA Forest Service Wildfire Risk to Communities · 2nd edition (2024), fuels as of 2020

Wildfire RiskLow
this street's cells rank at the 24th percentile of exposed land nationally · 8th in Florida
Wildfire LikelihoodLow — about 1 in 2,128 per year
ExposureDirect
2 of 4 cells directly exposed · 4 adjoin burnable vegetation

Property Records in Nearby Streets