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Olde Cypress Dr, Naples, FL Property Records

Collier County property records for 47 addresses on Olde Cypress Dr, Naples, FL · Last verified August 2026

Olde Cypress Dr Highlights

Properties 47
Median Sale Price $1,715,000
Deeds and Mortgages on File 50
Median Price per Sqft $525
Owner Occupied 77%
Median Annual Tax Bill $9,376
Median Year Built 2002
Median Ownership Tenure 12 years

Properties on Olde Cypress Dr

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

2701 Olde Cypress Dr

3,892 sqft · Built 2004 · 0.45 acres · Pool

Last Sale Tax Bill Prior Sale Owner Records
$1,132,500Oct 2009 $10,3902024 Amount on Record Apr 2004 2 Names on Record Owner Occupied AssessorUpdated Apr 2026

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2705 Olde Cypress Dr

3,918 sqft · Built 2006 · 0.269 acres · Pool

Last Sale Tax Bill Prior Sale Owner Records
$1,175,000Oct 2017 $13,7222024 Amount on Record Sep 2006 1 Name on Record Assessor + 1 DocumentUpdated Apr 2026

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2706 Olde Cypress Dr

3,763 sqft · Built 2004 · 0.36 acres · Pool

Last Sale Tax Bill Prior Sale Owner Records
$950,000Feb 2012 $9,6652025 —Oct 2004 2 Names on Record Owner Occupied AssessorUpdated Dec 2025

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2709 Olde Cypress Dr

3,011 sqft · Built 2005 · 0.35 acres · Pool

Last Sale Tax Bill Prior Sale Owner Records
$630,000Dec 2005 $6,0342025 Amount on Record Aug 2004 2 Names on Record Owner Occupied AssessorUpdated Aug 2026

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2710 Olde Cypress Dr

2,728 sqft · Built 2000 · 0.269 acres · Pool

Last Sale Tax Bill Prior Sale Owner Records
$550,000Mar 2010 $4,9182025 Amount on Record Apr 2000 2 Names on Record Owner Occupied AssessorUpdated Dec 2025

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2714 Olde Cypress Dr

3,239 sqft · Built 2002 · 0.25 acres · Pool

Last Sale Tax Bill Prior Sale Owner Records
$980,000May 2018 $8,7482025 Amount on Record Nov 2000 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Dec 2025

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2717 Olde Cypress Dr

3,440 sqft · Built 2006 · 0.289 acres · Pool

Last Sale Tax Bill Prior Sale Owner Records
$1,175,000Jul 2007 $13,0602025 Amount on Record Dec 2004 2 Names on Record AssessorUpdated Aug 2026

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2718 Olde Cypress Dr

2,888 sqft · Built 2004 · 0.25 acres · Pool

Last Sale Tax Bill Prior Sale Owner Records
$835,000Apr 2015 $6,1972024 Amount on Record May 2004 1 Name on Record Owner Occupied AssessorUpdated Apr 2026

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2721 Olde Cypress Dr

3,663 sqft · Built 2002 · 0.31 acres · Pool

Last Sale Tax Bill Prior Sale Owner Records
$1,100,000Feb 2022 $13,8872025 Amount on Record Apr 2018 1 Name on Record Assessor + 5 DocumentsUpdated Aug 2026

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2722 Olde Cypress Dr

2,786 sqft · Built 2001 · 0.319 acres · Pool

Last Sale Tax Bill Prior Sale Owner Records
$1,715,000Jul 2025 $10,5582024 Amount on Record Aug 2023 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Apr 2026

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2725 Olde Cypress Dr

3,118 sqft · Built 2001 · 0.43 acres · Pool

Last Sale Tax Bill Prior Sale Owner Records
$1,100,000Nov 2014 $7,1372025 Amount on Record Feb 2010 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Aug 2026

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2726 Olde Cypress Dr

2,949 sqft · Built 2002 · 0.319 acres · Pool

Last Sale Tax Bill Prior Sale Owner Records
—Jun 2024 $11,9432025 Amount on Record Dec 2001 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Dec 2025

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2730 Olde Cypress Dr

3,119 sqft · Built 2001 · 0.319 acres · Pool

Last Sale Tax Bill Prior Sale Owner Records
$55,000May 2018 $5,9712024 Amount on Record May 2000 2 Names on Record Owner Occupied Assessor + 4 DocumentsUpdated Apr 2026

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2731 Olde Cypress Dr

3,395 sqft · Built 2002 · 0.36 acres · Pool

Last Sale Tax Bill Prior Sale Owner Records
$175,000Jan 2001 $7,4582024 —Dec 2000 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

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2734 Olde Cypress Dr

3,308 sqft · Built 2006 · 0.319 acres · Pool

Last Sale Tax Bill Prior Sale Owner Records
$275,000May 2004 $12,5652024 Amount on Record Jun 2003 1 Name on Record Assessor + 1 DocumentUpdated Apr 2026

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2737 Olde Cypress Dr

3,613 sqft · Built 2002 · 0.319 acres · Pool

Last Sale Tax Bill Prior Sale Owner Records
$795,000May 2011 $8,6572025 Amount on Record May 2002 2 Names on Record Owner Occupied AssessorUpdated Dec 2025

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2738 Olde Cypress Dr

3,336 sqft · Built 2002 · 0.319 acres · Pool

Last Sale Tax Bill Prior Sale Owner Records
$1,800,000Aug 2023 $12,4982024 Amount on Record Mar 2023 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Apr 2026

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2742 Olde Cypress Dr

2,605 sqft · Built 2001 · 0.319 acres · Pool

Last Sale Tax Bill Prior Sale Owner Records
$750,000Dec 2014 $5,5612025 Amount on Record Oct 2003 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Dec 2025

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2743 Olde Cypress Dr

3,800 sqft · Built 2003 · 0.319 acres · Pool

Last Sale Tax Bill Prior Sale Owner Records
$1,998,000Jul 2025 $7,8472024 Amount on Record Jul 2005 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

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2746 Olde Cypress Dr

2,770 sqft · Built 2001 · 0.3 acres · Pool

Last Sale Tax Bill Prior Sale Owner Records
—Oct 2022 $10,6262025 —Oct 2003 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Dec 2025

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2747 Olde Cypress Dr

3,551 sqft · Built 2002 · 0.33 acres · Pool

Last Sale Tax Bill Prior Sale Owner Records
$1,048,000Jun 2021 $13,7032024 Amount on Record Jun 2014 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Apr 2026

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2750 Olde Cypress Dr

2,843 sqft · Built 2002 · 0.31 acres · Pool

Last Sale Tax Bill Prior Sale Owner Records
$157,500Jan 2001 $6,5102025 1 Name on Record Owner Occupied AssessorUpdated Dec 2025

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2753 Olde Cypress Dr

3,397 sqft · Built 2002 · 0.33 acres · Pool

Last Sale Tax Bill Prior Sale Owner Records
$900,000Feb 2017 $11,7642024 Amount on Record May 2003 1 Name on Record Assessor + 1 DocumentUpdated Apr 2026

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2754 Olde Cypress Dr

3,226 sqft · Built 2005 · 0.31 acres · Pool

Last Sale Tax Bill Prior Sale Owner Records
$250,000Mar 2004 $7,1982025 Amount on Record Dec 2001 3 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Dec 2025

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2757 Olde Cypress Dr

3,322 sqft · Built 2001 · 0.319 acres · Pool

Last Sale Tax Bill Prior Sale Owner Records
$70,000Oct 2007 $6,4262025 Amount on Record Jul 2004 1 Name on Record Owner Occupied AssessorUpdated Aug 2026

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2758 Olde Cypress Dr

3,627 sqft · Built 2001 · 0.319 acres · Pool

Last Sale Tax Bill Prior Sale Owner Records
$800,000Oct 2004 $7,3132024 Amount on Record Jan 2003 2 Names on Record Owner Occupied AssessorUpdated Apr 2026

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2761 Olde Cypress Dr

3,128 sqft · Built 2001 · 0.31 acres · Pool

Last Sale Tax Bill Prior Sale Owner Records
$900,000Jul 2025 $10,0502024 Amount on Record Apr 2002 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Apr 2026

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2762 Olde Cypress Dr

2,888 sqft · Built 2001 · 0.319 acres · Pool

Last Sale Tax Bill Prior Sale Owner Records
$700,000Jan 2014 $5,8082024 Amount on Record May 2000 2 Names on Record Owner Occupied Assessor + 4 DocumentsUpdated Apr 2026

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2766 Olde Cypress Dr

3,321 sqft · Built 2001 · 0.319 acres · Pool

Last Sale Tax Bill Prior Sale Owner Records
$920,000Apr 2015 $6,4522024 Amount on Record Jul 2005 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Apr 2026

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2767 Olde Cypress Dr

3,033 sqft · Built 2001 · 0.31 acres · Pool

Last Sale Tax Bill Prior Sale Owner Records
$1,438,000Apr 2024 $9,7072024 Amount on Record Jul 2009 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Apr 2026

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2770 Olde Cypress Dr

3,404 sqft · Built 2001 · 0.319 acres · Pool

Last Sale Tax Bill Prior Sale Owner Records
$825,000Apr 2009 $11,7092025 Amount on Record Apr 2000 2 Names on Record AssessorUpdated Aug 2026

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2773 Olde Cypress Dr

3,867 sqft · Built 2002 · 0.319 acres · Pool

Last Sale Tax Bill Prior Sale Owner Records
$1,000,000Dec 2004 $8,3592025 Amount on Record Jan 2001 1 Name on Record Owner Occupied AssessorUpdated Dec 2025

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2774 Olde Cypress Dr

3,087 sqft · Built 2003 · 0.31 acres · Pool

Last Sale Tax Bill Prior Sale Owner Records
$245,000Jun 2002 $6,6122025 —Mar 2002 2 Names on Record Owner Occupied AssessorUpdated Dec 2025

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2777 Olde Cypress Dr

3,763 sqft · Built 2001 · 0.33 acres · Pool

Last Sale Tax Bill Prior Sale Owner Records
$2,351,000Mar 2022 $15,7002025 Amount on Record Aug 2017 2 Names on Record Owner Occupied Assessor + 3 DocumentsUpdated Dec 2025

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2778 Olde Cypress Dr

3,220 sqft · Built 2001 · 0.31 acres · Pool

Last Sale Tax Bill Prior Sale Owner Records
$780,000Mar 2014 $6,4172025 Amount on Record May 2005 2 Names on Record Owner Occupied AssessorUpdated Dec 2025

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2781 Olde Cypress Dr

3,418 sqft · Built 2002 · 0.33 acres · Pool

Last Sale Tax Bill Prior Sale Owner Records
$950,000Mar 2015 $12,0522024 Amount on Record Feb 2001 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Aug 2026

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2782 Olde Cypress Dr

2,986 sqft · Built 2001 · 0.31 acres · Pool

Last Sale Tax Bill Prior Sale Owner Records
$1,980,000Oct 2023 $11,2602024 Amount on Record Mar 2017 2 Names on Record Assessor + 3 DocumentsUpdated Apr 2026

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2785 Olde Cypress Dr

3,327 sqft · Built 2002 · 0.33 acres · Pool

Last Sale Tax Bill Prior Sale Owner Records
$1,025,000Sep 2005 $7,8162024 Amount on Record Jan 2002 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Apr 2026

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2786 Olde Cypress Dr

3,956 sqft · Built 2002 · 0.31 acres · Pool

Last Sale Tax Bill Prior Sale Owner Records
$2,350,000May 2023 $9,3762025 Amount on Record Apr 2000 3 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Dec 2025

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2789 Olde Cypress Dr

3,803 sqft · Built 2003 · 0.33 acres · Pool

Last Sale Tax Bill Prior Sale Owner Records
$850,000Aug 2009 $14,2022025 —Aug 2004 2 Names on Record AssessorUpdated Dec 2025

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2790 Olde Cypress Dr

3,568 sqft · Built 2001 · 0.31 acres · Pool

Last Sale Tax Bill Prior Sale Owner Records
$1,227,200Jan 2021 $13,9282024 Amount on Record Mar 2007 2 Names on Record Assessor + 2 DocumentsUpdated Apr 2026

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2793 Olde Cypress Dr

3,309 sqft · Built 2005 · 0.33 acres · Pool

Last Sale Tax Bill Prior Sale Owner Records
$240,000Jul 2004 $7,7612024 Amount on Record Jun 2003 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Apr 2026

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2794 Olde Cypress Dr

3,411 sqft · Built 2004 · 0.319 acres · Pool

Last Sale Tax Bill Prior Sale Owner Records
$1,005,000Apr 2013 $12,7122024 Amount on Record Mar 2004 2 Names on Record Owner Occupied AssessorUpdated Apr 2026

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2797 Olde Cypress Dr

3,266 sqft · Built 2003 · 0.33 acres · Pool

Last Sale Tax Bill Prior Sale Owner Records
$950,000Jan 2019 $8,3722024 Amount on Record Jan 2015 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated Apr 2026

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2798 Olde Cypress Dr

3,275 sqft · Built 2004 · 0.369 acres · Pool

Last Sale Tax Bill Prior Sale Owner Records
$910,000Sep 2014 $12,2092024 Amount on Record Sep 2012 2 Names on Record Assessor + 2 DocumentsUpdated Apr 2026

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2801 Olde Cypress Dr

3,800 sqft · Built 2005 · 0.33 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$970,000Nov 2015 $8,7272025 Amount on Record Dec 2009 2 Names on Record Owner Occupied AssessorUpdated Dec 2025

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3071 Olde Cypress Dr

0.069 acres

Last Sale Tax Bill Prior Sale Owner Records
1 Name on Record AssessorUpdated Apr 2026

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Wildfire Risk on Olde Cypress Dr

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

Wildfire RiskModerate
this street's cells rank at the 49th percentile of exposed land nationally · 21st in Florida
Wildfire LikelihoodModerate — about 1 in 844 per year
ExposureDirect
2 of 4 cells directly exposed · 4 adjoin burnable vegetation

Property Records in Nearby Streets