47

Recently Sold Winding Cypress Homes

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  • /2

    $1,025,000

    Sold Jun 25, 2026

    7631 Winding Cypress Dr, Naples, FL 34114

    • 4 Beds
    • 2 Baths
    • 2,186 Sq Ft
    • Built 2018

    Last Sold Summary

    • 7% Below List Price
    • $469/SF
    • 0 Days On Market

    Current Estimated Value $1,060,530

    Last Listing Agent Comp Agent Marco Island Area Association Of Realtor

    7631 Winding Cypress Dr, Naples, FL 34114
  • /38

    $565,000

    Sold Jul 14, 2026

    7733 Jacaranda Ln, Naples, FL 34114

    • 2 Beds
    • 2 Baths
    • 1,554 Sq Ft
    • Built 2018

    Last Sold Summary

    • 6% Below List Price
    • $364/SF
    • 101 Days On Market

    Current Estimated Value $582,552

    Last Listing Agent Jeff Waldman Premiere Plus Realty Company

    7733 Jacaranda Ln, Naples, FL 34114
  • /50

    $905,000

    Sold May 22, 2026

    7545 Geranium Way, Naples, FL 34114

    • 2 Beds
    • 2 Baths
    • 2,036 Sq Ft
    • Built 2018

    Last Sold Summary

    • 8% Below List Price
    • $444/SF
    • 45 Days On Market

    Current Estimated Value $915,709

    Last Listing Agent Nina Llorca Coldwell Banker Realty

    7545 Geranium Way, Naples, FL 34114
  • /50

    $1,260,000

    Sold Nov 21, 2025

    6839 Winding Cypress Dr, Naples, FL 34114

    • 3 Beds
    • 3 Baths
    • 2,515 Sq Ft
    • Built 2021

    Last Sold Summary

    • 7% Below List Price
    • $501/SF
    • 76 Days On Market

    Current Estimated Value $1,267,098

    Last Listing Agent Kendra Hoefs Realty One Group MVP

    6839 Winding Cypress Dr, Naples, FL 34114
  • /44

    $635,000

    Sold Apr 09, 2026

    7717 Jacaranda Ln, Naples, FL 34114

    • 2 Beds
    • 2 Baths
    • 1,554 Sq Ft
    • Built 2017

    Last Sold Summary

    • 4% Below List Price
    • $409/SF
    • 12 Days On Market

    Current Estimated Value $633,338

    Last Listing Agent Kendra Hoefs Realty One Group MVP

    7717 Jacaranda Ln, Naples, FL 34114
  • /33

    $580,000

    Sold Jun 12, 2026

    7121 Live Oak Dr, Naples, FL 34114

    • 2 Beds
    • 2 Baths
    • 1,554 Sq Ft
    • Built 2016

    Last Sold Summary

    • 8% Below List Price
    • $373/SF
    • 121 Days On Market

    Current Estimated Value $577,085

    Last Listing Agent Julie Blanton John R Wood Properties

    7121 Live Oak Dr, Naples, FL 34114
  • /43

    $625,000

    Sold Apr 14, 2026

    7057 Live Oak Dr, Naples, FL 34114

    • 3 Beds
    • 2 Baths
    • 2,230 Sq Ft
    • Built 2016

    Last Sold Summary

    • 24% Below List Price
    • $280/SF
    • 152 Days On Market

    Current Estimated Value $655,561

    Last Listing Agent Craig Jerabeck John R Wood Properties

    7057 Live Oak Dr, Naples, FL 34114
  • /46

    $1,175,000

    Sold Sep 22, 2025

    7597 Blackberry Dr, Naples, FL 34114

    • 3 Beds
    • 3 Baths
    • 2,496 Sq Ft
    • Built 2017

    Last Sold Summary

    • 9% Below List Price
    • $471/SF
    • 132 Days On Market

    Current Estimated Value $1,175,486

    Last Listing Agent Robert Crovo Premier Sotheby's Int'l Realty

    7597 Blackberry Dr, Naples, FL 34114
  • /43

    $875,000

    Sold Dec 15, 2025

    7355 Mockingbird Ct, Naples, FL 34114

    • 3 Beds
    • 2 Baths
    • 2,198 Sq Ft
    • Built 2016

    Last Sold Summary

    • 3% Below List Price
    • $398/SF
    • 4 Days On Market

    Current Estimated Value $878,228

    Last Listing Agent Kendra Hoefs Realty One Group MVP

    7355 Mockingbird Ct, Naples, FL 34114
  • /39

    $700,000

    Sold Aug 07, 2026

    7022 Live Oak Dr, Naples, FL 34114

    • 3 Beds
    • 2 Baths
    • 2,078 Sq Ft
    • Built 2016

    Last Sold Summary

    • 12% Below List Price
    • $337/SF
    • 123 Days On Market

    Current Estimated Value $748,293

    Last Listing Agent Kathy Friedle John R. Wood Properties

    7022 Live Oak Dr, Naples, FL 34114
  • /48

    $470,000

    Sold Jun 24, 2026

    7638 Jacaranda Ln, Naples, FL 34114

    • 2 Beds
    • 2 Baths
    • 1,574 Sq Ft
    • Built 2017

    Last Sold Summary

    • 25% Below List Price
    • $299/SF
    • 629 Days On Market

    Current Estimated Value $477,822

    Last Listing Agent Taylor Smith Premier Sotheby's Int'l Realty

    7638 Jacaranda Ln, Naples, FL 34114
  • /50

    $550,000

    Sold Mar 30, 2026

    7785 Jacaranda Ln, Naples, FL 34114

    • 2 Beds
    • 2 Baths
    • 1,574 Sq Ft
    • Built 2018

    Last Sold Summary

    • $349/SF
    • 10 Days On Market

    Current Estimated Value $548,428

    Last Listing Agent Taylor Smith Premier Sotheby's Int'l Realty

    7785 Jacaranda Ln, Naples, FL 34114
  • /47

    $962,500

    Sold Jul 09, 2026

    7343 Mockingbird Ct, Naples, FL 34114

    • 3 Beds
    • 2 Baths
    • 2,107 Sq Ft
    • Built 2016

    Last Sold Summary

    • 1% Below List Price
    • $457/SF
    • 11 Days On Market

    Current Estimated Value $970,833

    Last Listing Agent Kendra Hoefs Realty One Group MVP

    7343 Mockingbird Ct, Naples, FL 34114
  • /50

    $858,000

    Sold Jan 16, 2026

    6856 Winding Cypress Dr, Naples, FL 34114

    • 3 Beds
    • 2 Baths
    • 2,076 Sq Ft
    • Built 2021

    Last Sold Summary

    • 5% Below List Price
    • $413/SF
    • 81 Days On Market

    Current Estimated Value $863,724

    Last Listing Agent Brian Stolliker BERKSHIRE HATHAWAY HOMESERVICES FLORIDA REALTY

    6856 Winding Cypress Dr, Naples, FL 34114
  • /48

    $860,000

    Sold Oct 09, 2025

    6870 Winding Cypress Dr, Naples, FL 34114

    • 3 Beds
    • 2 Baths
    • 2,084 Sq Ft
    • Built 2021

    Last Sold Summary

    • 7% Below List Price
    • $413/SF
    • 75 Days On Market

    Current Estimated Value $870,068

    Last Listing Agent Kendra Hoefs Realty One Group MVP

    6870 Winding Cypress Dr, Naples, FL 34114
  • /33

    $750,000

    Sold Sep 10, 2025

    7128 Lily Way, Naples, FL 34114

    • 2 Beds
    • 2 Baths
    • 1,685 Sq Ft
    • Built 2015

    Last Sold Summary

    • 17% Below List Price
    • $445/SF
    • 143 Days On Market

    Current Estimated Value $734,686

    Last Listing Agent Kate Pentelow Premiere Plus Realty Company

    7128 Lily Way, Naples, FL 34114
  • /50

    $800,000

    Sold May 08, 2026

    6754 Pennyroyal Dr, Naples, FL 34114

    • 3 Beds
    • 3 Baths
    • 2,158 Sq Ft
    • Built 2021

    Last Sold Summary

    • 9% Below List Price
    • $371/SF
    • 73 Days On Market

    Current Estimated Value $799,861

    Last Listing Agent Kendra Hoefs Realty One Group MVP

    6754 Pennyroyal Dr, Naples, FL 34114
  • /42

    $455,000

    Sold Nov 17, 2025

    7642 Jacaranda Ln, Naples, FL 34114

    • 2 Beds
    • 2 Baths
    • 1,554 Sq Ft
    • Built 2017

    Last Sold Summary

    • 15% Below List Price
    • $293/SF
    • 172 Days On Market

    Current Estimated Value $468,240

    Last Listing Agent Scott Bertha Downing Frye Realty Inc.

    7642 Jacaranda Ln, Naples, FL 34114
  • /46

    $990,000

    Sold Nov 17, 2025

    6767 Pennyroyal Dr, Naples, FL 34114

    • 3 Beds
    • 2 Baths
    • 2,185 Sq Ft
    • Built 2021

    Last Sold Summary

    • 10% Below List Price
    • $453/SF
    • 152 Days On Market

    Current Estimated Value $957,653

    Last Listing Agent Jeff Waldman Premiere Plus Realty Company

    6767 Pennyroyal Dr, Naples, FL 34114
  • /38

    $1,495,000

    Sold Mar 11, 2026

    7412 Winding Cypress Dr, Naples, FL 34114

    • 4 Beds
    • 4 Baths
    • 3,656 Sq Ft
    • Built 2017

    Last Sold Summary

    • 12% Below List Price
    • $409/SF
    • 127 Days On Market

    Current Estimated Value $1,470,008

    Last Listing Agent Manuela Schinagl Manuela Realty, Inc

    7412 Winding Cypress Dr, Naples, FL 34114
  • /50

    $615,000

    Sold May 28, 2026

    7639 Jacaranda Ln, Naples, FL 34114

    • 2 Beds
    • 2 Baths
    • 1,554 Sq Ft
    • Built 2017

    Last Sold Summary

    • 8% Below List Price
    • $396/SF
    • 73 Days On Market

    Current Estimated Value $614,684

    Last Listing Agent Taylor Smith Premier Sotheby's Int'l Realty

    7639 Jacaranda Ln, Naples, FL 34114
  • /50

    $815,000

    Sold Aug 10, 2026

    7460 Blackberry Dr, Naples, FL 34114

    • 3 Beds
    • 2 Baths
    • 2,188 Sq Ft
    • Built 2016

    Last Sold Summary

    • 9% Below List Price
    • $372/SF
    • 117 Days On Market

    Current Estimated Value $819,991

    Last Listing Agent Angelica Andrews Premier Sotheby's International Realty

    7460 Blackberry Dr, Naples, FL 34114
  • /49

    $850,000

    Sold Feb 10, 2026

    6699 Pennyroyal Dr, Naples, FL 34114

    • 3 Beds
    • 2 Baths
    • 2,094 Sq Ft
    • Built 2022

    Last Sold Summary

    • 8% Below List Price
    • $406/SF
    • 116 Days On Market

    Current Estimated Value $858,702

    Last Listing Agent Theresa Bocka William Raveis Real Estate

    6699 Pennyroyal Dr, Naples, FL 34114
  • /17

    $460,000

    Sold Mar 12, 2026

    7658 Jacaranda Ln, Naples, FL 34114

    • 2 Beds
    • 2 Baths
    • 1,554 Sq Ft
    • Built 2018

    Last Sold Summary

    • 8% Below List Price
    • $296/SF
    • 16 Days On Market

    Current Estimated Value $473,037

    Last Listing Agent Theresa Bocka William Raveis Real Estate

    7658 Jacaranda Ln, Naples, FL 34114
  • /25

    $1,475,000

    Sold May 13, 2026

    6912 Cocoplum St, Naples, FL 34114

    • 3 Beds
    • 3.5 Baths
    • 2,923 Sq Ft
    • Built 2019

    Last Sold Summary

    • 18% Below List Price
    • $505/SF
    • 406 Days On Market

    Current Estimated Value $1,437,210

    Last Listing Agent Theresa Bocka William Raveis Real Estate

    6912 Cocoplum St, Naples, FL 34114
  • /18

    $835,000

    Sold Mar 06, 2026

    7211 Live Oak Dr, Naples, FL 34114

    • 3 Beds
    • 2 Baths
    • 2,230 Sq Ft
    • Built 2015

    Last Sold Summary

    • 2% Below List Price
    • $374/SF
    • 66 Days On Market

    Current Estimated Value $843,017

    Last Listing Agent Theresa Bocka William Raveis Real Estate

    7211 Live Oak Dr, Naples, FL 34114
  • /50

    $890,000

    Sold Apr 23, 2026

    6698 Pennyroyal Dr, Naples, FL 34114

    • 3 Beds
    • 3 Baths
    • 2,150 Sq Ft
    • Built 2022

    Last Sold Summary

    • 6% Below List Price
    • $414/SF
    • 94 Days On Market

    Current Estimated Value $884,544

    Last Listing Agent Taylor Smith Premier Sotheby's Int'l Realty

    6698 Pennyroyal Dr, Naples, FL 34114
  • /49

    $599,900

    Sold Apr 30, 2026

    7255 Live Oak Dr, Naples, FL 34114

    • 2 Beds
    • 2 Baths
    • 1,659 Sq Ft
    • Built 2015

    Last Sold Summary

    • 17% Below List Price
    • $362/SF
    • 73 Days On Market

    Current Estimated Value $604,881

    Last Listing Agent Linda Covino Royal Shell Real Estate, Inc.

    7255 Live Oak Dr, Naples, FL 34114
  • /48

    $910,000

    Sold Feb 27, 2026

    6779 Winding Cypress Dr, Naples, FL 34114

    • 3 Beds
    • 2 Baths
    • 2,003 Sq Ft
    • Built 2021

    Last Sold Summary

    • 2% Below List Price
    • $454/SF
    • 9 Days On Market

    Current Estimated Value $908,464

    Last Listing Agent Kendra Hoefs Realty One Group MVP

    6779 Winding Cypress Dr, Naples, FL 34114
  • /3

    $710,000

    Sold Nov 06, 2025

    6787 Winding Cypress Dr, Naples, FL 34114

    • 2 Beds
    • 2 Baths
    • 1,654 Sq Ft
    • Built 2021

    Last Sold Summary

    • 1% Below List Price
    • $429/SF
    • 108 Days On Market

    Current Estimated Value $709,535

    Last Listing Agent Theresa Bocka William Raveis Real Estate

    6787 Winding Cypress Dr, Naples, FL 34114
  • /6

    $1,150,000

    Sold Feb 03, 2026

    7716 Winding Cypress Dr, Naples, FL 34114

    • 3 Beds
    • 3.5 Baths
    • 2,923 Sq Ft
    • Built 2018

    Last Sold Summary

    • 4% Below List Price
    • $393/SF
    • 7 Days On Market

    Current Estimated Value $1,165,347

    Last Listing Agent Theresa Bocka William Raveis Real Estate

    7716 Winding Cypress Dr, Naples, FL 34114
  • /36

    $835,000

    Sold May 05, 2026

    6902 Winding Cypress Dr, Naples, FL 34114

    • 3 Beds
    • 2 Baths
    • 2,084 Sq Ft
    • Built 2022

    Last Sold Summary

    • 12% Below List Price
    • $401/SF
    • 233 Days On Market

    Current Estimated Value $843,880

    Last Listing Agent Elliot Barton Waterfront Realty Group Inc

    6902 Winding Cypress Dr, Naples, FL 34114
  • /2

    $975,000

    Sold Jun 12, 2026

    6678 Pennyroyal Dr, Naples, FL 34114

    • 3 Beds
    • 3 Baths
    • 2,000 Sq Ft
    • Built 2022

    Last Sold Summary

    • 7% Below List Price
    • $488/SF
    • 0 Days On Market

    Current Estimated Value $994,085

    Last Listing Agent Comp Agent Marco Island Area Association Of Realtor

    6678 Pennyroyal Dr, Naples, FL 34114
  • /42

    $900,000

    Sold Jul 31, 2026

    7473 Winding Cypress Dr, Naples, FL 34114

    • 4 Beds
    • 2 Baths
    • 2,018 Sq Ft
    • Built 2018

    Last Sold Summary

    • 5% Below List Price
    • $446/SF
    • 13 Days On Market

    Current Estimated Value $935,239

    Last Listing Agent Kendra Hoefs Realty One Group MVP

    7473 Winding Cypress Dr, Naples, FL 34114
  • /39

    $520,000

    Sold Mar 06, 2026

    7176 Live Oak Dr, Naples, FL 34114

    • 3 Beds
    • 2 Baths
    • 1,554 Sq Ft
    • Built 2015

    Last Sold Summary

    • 5% Below List Price
    • $335/SF
    • 34 Days On Market

    Current Estimated Value $573,783

    Last Listing Agent David Burke John R Wood Properties

    7176 Live Oak Dr, Naples, FL 34114
  • /48

    $1,100,000

    Sold Mar 03, 2026

    7520 Blackberry Dr, Naples, FL 34114

    • 3 Beds
    • 3 Baths
    • 2,496 Sq Ft
    • Built 2017

    Last Sold Summary

    • 15% Below List Price
    • $441/SF
    • 296 Days On Market

    Current Estimated Value $1,078,912

    Last Listing Agent Taylor Smith Premier Sotheby's Int'l Realty

    7520 Blackberry Dr, Naples, FL 34114
  • /50

    $800,000

    Sold Nov 14, 2025

    7049 Live Oak Dr, Naples, FL 34114

    • 3 Beds
    • 2 Baths
    • 2,230 Sq Ft
    • Built 2015

    Last Sold Summary

    • 3% Below List Price
    • $359/SF
    • 26 Days On Market

    Current Estimated Value $806,858

    Last Listing Agent Taylor Smith Premier Sotheby's Int'l Realty

    7049 Live Oak Dr, Naples, FL 34114
  • /25

    $1,000,000

    Sold Oct 30, 2025

    7235 Clamshell Ln, Naples, FL 34114

    • 3 Beds
    • 3 Baths
    • 2,512 Sq Ft
    • Built 2015

    Last Sold Summary

    • 9% Below List Price
    • $398/SF
    • 5 Days On Market

    Current Estimated Value $1,053,407

    Last Listing Agent Tommy Ogiba Downing Frye Realty Inc.

    7235 Clamshell Ln, Naples, FL 34114
  • /10

    $595,000

    Sold May 22, 2026

    7248 Live Oak Dr, Naples, FL 34114

    • 2 Beds
    • 2 Baths
    • 1,685 Sq Ft
    • Built 2016

    Last Sold Summary

    • 8% Below List Price
    • $353/SF
    • 191 Days On Market

    Current Estimated Value $593,560

    Last Listing Agent Theresa Bocka William Raveis Real Estate

    7248 Live Oak Dr, Naples, FL 34114
  • /48

    $575,000

    Sold Mar 23, 2026

    7167 Live Oak Dr, Naples, FL 34114

    • 3 Beds
    • 2 Baths
    • 1,554 Sq Ft
    • Built 2015

    Last Sold Summary

    • 4% Below List Price
    • $370/SF
    • 104 Days On Market

    Current Estimated Value $582,039

    Last Listing Agent Taylor Smith Premier Sotheby's Int'l Realty

    7167 Live Oak Dr, Naples, FL 34114

Showing Results 1 - 40, Page 1 of 2

Frequently Asked Questions

What is the average time to sell a house in Winding Cypress, FL?
The houses for sale in Winding Cypress, FL spend an average of 139 days on the market.
What is the number of active homes for sale in Winding Cypress, FL?
There are 8 active homes for sale in Winding Cypress, FL.

Home Price Trends

Median Sale Price
$835,000
Median Single Family Sale Price
$866,750
Median Townhouse Sale Price
$575,000
Median 2 Bedroom Sale Price
$595,000
Average Price Per Sq Ft
$415
Number of Homes for Sale
8
Last 12 months Home Sales
99
Months of Supply
1.00
Median List Price
$900,000
Median Change From 1st List Price
8%
Median Home Sale Price YoY Change
-2%
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