48

Recently Sold Winding Cypress Homes

Section Image
  • /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 $980,162

    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 $1,247,216

    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 $651,440

    Last Listing Agent Kendra Hoefs Realty One Group MVP

    7717 Jacaranda Ln, 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 $679,336

    Last Listing Agent Craig Jerabeck Premiere Plus Realty Company

    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 $1,188,449

    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 $879,319

    Last Listing Agent Kendra Hoefs Realty One Group MVP

    7355 Mockingbird Ct, Naples, FL 34114
  • /2

    $530,000

    Sold Jun 23, 2025

    7702 Jacaranda Ln, Naples, FL 34114

    • 2 Beds
    • 2 Baths
    • 1,554 Sq Ft
    • Built 2019

    Last Sold Summary

    • 4% Below List Price
    • $341/SF
    • 0 Days On Market

    Current Estimated Value $548,081

    Last Listing Agent Comp Agent Marco Island Area Association Of Realtor

    7702 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 $547,845

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

    7785 Jacaranda Ln, Naples, FL 34114
  • /27

    $675,000

    Sold May 30, 2025

    7742 Jacaranda Ln, Naples, FL 34114

    • 2 Beds
    • 2 Baths
    • 1,554 Sq Ft
    • Built 2019

    Last Sold Summary

    • 6% Below List Price
    • $434/SF
    • 47 Days On Market

    Current Estimated Value $658,268

    Last Listing Agent Bob Bailey R L Bailey Realty Inc.

    7742 Jacaranda Ln, Naples, FL 34114
  • /42

    $855,000

    Sold Jul 11, 2025

    6906 Winding Cypress Dr, Naples, FL 34114

    • 3 Beds
    • 3 Baths
    • 2,124 Sq Ft
    • Built 2022

    Last Sold Summary

    • 14% Below List Price
    • $403/SF
    • 103 Days On Market

    Current Estimated Value $894,459

    Last Listing Agent Terence Trombetti Berkshire Hathaway FL Realty

    6906 Winding Cypress Dr, Naples, FL 34114
  • /46

    $975,000

    Sold Sep 09, 2025

    7788 Winding Cypress Dr, Naples, FL 34114

    • 3 Beds
    • 3 Baths
    • 2,496 Sq Ft
    • Built 2019

    Last Sold Summary

    • 37% Below List Price
    • $391/SF
    • 293 Days On Market

    Current Estimated Value $1,066,901

    Last Listing Agent Justine Hine John R. Wood Properties

    7788 Winding Cypress Dr, 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 $862,901

    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 $879,890

    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 $749,739

    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 $825,388

    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 $466,519

    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 $960,164

    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 $1,434,085

    Last Listing Agent Manuela Schinagl Manuela Realty, Inc

    7412 Winding Cypress 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 $858,957

    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 $472,254

    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 $1,361,232

    Last Listing Agent Paul Bocka William Raveis Real Estate

    6912 Cocoplum St, Naples, FL 34114
  • /48

    $900,000

    Sold Aug 07, 2025

    6848 Winding Cypress Dr, Naples, FL 34114

    • 2 Beds
    • 2 Baths
    • 1,901 Sq Ft
    • Built 2021

    Last Sold Summary

    • $473/SF
    • 23 Days On Market

    Current Estimated Value $893,907

    Last Listing Agent Kendra Hoefs Realty One Group MVP

    6848 Winding Cypress Dr, 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 $840,659

    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 $920,496

    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 $616,019

    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 $906,636

    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 $717,938

    Last Listing Agent Theresa Bocka William Raveis Real Estate

    6787 Winding Cypress Dr, Naples, FL 34114
  • /17

    $975,000

    Sold Jun 20, 2025

    7530 Geranium Way, Naples, FL 34114

    • 3 Beds
    • 3 Baths
    • 2,496 Sq Ft
    • Built 2018

    Last Sold Summary

    • 17% Below List Price
    • $391/SF
    • 41 Days On Market

    Current Estimated Value $1,016,508

    Last Listing Agent Theresa Bocka William Raveis Real Estate

    7530 Geranium Way, 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 $1,152,704

    Last Listing Agent Theresa Bocka William Raveis Real Estate

    7716 Winding Cypress Dr, Naples, FL 34114
  • /46

    $453,000

    Sold Jun 20, 2025

    7686 Jacaranda Ln, Naples, FL 34114

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

    Last Sold Summary

    • 21% Below List Price
    • $288/SF
    • 100 Days On Market

    Current Estimated Value $479,124

    Last Listing Agent Kendra Hoefs Realty One Group MVP

    7686 Jacaranda Ln, 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 $878,590

    Last Listing Agent Elliot Barton Waterfront Realty Group Inc

    6902 Winding Cypress Dr, Naples, FL 34114
  • /50

    $1,255,000

    Sold Jul 24, 2025

    7675 Winding Cypress Dr, Naples, FL 34114

    • 3 Beds
    • 3 Baths
    • 2,496 Sq Ft
    • Built 2020

    Last Sold Summary

    • 16% Below List Price
    • $503/SF
    • 161 Days On Market

    Current Estimated Value $1,262,363

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

    7675 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 $573,454

    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 $1,088,700

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

    7520 Blackberry Dr, Naples, FL 34114
  • /11

    $510,000

    Sold Jul 16, 2025

    7650 Jacaranda Ln, Naples, FL 34114

    • 2 Beds
    • 2 Baths
    • 1,579 Sq Ft
    • Built 2018

    Last Sold Summary

    • 7% Below List Price
    • $323/SF
    • 61 Days On Market

    Current Estimated Value $519,170

    Last Listing Agent Theresa Bocka William Raveis Real Estate

    7650 Jacaranda Ln, 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 $803,993

    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 $1,061,399

    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 $608,181

    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 $578,937

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

    7167 Live Oak Dr, Naples, FL 34114
  • /30

    $885,000

    Sold Aug 07, 2025

    7451 Blackberry Dr, Naples, FL 34114

    • 3 Beds
    • 2 Baths
    • 2,188 Sq Ft
    • Built 2017

    Last Sold Summary

    • 7% Below List Price
    • $404/SF
    • 82 Days On Market

    Current Estimated Value $900,538

    Last Listing Agent Brandi Chapman Downing Frye Realty Inc.

    7451 Blackberry 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 138 days on the market.
What is the number of active homes for sale in Winding Cypress, FL?
There are 11 active homes for sale in Winding Cypress, FL.

Home Trends in Winding Cypress, FL

Housing Trends

Median Sale Price
$835,000
Median Single Family Sale Price
$856,500
Median Townhouse Sale Price
$575,000
Median 2 Bedroom Sale Price
$550,000
Average Price Per Sq Ft
$410
Number of Homes for Sale
11
Last 12 months Home Sales
100
Months of Supply
1.30
Median List Price
$899,900
Median Change From 1st List Price
9%
Median Home Sale Price YoY Change
-3%
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