Recently Sold Winding Cypress Homes

/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 $1,232,916

Last Listing Agent Kendra Hoefs Realty One Group MVP

6839 Winding Cypress Dr, Naples, FL 34114
Explore Winding Cypress
/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 $1,151,485

Last Listing Agent Robert Crovo Coldwell Banker Realty

7597 Blackberry Dr, Naples, FL 34114
/50
$992,500 Sold Apr 17, 2025

7404 Winding Cypress Dr, Naples, FL 34114
- 2 Beds
- 2 Baths
- 2,062 Sq Ft
- Built 2016
Last Sold Summary
- 21% Below List Price
- $481/SF
- 115 Days On Market
Current Estimated Value $959,642

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

7404 Winding Cypress Dr, Naples, FL 34114
/20
$537,000 Sold May 01, 2025

7591 Jacaranda Ln, Naples, FL 34114
- 2 Beds
- 2 Baths
- 1,554 Sq Ft
- Built 2016
Last Sold Summary
- 2% Below List Price
- $346/SF
- 26 Days On Market
Current Estimated Value $579,970

Last Listing Agent william Romano Keller Williams Marco Realty

7591 Jacaranda Ln, 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 $865,381

Last Listing Agent Kendra Hoefs Realty One Group MVP

7355 Mockingbird Ct, 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 $654,902

Last Listing Agent Bob Bailey R L Bailey Realty Inc.

7742 Jacaranda Ln, Naples, FL 34114
/43
$890,000 Sold Mar 28, 2025

7556 Winding Cypress Dr, Naples, FL 34114
- 3 Beds
- 2 Baths
- 2,107 Sq Ft
- Built 2018
Last Sold Summary
- 1% Below List Price
- $422/SF
- 3 Days On Market
Current Estimated Value $860,306

Last Listing Agent Kimberly Springer Orchid Realty International

7556 Winding Cypress Dr, 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 $870,999

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 $1,023,735

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 $866,463

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 $851,990

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 $735,949

Last Listing Agent Kate Pentelow Premiere Plus Realty Company

7128 Lily Way, 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 $461,521

Last Listing Agent Scott Bertha Downing Frye Realty Inc.

7642 Jacaranda Ln, Naples, FL 34114
/50
$635,000 Sold Apr 08, 2025

7199 Live Oak Dr, Naples, FL 34114
- 2 Beds
- 2 Baths
- 1,554 Sq Ft
- Built 2015
Last Sold Summary
- 4% Below List Price
- $409/SF
- 40 Days On Market
Current Estimated Value $625,248

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

7199 Live Oak Dr, 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 $955,080

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 $1,521,798

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 $877,117

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 $534,618

Last Listing Agent Theresa Bocka William Raveis Real Estate

7658 Jacaranda Ln, 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 $893,357

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 $839,651

Last Listing Agent Theresa Bocka William Raveis Real Estate

7211 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 $911,356

Last Listing Agent Kendra Hoefs Realty One Group MVP

6779 Winding Cypress Dr, Naples, FL 34114
/27
$530,000 Sold Jun 20, 2025

7702 Jacaranda Ln, Naples, FL 34114
- 2 Beds
- 2 Baths
- 1,554 Sq Ft
- Built 2019
Last Sold Summary
- 24% Below List Price
- $341/SF
- 271 Days On Market
Current Estimated Value $532,843

Last Listing Agent Mike Miller Berkshire Hathaway FL Realty

7702 Jacaranda Ln, 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 $705,271

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 $974,393

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 $1,178,734

Last Listing Agent Theresa Bocka William Raveis Real Estate

7716 Winding Cypress Dr, Naples, FL 34114
/47
$935,000 Sold Apr 01, 2025

7683 Winding Cypress Dr, Naples, FL 34114
- 3 Beds
- 2 Baths
- 2,018 Sq Ft
- Built 2018
Last Sold Summary
- 6% Below List Price
- $463/SF
- 146 Days On Market
Current Estimated Value $909,151

Last Listing Agent Kimberly Alvord John R Wood Properties

7683 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 $471,645

Last Listing Agent Kendra Hoefs Realty One Group MVP

7686 Jacaranda Ln, 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 $1,237,983

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

7675 Winding Cypress 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 $1,110,134

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 $504,133

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 $796,102

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 $1,008,099

Last Listing Agent Tommy Ogiba Downing Frye Realty Inc.

7235 Clamshell Ln, Naples, FL 34114
/13
$860,000 Sold May 02, 2025

6763 Pennyroyal Dr, Naples, FL 34114
- 3 Beds
- 2 Baths
- 2,208 Sq Ft
- Built 2020
Last Sold Summary
- 14% Below List Price
- $389/SF
- 66 Days On Market
Current Estimated Value $858,526

Last Listing Agent Theresa Bocka William Raveis Real Estate

6763 Pennyroyal 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 $882,655

Last Listing Agent Brandi Chapman Downing Frye Realty Inc.

7451 Blackberry Dr, Naples, FL 34114
/28
$645,000 Sold Dec 05, 2025

7370 Mockingbird Ct, Naples, FL 34114
- 2 Beds
- 2 Baths
- 1,805 Sq Ft
- Built 2016
Last Sold Summary
- 19% Below List Price
- $357/SF
- 307 Days On Market
Current Estimated Value $647,468

Last Listing Agent Joseph Scott Compass Florida LLC

7370 Mockingbird Ct, Naples, FL 34114
/50
$880,000 Sold Aug 18, 2025

6763 Winding Cypress Dr, Naples, FL 34114
- 3 Beds
- 2 Baths
- 2,107 Sq Ft
- Built 2021
Last Sold Summary
- 9% Below List Price
- $418/SF
- 272 Days On Market
Current Estimated Value $889,153

Last Listing Agent Ryan Finnegan Coldwell Banker Sunstar Realty

6763 Winding Cypress Dr, Naples, FL 34114
/11
$830,000 Sold Aug 08, 2025

7544 Winding Cypress Dr, Naples, FL 34114
- 3 Beds
- 3 Baths
- 2,532 Sq Ft
- Built 2018
Last Sold Summary
- 28% Below List Price
- $328/SF
- 253 Days On Market
Current Estimated Value $846,787

Last Listing Agent Theresa Bocka William Raveis Real Estate

7544 Winding Cypress Dr, Naples, FL 34114
/45
$575,000 Sold Jan 27, 2026

7659 Jacaranda Ln, Naples, FL 34114
- 2 Beds
- 2 Baths
- 1,544 Sq Ft
- Built 2017
Last Sold Summary
- 8% Below List Price
- $372/SF
- 69 Days On Market
Current Estimated Value $585,362

Last Listing Agent Stanley Whitcomb Premiere Plus Realty Company

7659 Jacaranda Ln, Naples, FL 34114
/44
$575,000 Sold Mar 16, 2026

7690 Jacaranda Ln, Naples, FL 34114
- 2 Beds
- 2 Baths
- 1,554 Sq Ft
- Built 2018
Last Sold Summary
- 10% Below List Price
- $370/SF
- 241 Days On Market
Current Estimated Value $604,547

Last Listing Agent Michelle Thomas Premier Sotheby's International Realty

7690 Jacaranda Ln, Naples, FL 34114
/47
$760,000 Sold May 08, 2025

6758 Pennyroyal Dr, Naples, FL 34114
- 2 Beds
- 2 Baths
- 1,921 Sq Ft
- Built 2021
Last Sold Summary
- 22% Below List Price
- $396/SF
- 52 Days On Market
Current Estimated Value $769,442

Last Listing Agent Kendra Hoefs Realty One Group MVP

6758 Pennyroyal Dr, Naples, FL 34114

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Florida Collier County Naples Winding Cypress

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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 130 days on the market.

What is the number of active homes for sale in Winding Cypress, FL?

There are 20 active homes for sale in Winding Cypress, FL.

Home Trends in Winding Cypress, FL

On average, homes in Winding Cypress, Naples sell after 130 days on the market compared to the national average of 55 days. The median sale price for homes in Winding Cypress, Naples over the last 12 months is $858,000, up 1% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price

$858,000

Median Single Family Sale Price

$858,500

Median Townhouse Sale Price

$602,500

Median 2 Bedroom Sale Price

$556,000

Average Price Per Sq Ft

$417

Number of Homes for Sale

Last 12 months Home Sales

Months of Supply

2.60

Median List Price

$900,000

Median Change From 1st List Price

Median Home Sale Price YoY Change

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