Winding Cypress Homes

/50
$1,499,900
- 4 Beds
- 4 Baths
- 3,350 Sq Ft
7072 Live Oak Dr, Naples, FL 34114

Welcome to this stunning Tangerly Oak model home, thoughtfully designed with space, style, and Florida living in mind. This expansive 4-bedroom residence with a generous loft offers a flexible floor plan ideal for both everyday living and hosting guests, all enhanced by beautiful designer upgrades throughout. Step outside to an exceptional outdoor living space featuring a large covered lanai,

Reilly McGregor Harborview Realty Inc

7072 Live Oak 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 $796,854

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

7049 Live Oak Dr, Naples, FL 34114

/38
Est $891,698 Not Listed For Sale
- 2 Beds
- 2.5 Baths
- 2,117 Sq Ft
6898 Winding Cypress Dr, Naples, FL 34114

6898 Winding Cypress Dr, Naples, FL 34114

/44
$610,000 Pending
- 2 Beds
- 2 Baths
- 1,554 Sq Ft
7690 Jacaranda Ln, Naples, FL 34114

Set against private garden views with tranquil eastern exposure, this beautifully appointed villa in Winding Cypress offers a peaceful retreat and effortless indoor-outdoor living. Featuring two bedrooms plus a den, two baths, and a two-car garage, this thoughtfully designed residence combines quiet luxury with meticulous updates in one of Naples' most dynamic lifestyle communities. The screened

Michelle Thomas Premier Sotheby's International Realty

7690 Jacaranda Ln, 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 $1,023,348

Last Listing Agent Tommy Ogiba Downing Frye Realty Inc.

7235 Clamshell Ln, Naples, FL 34114

/48
Est $918,423 Not Listed For Sale
- 3 Beds
- 3 Baths
- 2,998 Sq Ft
7123 Lily Way, Naples, FL 34114

7123 Lily Way, Naples, FL 34114

/44
$699,900 Open Sun 3PM - 4PM
- 2 Beds
- 2 Baths
- 1,659 Sq Ft
7255 Live Oak Dr, Naples, FL 34114

This home has just been freshly painted inside and out. professionally painted kitchen and bath cabinets, nice private south west waterview , screened lanai able to enlarge or even add a pool. Previous owner had a great workshop in garage with 8 overhead lights, charging station for a Tesla , framed peg boards for hanging tools , custom storage cabinets and a pull down staircase for added

Linda Covino Royal Shell Real Estate, Inc.

7255 Live Oak Dr, 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 $874,467

Last Listing Agent Theresa Bocka William Raveis Real Estate

6763 Pennyroyal Dr, Naples, FL 34114

/33
Est $668,583 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,685 Sq Ft
7108 Lily Way, Naples, FL 34114

7108 Lily Way, 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 $872,224

Last Listing Agent Brandi Chapman Downing Frye Realty Inc.

7451 Blackberry Dr, Naples, FL 34114

/34
Est $659,828 Not Listed For Sale
- 3 Beds
- 2 Baths
- 2,230 Sq Ft
7267 Live Oak Dr, Naples, FL 34114

7267 Live Oak 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
Last Listing Agent Joseph Scott Compass Florida LLC

7370 Mockingbird Ct, Naples, FL 34114

/37
Est $692,436 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,910 Sq Ft
7247 Live Oak Dr, Naples, FL 34114

7247 Live Oak Dr, 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 $886,671

Last Listing Agent Ryan Finnegan Coldwell Banker Sunstar Realty

6763 Winding Cypress Dr, Naples, FL 34114

/32
Est $531,771 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,554 Sq Ft
7191 Live Oak Dr, Naples, FL 34114

7191 Live Oak 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 $843,033

Last Listing Agent Theresa Bocka William Raveis Real Estate

7544 Winding Cypress Dr, Naples, FL 34114

/19
Est $600,790 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,554 Sq Ft
7175 Live Oak Dr, Naples, FL 34114

7175 Live Oak 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
Last Listing Agent Stanley Whitcomb Premiere Plus Realty Company

7659 Jacaranda Ln, Naples, FL 34114

/34
Est $562,545 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,542 Sq Ft
7097 Live Oak Dr, Naples, FL 34114

7097 Live Oak Dr, 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 $768,986

Last Listing Agent Kendra Hoefs Realty One Group MVP

6758 Pennyroyal Dr, Naples, FL 34114

/50
Est $854,050 Not Listed For Sale
- 4 Beds
- 3 Baths
- 2,350 Sq Ft
7021 Live Oak Dr, Naples, FL 34114

7021 Live Oak Dr, Naples, FL 34114

/47
$615,000 Sold Mar 24, 2025

7113 Live Oak Dr, Naples, FL 34114
- 2 Beds
- 2 Baths
- 1,554 Sq Ft
- Built 2016
Last Sold Summary
- 14% Below List Price
- $396/SF
- 330 Days On Market
Current Estimated Value $590,336

Last Listing Agent James Trzyna Realty One Group MVP

7113 Live Oak Dr, Naples, FL 34114

/29
Est $956,642 Not Listed For Sale
- 3 Beds
- 3 Baths
- 2,496 Sq Ft
7063 Winding Cypress Dr, Naples, FL 34114

7063 Winding Cypress Dr, Naples, FL 34114

/50
$635,000 Sold Sep 29, 2025

7773 Jacaranda Ln, Naples, FL 34114
- 2 Beds
- 2 Baths
- 1,554 Sq Ft
- Built 2018
Last Sold Summary
- 5% Below List Price
- $409/SF
- 94 Days On Market
Current Estimated Value $632,452

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

7773 Jacaranda Ln, Naples, FL 34114

/24
Est $504,574 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,554 Sq Ft
7202 Live Oak Dr, Naples, FL 34114

7202 Live Oak Dr, Naples, FL 34114

/49
$674,000 Sold Aug 19, 2025

7445 Winding Cypress Dr, Naples, FL 34114
- 3 Beds
- 2 Baths
- 2,198 Sq Ft
- Built 2016
Last Sold Summary
- 16% Below List Price
- $307/SF
- 65 Days On Market
Current Estimated Value $695,650

Last Listing Agent Drayton Herold KW Elevate Luxury

7445 Winding Cypress Dr, Naples, FL 34114

/36
Est $1,412,022 Not Listed For Sale
- 4 Beds
- 4 Baths
- 3,696 Sq Ft
7383 Mockingbird Ct, Naples, FL 34114

7383 Mockingbird Ct, Naples, FL 34114

/49
$775,000 Sold Mar 11, 2025

6852 Winding Cypress Dr, Naples, FL 34114
- 2 Beds
- 2 Baths
- 1,804 Sq Ft
- Built 2021
Last Sold Summary
- 7% Below List Price
- $430/SF
- 117 Days On Market
Current Estimated Value $688,013

Last Listing Agent Ashley Prescott DomainRealty.com LLC

6852 Winding Cypress Dr, Naples, FL 34114

/50
Est $814,688 Not Listed For Sale
- 4 Beds
- 2 Baths
- 2,230 Sq Ft
7346 Mockingbird Ct, Naples, FL 34114

7346 Mockingbird Ct, Naples, FL 34114

/17
$925,000 Sold May 14, 2025

6854 Greenbriar Ct, Naples, FL 34114
- 3 Beds
- 2 Baths
- 2,118 Sq Ft
- Built 2020
Last Sold Summary
- $437/SF
- 8 Days On Market
Current Estimated Value $903,334

Last Listing Agent Theresa Bocka William Raveis Real Estate

6854 Greenbriar Ct, Naples, FL 34114

/50
Est $847,366 Not Listed For Sale
- 4 Beds
- 2 Baths
- 2,198 Sq Ft
7408 Winding Cypress Dr, Naples, FL 34114

7408 Winding Cypress Dr, Naples, FL 34114

/32
$620,000 Sold Jan 27, 2026

7815 Jacaranda Ln, Naples, FL 34114
- 2 Beds
- 2 Baths
- 1,574 Sq Ft
- Built 2019
Last Sold Summary
- 17% Below List Price
- $394/SF
- 255 Days On Market
Last Listing Agent Kati Bepko Coldwell Banker Realty

7815 Jacaranda Ln, Naples, FL 34114

/50
Est $829,598 Not Listed For Sale
- 4 Beds
- 2 Baths
- 2,198 Sq Ft
7420 Winding Cypress Dr, Naples, FL 34114

7420 Winding Cypress Dr, Naples, FL 34114

/4
Est $680,517 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,685 Sq Ft
7441 Winding Cypress Dr, Naples, FL 34114

7441 Winding Cypress Dr, Naples, FL 34114

/50
Est $1,137,365 Not Listed For Sale
- 3 Beds
- 3 Baths
- 2,496 Sq Ft
7453 Winding Cypress Dr, Naples, FL 34114

7453 Winding Cypress Dr, Naples, FL 34114

/34
Est $725,288 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,910 Sq Ft
7465 Winding Cypress Dr, Naples, FL 34114

7465 Winding Cypress Dr, Naples, FL 34114

/41
Est $1,066,445 Not Listed For Sale
- 4 Beds
- 3 Baths
- 2,914 Sq Ft
7493 Winding Cypress Dr, Naples, FL 34114

7493 Winding Cypress Dr, Naples, FL 34114

/35
Est $1,447,958 Not Listed For Sale
- 3 Beds
- 3.5 Baths
- 2,900 Sq Ft
7513 Winding Cypress Dr, Naples, FL 34114

7513 Winding Cypress Dr, Naples, FL 34114

/32
Est $838,355 Not Listed For Sale
- 3 Beds
- 2 Baths
- 2,230 Sq Ft
7452 Blackberry Dr, Naples, FL 34114

7452 Blackberry Dr, Naples, FL 34114

/40
Est $866,683 Not Listed For Sale
- 3 Beds
- 2 Baths
- 2,107 Sq Ft
7464 Blackberry Dr, Naples, FL 34114

7464 Blackberry Dr, Naples, FL 34114

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