Winding Cypress Homes

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  /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 $880,073

  Last Listing Agent Kendra Hoefs Realty One Group MVP

  6870 Winding Cypress Dr, Naples, FL 34114
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  /50

  Est $1,212,371 Not Listed For Sale

  6932 Cocoplum St, Naples, FL 34114

  • 3 Beds
  • 3 Baths
  • 2,515 Sq Ft
  • Built 2019

  6932 Cocoplum St, Naples, FL 34114

  Last Sold Summary

  • 21% Below List Price
  • $606/SF
  • 146 Days On Market

  • Last Sold Price $1,525,000
  • Sep 20, 2024

  Last Listing Agent Joy Selby Real Estate of South Florida
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  /39

  $799,900

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

  7022 Live Oak Dr, Naples, FL 34114

  Welcome to your beautiful Summerwood floor plan home ... Enjoy Florida living in this IMPECCABLY maintained STUNNING home featuring 3 bedrooms, den/sitting room, 2 full bathrooms. Enjoy a spacious living room which is open to the gourmet kitchen featuring a NATURAL GAS range, a large pantry and an island, with ample prep space, for gathering with friends and family. There is tile flooring

  Kathy Friedle John R. Wood Properties

  7022 Live Oak Dr, Naples, FL 34114
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  /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 $744,819

  Last Listing Agent Kate Pentelow Premiere Plus Realty Company

  7128 Lily Way, Naples, FL 34114
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  /39

  Est $878,694 Not Listed For Sale

  6828 Winding Cypress Dr, Naples, FL 34114

  • 3 Beds
  • 2 Baths
  • 2,089 Sq Ft
  • Built 2021

  6828 Winding Cypress Dr, Naples, FL 34114

  Last Sold Summary

  • 5% Above List Price
  • $402/SF
  • 11 Days On Market

  • Last Sold Price $840,000
  • Apr 30, 2024

  Last Listing Agent Heidi Varsames John R Wood Properties
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  /50

  $850,000

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

  7460 Blackberry Dr, Naples, FL 34114

  Paradise at your fingertips. This modern three-bedroom plus den residence in the prestigious resort style living gated community of Winding Cypress, offers a bright, expansive open floor plan, breathtaking lake views, ceramic tile throughout and a gorgeous and functional updated kitchen featuring solid maple shaker cabinetry, premium hardware, and spacious pantry. This residence is also equipped

  Angelica Andrews Premier Sotheby's Int'l Realty

  7460 Blackberry Dr, Naples, FL 34114
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  /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 $466,141

  Last Listing Agent Scott Bertha Downing Frye Realty Inc.

  7642 Jacaranda Ln, Naples, FL 34114
• 

  

  /41

  Est $1,277,676 Not Listed For Sale

  6880 Cocoplum St, Naples, FL 34114

  • 3 Beds
  • 3 Baths
  • 2,515 Sq Ft
  • Built 2020

  6880 Cocoplum St, Naples, FL 34114

  Last Sold Summary

  • 18% Below List Price
  • $622/SF
  • 9 Days On Market

  • Last Sold Price $1,565,000
  • May 20, 2024

  Last Listing Agent Kendra Hoefs Realty One Group MVP
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  /50

  $649,000 Pending

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

  7639 Jacaranda Ln, Naples, FL 34114

  Sunset water views stretch across a sparkling long lake from your private pool and spa, creating a breathtaking backdrop for everyday living and entertaining from the fully equipped natural gas outdoor kitchen. This beautifully maintained home stands out with major recent upgrades including a brand new AC system (2026), new washer and dryer, new hot water heater, and new carpet, offering peace of

  Taylor Smith Premier Sotheby's Int'l Realty

  7639 Jacaranda Ln, Naples, FL 34114
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  /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 $1,543,740

  Last Listing Agent Manuela Schinagl Manuela Realty, Inc

  7412 Winding Cypress Dr, Naples, FL 34114
• 

  

  /22

  Est $913,754 Not Listed For Sale

  6801 Greenbriar Ct, Naples, FL 34114

  • 4 Beds
  • 3 Baths
  • 2,152 Sq Ft
  • Built 2022

  6801 Greenbriar Ct, Naples, FL 34114

  Last Sold Summary

  • 3% Below List Price
  • $439/SF
  • 63 Days On Market

  • Last Sold Price $945,000
  • Sep 30, 2024

  Last Listing Agent Yuri Granovsky Realty One Group MVP
• 

  

  /25

  $1,799,900 Pending

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

  6912 Cocoplum St, Naples, FL 34114

  3 bedroom and 3 bath home in Winding Cypress

  Paul Bocka William Raveis Real Estate

  6912 Cocoplum St, Naples, FL 34114
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  /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 $861,834

  Last Listing Agent Theresa Bocka William Raveis Real Estate

  6699 Pennyroyal Dr, Naples, FL 34114
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  /50

  Est $885,812 Not Listed For Sale

  6830 Greenbriar Ct, Naples, FL 34114

  • 2 Beds
  • 2.5 Baths
  • 2,105 Sq Ft
  • Built 2021

  6830 Greenbriar Ct, Naples, FL 34114

  Last Sold Summary

  • 16% Below List Price
  • $499/SF
  • 34 Days On Market

  • Last Sold Price $1,050,000
  • Apr 19, 2024

  Last Listing Agent Paul Fonseca Berkshire Hathaway FL Realty
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  /33

  $599,000 Pending

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

  7121 Live Oak Dr, Naples, FL 34114

  Nestled within the gated, amenity-rich community of Winding Cypress, this thoughtfully designed turnkey furnished two-bedroom plus den, two-bath residence offers an exceptional blend of comfort, quality, and relaxed Florida living. The open floor plan is enhanced by wood flooring throughout the main living areas, along with crown molding, and a distinctive coffered ceiling in the living and

  Julie Blanton John R Wood Properties

  7121 Live Oak Dr, Naples, FL 34114
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  /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 $500,014

  Last Listing Agent Theresa Bocka William Raveis Real Estate

  7658 Jacaranda Ln, Naples, FL 34114
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  /48

  Est $964,276 Not Listed For Sale

  6846 Greenbriar Ct, Naples, FL 34114

  • 3 Beds
  • 2 Baths
  • 2,107 Sq Ft
  • Built 2020

  6846 Greenbriar Ct, Naples, FL 34114

  Last Sold Summary

  • 8% Below List Price
  • $495/SF
  • 27 Days On Market

  • Last Sold Price $1,043,000
  • Feb 21, 2024

  Last Listing Agent Kendra Hoefs Realty One Group MVP
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  /41

  $698,500

  • 3 Beds
  • 2 Baths
  • 1,594 Sq Ft

  7670 Jacaranda Ln, Naples, FL 34114

  Discover refined living with this beautifully appointed villa in Winding Cypress, where luxury and comfort meet in perfect balance. Designed for those who appreciate both elegance and ease, this home offers an unparalleled lifestyle inside and out.Arriving fully furnished and enhanced by the sellers’ two-seater Club Car golf cart, this property delivers a true move-in ready experience. Every

  Sean Smuk Coldwell Banker Realty

  7670 Jacaranda Ln, Naples, FL 34114
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  /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 $891,501

  Last Listing Agent Kendra Hoefs Realty One Group MVP

  6848 Winding Cypress Dr, Naples, FL 34114
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  /34

  Est $920,120 Not Listed For Sale

  6723 Pennyroyal Dr, Naples, FL 34114

  • 3 Beds
  • 2 Baths
  • 2,094 Sq Ft
  • Built 2021

  6723 Pennyroyal Dr, Naples, FL 34114

  Last Sold Summary

  • 9% Below List Price
  • $485/SF
  • 19 Days On Market

  • Last Sold Price $1,015,000
  • Dec 12, 2023

  Last Listing Agent Brian Walsh INACTIVE AGENT ACCT
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  /50

  $799,000 Pending

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

  6754 Pennyroyal Dr, Naples, FL 34114

  This gorgeous Mystique floor plan features 3 bedrooms, a den, a rare 3 full bathrooms, heated pool, and a 2-car garage. Inside the home is loaded with upgrades, impact windows and doors, custom built-in cabinetry in the living & laundry room, crown molding, tray ceilings, recessed lighting, electric blinds, designer hardware and lighting, and abundant storage throughout. Embrace the Florida

  Kendra Hoefs Realty One Group MVP

  6754 Pennyroyal Dr, Naples, FL 34114
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  /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 $833,552

  Last Listing Agent Theresa Bocka William Raveis Real Estate

  7211 Live Oak Dr, Naples, FL 34114
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  /29

  Est $1,282,779 Not Listed For Sale

  6962 Winding Cypress Dr, Naples, FL 34114

  • 3 Beds
  • 3.5 Baths
  • 2,952 Sq Ft
  • Built 2020

  6962 Winding Cypress Dr, Naples, FL 34114

  Last Sold Summary

  • 14% Below List Price
  • $506/SF
  • 100 Days On Market

  • Last Sold Price $1,495,000
  • Oct 08, 2024

  Last Listing Agent Linda Covino Royal Shell Real Estate, Inc.
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  /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
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  /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
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  /50

  Est $1,494,366 Not Listed For Sale

  6903 Cocoplum St, Naples, FL 34114

  • 4 Beds
  • 4 Baths
  • 3,656 Sq Ft
  • Built 2021

  6903 Cocoplum St, Naples, FL 34114

  Last Sold Summary

  • 3% Above List Price
  • $397/SF
  • 108 Days On Market

  • Last Sold Price $1,450,000
  • Sep 17, 2024

  Last Listing Agent Lauren Trethewey Realty One Group MVP
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  /34

  $1,645,000

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

  7247 Clamshell Ln, Naples, FL 34114

  A must-see opportunity—spacious, stunning views, showpiece home and resort style Florida living. A rare opportunity to own a 4 bedroom estate home with breathtaking views in the sought-after community of Winding Cypress, offering top-tier amenities at surprisingly low HOA fees. This award-winning Pinnacle model boasts numerous upgrades and interiors like the builder’s model home and is on one of

  Sheila Kumar Real Broker, LLC

  7247 Clamshell Ln, Naples, FL 34114
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  /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
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  /43

  Est $941,475 Not Listed For Sale

  6762 Pennyroyal Dr, Naples, FL 34114

  • 3 Beds
  • 3 Baths
  • 2,884 Sq Ft
  • Built 2021

  6762 Pennyroyal Dr, Naples, FL 34114

  Last Sold Summary

  • 5% Above List Price
  • $312/SF
  • 126 Days On Market

  • Last Sold Price $900,000
  • Jul 14, 2023

  Last Listing Agent Vivian Lugo Berkshire Hathaway FL Realty
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  /37

  $825,000

  • 3 Beds
  • 3 Baths
  • 2,128 Sq Ft

  6770 Pennyroyal Dr, Naples, FL 34114

  Discover your dream home in the prestigious Winding Cypress community! This newly constructed, pet-friendly residence boasts 3 spacious bedrooms plus a versatile den, perfect for guests or a home office. Designed for seamless entertaining, the open-concept floor plan flows effortlessly, with zero-corner sliders merging the indoor living area with a stylish outdoor kitchen and bar—ideal for

  Ryan Buchalter William Raveis Real Estate

  6770 Pennyroyal Dr, Naples, FL 34114
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  /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 $913,362

  Last Listing Agent Kendra Hoefs Realty One Group MVP

  6779 Winding Cypress Dr, Naples, FL 34114
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  /47

  Est $963,851 Not Listed For Sale

  7454 Winding Cypress Dr, Naples, FL 34114

  • 3 Beds
  • 3 Baths
  • 2,673 Sq Ft
  • Built 2016

  7454 Winding Cypress Dr, Naples, FL 34114

  Last Sold Summary

  • 13% Above List Price
  • $318/SF
  • 53 Days On Market

  • Last Sold Price $850,000
  • Jul 17, 2024

  Last Listing Agent Kimberly Hill Schulz Realty LLC
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  /52

  $1,750,000

  • 4 Beds
  • 4.5 Baths
  • 3,965 Sq Ft

  7229 Wiregrass Ct, Naples, FL 34114

  Rare to find, this light-filled 2-story Stonewater model offering 4 bedrooms, den and 4.5 baths on a pie shaped waterfront lot in the highly desirable gated community of Winding Cypress in Naples. This home has been upgraded to include all available options totaling over $650,000 including 2nd floor loft, hurricane windows and doors, upgraded finishes throughout including smooth drywall, seamless

  Manuela Schinagl Manuela Realty, Inc

  7229 Wiregrass Ct, Naples, FL 34114
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  /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 $719,083

  Last Listing Agent Theresa Bocka William Raveis Real Estate

  6787 Winding Cypress Dr, Naples, FL 34114
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  /51

  Est $1,344,028 Not Listed For Sale

  6907 Cocoplum St, Naples, FL 34114

  • 3 Beds
  • 3 Baths
  • 2,515 Sq Ft
  • Built 2020

  6907 Cocoplum St, Naples, FL 34114

  Last Sold Summary

  • 13% Below List Price
  • $616/SF
  • 6 Days On Market

  • Last Sold Price $1,550,000
  • Oct 18, 2023

  Last Listing Agent Todd Lawler Premiere Plus Realty Company
• 

  /2

  $575,000

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

  7666 Jacaranda Ln, Naples, FL 34114

  Experience elevated resort-style living in the highly desirable community of Winding Cypress. This impeccably maintained and tastefully updated 2-bedroom plus den, 2-bath villa offers soaring 9’4” ceilings and an attached two-car garage, delivering both comfort and functionality in a truly move-in-ready residence. Thoughtful upgrades include a newer refrigerator and hot water heater, upgraded

  Susan Heller EXP Realty LLC

  7666 Jacaranda Ln, Naples, FL 34114
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  /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 $1,009,381

  Last Listing Agent Theresa Bocka William Raveis Real Estate

  7530 Geranium Way, Naples, FL 34114
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  /50

  Est $934,743 Not Listed For Sale

  6818 Greenbriar Ct, Naples, FL 34114

  • 3 Beds
  • 3 Baths
  • 2,152 Sq Ft
  • Built 2021

  6818 Greenbriar Ct, Naples, FL 34114

  Last Sold Summary

  • 18% Below List Price
  • $532/SF
  • 16 Days On Market

  • Last Sold Price $1,145,000
  • Feb 06, 2024

  Last Listing Agent Michelle Thomas Premier Sotheby's International Realty
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  /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 $1,149,228

  Last Listing Agent Theresa Bocka William Raveis Real Estate

  7716 Winding Cypress Dr, Naples, FL 34114
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  /43

  Est $969,274 Not Listed For Sale

  6695 Pennyroyal Dr, Naples, FL 34114

  • 3 Beds
  • 3 Baths
  • 2,148 Sq Ft
  • Built 2022

  6695 Pennyroyal Dr, Naples, FL 34114

  Last Sold Summary

  • 19% Below List Price
  • $559/SF
  • 8 Days On Market

  • Last Sold Price $1,200,000
  • Apr 05, 2024

  Last Listing Agent Marc Middleton Cachon Realty Group. LLC

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