Winding Cypress Homes

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  $534,500

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

  7658 Jacaranda Ln, Naples, FL 34114

  This beautiful Winding Cypress Serenity Villa home offers 1,554 sq. ft. of comfort with 2 bedroom plus den, 2 bathrooms, screened lanai, and a 2-car garage. It features multiple quality upgrades including stainless appliances with both gas and electric connectivity for the stove, 22" porcelain tile on the diagonal throughout, plantation shutters, Quartz countertops in kitchen and bathrooms, den

  Bob Lashenka Downing Frye Realty Inc.

  7658 Jacaranda Ln, Naples, FL 34114
• Explore Winding Cypress

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  /20

  $4,447 per month

  • 2 Beds
  • 2 Baths
  • 1,555 Sq Ft
  • House for Rent

  7662 Jacaranda Ln, Naples, FL 34114

  Property Id: 9571066 to 24-monthsAvailable January 2026Escape from stress in this clean, like-new ELEGANT POOL VILLA, maintained, updated & FURNISHED. Incomparably upgraded for discriminating guests. CENTRALLY LOCATED, gated resort living, MINUTES to Marco Island, Naples Pier, shopping, beaches, golf, downtown & I75. THREE BEDS, including thick mattress QUEEN PULL-OUT in DEN.

  7662 Jacaranda Ln, Naples, FL 34114
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  $1,495,000 Sold Jan 21, 2025

  6883 Cocoplum St, Naples, FL 34114

  • 3 Beds
  • 3 Baths
  • 2,519 Sq Ft
  • Built 2021

  Last Sold Summary

  • 4% Below List Price
  • $593/SF
  • 56 Days On Market

  Current Estimated Value $1,402,081

  Last Listing Agent Theresa Bocka William Raveis Real Estate

  6883 Cocoplum St, Naples, FL 34114
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  /50

  Est $760,116 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,774 Sq Ft

  6792 Bromeliad Dr, Naples, FL 34114

  6792 Bromeliad Dr, Naples, FL 34114
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  /49

  $925,000 Open Sun 1PM - 4PM

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

  6699 Pennyroyal Dr, Naples, FL 34114

  Perfection is the only way to describe this home! It shows like a model as it has been rarely lived in since built barely three years ago. Welcome to the desirable Pulte/DiVosta Mystique Model located in the popular amenity rich community of Winding Cypress. This waterfront property sits on a dead-end cul-de-sac and is loaded with owner and builder upgrades. It's impeccably decorated and

  Theresa Bocka William Raveis Real Estate

  6699 Pennyroyal Dr, Naples, FL 34114
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  /46

  $10,500 per month

  • 3 Beds
  • 2 Baths
  • 2,185 Sq Ft
  • House for Rent

  6767 Pennyroyal Dr, Naples, FL 34114

  Available for Season 2026 and 2027! Beautifully furnished 3+Den single family home in the highly sought-after, gated community of Winding Cypress in Naples. This thoughtfully appointed home offers a comfortable and stylish escape, perfect for enjoying the Southwest Florida lifestyle during season. The residence features an open-concept layout filled with natural light, a well-equipped kitchen

  Lauren Wells Premier Sotheby's Int'l Realty

  6767 Pennyroyal Dr, Naples, FL 34114
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  /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

  Last Listing Agent Kendra Hoefs Realty One Group MVP

  6839 Winding Cypress Dr, Naples, FL 34114
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  /46

  Est $547,107 Not Listed For Sale

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

  7694 Jacaranda Ln, Naples, FL 34114

  7694 Jacaranda Ln, Naples, FL 34114
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  /37

  $1,595,000

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

  7412 Winding Cypress Dr, Naples, FL 34114

  Motivated Seller! Luxurious Lakeside Living in Winding Cypress – Rare One Owner Pinnacle Model! Welcome to this stunning lake view home offering 3,656 sq. ft. of modern elegance in the prestigious, amenity-rich community of Winding Cypress. With 4 bedrooms, 4 bathrooms, a den, bonus room, and 2,5-car garage, this home is thoughtfully designed for both everyday living and entertaining on a grand

  Manuela Schinagl Manuela Realty

  7412 Winding Cypress Dr, Naples, FL 34114
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  /50

  $9,995 per month

  • 3 Beds
  • 2 Baths
  • 2,496 Sq Ft
  • House for Rent

  7611 Winding Cypress Dr, Naples, FL 34114

  Available for 2026 season! Welcome to this beautifully appointed seasonal rental located in the highly sought after Winding Cypress community. This spacious home offers three bedrooms plus a den, three full bathrooms, and a two and a half car garage. Fully turnkey furnished and thoughtfully designed, the home features an open concept floor plan that flows seamlessly from the interior living

  Josh Yelensky Current Property Management

  7611 Winding Cypress Dr, Naples, FL 34114
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  /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 $1,163,984

  Last Listing Agent Robert Crovo Coldwell Banker Realty

  7597 Blackberry Dr, Naples, FL 34114
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  /50

  Est $1,060,651 Not Listed For Sale

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

  7628 Winding Cypress Dr, Naples, FL 34114

  7628 Winding Cypress Dr, Naples, FL 34114
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  $1,150,000 Open Sun 1PM - 4PM

  • 4 Beds
  • 3 Baths
  • 3,036 Sq Ft

  6825 Greenbriar Ct, Naples, FL 34114

  Spacious & Immaculate accurately describe this outstanding retreat in the sought-after community of Winding Cypress. This rare, two-story Mystique footprint boasts 4 bedrooms, 3 full baths, a large den/office, and over 3160 square feet of adjusted living space, 3036 square feet under air. This residence was one of the last built in the community, 3 years new, and shows like a model home. Located

  Theresa Bocka William Raveis Real Estate

  6825 Greenbriar Ct, Naples, FL 34114
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  /24

  $11,500 per month

  • 3 Beds
  • 2 Baths
  • 1,805 Sq Ft
  • House for Rent

  7567 Winding Cypress Dr, Naples, FL 34114

  From the moment you arrive at the stunning entry, Winding Cypress invites you into this wonderful community. This natural gas, resort-style community, remaining almost 2/3 preserve, welcomes you with a streetscape of superb views and new homes designed for the way you live. This premier Naples location offers highly attractive fees for the variety of world-class amenities right in your own

  Dave Garafola Reed Property Mgt. & Sales

  7567 Winding Cypress Dr, Naples, FL 34114
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  /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 $950,308

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

  7404 Winding Cypress Dr, Naples, FL 34114
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  /44

  Est $628,119 Not Listed For Sale

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

  7682 Jacaranda Ln, Naples, FL 34114

  7682 Jacaranda Ln, Naples, FL 34114
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  $959,900 Open Sun 1PM - 3PM

  • 3 Beds
  • 2 Baths
  • 2,186 Sq Ft

  6787 Pennyroyal Dr, Naples, FL 34114

  Move in Ready 3 year old 3 bdrm den 2bath Mystic model at Winding Cypress. Here are some of the reasons we are we different from the rest . widened paved driveway comfortablly fitting 2 cars side by side, corner lot for privacy, beautiful long lake view on WC largest lakes, 4ft extended garage for larger vehicles plus overhead storage with Mini a/c split in garage. whole house generator, impact

  Linda Covino Royal Shell Real Estate, Inc.

  6787 Pennyroyal Dr, Naples, FL 34114
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  /50

  $5,900 per month

  • 2 Beds
  • 2 Baths
  • 1,574 Sq Ft
  • Apartment for Rent

  7638 Jacaranda Ln, Naples, FL 34114

  Discover Your Dream Home in Naples! Presenting the rare Winding Cypress model, the stunning Cressida villa. This beautiful home features a spacious private yard and lanai, perfect for entertaining or relaxing in paradise. Inside, a dedicated front entrance and a large foyer welcome you into an open yet well-defined living area. The master bedroom has a king-size bed, the guest bedroom includes a

  Aniledif Ayala Burger Premier Sotheby's Int'l Realty

  7638 Jacaranda Ln, Naples, FL 34114
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  /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 $537,237

  Last Listing Agent william Romano Keller Williams Marco Realty

  7591 Jacaranda Ln, Naples, FL 34114
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  /36

  Est $593,482 Not Listed For Sale

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

  7627 Jacaranda Ln, Naples, FL 34114

  7627 Jacaranda Ln, Naples, FL 34114
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  $1,599,900

  • 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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  /46

  $6,800 per month

  • 2 Beds
  • 2 Baths
  • 1,542 Sq Ft
  • House for Rent

  7631 Jacaranda Ln, Naples, FL 34114

  Beautiful two bedrooms plus den, two bath attached villa pool home in the amenity rich gated community of Winding Cypress. Main bedroom has a king bed, second bedroom has a queen bed and den has a full size pullout couch that sleeps 2 and includes a full wardrobe armoire for clothing . Spacious attached 2-car garage. Relax on the spacious lanai that overlooks the private pool and peaceful lake

  Amber Jasper Grice Realty Inc

  7631 Jacaranda Ln, Naples, FL 34114
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  /34

  $650,000 Sold Feb 13, 2025

  7267 Live Oak Dr, Naples, FL 34114

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

  Last Sold Summary

  • 28% Below List Price
  • $291/SF
  • 376 Days On Market

  Current Estimated Value $654,687

  Last Listing Agent Heidi Varsames John R Wood Properties

  7267 Live Oak Dr, Naples, FL 34114
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  /42

  Est $658,550 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,685 Sq Ft

  7256 Live Oak Dr, Naples, FL 34114

  7256 Live Oak Dr, Naples, FL 34114
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  /35

  $849,900 Open Sun 1PM - 4PM

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

  7211 Live Oak Dr, Naples, FL 34114

  This impeccably maintained residence offers an exceptional living experience. The open floor plan features three spacious bedrooms, a versatile den or flex room, and two full bathrooms. Elegant details include crown molding, tray ceilings, plantation shutters, Hunter Douglas blinds, and updated flooring. The added sunroom provides a tranquil space for relaxation or entertaining.The custom

  Theresa Bocka William Raveis Real Estate

  7211 Live Oak Dr, Naples, FL 34114
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  /49

  $6,500 per month

  • 2 Beds
  • 2 Baths
  • 1,554 Sq Ft
  • Apartment for Rent

  7627 Jacaranda Ln, Naples, FL 34114

  Light, bright and beautifully updated two bedroom plus den, two bath attached villa pool home in the amenity rich gated community of Winding Cypress. Main bedroom has a king bed, second bedroom has a queen size bed and den has a queen size Murphy bed. Spacious attached 2-car garage. Water filter system purifies all water throughout the villa. Sit back and relax with your coffee in the morning or

  Amber Jasper Grice Realty Inc

  7627 Jacaranda Ln, Naples, FL 34114
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  /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

  Last Listing Agent Kendra Hoefs Realty One Group MVP

  7355 Mockingbird Ct, Naples, FL 34114
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  /29

  Est $690,566 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,878 Sq Ft

  7244 Live Oak Dr, Naples, FL 34114

  7244 Live Oak Dr, Naples, FL 34114
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  /49

  $899,000 Pending

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

  6856 Winding Cypress Dr, Naples, FL 34114

  Sense the comfort and beauty of this magnificent home the minute you enter the foyer and see the view out to the inviting pool and spa. This 3 bedroom, plus separate den, great room floor-plan is perfect for entertaining or just a lovely place to call home. These original owners have impeccably maintained the home making it feel brand new. Built in 2021 it boasts a chef's delight kitchen with

  Brian Stolliker Berkshire Hathaway FL Realty

  6856 Winding Cypress Dr, Naples, FL 34114
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  /37

  $720,000 Sold Feb 13, 2025

  7247 Live Oak Dr, Naples, FL 34114

  • 2 Beds
  • 2 Baths
  • 1,910 Sq Ft
  • Built 2015

  Last Sold Summary

  • 9% Below List Price
  • $377/SF
  • 265 Days On Market

  Current Estimated Value $694,510

  Last Listing Agent Kati Bepko Coldwell Banker Realty

  7247 Live Oak Dr, Naples, FL 34114
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  /50

  Est $615,396 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,544 Sq Ft

  7611 Jacaranda Ln, Naples, FL 34114

  7611 Jacaranda Ln, Naples, FL 34114
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  /50

  $943,000

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

  6698 Pennyroyal Dr, Naples, FL 34114

  Discover resort-style living in this rare three-bedroom plus den, three-bath natural gas home in the highly sought-after community of Winding Cypress. Designed for privacy and effortless indoor–outdoor living, it features an oversized fully custom pool with integrated seamless spa and a panoramic barless screen lanai, integrated home theater sound, all overlooking lush, tranquil landscaping. The

  Taylor Smith Premier Sotheby's Int'l Realty

  6698 Pennyroyal Dr, Naples, FL 34114
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  /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 $648,815

  Last Listing Agent Bob Bailey R L Bailey Realty Inc.

  7742 Jacaranda Ln, Naples, FL 34114
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  /50

  Est $1,307,685 Not Listed For Sale

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

  6932 Cocoplum St, Naples, FL 34114

  6932 Cocoplum St, Naples, FL 34114
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  /48

  $600,000

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

  7167 Live Oak Dr, Naples, FL 34114

  Rare villa opportunity in Winding Cypress! This turnkey, fully furnished villa sits on an extra-large, ultra-private lot with exceptional spacing between neighbors, creating a peaceful and open feel that is hard to find. The backyard is a retreat, featuring a saltwater private pool framed by mature cypress trees, colorful landscaping and wide natural preserve views. Inside, the home offers

  Taylor Smith Premier Sotheby's Int'l Realty

  7167 Live Oak Dr, Naples, FL 34114
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  /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 $854,572

  Last Listing Agent Kimberly Springer Orchid Realty International

  7556 Winding Cypress Dr, Naples, FL 34114
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  /39

  Est $824,255 Not Listed For Sale

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

  6828 Winding Cypress Dr, Naples, FL 34114

  6828 Winding Cypress Dr, Naples, FL 34114
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  /43

  $819,000 Pre-Foreclosure

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

  7057 Live Oak Dr, Naples, FL 34114

  Winding Cypress – Resort-Style Living in Naples - Priced to sell!Welcome to your Florida dream home in the sought-after gated community of Winding Cypress! This immaculate residence built in 2016, offers the perfect blend of modern luxury and relaxed coastal living. Featuring 2,230’sq under air, 3 bedrooms plus a den, 2 full baths, and an open-concept floor plan, this home is designed for

  Craig Jerabeck Premiere Plus Realty Company

  7057 Live Oak Dr, Naples, FL 34114
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  /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 $860,161

  Last Listing Agent Terence Trombetti Berkshire Hathaway FL Realty

  6906 Winding Cypress Dr, Naples, FL 34114
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  /41

  Est $1,349,321 Not Listed For Sale

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

  6880 Cocoplum St, Naples, FL 34114

  6880 Cocoplum St, Naples, FL 34114

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