Winding Cypress Homes

• 

  

  

  /45

  $1,050,000

  • 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

  (239) 488-2755

  6825 Greenbriar Ct, Naples, FL 34114
• Explore Winding Cypress

• 

  

  

  /20

  $3,990 per month

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

  7662 Jacaranda Ln, Naples, FL 34114

  Property Id: 957106Escape from stress in this clean, like-new ELEGANT POOL VILLA, completely updated & FURNISHED. Incomparably upgraded for our discriminating guests. #Lease Options (All Taxes Included)||Monthly Season (April) $5,330/month. Tax & utilities included, and $0 pet fee!||6-17 Month Lease$4,247/month + utilities||18+ Month LeaseBest

  7662 Jacaranda Ln, 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

  Last Listing Agent Kendra Hoefs Realty One Group MVP

  6839 Winding Cypress Dr, Naples, FL 34114
• 

  

  

  /46

  Est $558,357 Not Listed For Sale

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

  7694 Jacaranda Ln, Naples, FL 34114

  7694 Jacaranda Ln, Naples, FL 34114
• 

  

  

  /30

  $499,000

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

  7658 Jacaranda Ln, Naples, FL 34114

  Experience luxury living in this beautifully appointed Serenity villa, greats you with LED walkway lighting along the entrance pathway. This property is nestled in one of Naples’ most desirable communities. This home features two spacious bedrooms, two elegant baths, and a flexible den—perfect for a home office, hobby room or additional guest area. The upgraded kitchen is equipped with stainless

  

  Theresa Bocka

  William Raveis Real Estate

  (239) 329-1331

  7658 Jacaranda Ln, Naples, FL 34114
• 

  

  /39

  $16,000 per month

  • 4 Beds
  • 3 Baths
  • 3,077 Sq Ft
  • House for Rent

  7763 Winding Cypress Dr, Naples, FL 34114

  Seasonal Rental available for 2027. Turnkey Furnished, and ready for you to enjoy. This 2 story Summerwood model home with Breathtaking Pool and Spa offers a spectacular open floor plan. This home has a very large, beautiful Gourmet kitchen with Dining area, generous Great room with baby Grand Piano, 3 Bedrooms, 3 bathrooms on the main floor, 1 bedroom, 1 bathroom, plus a very large loft on the

  Melanie Listrom REMAX Affinity Mercato

  7763 Winding Cypress 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 $1,163,984

  Last Listing Agent Robert Crovo Coldwell Banker Realty

  7597 Blackberry Dr, Naples, FL 34114
• 

  

  /50

  Est $1,070,096 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
• 

  

  /35

  $835,000 Open Sun 1PM - 4PM

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

  7211 Live Oak Dr, Naples, FL 34114

  Over 2200 Sq ft complete with your own POOL this is a great opportunity! Don't waitCheck out 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 bathroom. Elegant details include crown molding, tray ceilings, plantation shutters, Hunter Douglas blinds, and updated LVP

  

  Theresa Bocka

  William Raveis Real Estate

  (239) 266-8980

  7211 Live Oak Dr, Naples, FL 34114
• 

  

  /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
• 

  

  /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
• 

  

  /44

  Est $632,374 Not Listed For Sale

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

  7682 Jacaranda Ln, Naples, FL 34114

  7682 Jacaranda Ln, Naples, FL 34114
• 

  

  /36

  $634,999 Open Sun 1PM - 4PM

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

  7248 Live Oak Dr, Naples, FL 34114

  Single Family home in Winding Cypress -Ready for the season!! This charming model is the perfect fit featuring an inviting open-floor concept where natural light streams through the windows. The kitchen boasts granite counters, stainless appliances and a center island and extra storage for everyday use and easy entertaining. The pantry closet has plenty of space for all of your staple goods. Tile

  

  Theresa Bocka

  William Raveis Real Estate

  (239) 456-3829

  7248 Live Oak Dr, Naples, FL 34114
• 

  

  /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
• 

  

  /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 $536,710

  Last Listing Agent william Romano Keller Williams Marco Realty

  7591 Jacaranda Ln, Naples, FL 34114
• 

  

  /36

  Est $605,742 Not Listed For Sale

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

  7627 Jacaranda Ln, Naples, FL 34114

  7627 Jacaranda Ln, Naples, FL 34114
• 

  

  /47

  $949,900 Open Sun 2PM - 3PM

  • 3 Beds
  • 2 Baths
  • 2,100 Sq Ft

  6844 Winding Cypress Dr, Naples, FL 34114

  Welcome to newest and last phase of homes built in 2020 in the vibrant well maintained community of Winding Cypress. Located just off Collier and 41 and minutes to 75 , Marco Island and downtown NaplesThis summer wood model is sure to please with 3 bdrms 2 baths with full showers , primary bath with custom mirrors. custom closet , plantation shutters mini a/c in garage, whole house water

  Linda Covino Royal Shell Real Estate, Inc.

  6844 Winding Cypress Dr, Naples, FL 34114
• 

  

  /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
• 

  

  /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
• 

  

  /42

  Est $663,095 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
• 

  

  /36

  $919,000 Open Sun 1PM - 2PM

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

  6787 Pennyroyal Dr, Naples, FL 34114

  The View !!!!!!!! built in 2022 Move in Ready ! Like new Contemporary style mystique model 3 bdrm den 2bath in Winding Cypress. Location Location with this breathtaking long lake view , last home on street on long landscaped corner affords plenty of privacy.Some of the Upgraded features consist of a widened paved recently sealed driveway comfortably fitting 2 cars side by side, zero clearance

  Linda Covino Royal Shell Real Estate, Inc.

  6787 Pennyroyal Dr, 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 $643,211

  Last Listing Agent Bob Bailey R L Bailey Realty Inc.

  7742 Jacaranda Ln, Naples, FL 34114
• 

  

  /49

  Est $1,390,064 Not Listed For Sale

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

  6883 Cocoplum St, Naples, FL 34114

  6883 Cocoplum St, Naples, FL 34114
• 

  

  /53

  $949,000

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

  7679 Winding Cypress Dr, Naples, FL 34114

  Welcome to this beautifully designed residence located within one of Naples' most desirable gated communities. The open-concept floor plan is enhanced by volume and tray ceilings, crown molding, plantation shutters throughout, and an extended driveway, adding both elegance and curb appeal. The spacious kitchen features granite countertops, a gas cooktop, wall oven, and ample cabinetry—making it

  Joseph Bartos Premiere Plus Realty Company

  7679 Winding Cypress Dr, 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 $849,616

  Last Listing Agent Kimberly Springer Orchid Realty International

  7556 Winding Cypress Dr, Naples, FL 34114
• 

  

  /29

  Est $701,784 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
• 

  

  /50

  $899,000

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

  7460 Blackberry Dr, Naples, FL 34114

  Experience resort-style luxury in the prestigious gated community of Winding Cypress. This modern 3-bedroom plus den residence features a bright, open floor plan and a gourmet kitchen equipped with a gas stove, ample storage, and full hurricane protection. The expansive living area flows seamlessly to a spectacular enclosed lanai--your private sanctuary featuring an outdoor kitchen, firepit, and

  Angelica Andrews Premier Sotheby's International Realty

  7460 Blackberry 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 $883,300

  Last Listing Agent Terence Trombetti Berkshire Hathaway FL Realty

  6906 Winding Cypress Dr, Naples, FL 34114
• 

  

  /50

  Est $614,435 Not Listed For Sale

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

  7611 Jacaranda Ln, Naples, FL 34114

  7611 Jacaranda Ln, Naples, FL 34114
• 

  

  /50

  $943,000 Open Sun 1PM - 4PM

  • 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
• 

  

  /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 $1,011,534

  Last Listing Agent Justine Hine John R. Wood Properties

  7788 Winding Cypress Dr, Naples, FL 34114
• 

  

  /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
• 

  

  /36

  $899,000

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

  6902 Winding Cypress Dr, Naples, FL 34114

  Stunning 3-Bedroom + Den Home in Sought-After Winding Cypress – Welcome to your dream home in the prestigious, resort-style community of Winding Cypress in Naples, FL. Built in 2022, this impeccably maintained 3-bedroom + den, 2-bathroom residence blends modern design with everyday comfort. Step inside to find an open-concept floor plan featuring, abundant natural light, and contemporary finishes

  Elliot Barton Waterfront Realty Group Inc

  6902 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

  Last Listing Agent Brian Stolliker BERKSHIRE HATHAWAY HOMESERVICES FLORIDA REALTY

  6856 Winding Cypress Dr, Naples, FL 34114
• 

  

  /50

  Est $1,297,863 Not Listed For Sale

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

  6932 Cocoplum St, Naples, FL 34114

  6932 Cocoplum St, Naples, FL 34114
• 

  

  /50

  $875,000

  • 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
• 

  

  /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 $858,714

  Last Listing Agent Kendra Hoefs Realty One Group MVP

  6870 Winding Cypress Dr, Naples, FL 34114
• 

  

  /39

  Est $848,904 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
• 

  

  /50

  $925,000 Pending

  • 3 Beds
  • 2 Baths
  • 2,003 Sq Ft

  6779 Winding Cypress Dr, Naples, FL 34114

  This Summerwood floorplan is situated on a gorgeous lake and features 3 bedrooms, a den, 2 bathrooms, a gas heated pool and spa, and an extended 2-car garage. The home includes valuable storm-ready features such as a whole-home generator, impact-resistant windows and doors, and electric hurricane screens for added protection. Inside, the home is loaded with upgrades such as a custom built-in bar,

  Kendra Hoefs Realty One Group MVP

  6779 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 $731,793

  Last Listing Agent Kate Pentelow Premiere Plus Realty Company

  7128 Lily Way, Naples, FL 34114

Showing Results 1 - 40, Page 1 of 18