Winding Cypress Homes

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  $1,299,000 Open Sun 1PM - 4PM

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

  7520 Blackberry Dr, Naples, FL 34114

  Introducing a luxury estate site with landscaped privacy corner lot home in Winding Cypress with pool and spa. Step into elegance with this stunning Pinnacle model estate home, set in the prestigious, gated community of Winding Cypress. This home stands out with its soaring raised tray ceilings, rare privacy and spacious yard, impact glass for peace of mind, and an expansive open layout filled

  Taylor Smith Premier Sotheby's Int'l Realty

  7520 Blackberry Dr, Naples, FL 34114
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  /39

  $6,700 per month

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

  7763 Winding Cypress Dr, Naples, FL 34114

  Annual Rental available for immediate occupancy. 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

  

  Melanie Listrom

  REMAX Affinity Mercato

  (239) 323-6669

  7763 Winding Cypress Dr, Naples, FL 34114
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  /13

  $860,000 Sold May 02, 2025

  • 2,208 Sq Ft
  • $389/SF
  • 66 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2020

  6763 Pennyroyal Dr, Naples, FL 34114

  Don't miss out on this stunning impeccably maintained Summerwood model in the highly coveted Winding Cypress community. This beautifully designed home offers 3 bedrooms, plus a dedicated home office, perfect for today’s lifestyle. The charming front porch, an inviting space to unwind with your morning coffee, and be greeted by a designer glass entry door. Inside, you’ll find a bright and open

  Theresa Bocka William Raveis Real Estate

  6763 Pennyroyal Dr, Naples, FL 34114
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  /46

  Est $617,880 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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  /45

  $999,900 Open Sun 1PM - 4PM

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

  7530 Geranium Way, Naples, FL 34114

  This home is an amazing value for Winding Cypress!! Once you compare, you'll agree. The Pinnacle model is clearly the most popular floorplan in The Community. The sought after "open area concept" footprint boasts 3 expansive bedrooms including a most impressive owner's suite, 3 full baths, a large den, desirable 3 car garage, and 2496 square feet of indoor living space under air. Builder and

  Theresa Bocka William Raveis Real Estate

  7530 Geranium Way, Naples, FL 34114
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  /35

  $6,250 per month

  • 3 Beds
  • 2 Baths
  • 2,100 Sq Ft
  • House for Rent

  6856 Winding Cypress Dr, Naples, FL 34114

  Gorgeous kitchen with an oversized island is open to the bright and airy great room as well as your very own private pool and spa! Sliding doors fold all the way back allowing for fabulous inside/outside entertaining. The chef's dream kitchen offers GAS cooking, a huge pantry and counter island seating. Your private pool and spa is heated by gas as well! Be sure to notice the unique lighting

  Maureen Vita Berkshire Hathaway FL Realty

  6856 Winding Cypress Dr, Naples, FL 34114
• 

  

  /20

  $537,000 Sold May 01, 2025

  • 1,554 Sq Ft
  • $346/SF
  • 26 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 2016

  7591 Jacaranda Ln, Naples, FL 34114

  Price Negotiable! Seller is highly motivated!! Discover your slice of paradise in this stunning 2-bedroom plus den villa, located in the resort-style community of Winding Cypress. With exquisite builder-installed upgrades, this home features a sleek open floor plan, granite countertops, and elegant porcelain tile throughout. The kitchen is outfitted with stainless appliances and gas stove

  william Romano Keller Williams Marco Realty

  7591 Jacaranda Ln, Naples, FL 34114
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  /44

  Est $723,998 Not Listed For Sale

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

  7682 Jacaranda Ln, Naples, FL 34114

  7682 Jacaranda Ln, Naples, FL 34114
• 

  

  /46

  $1,049,000

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

  7679 Winding Cypress Dr, Naples, FL 34114

  Imagine waking up each morning in your dream home,Nestled in one of Naples' most sought-after gated communities. As you walk into this beautiful home you are greeted with the open-concept floor plan that welcomes you, with the warmth of granite countertops and the added upgrades of a gas stove and wall oven in your chef-inspired kitchen. Your home is more than just a place to live, it’s a

  Joseph Bartos Premiere Plus Realty Company

  7679 Winding Cypress Dr, Naples, FL 34114
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  /50

  $5,250 per month

  • 3 Beds
  • 2 Baths
  • 1,896 Sq Ft
  • House for Rent

  6775 Winding Cypress Dr, Naples, FL 34114

  Welcome to this inviting home in the sought-after Winding Cypress community. With 3 generous bedrooms and 2 bathrooms, this nearly 2,000 square feet home harmoniously merges modern design with everyday comfort. It is in immaculate condition, with quality upgrades throughout. Finding a rental of this caliber is rare; it is sparkling clean and meticulously cared for, with an unfurnished setup that

  Aimee O'Connor Coldwell Banker Realty

  6775 Winding Cypress Dr, Naples, FL 34114
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  /50

  $992,500 Sold Apr 17, 2025

  • 2,062 Sq Ft
  • $481/SF
  • 115 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 2016

  7404 Winding Cypress Dr, Naples, FL 34114

  The most private homesite in Winding Cypress Resort community, this exceptional home offers views abundant with trees and lake, bordered by a lush preserve and expansive buffer zones. Breathtaking southwestern water views provide the ideal backdrop, rivaling the most stunning beach sunsets. Step outside to the largest covered lanai in the community, complete with a sparkling pool and spa,

  Taylor Smith Premier Sotheby's Int'l Realty

  7404 Winding Cypress Dr, Naples, FL 34114
• 

  

  /29

  Est $740,471 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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  /47

  $995,000

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

  6699 Pennyroyal Dr, Naples, FL 34114

  Welcome to this Winding Cypress beauty! Why wait months to build and spend twice as much to get less in a home and amenities. This 2022 built classic Summerwood Model has everything you'll ever need in a home and is located in Naples best hidden secret.....Winding Cypress! Located on a private, quiet, dead-end cul-de-sac, this home has many builder upgrades. The home is impeccably decorated and

  Theresa Bocka William Raveis Real Estate

  6699 Pennyroyal Dr, Naples, FL 34114
• 

  

  /19

  $7,000 per month

  • 2 Beds
  • 2 Baths
  • 1,654 Sq Ft
  • House for Rent

  6787 Winding Cypress Dr, Naples, FL 34114

  Home away from home! Enjoy a newly built, barely lived in home, in one of the most amenity rich communities in all of Naples. Featuring 2 Bedrooms + Den, 2 Full Bathrooms, screened-in lanai, 10' foot ceilings, and a large open floor plan, this property has everything one needs in order to ensure a relaxing, comfortable, and entertaining/active stay. Winding Cypress is a vibrant community offering

  Ryan Gaumer William Raveis Real Estate

  6787 Winding Cypress Dr, Naples, FL 34114
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  /50

  $635,000 Sold Apr 08, 2025

  • 1,554 Sq Ft
  • $409/SF
  • 40 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 2015

  7199 Live Oak Dr, Naples, FL 34114

  Rare villa opportunity in Winding Cypress! For the first time in over a year, a villa with a private pool and spa on an extra-large lot is available. Enjoy unmatched privacy with huge space between neighbors and serene ultra-private preserve views. This turnkey, fully furnished home features impact windows, 8-foot doors, new bedroom flooring, fresh landscaping and more. This natural gas community

  Taylor Smith Premier Sotheby's Int'l Realty

  7199 Live Oak Dr, Naples, FL 34114
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  /39

  Est $878,279 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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  /46

  $1,100,000 Open Sun 1PM - 4PM

  • 3 Beds
  • 2 Baths
  • 2,198 Sq Ft

  7355 Mockingbird Ct, Naples, FL 34114

  Welcome to your new home in Winding Cypress, a vibrant community in the heart of Southeast Naples. Surrounded by 800 acres of lush preserves and 80 acres of peaceful lakes, this is the ideal setting to enjoy a serene, nature-filled lifestyle. Yet, with Downtown Naples and the iconic 5th Avenue—one of America’s most beautiful streets—just 20 minutes away, you’ll always be close to the best of city

  Mike Zecchino The Agency Naples

  7355 Mockingbird Ct, Naples, FL 34114
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  /50

  $9,500 per month

  • 3 Beds
  • 3 Baths
  • 2,272 Sq Ft
  • House for Rent

  6779 Pennyroyal Dr, Naples, FL 34114

  A stunning new pool and outdoor lanai, complement this exquisitely designed home, which offers tranquil views of the lake. This property features three bedrooms plus a den and three bathrooms, making it ideal for vacationing. The interior boasts a bright and airy coastal contemporary style with an open floor plan.This is a perfect vacation rental!

  Patricia Moreno Naples Homes and Rentals Inc

  6779 Pennyroyal Dr, Naples, FL 34114
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  /47

  $935,000 Sold Apr 01, 2025

  • 2,018 Sq Ft
  • $463/SF
  • 146 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2018

  7683 Winding Cypress Dr, Naples, FL 34114

  Live the Vacation Lifestyle Every Day in Winding CypressWelcome to a home that feels like a never-ending vacation. This stunning Summerwood residence, nestled in the resort-style community of Winding Cypress, is more than a home—it’s a lifestyle.From the moment you step through the dramatic entry hall, you’re greeted by breathtaking lake views that set the tone for tranquility and

  Kimberly Alvord John R Wood Properties

  7683 Winding Cypress Dr, Naples, FL 34114
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  /50

  Est $1,055,646 Not Listed For Sale

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

  6830 Greenbriar Ct, Naples, FL 34114

  6830 Greenbriar Ct, Naples, FL 34114
• 

  

  /37

  $995,000

  • 3 Beds
  • 2 Baths
  • 2,185 Sq Ft

  6949 Winding Cypress Dr, Naples, FL 34114

  Welcome to this stunning Summerwood floor plan with an extended great room. As you enter this 3 bedroom plus den home the quality of finishes is evident. The great room open plan concept allows for a great entertainment area with a large island kitchen and beautiful quartz countertops open to the dining and living area. Step out onto the large paver lanai area and enjoy the exceptional location

  Michelle Combs Keller Williams Realty Naples

  6949 Winding Cypress Dr, Naples, FL 34114
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  /29

  $12,000 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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  /43

  $890,000 Sold Mar 28, 2025

  • 2,107 Sq Ft
  • $422/SF
  • 3 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2018

  7556 Winding Cypress Dr, Naples, FL 34114

  Discover luxury living in this modern and bright single-family Martin Ray home, located in the resort-style community of Winding Cypress. With 2,107 square feet of living space, this open concept 3-bedroom plus den, 2-bathroom home offers a harmonious blend of elegance and functionality. Natural light and coffered ceiling details create a bright and airy atmosphere while modern design and neutral

  Kimberly Springer Orchid Realty International

  7556 Winding Cypress Dr, Naples, FL 34114
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  /48

  Est $1,063,560 Not Listed For Sale

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

  6846 Greenbriar Ct, Naples, FL 34114

  6846 Greenbriar Ct, Naples, FL 34114
• 

  

  /46

  $1,099,000

  • 3 Beds
  • 2 Baths
  • 2,185 Sq Ft

  6767 Pennyroyal Dr, Naples, FL 34114

  Wow! This beautifully designed and meticulously maintained home checks all the right boxes. Featuring the highly desirable Summerwood floor plan with Great Room extension, it is perfect for entertaining or simply relaxing at home after a nice day out in beautiful Naples, FL. The kitchen features upgraded appliances, quartz countertops, an oversized island and walk-in pantry. The two guest

  Jeff Waldman Premiere Plus Realty Company

  6767 Pennyroyal Dr, Naples, FL 34114
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  /35

  $8,500 per month

  • 3 Beds
  • 2 Baths
  • 2,175 Sq Ft
  • House for Rent

  6694 Pennyroyal Dr, Naples, FL 34114

  Unwind in this brand new, pristine vacation rental. Revel in the allure of a splendid pet-friendly home with a dazzling outdoor lanai, designed for the ultimateoutdoor living experience. This residence boasts abundant natural light, a refreshing coastal contemporary interior, and an inviting open floor plan. With three bedrooms plus a versatile office you'll have ample space to accommodate

  Jocelyn Lujen Coldwell Banker Realty

  6694 Pennyroyal Dr, Naples, FL 34114
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  /47

  $615,000 Sold Mar 24, 2025

  • 1,554 Sq Ft
  • $396/SF
  • 330 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 2016

  7113 Live Oak Dr, Naples, FL 34114

  BIG PRICE REDUCTION! THIS IS ONE OF THE LOWEST PRICED VILLA POOL HOME! Discover this stunning 3-bedroom, 2-bathroom villa with a 2-car garage and a luxurious gas heated pool that is ideally situated on a premium pie-shaped lot adjacent to nature preserve and near to the vibrant Winding Cypress Amenity Center is the perfect place to make your own paradise. The flex room offers endless

  James Trzyna Realty One Group MVP

  7113 Live Oak Dr, Naples, FL 34114
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  /34

  Est $1,047,135 Not Listed For Sale

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

  6723 Pennyroyal Dr, Naples, FL 34114

  6723 Pennyroyal Dr, Naples, FL 34114
• 

  

  /81

  $899,000

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

  6763 Winding Cypress Dr, Naples, FL 34114

  The Martin Ray floor plan is a breathtaking home located in the serene Winding Cypress community, overlooking a picturesque lake. This exquisite 2021 residence showcases the meticulous care of its single owner and boasts numerous upgrades throughout. It features a heated pool, three bedrooms, two bathrooms, and a den, providing ample space for living and entertaining. The heart of the home is a

  Ryan Finnegan COLDWELL BANKER SUNSTAR REALTY

  6763 Winding Cypress Dr, Naples, FL 34114
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  /41

  $7,000 per month

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

  7631 Jacaranda Ln, Naples, FL 34114

  Beautiful 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 bed and den has a full size pullout couch that sleeps 2 and includes a full wardrobe armor for clothing . Spacious attached 2-car garage. Relax on the spacious lanai that overlooks the private pool with peaceful lake

  Amber Jasper Grice Realty Inc

  7631 Jacaranda Ln, Naples, FL 34114
• 

  

  /49

  $775,000 Sold Mar 11, 2025

  • 1,804 Sq Ft
  • $430/SF
  • 117 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 2021

  6852 Winding Cypress Dr, Naples, FL 34114

  This pristine Abbeyville home in Winding Cypress has it all and is not to be missed! Built in 2021, this property has a fresh neutral palate and features a spacious open split bedroom floor plan with 2 bedrooms + den + sunroom and 2 full bathrooms. The 2-car garage has upgraded features including AC, an insulated garage door, a 4' extension, and extra lighting. 10' ceilings add to the

  Ashley Prescott DomainRealty.com LLC

  6852 Winding Cypress Dr, Naples, FL 34114
• 

  

  /43

  Est $1,078,410 Not Listed For Sale

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

  6762 Pennyroyal Dr, Naples, FL 34114

  6762 Pennyroyal Dr, Naples, FL 34114
• 

  

  /42

  $950,000

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

  7211 Live Oak Dr, Naples, FL 34114

  Lakefront Paradise Awaits in Winding Cypress! Imagine waking up to serene lake views every day in this meticulously maintained 3-bedroom, 2-bathroom haven located in the highly sought-after Winding Cypress community of Naples. Situated on an oversized, pie-shaped lot, this stunning Summerville extended model by Pulte offers the ultimate in Florida living.Step inside and be greeted by a

  Felicia Saraceno Keller Williams Marco Realty

  7211 Live Oak Dr, Naples, FL 34114
• 

  

  /25

  $12,000 per month

  • 3 Beds
  • 3 Baths
  • 2,128 Sq Ft
  • House for Rent

  6770 Pennyroyal Dr, Naples, FL 34114

  This newly completed and spacious PET FRIENDLY home offers 3 bedrooms (King, King & 2 Twins) plus a den that is equipped with a queen-size murphy bed. This home is full of entertaining options that allow you to bring the extended family along. With its open floor plan as well as zero-corner sliders that blend the interior seating with the outside kitchen and bar. As soon as you drive through the

  Ryan Buchalter William Raveis Real Estate

  6770 Pennyroyal Dr, Naples, FL 34114
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  /50

  $850,000 Sold Feb 27, 2025

  • 2,867 Sq Ft
  • $296/SF
  • 23 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 2016

  7073 Live Oak Dr, Naples, FL 34114

  Welcome to the award-winning Martin Ray home in the prestigious and centrally located Winding Cypress resort community in Naples. This exceptional home features an expansive lanai set on a protected and private preserve, with room for a pool, providing the perfect space to enjoy the serene Florida sunshine. Inside, the bright and airy ambiance is enhanced by a newly enlarged center island with

  Taylor Smith Premier Sotheby's Int'l Realty

  7073 Live Oak Dr, Naples, FL 34114
• 

  

  /38

  Est $1,534,931 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,852 Sq Ft

  6871 Cocoplum St, Naples, FL 34114

  6871 Cocoplum St, Naples, FL 34114
• 

  

  /42

  $537,000

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

  7642 Jacaranda Ln, Naples, FL 34114

  Tucked Away Treasure in Winding Cypress- Step into a slice of serenity with this charming attached villa, nestled in one of the most peaceful corners of Naples. Unlike the typical coastal designs so common in the area, this home offers a more rustic warmth—perfect for those who appreciate natural textures, cozy finishes, and a relaxed, grounded lifestyle. With 2 bedrooms, a versatile den, 2

  Scott Bertha Downing Frye Realty Inc.

  7642 Jacaranda Ln, Naples, FL 34114
• 

  

  /44

  $7,000 per month

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

  7627 Jacaranda Ln, Naples, FL 34114

  Available for season 2025. 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

  Amber Jasper Grice Realty Inc

  7627 Jacaranda Ln, Naples, FL 34114
• 

  

  /37

  $720,000 Sold Feb 13, 2025

  • 1,910 Sq Ft
  • $377/SF
  • 265 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 2015

  7247 Live Oak Dr, Naples, FL 34114

  JUST REDUCED AND PRICED TO SELL! Welcome to one of the most desirable neighborhoods in Naples. Winding Cypress boasts resort style living with pickleball, tennis, bocci, large gym, movement room, library, internet cafe, banquet room with kitchen, restaurant, and resort style pool with waterfall and lap lane. Currently the only Summerwood model for sale with peaceful panoramic water and preserve

  Kati Bepko Coldwell Banker Realty

  7247 Live Oak Dr, Naples, FL 34114
• 

  

  /51

  Est $1,388,492 Not Listed For Sale

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

  6907 Cocoplum St, Naples, FL 34114

  6907 Cocoplum St, Naples, FL 34114

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