The community of Winding Cypress is found in Naples. Superbly situated for access to all of the Naples region amenities and comforts has to offer.

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7073 Live Oak Dr   Naples
  • 3Bedrooms
  • 3Bathrooms
  • 2867Sq Ft
  • 2016Year Built
$925,000

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…

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7675 Winding Cypress Dr   Naples
  • 3Bedrooms
  • 3Bathrooms
  • 2496Sq Ft
  • 2020Year Built
$1,499,000

Discover luxury living in this breathtaking Pinnacle estate home, situated on one of the most coveted lakefront sites in the south Naples resort community of Winding Cypress. Step inside to an open and spacious floor plan, enhanced by soaring tray ceilings, architecturally stunning alcoves and graceful arches. The home’s designer kitchen serves as the centerpiece,…

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6754 Pennyroyal Dr   Naples
  • 3Bedrooms
  • 3Bathrooms
  • 2158Sq Ft
  • 2021Year Built
$1,100,000

From the moment you drive into the beautiful community of Winding Cypress you will feel welcomed. The stunning entry to this picturesque enclave will be a place you can truly call HOME! This is a natural gas, resort-style community, with over 2/3rds of the neighborhood remaining a preserve! You are surrounded by nature, yet close…

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7370 Mockingbird Ct   Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1805Sq Ft
  • 2016Year Built
$795,900

Welcome to your dream home at 7370 Mockingbird Court in beautiful Naples, FL! This charming 2-bedroom, 2-bathroom residence, with a versatile den that can easily be converted into a third bedroom, offers a spacious 1,805 square feet of living space, perfectly nestled on an 8,276 square foot lot. Step inside to discover a welcoming interior featuring…

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7248 Live Oak Dr   Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1685Sq Ft
  • 2016Year Built
$689,900

This home is a true single famly NOT an attached villa. Wonderful community with over 800 acres giving room for custom homes and large back yards, nature trails and room to relax. So well cared for. Enjoy the private park like back yard. Extended screened patio with outdoor kitchen perfect for dining al fresco. Light…

Active
7355 Mockingbird Ct   Naples
  • 3Bedrooms
  • 2Bathrooms
  • 2198Sq Ft
  • 2016Year Built
$1,150,000

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…

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6906 Winding Cypress Dr   Naples
  • 3Bedrooms
  • 3Bathrooms
  • 2124Sq Ft
  • 2022Year Built
$1,175,000

This exquisite 3-bedroom + den, 3-bathroom pool home offers a perfect blend of luxury and comfort in the prestigious gated community of Winding Cypress. As you step inside, you'll be greeted by a spacious open floor plan with elegant tile flooring, neutral tones, and designer fixtures that create a warm and inviting atmosphere. The beautifully…

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6763 Winding Cypress Dr   Naples
  • 3Bedrooms
  • 2Bathrooms
  • 2107Sq Ft
  • 2021Year Built
$970,000

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…

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6851 Winding Cypress Dr   Naples
  • 3Bedrooms
  • 3Bathrooms
  • 2789Sq Ft
  • 2020Year Built
$1,699,000

Indulge in breathtaking lake and sunset views from this exquisite Stonewater model home, ideally on a premium lot in the prestigious guard-gated low HOA fee community of Winding Cypress. From the moment you step inside, the meticulous attention to detail and timeless elegance will captivate you. This sophisticated residence features three bedrooms plus a den,…

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7602 Jacaranda Ln   Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1554Sq Ft
  • 2017Year Built
$599,000

Welcome to this stunning 2+Den, 2 Bath home in the preserve-like community of Winding Cypress. As its name suggests, you will be ushered away from the worries of the world as you are greeted by this serene and natural, resort-style community boasting a poolside restaurant, 5 tennis courts, 4 bocce courts, 4 pickle ball courts,…

Active
6949 Winding Cypress Dr   Naples
  • 3Bedrooms
  • 2Bathrooms
  • 2185Sq Ft
  • 2020Year Built
$1,045,000

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.…

Active
6852 Winding Cypress Dr   Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1804Sq Ft
  • 2021Year Built
$810,000

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…

Active
7404 Winding Cypress Dr   Naples
  • 2Bedrooms
  • 2Bathrooms
  • 2062Sq Ft
  • 2016Year Built
$1,250,000

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…

Active
7788 Winding Cypress Dr   Naples
  • 3Bedrooms
  • 3Bathrooms
  • 2496Sq Ft
  • 2019Year Built
$1,550,000

Nestled within an exclusive gated community and surrounded by a serene nature preserve, this elegant 3-bedroom, 3-bathroom home with a spacious den/office is the epitome of refined Florida living. The open, airy floor plan flows seamlessly, with high ceilings and large windows that capture abundant natural light and offer unobstructed views of the lush preserve…

Active
7544 Winding Cypress Dr   Naples
  • 3Bedrooms
  • 3Bathrooms
  • 2532Sq Ft
  • 2018Year Built
$1,150,000

Welcome to a beautiful Pinnacle Model in the desirable, amenity rich community of Winding Cypress. This waterfront home is offered at an incredible value. Original owner care is apparent throughout. Builder and owner upgrades include; chef's kitchen with upgraded appliances, sink & faucet, soft close pull out cabinets including under-side lighting, custom quartz countertops, custom…

Active
7683 Winding Cypress Dr   Naples
  • 3Bedrooms
  • 2Bathrooms
  • 2018Sq Ft
  • 2018Year Built
$998,000

Live the Vacation Lifestyle Every Day in Winding Cypress Welcome 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…

Active
7171 Live Oak Dr   Naples
  • 3Bedrooms
  • 2Bathrooms
  • 1554Sq Ft
  • 2016Year Built
$585,000

Here is the best priced villa at this time! A lovely, comfortable 3 bedroom home, located in the amenity-filled Winding Cypress community, one of only a few that offer natural gas. Loaded with upgrades, it features stainless steel appliances, granite counters and vanities, under cabinet lighting, custom kitchen pantry with pull out shelves, full…

Active
7638 Jacaranda Ln   Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1574Sq Ft
  • 2017Year Built
$599,900

Introducing the incredibly rare Winding Cypress model, the Cressida villa, now available with expansive private yard and lanai space. This unique villa features a dedicated private front entrance and an expanded foyer, complemented by an open yet defined living concept. The home boasts a wealth of builder-installed upgrades, including granite finishes, high-end porcelain floors, a…

Active
6823 Winding Cypress Dr   Naples
  • 3Bedrooms
  • 3Bathrooms
  • 2515Sq Ft
  • 2021Year Built
$1,649,000

Massive $200K price reduction!! STUNNING lake and sunset views await from the lanai of this Pinnacle model home situated on an oversized lot in Winding Cypress. At just over 2,500 square feet, you will notice the attention to detail from the moment you walk in the front door. Features of this gorgeous home include: 3…

Active
7702 Jacaranda Ln   Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1554Sq Ft
  • 2019Year Built
$634,900

What's Special: *Open floor plan *Epoxy garage floor *Granite countertops *3 ft. bathroom countertops *Remote controlled garage screen *Remote controlled hurricane shutters on the lanai *California Closets in all bedrooms *Pool. Den can be converted to a 3rd bedroom too. Come see this beautifully designed pool home boasting of an inviting open floor plan, perfect for entertaining…

Active
6767 Pennyroyal Dr   Naples
  • 3Bedrooms
  • 2Bathrooms
  • 2185Sq Ft
  • 2021Year Built
$1,274,900

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…

Active
7670 Jacaranda Ln   Naples
  • 3Bedrooms
  • 2Bathrooms
  • 1594Sq Ft
  • 2018Year Built
$789,900

Step into the lap of luxury with this stunning villa in Winding Cypress. This exquisite property is not just a home; it's an embodiment of sophistication and comfort, offering a lifestyle that is truly unparalleled. The villa is being offered fully furnished, ensuring that every inch of this residence reflects a tasteful and cohesive design.…

Active
7619 Jacaranda Ln   Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1554Sq Ft
  • 2016Year Built
$592,500

No storm damage from recent hurricanes! This impeccably maintained residence, boasting serene lake vistas, presents an array of desirable features. Comprising two bedrooms, two bathrooms, a den complete with a Murphy bed, a two-car garage, and a utility-equipped laundry room, this property epitomizes comfort and functionality. Nestled within the highly coveted and rapidly flourishing community…

Active
7235 Live Oak Dr   Naples
  • 3Bedrooms
  • 3Bathrooms
  • 2640Sq Ft
  • 2015Year Built
$995,000

Luxury living in this extraordinary Naples FL home and coveted community of Winding Cypress! Built in 2015 by Divosta homes this 3 bed, 3 bath, plus a den with a second story loft known as the Martin Ray flood plan. This home with over 2,600 sq feet under air, it's the perfect layout. Walk into…

Active
7247 Live Oak Dr   Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1910Sq Ft
  • 2015Year Built
$789,000

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…

Active
7663 Jacaranda Ln   Naples
  • 3Bedrooms
  • 2Bathrooms
  • 1554Sq Ft
  • 2017Year Built
$620,000

Welcome to your new home, a rare opportunity to own a unique three-bedroom Serenity model with a newly added whole-home generator powered by direct natural gas and motorized retractable lanai storm shutter screens. Enjoy the outstanding ample space inside and out, with a fully expanded screened and paver lanai with beautiful, lush landscaping for privacy.…

Active
7113 Live Oak Dr   Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1554Sq Ft
  • 2016Year Built
$635,000

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…

Active
7658 Jacaranda Ln   Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1554Sq Ft
  • 2018Year Built
$604,500

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…

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