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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18 listings match your search criteria.
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7638 Jacaranda Ln   Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1574Sq Ft
  • 2017Year Built
$629,000

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…

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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…

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7702 Jacaranda Ln   Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1554Sq Ft
  • 2019Year Built
$679,900

What's Special: *Open floor plan *Epoxy garage floor *Granite countertops *3 feet bathroom countertops *Remote controlled garage screen *Remote controlled hurricane shutters on the lanai *California Closets in all bedrooms *Pool. Come see this beautifully designed pool home boasting of an inviting open floor plan, perfect for entertaining and family living. The kitchen highlights its elegant…

Active
6792 Bromeliad Dr   Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1774Sq Ft
  • 2021Year Built
$799,000

Welcome to Winding Cypress, where modern elegance meets comfort in this stunning Abbeyville model, Pulte home built in 2021. A beautiful lake view frames the backyard of this meticulously maintained, well designed residence featuring two spacious bedrooms plus a versatile den, perfect for a home office or additional guest space. Step inside to…

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6767 Pennyroyal Dr   Naples
  • 3Bedrooms
  • 2Bathrooms
  • 2185Sq Ft
  • 2021Year Built
$1,299,000

Wow! This beautifully designed and meticulously maintained home is absolutely spectacular. 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…

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7670 Jacaranda Ln   Naples
  • 3Bedrooms
  • 2Bathrooms
  • 1594Sq Ft
  • 2018Year Built
$799,900

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.…

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

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 of Winding Cypress in Naples, the…

Active
6906 Winding Cypress Dr   Naples
  • 3Bedrooms
  • 3Bathrooms
  • 2124Sq Ft
  • 2022Year Built
$1,199,900

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…

Active
7716 Winding Cypress Dr   Naples
  • 3Bedrooms
  • 3Bathrooms
  • 2923Sq Ft
  • 2018Year Built
$1,395,000

Welcome to the rare opportunity to own the prestigious Stonewater model home in the desirable, amenity filled community of Winding Cypress. This property sits on one of the most beautiful and private waterfront lots. View spectacular sunsets over a big water lake with a wildlife-rich preserve as a private backdrop. As soon as you walk through…

Active
7248 Live Oak Dr   Naples
  • 3Bedrooms
  • 2Bathrooms
  • 1685Sq Ft
  • 2016Year Built
$699,900

Time to enjoy life. 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…

Active
7626 Jacaranda Ln   Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1554Sq Ft
  • 2017Year Built
$649,500

Welcome to your dream home in the highly sought-after Winding Cypress community! This beautifully maintained 2-bedroom plus den, 2-bathroom pool home features an inviting open floor plan, perfect for modern living and entertaining. The kitchen is a chef's delight, boasting a breakfast bar and sleek stainless steel appliances. The generous primary bedroom offers a serene retreat…

Active
7235 Live Oak Dr   Naples
  • 3Bedrooms
  • 3Bathrooms
  • 2640Sq Ft
  • 2015Year Built
$1,050,000

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
$645,000

BIG PRICE REDUCTION! THIS IS 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…

Active
7658 Jacaranda Ln   Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1554Sq Ft
  • 2018Year Built
$609,500

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…

Active
7267 Live Oak Dr   Naples
  • 3Bedrooms
  • 2Bathrooms
  • 2230Sq Ft
  • 2015Year Built
$725,000

This pre-inspected, intelligently-priced single family home is located in a stunning natural gas community and perfectly situated between Marco Island and downtown Naples. Among other amenities, this community has TWO dog parks! Stunning landscaping greets you at the front door, and you can step outdoors and savor a sanctuary of comfort and tranquility from the…

Active
7602 Jacaranda Ln   Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1554Sq Ft
  • 2017Year Built
$599,900

Discover EXCEPTIONAL VALUE in this captivating attached villa nestled in the HIGHLY SOUGHT-AFTER Naples locale within the vibrant community of Winding Cypress. Boasting 2 bedrooms, 2 full bathrooms, a den, and a two-car garage, this residence is meticulously designed for comfort and style. The bright and white kitchen, adorned with popular finishes, complements the seamless…

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