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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34 listings match your search criteria.
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7663 Jacaranda Ln   Naples
  • 3Bedrooms
  • 2Bathrooms
  • 1554Sq Ft
  • 2017Year Built
$665,000

Welcome to the ultimate villa in Winding Cypress. This is the rare opportunity to own the unique and wildly popular Serenity model with the fully expanded lanai screened and pavered play deck with the bonus third bedroom den option and newly added whole-home generator powered by direct natural gas. Enjoy outstanding privacy and ample space…

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7039 Winding Cypress Dr   Naples
  • 3Bedrooms
  • 3Bathrooms
  • 2496Sq Ft
  • 2016Year Built
$1,499,900

Beautiful Pinnacle style Estate home located within walking distance to Winding Cypress beautiful amenity center, dog park and the community gardens. When you enter this home you will be pleasantly surprised with the attention to details thoughtfully placed in this home. A few of the upgraded extras are custom California Closets, motorized…

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7202 Live Oak Dr   Naples
  • 3Bedrooms
  • 2Bathrooms
  • 1554Sq Ft
  • 2015Year Built
$549,000

This Villa is a true masterpiece of design and comfort. Enjoy your new Naples lifestyle, total relaxation and resort living or use it as a rental income property investment. A gorgeous unit featuring a tasteful interior that's highlighted with palm trees, tropical flowers & foliage to view from a private lanai with room…

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6903 Cocoplum St   Naples
  • 4Bedrooms
  • 4Bathrooms
  • 3656Sq Ft
  • 2021Year Built
$12,500

Live every day as if on a luxury resort vacation in Winding Cypress! The magic unfolds as you open the pocketing sliders, dissolving the boundaries between the interior & enchanting outdoor lanai--where you can enjoy 5-star resort amenities right at home, from the azure pool waters & sun shelf that beckons and a rejuvenating spa…

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7592 Winding Cypress Dr   Naples
  • 4Bedrooms
  • 2Bathrooms
  • 2159Sq Ft
  • 2021Year Built
$1,150,000

Welcome to your FULLY FURNISHED TURNKEY dream home nestled in the amenity rich community of Winding Cypress, where luxury living meets serene surroundings in beautiful Naples. This meticulously maintained residence presents a rare opportunity to indulge in modern elegance and comfort. Upon entering through the leaded glass front door, you're greeted by an inviting atmosphere accentuated…

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6932 Cocoplum St   Naples
  • 3Bedrooms
  • 3Bathrooms
  • 2515Sq Ft
  • 2019Year Built
$1,850,000

A staggering mix of natural beauty and fabulous Naples living. This jewel box home is situated on one of the most desirable lots in Winding Cypress. Look at the aerial view, simply breathtaking. Lot location had a $125,000 premium. Peaceful and full of nature. Well-designed, expansive floor plan offering generous size rooms, an outstanding…

Active
6906 Winding Cypress Dr   Naples
  • 3Bedrooms
  • 3Bathrooms
  • 2124Sq Ft
  • 2022Year Built
$1,350,000

This gorgeous pool home is being offered turnkey furnished and was inspired by the model home. It features 3 bedrooms, plus a den, 3 full bathrooms, and a 2 car extended garage. The endless upgrades feature zero corner sliders, tile throughout, Hunter Douglas electric blinds, exterior cameras, two toned cabinets, upgraded and built in…

Active
7420 Winding Cypress Dr   Naples
  • 4Bedrooms
  • 2Bathrooms
  • 2198Sq Ft
  • 2017Year Built
$925,000

Winding Cypress is the ultimate Naples resort community, and this home serves as the ultimate poolside retreat. The long southwest water views seamlessly blend waterfront serenity, preserved nature, and privacy. Adorning the oversized covered lanai is a deluxe outdoor kitchen complete with every conceivable feature and top-grade finishes. This award-winning Summerwood floor plan boasts every…

Active
7465 Winding Cypress Dr   Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1910Sq Ft
  • 2018Year Built
$789,000

Beautiful selected finishes and colors. A peaceful beach sand pallet will take away the stress and bring you to your happy place. Casual comfort. 3 bedrooms presently featuring one designed as a den open to living area. Custom upgraded Kitchen cabinets. Stainless appliance with a GAS range. Nice size pantry. Generous laundry room. The Living…

Active
7113 Live Oak Dr   Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1554Sq Ft
  • 2016Year Built
$687,000

Step into your own slice of paradise with this stunning 2-bedroom + den, 2-bathroom villa boasting a 2-car garage and a luxurious gas heated pool, nestled on a premium pie-shaped lot adjacent to the vibrant Winding Cypress Amenity Center. The Serenity Model, a highly coveted gem, offers the perfect blend of charm and sophistication, whether…

Active
7658 Jacaranda Ln   Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1554Sq Ft
  • 2018Year Built
$614,500

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
7063 Winding Cypress Dr   Naples
  • 3Bedrooms
  • 3Bathrooms
  • 2496Sq Ft
  • 2016Year Built
$1,199,900

Look no further. This Pinnacle model in the beautiful community of Winding Cypress rarely comes available and features a great open floor plan for entertaining. 3 bdrms den/office 3 full baths and a 3 car garage plenty of space for guests and family. Some of the extras include an oversize extended lanai overlooking…

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7627 Jacaranda Ln   Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1554Sq Ft
  • 2017Year Built
$679,000

This stunning lake view villa pool home with 2 car garage in the low fee community of Winding Cypress offers a luxurious lifestyle with its serene lake views and exceptional amenities. Home features include: Premium Wide Lake View: Step out onto your patio and soak in the breathtaking vistas of the tranquil lake. Whether it’s morning…

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6801 Greenbriar Ct   Naples
  • 4Bedrooms
  • 3Bathrooms
  • 2152Sq Ft
  • 2022Year Built
$1,099,000

Like new, two years old three-bedroom plus den, three-bathroom residence in Winding Cypress. House has been totally custom remodeled. This furnished home showcases new furniture and TVs, finished with 9’ ceilings, 8’ doors, pristine tile floors. The gourmet kitchen features high end appliances with gas cooking, pullout drawer cabinets, designer backsplash, pantry, and a large…

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7447 Chenille Ct   Naples
  • 4Bedrooms
  • 3Bathrooms
  • 2400Sq Ft
  • 2016Year Built
$3,595

Better then new 4 bedroom 3 bathroom with a loft home in Winding Cypress. This extraordinary home features stainless steel appliances with granite countertop in kitchen, spacious dinning & living room for easy entertaining, Master suite with walk-in closet looks out onto the landscape backyard, tile in living areas, carpet in bedrooms, upstairs you have…

Active
7670 Jacaranda Ln   Naples
  • 3Bedrooms
  • 2Bathrooms
  • 1594Sq Ft
  • 2018Year Built
$825,000

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
7574 Jacaranda Ln   Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1554Sq Ft
  • 2016Year Built
$650,000

Villa w/ PEACEFUL view! Attached villa Serenity floor plan that lives like a single family home w/ luxury features throughout- tray ceilings, 18" tile flooring, quartz countertops, custom tile backsplash in kitchen, convection double oven, designer light fixtures, high-end cabinetry, crown molding, French door entry to den, frameless glass enclosure in master shower, custom built…

Active
7103 Lily Way   Naples
  • 4Bedrooms
  • 3Bathrooms
  • 2654Sq Ft
  • 2015Year Built
$6,500

ANNUAL FURNISHED RENTAL APRIL 2024-MARCH 2025 available in elegant Winding Cypress...Contemporary and comfortable 4+ loft / 3 bathroom single family home located steps away from the RESORT STYLE club house. Amenities include a resort style pool, exercise room, and large yoga/dance studio, 4 pickleball courts, 6 tennis courts and a restaurant with an outdoor cabana.…

Active
6787 Winding Cypress Dr   Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1654Sq Ft
  • 2021Year Built
$7,000

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…

Active
7781 Jacaranda Ln   Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1554Sq Ft
  • 2018Year Built
$700,000

Arguably one of the best views in Winding Cypress! Don't miss your chance to snag this 2 bedroom plus den, 2 bath, 2 car garage Serenity villa with a heated saltwater pool! This home features a view that can't be beat, a huge pie shaped lot offering extensive privacy, a pool water feature, granite countertops,…

Active
7248 Live Oak Dr   Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1685Sq Ft
  • 2016Year Built
$745,900

You will think this home is new. So well cared for. 2+Den but den could have a closet making it a 3/2. Enjoy the private park like back yard. Extended screened patio with outdoor kitchen perfect for dining al fresco. Light bright home with all the goodies. Community even has…

Active
7267 Live Oak Dr   Naples
  • 3Bedrooms
  • 2Bathrooms
  • 2230Sq Ft
  • 2015Year Built
$789,000

Incredible value in Naples located in an intimate community with lovely amenities yet low HOA fees. This state-of-the art designed single family home enjoys both privacy and a lush botanical view, with its glorious gardens and plantings. The gourmet kitchen boasts walnut cabinets, high-end granite countertops, a large center island with breakfast bar and stainless-steel…

Active
6903 Cocoplum St   Naples
  • 4Bedrooms
  • 4Bathrooms
  • 3656Sq Ft
  • 2021Year Built
$1,699,500

.An exquisite residence offering a blend of timeless elegance & resort-style living that sets it apart in a class of its own in Winding Cypress. The open floor plan harmoniously integrates the kitchen, dining area & great room, creating a central hub where daily life unfolds w/effortles s elegance. The gourmet kitchen is a chef's…

Active
7602 Jacaranda Ln   Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1554Sq Ft
  • 2017Year Built
$609,900

NEW IMPROVED PRICE...WHAT A DEAL! 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…

Active
7763 Winding Cypress Dr   Naples
  • 4Bedrooms
  • 3Bathrooms
  • 3077Sq Ft
  • 2019Year Built
$7,800

ANNUAL Rental available May 1 2024. 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…

Active
7467 Blackberry Dr   Naples
  • 3Bedrooms
  • 2Bathrooms
  • 2198Sq Ft
  • 2017Year Built
$924,900

Welcome home to the popular Winding Cypress gated community! Spectacular private water and nature preserve views from your own premium lot’s lanai and backyard. This fresh and pristine home will exceed your expectations. An impressive custom door welcomes you inside to an open great room with elevated, coffered ceilings & high end…

Active
7567 Winding Cypress Dr   Naples
  • 3Bedrooms
  • 2Bathrooms
  • 1805Sq Ft
  • 2018Year Built
$10,000

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…

Active
7579 Jacaranda Ln   Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1554Sq Ft
  • 2016Year Built
$615,000

Beautiful, well-kept, light-and-bright villa with a long lake view to the Southwest to catch the all-day sun. Tile floors throughout for comfort and cleanliness. Lanai has no-see-um netting for year-round use. Bright kitchen with desirable gas cooktop. Split bedroom floor plan for guest privacy. Den and office with glass doors. Superb seasonal home or full-time…

Active
7662 Jacaranda Ln   Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1554Sq Ft
  • 2018Year Built
$4,400

Escape from stress in this immaculate ELEGANT POOL VILLA completely updated & FURNISHED. CENTRALLY LOCATED, gated resort living, minutes to Marco Island and Naples Pier, beaches, downtown & I75. Three beds, including NEW QUEEN PULL-OUT in DEN. Plank flooring throughout, FULL-SIZED private heated SALT WATER POOL w/ fountain & **RARE OUTDOOR KITCHEN** and FIRE PIT.…

Active
7631 Jacaranda Ln   Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1542Sq Ft
  • 2017Year Built
$7,000

Available for season 2025. 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…

Active
6694 Pennyroyal Dr   Naples
  • 3Bedrooms
  • 2Bathrooms
  • 2175Sq Ft
  • 2023Year Built
$6,000

*** Available May 2024-October 2024 ($4,000/month) November & December 2024 ($5,000/month) and January 2025 ($6,000/month) *** 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 ultimate outdoor living experience. This residence boasts abundant natural light, a refreshing coastal contemporary…

Active
6754 Pennyroyal Dr   Naples
  • 3Bedrooms
  • 3Bathrooms
  • 2158Sq Ft
  • 2021Year Built
$12,000

NOT AVAILABLE January, February and March 2025!! Step into paradise! ONE SMALL DOG ALLOWED! Built in 2021, this newly decorated and spacious pool home offers 3 bedrooms (King, King & 2 Twins) plus a den and 3 FULL bathrooms. Features include a wonderful open floor plan with zero-corner sliders that bring the outside…

Active
6779 Pennyroyal Dr   Naples
  • 3Bedrooms
  • 3Bathrooms
  • 2175Sq Ft
  • 2021Year Built
$13,000

A stunning new pool, outdoor lanai and outdoor kitchen. Spectacularly designed home. Serene lake views. Three-bedroom plus den, 3 bath property is perfect for vacationing. Light. Bright. Airy. Coastal Contemporary Interior. Open Floor Plan. The master bedroom has a king bed, and the two other bedrooms have queen beds. Another Futon has sleeping capabilities. Gas…

Active
7638 Jacaranda Ln   Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1574Sq Ft
  • 2018Year Built
$5,950

***WINDING CYPRESS - NEW - FURNISHED *** Beautifully furnished two bedrooms plus a den and two full bathrooms with two car garage. King size bed in master bedroom with a walk in closet, big walk in shower, and dual sinks. Guest bedroom has Twin size bed with a roll out second mattress and Full bathroom…

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