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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22 listings match your search criteria.
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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…

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6962 Winding Cypress Dr   Naples
  • 3Bedrooms
  • 3Bathrooms
  • 2952Sq Ft
  • 2020Year Built
$1,629,000

Presenting the exclusive Stonewater model in Winding Cypress. This impeccably maintained home is nearly new, offering three bedrooms, a versatile den and three baths, plus a pool bath. Step onto the expansive panoramic screened lanai, featuring a custom pool, built-in outdoor kitchen, and be captivated by the serene lake and tree-lined backdrop for privacy. The…

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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7615 Winding Cypress Dr   Naples
  • 3Bedrooms
  • 2Bathrooms
  • 2018Sq Ft
  • 2019Year Built
$1,150,000

Ideally located equidistant between Downtown Naples and Marco Island, Winding Cypress coexists with the natural flora and fauna of Southwest Florida. Enjoy bird songs along with deer and wild turkey sightings while walking or biking through the community. Get to know your neighbors while basking in the sun at the resort style community…

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6801 Greenbriar Ct   Naples
  • 4Bedrooms
  • 3Bathrooms
  • 2152Sq Ft
  • 2022Year Built
$1,145,000

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…

Active
7123 Lily Way   Naples
  • 3Bedrooms
  • 3Bathrooms
  • 2998Sq Ft
  • 2015Year Built
$998,500

Welcome to the ultimate Naples resort community of Winding Cypress. Presenting this lakeview Summerwood home, set on an exceptionally private homesite with a beautiful, long lake view. Features include every builder option and upgrade, plus a very cool upstairs bonus loft bedroom and living room, perfect for guests or as a homeowner's retreat. This home…

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…

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7673 Jacaranda Ln   Naples
  • 3Bedrooms
  • 3Bathrooms
  • 2063Sq Ft
  • 2019Year Built
$895,000

Furnished, 1-1/2 story, 2019 pool home at Winding Cypress blends luxurious amenities with top-tier safety features. Nestled on a preserve and corner lot, it offers extra privacy at the pool and a serene environment. The main floor presents a versatile layout with (1) the primary suite with a lavish bath and large walk-in closet, (2)…

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

Looking for an intimate community with lovely amenities yet low HOA fees? Situated on a private lot, 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 with walnut cabinets, high-end granite countertops, a large center island with breakfast bar and…

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
7248 Live Oak Dr   Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1685Sq Ft
  • 2016Year Built
$754,900

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…

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7627 Jacaranda Ln   Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1554Sq Ft
  • 2017Year Built
$720,000

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…

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
7113 Live Oak Dr   Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1554Sq Ft
  • 2016Year Built
$699,000

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
7574 Jacaranda Ln   Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1554Sq Ft
  • 2016Year Built
$675,000

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
7175 Live Oak Dr   Naples
  • 3Bedrooms
  • 2Bathrooms
  • 1554Sq Ft
  • 2016Year Built
$639,900

This beautiful Winding Cypress Villa home offers 1,554 sq. ft. of comfort has 3 bedrooms, 2 full bathrooms, Screened in lanai, salt water pool and spa and a 2-car garage also has lots of upgrades. The list is attached in the Supplements section. Located just minutes to Marco Island and downtown Naples, the community features…

Active
7658 Jacaranda Ln   Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1554Sq Ft
  • 2018Year Built
$624,500

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
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
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
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…

Active
7191 Live Oak Dr   Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1554Sq Ft
  • 2015Year Built
$529,000

Incredible opportunity to own an attached villa in amenity rich Winding Cypress in spectacular Naples Florida. This home features 2 split bedrooms, each with walk in closets, plus a den with French doors. Granite countertops in both bathrooms, Plantation Shutters, tile flooring throughout and designer light fixtures. Kitchen has upgraded 42” cabinets, granite countertops…

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