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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28 listings match your search criteria.
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6903 Cocoplum St   Naples
  • 4Bedrooms
  • 4Bathrooms
  • 3656Sq Ft
  • 2021Year Built
$1,870,000

SELLER WILL CONTRIBUTE TOWARD A 3-2-1 INTEREST RATE BUY DOWN for full price offers received within the next 30 days.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 &…

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6920 Cocoplum St   Naples
  • 3Bedrooms
  • 3Bathrooms
  • 2952Sq Ft
  • 2019Year Built
$1,649,000

Discover luxury living in this exquisite Stonewater resort home in one of the most outstanding communities in South Naples on one of the best lakefront land sites imaginable. Boasting nearly 3,000 square feet of living space, this residence offers a spacious and open floor plan with high tray ceilings, architecturally stunning alcoves and arches, and…

Active
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…

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7565 Blackberry Dr   Naples
  • 3Bedrooms
  • 3Bathrooms
  • 2948Sq Ft
  • 2017Year Built
$1,450,000

Located in the highly sought after and amenity rich community of Winding Cypress, this 3 Bedroom + Den, 3 Bath Summerwood boasts a hard to find spacious loft that adds an additional 900+ sq ft of living area. The meticulously maintained home has numerous upgrades that include an extended finished garage with utility…

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6801 Greenbriar Ct   Naples
  • 4Bedrooms
  • 3Bathrooms
  • 2152Sq Ft
  • 2022Year Built
$1,275,000

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
7063 Winding Cypress Dr   Naples
  • 3Bedrooms
  • 3Bathrooms
  • 2496Sq Ft
  • 2016Year Built
$1,275,000

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…

Active
7615 Winding Cypress Dr   Naples
  • 3Bedrooms
  • 2Bathrooms
  • 2018Sq Ft
  • 2019Year Built
$1,200,000

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…

Active
6830 Greenbriar Ct   Naples
  • 2Bedrooms
  • 2Bathrooms
  • 2105Sq Ft
  • 2021Year Built
$1,190,000

LIKE NO OTHER FOR SALE IN WINDING CYPRESS! This "PRESTIGE MODEL" POOL home must be seen to be appreciated for all that it has to offer! BEING SOLD TURNKEY WITH ALL DESIGNER DECOR ALL YOU NEED TO DO IS BRING YOUR TOOTHBRUSH AND CLOTHES! GORGEOUS LAKE VIEWS THROUGH THE PICTURE WINDOW SCREEN! This home has…

Active
7634 Arrowhead Way   Naples
  • 3Bedrooms
  • 2Bathrooms
  • 2230Sq Ft
  • 2019Year Built
$1,095,000

Discover Your Dream Home Nestled W/in The Prestigious Community Of Winding Cypress. This Exquisite Residence Epitomizes Luxury Living W/ Its Open-Concept Design Seamlessly Integrating The Spacious Living Areas, Creating An Inviting Atmosphere For Both Relaxation & Entertainment. As You Step Inside, You'll Be Greeted By A Breathtaking Long Lake View That Sets The Stage For…

Active
7673 Jacaranda Ln   Naples
  • 3Bedrooms
  • 3Bathrooms
  • 2063Sq Ft
  • 2019Year Built
$999,000

This immaculate & move-in-ready 2019 pool home at Winding Cypress stands as a true gem, blending luxurious amenities with top-tier safety features. Nestled on a preserve and corner lot, it offers extra privacy at the pool & a serene environment. The main floor presents a versatile layout with a spare bedroom, full bath, and a…

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

Exquisite Summerwood floor plan featuring a Prime lot Location with Views of the Pond and Preserve. A Beautiful and Peaceful respite that can be enjoyed from the panoramic screened Lanai. The entire home comes with Upgraded Flooring, no carpet. 3 Bedrooms, with Wide Oak, blonde Plank Wood, the Den offers Hand Scraped Wood Flooring with…

Active
7491 Blackberry Dr   Naples
  • 3Bedrooms
  • 3Bathrooms
  • 2282Sq Ft
  • 2017Year Built
$895,000

This rarely available two-story “Abbeyville” model with a Premium Waterfront Location has a preferred Southern Exposure and has been meticulously maintained. Located in the highly sought-after, gated, amenity rich community of Winding Cypress. There is a ground floor Primary Suite with spacious walk-in closet, a guest bedroom and bath, and a den/office. Plus, the home…

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7346 Mockingbird Ct   Naples
  • 4Bedrooms
  • 2Bathrooms
  • 2230Sq Ft
  • 2016Year Built
$875,000

In the ultimate Naples resort community, this exceptional property in Winding Cypress stands out for its distinctive features, offering an ideal blend of waterfront tranquility, preserved nature and the allure of privacy. This award-winning Summerwood floor plan boasts every builder option and upgrade, on a completely private corner lot on a tranquil cul-de-sac. Highlights include…

Active
7267 Live Oak Dr   Naples
  • 3Bedrooms
  • 2Bathrooms
  • 2230Sq Ft
  • 2015Year Built
$869,000

H13764 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 stunning 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…

Active
7670 Jacaranda Ln   Naples
  • 3Bedrooms
  • 2Bathrooms
  • 1594Sq Ft
  • 2018Year Built
$849,900

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
7682 Jacaranda Ln   Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1594Sq Ft
  • 2018Year Built
$760,000

Must See this Beautiful two bedrooms, two bathroom, plus den Cresida Model. Features include pro series cabinets in the 2 car garage, french doors, kitchen with quartz counter tops, breakfast island, large pantry, stainless steel appliances, tile back splash , accent wall with built in bar and wine cooler , tile throughout, led…

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…

Active
7601 Blackberry Dr   Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1805Sq Ft
  • 2018Year Built
$749,900

Enjoy the relaxing and private views of the lake and preserve with no houses across from you. Some of the many upgrades in this lightly used, two-bedroom plus den, two-bath home are tile throughout, a sunroom addition, all California Closets, volume ceilings, huge walk-in shower, upgraded cabinets and an extended garage. The club at Winding…

Active
7108 Lily Way   Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1685Sq Ft
  • 2015Year Built
$749,900

Located within the amenity-rich Winding Cypress community, this 2-bedroom plus den, 2-bathroom Abbeyville has been meticulously maintained. Builder upgrades include additional drawers added in primary bathroom dual sink vanity, outdoor kitchen plumbed for water along with gas line, floor tile set on diagonal, Whirlpool stainless appliances, granite, garage utility sink, upgraded lighting package in garage…

Active
7627 Jacaranda Ln   Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1554Sq Ft
  • 2017Year Built
$749,000

This stunning lake view villa pool home with 2 car garage in 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 coffee or evening sunsets, this…

Active
7781 Jacaranda Ln   Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1554Sq Ft
  • 2018Year Built
$720,000

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
7574 Jacaranda Ln   Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1554Sq Ft
  • 2016Year Built
$700,000

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
$660,000

V11010 Beautifully updated 3 bedroom in Winding Cypress. This Serenity floorplan features granite kitchen with under cabinet lighting, pantry plus a hands-free faucet. Open living/dining area with tile, plantation shutters and large slider overlooking heated salt water pool. Private preserve views, ample closets plus a 2-car garage with AC and built-in storage. Impact glass throughout…

Active
7579 Jacaranda Ln   Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1554Sq Ft
  • 2016Year Built
$639,900

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
7790 Jacaranda Ln   Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1554Sq Ft
  • 2019Year Built
$629,000

Beautiful, like-new furnished single family attached villa with long lake view. Built in 2019, this move-in ready Serenity floor plan includes two bedrooms plus den, two bathrooms, upgraded tile floors, extended lanai with Storm Smart hurricane screens, hurricane impact windows/doors throughout. Southern exposure. Natural gas community. Quartz countertops, stainless appliances, plantation shutters. A highly sought…

Active
7602 Jacaranda Ln   Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1554Sq Ft
  • 2017Year Built
$624,900

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…

Active
7191 Live Oak Dr   Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1554Sq Ft
  • 2015Year Built
$559,000

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…

Active
7202 Live Oak Dr   Naples
  • 3Bedrooms
  • 2Bathrooms
  • 1554Sq Ft
  • 2015Year Built
$559,000

V14601 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…

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