Winding Cypress Homes with Patio Exterior

Winding Cypress Homes with Patio Exterior

Welcome to Winding Cypress, an exquisite community nestled in the heart of Naples, Florida, within the picturesque Collier County. This stunning development is designed for those who seek a harmonious blend of luxury, comfort, and the quintessential Florida lifestyle.

Winding Cypress features beautifully crafted homes that embody the essence of modern living, with an emphasis on outdoor enjoyment. Each residence boasts charming patio exteriors, inviting you to bask in the warm Florida sunshine or entertain guests under the stars. These outdoor spaces are perfect for hosting barbecues, enjoying morning coffee, or simply unwinding after a long day, creating an ideal setting for both relaxation and social gatherings.

The community itself is surrounded by lush landscapes and serene water features, providing a tranquil backdrop that enhances the overall appeal of Winding Cypress. Residents can indulge in a range of top-notch amenities, including a state-of-the-art clubhouse, sparkling swimming pools, and well-maintained walking trails that encourage an active lifestyle.

Located just minutes from Naples’ pristine beaches, upscale shopping, and gourmet dining, Winding Cypress offers the perfect balance of seclusion and accessibility. Whether you are a retiree seeking a peaceful retreat or a family looking for a vibrant community, Winding Cypress is the perfect place to call home. With its impeccable homes featuring delightful patio exteriors, this development invites you to experience the beauty and charm of Naples living at its finest. Come discover your dream home in Winding Cypress today!

Newest Winding Cypress Homes with Patio Exterior

7259 Live Oak Drive, Naples
$969,000
3 Beds ⋅ 3 Baths ⋅ 226040604 MLS
An opportunity to unlock value! Great opportunity for buyers looking to build equity through a little hard work and personal vision. This home offers solid potential for someone willing to invest time, effort and updates to make it their own. What has been done is new luxury vinyl flooring , painting , new kitchen backsplash and new sink, and new tile in primary bath shower. Bring your vision and creativity, Roll up your sleeves and transform this home to something special. The lanai is just the right size to take in the sunsets, or better yet plan to design your own pool/spa on this south west exposure lot with views of the lake. Winding Cypress is an amenity rich community to suit any lifestyle, resort style pool, restaurant and so much more. Just mins to 75 , downtown and Marco Island

7259 Live Oak Drive, Naples
6932 Cocoplum Street, Naples
$1,575,000
3 Beds ⋅ 3 Baths ⋅ 226033394 MLS
Exceptional southern exposure, breathtaking preserve and water views, and one of the most desirable homesites in Winding Cypress set the stage for this highly upgraded Pinnacle residence. Originally selected with a $125,000 lot premium, this exceptional property is tucked away on a quiet cul-de-sac street and offers a rare combination of privacy, natural beauty, and refined Naples living. Far beyond the standard Pinnacle floor plan, the home features soaring ceilings, expansive living spaces, abundant storage, and a sophisticated kitchen designed for entertaining with an oversized island, wine cooler, natural gas cooking, and impressive walk-in pantry. The private owner’s wing offers a spacious retreat with an oversized walk-in closet. A three-car, fully air-conditioned garage provides exceptional versatility, whether used for vehicles, additional storage, a workshop, or climate-controlled space for prized possessions. The outdoor living experience is equally impressive. Coveted southern exposure fills the lanai with beautiful natural light while providing comfortable year-round enjoyment. Relax in the saltwater pool and spa with sun shelf, entertain from the outdoor kitchen, or simply take in the peaceful preserve and water views. Impact-resistant windows and doors and a whole-home generator provide additional peace of mind. Winding Cypress offers more than 800 acres of natural preserves and an outstanding collection of resort-style amenities, including a 17,500-square-foot clubhouse, resort pool and spa, fitness center, Barefoot Bar & Grill, tennis, pickleball, bocce, dog park, community garden, boardwalk and more, all with lawn maintenance included and a staffed gated entrance. Ideally located near US-41 and I-75 with convenient access to Fifth Avenue South, Third Street South, Naples beaches, and Marco Island. This is elevated Winding Cypress living in a truly exceptional setting.

6932 Cocoplum Street, Naples
7775 Winding Cypress Drive, Naples
$990,000
4 Beds ⋅ 3 Baths ⋅ 226037594 MLS
Thank you for taking a look at the best value in sought after Winding Cypress! This pristine, 2-Story Summerwood Model, is loaded with options and is located on one of the nicest, private, and quiet lots in the entire community. This amazing home is perfectly situated on a lake's edge with a preserve backdrop. It's on a cul-de-sac with no thru traffic, and miles off of major roadways so it's incredibly quiet, private, with no road noise. If you are looking for a luxurious and functional space to entertain guests, or have them spend some overnights visiting, this is the property for you. Pride of original ownership is clear. With over 3200 square feet there's incredible room to entertain while also providing privacy for visitors. This home boasts 4 bedrooms, 3 full baths, and a large office or flex room that can be used as the new owner desires. The upstairs area is expansive with a huge gathering space that can be used as a theater room, craft area, media room, or office. The upstairs has it's own large bedroom and full bathroom. The 2nd floor also has it's own zoned climate control with a dedicated additional HVAC unit. The upgrades and amenities that this property offers are impressive. These features include: an upgraded kitchen package that adds optional cabinets, quartz counters & premium appliances, plank tile flooring, an incredible extended great room gathering space, built-in saltwater pool w/integral spa, a whole house generator, easy-use accordion shutters, hurricane rated electric shades enclosing the lanai, an outdoor summer kitchen, surround sound ceiling speakers, an upgraded, private owner's suite, built-in closet organizers, convenient interior plantation shutters, and a deep 2 car garage with epoxy flooring and a must have 2nd refrigerator. Winding Cypress is an amenity rich, natural gas community and a hidden gem of Naples. Meet friends and neighbors at the resident's only, full-service restaurant and bar that's conveniently located at the edge of the incredible resort pool. Play pickleball, tennis, or bocce on the premium lighted courts. Take advantage of the world-class fitness center. Enjoy the nature trail boardwalk, dog parks, and community garden. Participate in any of the huge selection of activities that the community and HOA offers. Speaking of the HOA, you will not find a better value for cost anywhere in Naples. It's not even close. The HOA General Manager, Assistant Manager, Activities Director, and Support Staff are all full-time and on site to better assist the residents. Winding Cypress is conveniently located just 10 minutes to the beaches and entertainment on Marco Island, 15 minutes to all that downtown Olde Naples has to offer, 10 minutes to I75, and just 35 minutes to RSW Airport.

7775 Winding Cypress Drive, Naples
7247 Clamshell Lane, Naples
$1,549,000
4 Beds ⋅ 4 Baths ⋅ 226035902 MLS
A MUST-SEE HOME IN A MUST SEE COMMUNITY Extensive upgrades and designer elements elevate this home, based on an award winning model. Gorgeous water/preserve views are seen both back and front. This quiet, lush green street is just a short walk to the recreation center where several activities, amenities and social events can be enjoyed. Winding Cypress has low HOA fees, numerous inclusions and is full of natural beauty. Motivated seller. All of which make this a must-see home and community. Inside, beautiful design blends elegance with functionality. The roomy open floor plan is ideal for easy mingling but has plenty of private spaces for everyday life. Enter a spacious foyer leading to the great room. Here, defined living and dining areas border a showpiece kitchen with a huge 10-foot island, gas cooking and a walk-in pantry, enhanced by several upgrades such as premium cabinetry and appliances, quartz countertops, generous crown molding and wainscoting, upgraded porcelain tile flooring, custom lighting and other designer finishes. Zero-corner doors enable fabulous indoor-outdoor entertaining, opening up the house to a beautiful lanai which has uncommon, high-impact, structural upgrades. It is oversized/extended to create a wide open feel and multiple spaces for relaxing and entertaining. The pool with spa and Baja shelf is also oversized for daytime full family fun and a dramatic lit atmosphere at night. The picture-frame screen enclosure is yet another upgrade for best showcasing the stunning views of water, preserve and large flocks of birds in winter. The ground floor primary suite offers a private retreat with a poolside bedroom, spa-like bathroom, coastal design enhancements and large walk-in closet. This floor also has two more bedrooms, each with a walk-in closet, and a den that can be used as a study, sitting room, TV room, or flex space. Upstairs is a large bedroom that comfortably sleeps up to 6 people; a full bath and a huge 34X21 loft that can be used as a quiet home office, fitness room, media room or play area for example. The floor plan has lots of storage and works well for a variety of lifestyles/needs like hosting large family gatherings, working from home, or multigenerational living. Other upgrades include full impact glass, an oversized, shelved, three vehicle garage with epoxy flooring. This home is situated on one of the most desirable, tranquil lots and is a one owner home. Winding Cypress has a guard-gate, all landscaping and a wow amenity center included in the low HOA, as are pickleball, tennis, bocce, fitness center, resort-style pool, on-site restaurant and bar, dog park, scenic walking trails and a full schedule of entertainment and social activities—providing a resort style country club lifestyle without country club fees. It is just minutes to Marco Island, downtown Naples, beaches, boating, golf, shopping, restaurants, hospitals, I-75.

7247 Clamshell Lane, Naples
7072 Live Oak Drive, Naples
$1,350,000
4 Beds ⋅ 4 Baths ⋅ 226031553 MLS
Welcome to this beautifully appointed 4-bedroom, 4-bath residence offering approximately 3,350 square feet and a custom, one-of-a-kind floor plan not found elsewhere in the community. Designed for effortless Florida living, the spacious interior features multiple living and dining areas, a private office, elegant architectural details and an impressive kitchen with white cabinetry, a large island and abundant workspace. A built-in wine bar adds the perfect touch for entertaining. Expansive sliders open to a screened lanai with an outdoor kitchen, private pool and spa, fire pit and peaceful water views. Additional highlights include generously sized bedrooms, well-appointed baths, a walk-in closet, separate laundry room and attached garage. Located in a sought-after natural gas community with beautiful surroundings and resort-style amenities, this exceptional home combines custom design, comfort and the indoor-outdoor lifestyle Southwest Florida is known for.

7072 Live Oak Drive, Naples
7230 Live Oak Drive, Naples
$1,100,000
3 Beds ⋅ 3 Baths ⋅ 226034017 MLS
Beautiful home on a premium pie shaped lot with lots of privacy. Seller keeps his landscaping impeccable. This home features 3 generous size bedrooms, 3 full bath , 3 car garage . with 2500 sq ft of indoor living space. Beautiful Custom oversized salt water heated pool with stairs , sunshelf, 3 waterfall features and an oversized hot tub all surrounded by beautiful landscaping. All impact resistance doors and windows, zero corner slider and a transfer switch with portable generator which handles lights, refrigerator and tv. Located close to the amenity center , dog park etc and all that Winding Cypress community offers, The Shady Palm restaurant, resort pool and spa, incredible gym and motion room for active fitness classes, library and an event room for social events. Winding Cypress can be as active as you wish to be or to just chill in your own backyard oasis, either way you will fall in love with the Winding Cypress community. A great location Just 15 mins to 75, 15 mins to marco and downtown.

7230 Live Oak Drive, Naples
6825 Greenbriar Court, Naples
$945,000
4 Beds ⋅ 3 Baths ⋅ 226034030 MLS
Preserve views on a quiet cul-de-sac street define this two-story Mystique residence in Winding Cypress, where a saltwater pool with spillover spa, expansive outdoor living and flexible interior spaces create a home designed for relaxation and entertaining. With four bedrooms, a den, an upstairs flex room, three baths and a two-car garage, the floor plan offers exceptional versatility while maintaining an open, connected feel throughout the main living areas. A whole-house generator is on-site, providing added peace of mind during storm-related power outages. A brick paver driveway, tile roof and professional landscaping establish a polished arrival. Inside, wood-look tile flooring, recessed lighting and white plantation shutters carry a clean, cohesive aesthetic throughout the home. The living room is filled with natural light from five windows and anchored by a modern ceiling fan, while the adjacent dining area draws additional light through its windows and sliding glass door, creating an easy transition between indoor and outdoor spaces. Open to the living and dining areas, the kitchen serves as the center of the main level with white shaker-style cabinetry, quartz countertops and a designer marble tile backsplash. A three-seat island provides a natural gathering place, complemented by stainless steel gas cooking appliances and a pantry. Positioned just off the kitchen, the primary suite offers a private retreat with a tray ceiling, walk-in closet and well-appointed en-suite bath. A dual-sink white vanity provides generous preparation space, while the floor-to-ceiling tiled walk-in shower features a built-in bench. A dedicated linen closet adds further storage. Additional guest bedrooms and baths provide comfortable accommodations, while a downstairs den with French doors creates a quiet setting for work or study. Upstairs, the carpeted flex room expands the home’s versatility and can readily serve as a media room, fitness space, office, playroom or secondary lounge. The upstairs bedroom and full bath create a private retreat that is especially well suited for extended family or out-of-town guests, offering added separation and privacy from the main living areas. Outdoors, a covered living area with paver flooring overlooks the screened saltwater pool and spillover spa, both framed by brick pavers. Beyond the pool enclosure, the home backs to a preserve and small creek, providing a natural backdrop and an added sense of privacy. Residents of Winding Cypress enjoy access to a private clubhouse with year-round gatherings, live music, holiday events and community activities. Ideally between downtown Naples and beaches of Marco Island, this residence combines preserve-side privacy, substantial indoor-outdoor living, flexible accommodations and the added security of a whole-house generator in one of Southwest Florida’s well-established communities.

6825 Greenbriar Court, Naples
7700 Winding Cypress Drive, Naples
$1,125,000
5 Beds ⋅ 3 Baths ⋅ 226032436 MLS
BEAUTIFUL AND METICULOUSLY MAINTAINED 5 BEDROOM, 3 BATH HOME IN DIVOSTA’S GATED WINDING CYPRESS COMMUNITY, ONE OF NAPLES MOST DESIRABLE LOCATIONS, CONVENIENT TO DOWNTOWN NAPLES, MARCO ISLAND’S PRISTINE BEACHES AS WELL AS NEARBY SHOPPING AND RESTAURANTS, THIS SUMMERWOOD FLOORPLAN FEATURES A MASTER ON MAIN LIVING FLOOR WITH LARGE BATH AND WALK-IN CLOSET, A LARGE LOFT SPACE UPSTAIRS WITH A SEPARATE BEDROOM AND FULL BATH, AND 3 OTHER BEDROOMS AND BATH ON THE MAIN LIVING LEVEL. NUMEROUS UPGRADES INCLUDE OVERSIZED POOL AND SPA, EXTENDED LANAI AND GARAGE, ZERO CORNER SLIDING DOORS LEADING TO LANAI, FRAMED DROP SOFFIT IN MASTER, FLOOR OUTLET, DECORATIVE GLASS FRONT DOOR, OVERSIZED KITCHEN ISLAND, OUTDOOR KITCHEN WITH BUILT-IN GRILL AND COOLER, TANKLESS WATER HEATER, AND CUSTOM CABINETRY AND TILE. WINDING CYPRESS FEATURES A GATED ENTRANCE WITH GUARD, DOG PARK, COMMUNITY GARDEN, TENNIS, PICKLEBALL, BEAUTIFUL CLUBHOUSE WITH BAR AND GRILL, LARGE RESORT POOL AND DECKS…TRULY A GEM IN SOUTH NAPLES! AND NO FLOOD INSURANCE REQUIRED!!

7700 Winding Cypress Drive, Naples
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