Winding Cypress Property - Search Winding Cypress Properties

Welcome to Winding Cypress | Naples Florida

From the moment you arrive at the stunning entry, Winding Cypress invites you in. Remaining almost 2/3 natural preserve, this natural gas, resort-style community welcomes you with a streetscape of superb views and homes designed for the way you live. This premier Naples location offers highly attractive fees for the variety of world-class amenities right in your own backyard, including a grand clubhouse, resort pool, sports courts, dog park, community garden, and more. Resort-style living and a welcoming community await you at Winding Cypress. Relax by the resort pool and spa, play a pick-up game at the sports courts, or pick fresh produce from the community garden. Headed into town?

Enjoy easy access to upscale shopping and dining in Downtown Naples, or when plans call for escaping to the sugar-white sand beaches, breeze over to Marco Island just minutes away.

Newly Listed Properties in Winding Cypress

$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, 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 gracious open floor plan is ideal for easy mingling but has plenty of private spaces for everyday life. Enter the spacious foyer to a great room. Defined living and dining areas border a showpiece kitchen with a huge 10-foot island, gas cooking, and a spacious walk-in pantry, enhanced by several upgrades such as premium cabinetry, quartz countertops, upgraded appliances, generous crown molding and wainscoting upgraded porcelain tile flooring, custom lighting, and other designer finishes. Zero-corner doors (another upgrade) enable fabulous indoor-outdoor entertaining and open to the stunning lanai which also boasts several upgrades. The lanai is extended/oversized for a spacious open feel and multiple spaces for relaxing and entertaining. The pool with spa and Baja shelf is oversized for full family fun during the day and a dramatic lit atmosphere at night. The premium picture-frame screen enclosure is yet another upgrade that showcases the stunning views overlooking water, preserve - and occasionally, wildlife. The primary suite offers a private retreat with a poolside bedroom, spa-like bathroom, coastal design enhancements and large walk-in closet. On the other side of the house are two 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 huge bedroom that comfortably sleeps up to 6 people; a full bath, and a huge loft area 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 and needs, including hosting large family gatherings, working from home, or multigenerational living. Other upgrades include full impact glass, an oversized, fully shelved three-car garage with epoxy flooring. This home is situated on one of the most desirable, tranquil, lots in the community and is a single owner home. Winding Cypress has guard-gated security, landscaping and a wow amenity center included in the HOA, as are pickleball, tennis, bocce, a state-of-the-art fitness center, a resort-style pool, an on-site restaurant and bar, a dog park, scenic walking trails and a full calendar of entertainment and social activities—providing a resort style country club lifestyle without country club fees. Just minutes from Marco Island, downtown Naples, beaches, boating, golf, shopping, restaurants, hospitals, I-75.

7247 Clamshell LN, Naples

$579,000

2 Beds ⋅ 2 Baths ⋅ 226035971 MLS

**Motivated sellers!! This freshly painted, light-filled attached villa in Winding Cypress features two bedrooms plus a den with easy conversion to a third bedroom, two full bathrooms, and a two-car garage. An open floor plan, bright kitchen with stainless-steel Whirlpool appliances, granite counters and an in-residence laundry room with a newer washer and dryer make everyday living comfortable. A newly screened lanai overlooks a very private backyard, creating a relaxing setting.Winding Cypress offers an exceptional collection of resort amenities, including a resort-style pool and spa, poolside restaurant, attended fitness center, yoga lawn, outdoor fireplace, five tennis courts, eight pickleball courts, and four bocce courts. Explore the nature boardwalk and walking paths, community garden,visit the covered dog park, or enjoy an active calendar of social events. This home has 100% hurricane coverage. Conveniently located between downtown Naples and Marco Island, this home provides easy access to white-sand beaches, Fifth Avenue shopping and dining, and I-75. Make the Southwest Florida lifestyle your own. Furnishings negotiable!

7602 Jacaranda LN, Naples

$1,450,000

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 DR, Naples

$1,195,000

3 Beds ⋅ 3 Baths ⋅ 226034017 MLS

Beautiful home inside and out Pinnacle style home in Winding Cypress. This home features 3 generous size bedrooms, 3 full bath , 2 car plus golf cart garage . Custom oversized salt water heated pool with stairs , sunshelf, 3 waterfall features and oversized hot tub all surrounded by beautiful landscaping on an oversized lot with plenty of privacy. 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 classes, library , event room . Winding Cypress can be as active as you wish to be or to chill , either way you will fall in love with this community

7230 Live Oak DR, Naples

$965,000

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 CT, Naples

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The data relating to real estate for sale on this web site comes in part from the Broker Reciprocity Program (BR Program) of M.L.S. of Naples, Inc. Properties listed with brokerage firms other than this company are marked with the BR Program Icon or the BR House Icon and detailed information about them includes the name of the listing brokers. The properties displayed may not be all the properties available through the BR Program. The information provided is for consumers’ personal, non-commercial use and may not be used for any other purpose.