Winding Cypress Real Estate

Winding Cypress Real Estate

Welcome to Winding Cypress, a breathtaking community nestled in the heart of Naples, Florida, within the picturesque Collier County. This stunning development redefines the concept of luxury living, offering an idyllic blend of natural beauty and modern conveniences.

Winding Cypress is thoughtfully designed to embrace the lush landscapes and serene surroundings that Naples is renowned for. With an array of meticulously crafted single-family homes, each residence showcases contemporary architecture paired with timeless elegance. The community features spacious floor plans, high-end finishes, and expansive outdoor living spaces that invite you to enjoy the Florida sunshine year-round.

Nature enthusiasts will find Winding Cypress particularly appealing, as it is surrounded by stunning preserves and tranquil lakes, providing a perfect backdrop for outdoor activities. Residents can indulge in a variety of amenities, including a resort-style pool, a state-of-the-art fitness center, and walking trails that wind through the lush greenery. The community clubhouse serves as a social hub, where neighbors can gather for events, activities, and shared experiences.

Located just minutes from the vibrant downtown Naples, Winding Cypress offers easy access to world-class dining, shopping, and pristine beaches. Whether you’re exploring the local art scene or enjoying a sunset stroll along the Gulf Coast, the lifestyle here is nothing short of exceptional.

Discover the charm of Winding Cypress, where luxury meets nature, and make this beautiful community your new home in Naples, Florida. Embrace the lifestyle you’ve always dreamed of in a place that truly feels like paradise.

Newest Listings in Winding Cypress

7383 Mockingbird Court, Naples
$1,550,000
4 Beds ⋅ 4 Baths ⋅ 226038449 MLS
Situated on a private .29 acre, end lot in the highly sought-after gated community of Winding Cypress, this home offers 3,696 square feet of refined Naples living space. Built in 2016, this two-story Pinnacle floor plan features 4 bedrooms, 4 full bathrooms, a versatile den and a spacious 3 car garage. The extended lanai with a premium long lake water view features a custom-built saltwater pool and spa combo plus a fully equipped built-in outdoor gas kitchen, a wonderful place to entertain family and friends. Step inside to discover wood-look tile flooring leading to a gourmet chef’s kitchen, stainless-steel appliances, natural gas cook top, a walk-in pantry and an expansive center island with seating for five or more. The main floor hosts a sizable primary suite with a generous custom walk-in closet and a luxurious primary bath. Upstairs, a massive loft area offers an expansive living and sitting area space accompanied by a private guest bedroom and a full bath, ensuring ideal privacy for visitors or multi-generational living. Winding Cypress residents enjoy an active social calendar and lifestyle including a resort -style pool, a poolside bar and grill, state-of-the-art fitness center, tennis, pickleball, bocce ball and miles of boardwalk trails traversing acres of natural preserves. Winding Cypress is located just minutes from downtown Naples restaurants, pristine beaches and world class golf.

7383 Mockingbird Court, 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
7591 Jacaranda Lane, Naples
$539,000
2 Beds ⋅ 2 Baths ⋅ 226038979 MLS
Western sunset views, peaceful pond vistas, and added privacy, this Winding Cypress villa offers a setting that’s truly special! Beautifully upgraded, this unfurnished 2 Bedroom + Den residence enjoys desirable western exposure overlooking a picturesque pond, complemented by private green space adjacent to the property, creating a serene and tranquil retreat. Inside, an inviting open floor plan showcases builder-installed upgrades, elegant porcelain tile, granite countertops, and a stylish kitchen featuring stainless steel appliances and decorative backsplash. The spacious den offers flexibility as a third bedroom or home office. Additional highlights include California Closets throughout, plantation shutters, and a two-car garage. Enjoy the best of resort-style living with an on-site restaurant and bar, pools, fitness center, pickleball, tennis, bocce, and scenic nature trails with bird-watching overlooks. Ideally located between downtown Naples and Marco Island, this exceptional villa combines privacy and beautiful surroundings. Come for the views and stay for the lifestyle. Fall in love with everything Winding Cypress has to offer! Seller is a licensed FL Realtor.

7591 Jacaranda Lane, 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
7098 Live Oak Drive, Naples
$520,000
3 Beds ⋅ 2 Baths ⋅ 226038340 MLS
Enjoy the ease of Florida living in this beautifully maintained, Serenity floor plan single family villa, ideally situated on a corner lot in the gated, amenity-rich community of Winding Cypress. Being offered turnkey furnished, this thoughtfully designed residence has three bedrooms, two baths, and an inviting open-concept design, while combining comfortable living with effortless indoor-outdoor enjoyment. Tile flooring throughout, granite countertops, tile backsplash, and stainless-steel appliances create a timeless, welcoming kitchen. New AC in 2021. Plantation shutters throughout and a freshly painted interior add to the appeal, while the extended screened lanai provides a relaxing outdoor retreat overlooking a peaceful, landscaped view. A newly added privacy hedge (2025) enhances the setting, creating an ideal space to enjoy morning coffee or unwind at the end of the day. Impact-resistant doors and windows, hurricane fabric screens for the lanai, and an attached two-car garage offer added convenience and peace of mind. Winding Cypress, a natural gas community carefully designed around preserved natural beauty, is known for its active, social lifestyle and impressive amenities. Residents enjoy a welcoming clubhouse, heated resort-style pool and spa, poolside dining at the Shady Palm, fitness center, library, and community gathering rooms. Pickleball, tennis, and bocce courts offer opportunities to stay active, while two dog parks, a community garden, and scenic walking and nature trails invite residents to enjoy the outdoors. Whether seeking a seasonal retreat or a year-round residence, this residence offers an appealing combination of comfort, convenience, and the vibrant Winding Cypress lifestyle, conveniently close to everything Naples has to offer.

7098 Live Oak Drive, Naples
7235 Live Oak Drive, Naples
$925,000
3 Beds ⋅ 3 Baths ⋅ 226036844 MLS
This home has had a complete refresh with a lot of new improvements, new heat/ac units on both floors new pool pump and heater, new roof vents, new lanai screen, pavers on front and side with a refresh landscaping with sitting area, new epoxy garage flooring in extended garage to add a golf cart or storage, interior freshly painted, . this home is a martin ray style 2 story home features 2 split bedrooms on the first floor 2 full baths and office/ den , expanded kitchen with extended coffee /wine station and full pantry and new refridgerator. 2nd floor features a great room , private bedroom and full bath, great for guests or a needed private suite , The pool has a beautiful expanded private view of the lake and the preserve This home is a must see and is in move in condition

7235 Live Oak 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
7602 Jacaranda Lane, Naples
$548,000
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 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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