Winding Cypress Naples Florida - 26 Homes For Sale

Indulge in breathtaking lake and sunset views from this exquisite Stonewater model home, ideally on a premium lot in the prestigious guard-gated low HOA fee community of Winding Cypress. From the moment you step inside, the meticulous attention to detail and timeless elegance will captivate you. This sophisticated residence features three bedrooms plus a den, three full baths and a spacious three-car garage, blending luxury and functionality seamlessly. The chef-inspired open kitchen is the heart of the home, showcasing KitchenAid appliances, quartz countertops, white cabinetry, a walk-in pantry, and natural gas cooktop, designed for everyday comfort and entertaining. Step out onto the expansive covered lanai, equipped with an upgraded natural gas summer kitchen, ideal for hosting gatherings. The extended screened enclosure boasts a large heated saltwater pool with three spillover waterfall features, creating an entertainer’s dream space with ample room for dining, lounging and relaxation. Inside, the open-concept great room design offers an effortless flow between indoor and outdoor living spaces, making it ideal for family gatherings and celebrations. The luxurious spacious primary suite features a custom-designed walk-in closet system, dual sinks and an oversized walk-in shower, embodying comfort and sophistication. Other exceptional highlights of the home include volume coffered ceilings, upgraded tile plank-style flooring, custom light fixtures and ceiling fans, a striking impact-resistant custom front door, landscape lighting, a whole home water filtration and softener system, and rolldown storm shades on the outdoor covered lanai for peace of mind and effortless living to name a few. Winding Cypress is renowned for its impressive amenities, offering an active and vibrant lifestyle. Enjoy the resort-style pool, on-site restaurant Shady Palm, tennis, bocce and pickleball, along with additional features like a dog park, state-of-the-art fitness center, internet café and over 800 acres of lush natural preserves to explore. Conveniently just minutes from world-class dining, shopping, pristine beaches, boating and spectacular sunsets, this home delivers the ultimate Florida lifestyle. Don’t miss the opportunity to make this piece of paradise your own!

Massive $200K price reduction!! STUNNING lake and sunset views await from the lanai of this Pinnacle model home situated on an oversized lot in Winding Cypress. At just over 2,500 square feet, you will notice the attention to detail from the moment you walk in the front door. Features of this gorgeous home include: 3 bedrooms and 3 full baths, 3 car garage, faux paint accents on walls & ceilings, custom light fixtures and ceiling fans, zero corner slider, impact resistant doors and windows, KitchenAid appliances, Quartz countertops, natural gas (cooktop, grill and pool equipment), dry bar with wine fridge, high-end carpeting in the bedrooms, plantation shutters throughout and SO MUCH MORE! This home is perfect for entertaining! The large, open kitchen & living room is ideal for family gatherings. Open the sliders to seamlessly bring the indoor living space, outdoors. The summer kitchen and large dining area is perfect after a day of relaxing by the pool & spa. The primary suite features a massive walk-in closet that will fit the needs of those with the largest of wardrobes. There are plenty of amenities in Winding Cypress for those looking to stay active outside of the residence, featuring a resort-style pool, on-site restaurant (Shady Palm), tennis, bocce, and the hottest new sport - pickleball. Additional amenities include a dog park, well-appointed fitness center, and internet cafe. All of this is just a short drive to some of the finest dining, shopping, beaches, boating and sunsets in all of Florida - Downtown Naples/5th Ave and Marco Island. Close to I-75 and 30 minutes to Southwest Florida International Airport. Come live in paradise!

Nestled within an exclusive gated community and surrounded by a serene nature preserve, this elegant 3-bedroom, 3-bathroom home with a spacious den/office is the epitome of refined Florida living. The open, airy floor plan flows seamlessly, with high ceilings and large windows that capture abundant natural light and offer unobstructed views of the lush preserve behind the home. This home has natural gas, generator, Sentricon system, central vac system, and many more upgrades. Step into the gourmet kitchen, complete with premium appliances, custom cabinetry, and an expansive island that's perfect for entertaining or family gatherings. Each bedroom is generously sized, featuring high-end finishes and ample storage, while the den/office provides an ideal, private space for working from home or additional relaxation. The master suite is a tranquil retreat with a luxurious en-suite bathroom featuring dual vanities, and a walk-in shower. Outdoors, your private paradise awaits, with a sparkling gas heated salt water pool and spa surrounded by a spacious patio, perfect for sunbathing, al fresco dining, or evening cocktails under the stars. The 3-car garage offers plenty of room for vehicles, storage, and hobbies. Living in this community comes with exceptional amenities that rival a luxury resort. Enjoy an on-site restaurant, a spectacular resort-style pool, tennis courts, pickleball, bocce, and a dog park, all thoughtfully designed to elevate your lifestyle. The well-appointed fitness center, internet café, and an engaging calendar of year-round social events ensure that there's always something to do. Centrally located between the pristine beaches of Marco Island and Naples, this home places you just moments away from world-class shopping, dining, and entertainment, yet offers a peaceful, nature-filled escape in your own backyard. Don't miss the opportunity to make this luxurious haven yours!

This popular DiVosta Pinnacle Model is situated in the amenity rich community of Winding Cypress. It is possible to purchase this beauty either furnished or turnkey furnished as negotiated and agreed upon. This property is a one owner home that's loaded with builder and owner upgrades to include: custom tile plank flooring throughout, 12'+ coffered/tray ceilings with crown molding and custom detail wall, saltwater pool w/integral spa, whole house generator, hurricane impact windows, zero corner slider with impact glass, Storm Smart Kevlar screen across lanai, leaded glass front door, upgraded kitchen appliance package, upgraded kitchen & bath cabinet package, plantation shutters throughout, home security system, extended 3 car garage w/epoxy floor, additional refrigerator/freezer & built in cabinets, custom closet and pantry storage systems, upgraded laundry room w/built in cabinets and utility sink, den complete with built in desk & storage system, upgraded electrical include custom fixtures, ceiling fans and dimmer switches. The exterior has beautiful Bohemian shutters along with a paver walkaround. This gorgeous home sits on an oversized private lot at the end of a dead-end cul-de-sac. Winding Cypress boasts one of the most outstanding set of community amenities anywhere in Naples and at an incredible value. They include a private, residents only restaurant, spectacular resort pool, spa & beach cabana, expansive clubhouse w/an amazing fitness center w/men's/women's locker rooms, conference & meeting rooms, library, community kitchen, pickleball, tennis, & bocce courts, dog park, nature boardwalk, and a community garden. Winding Cypress is perfectly located 10 minutes from Marco Island & 15 minutes from downtown Olde Naples.

Welcome to the rare opportunity to own the prestigious Stonewater model home in the desirable, amenity filled community of Winding Cypress. This property sits on one of the most beautiful and private waterfront lots. View spectacular sunsets over a big water lake with a wildlife-rich preserve as a private backdrop. As soon as you walk through the double-door front entrance, your breath will be taken away as you marvel at the grandeur of the open living space highlighted by a 12 foot ceiling accented with built-in trays. The split bedrooms and open living area floorplan is most popular and sought after as it is perfect for large gatherings and entertaining with family and friends while offering a quiet and separate space for guests during the overnights. The primary suite is expansive, big enough for king bed furniture and additional sitting area. The bath area boasts a beautiful walk-in tiled shower, large dual sink vanity, and oversized walk-in closet. The entrance to the two other bedrooms and baths can be closed off from the main living area by pocket doors giving a private feel of additional suites. The chef's kitchen boasts a beautiful quartz center island with sink, upgraded appliances that include a natural gas cook top, double built-in oven, custom cabinets with underside lighting and a huge walk-in pantry. There's also a formal dining area adjacent to kitchen and great room gathering space. Open up the French doors and enjoy the quaintness of your added den, study or office. This is an extra large space perfect to be set up with your personal wants and needs in mind. Nothing helps out a homeowner more than a three car garage. This one has a ton of built-in ceiling and wall storage racks for everything imaginable including bicycles. The garage doors are insulated as well as the attic above. As you step outside onto the custom upgraded pavers and look out over the big water lake, you can't help but admire the beautiful salt water pool with optional integral infinity spa. On the far side of the lake is a stunning and private preserve that speaks to tranquility, relaxation, and peacefulness as you sit in your lanai, swim in your pool, or unwind in your spa. Winding Cypress is a well designed community of over 1200 acres total with 850 acres of green space. It is amenity rich to include a resident's only full-scale restaurant, pickleball, tennis, & bocce courts, a spectacular community pool and clubhouse, awesome fitness center, dog park, community garden, boardwalk nature trail, and a full-time activities program that offers something for everyone on a weekly, regular basis.Located just 15 minutes to the beaches of Marco Island and 20 minutes to restaurants and shoppes in Olde Naples.

Wow! This beautifully designed and meticulously maintained home is absolutely spectacular. Featuring the highly desirable Summerwood floor plan with Great Room extension, it is perfect for entertaining or simply relaxing at home after a nice day out in beautiful Naples, FL. The kitchen features upgraded appliances, quartz countertops, an oversized island and walk-in pantry. The two guest bedrooms provide ample room for guests. The office/den can easily serve as a 4th bedroom if desired. Other interior features include high-grade porcelain tile throughout, a laundry/utility room with plenty of storage and natural gas for cooking, heated water and clothes drying. Exterior upgrades abound with a one-of-a-kind extended lanai with custom pavers and a built-in outdoor kitchen. There is plenty of space for outdoor gatherings, cookouts, an afternoon nap, a dip in the pool or just taking in some Florida sunshine. Looking through the huge portrait "no-see" lanai screen is one of the very best long water views in the entire community. The view is simply gorgeous, inspiring "wows" from all. Construction is top-notch with hurricane impact doors and windows throughout and there is a whole home gas generator too should the need arise. The driveway and side walkway are extended. There is over $100k in upgrades to this magnificent home. It is offered fully furnished. Just pack your bags and head on down to enjoy our very special slice of tropical paradise. To top it all off, this sensational home resides in the highly prized community of Winding Cypress. An onsite restaurant, modern fitness center, community pool and a full calendar of social gatherings with some of the best Naples residents around are a nice walk, bike or golf cart ride away. Also, located conveniently between downtown Naples and Marco Island, opportunities to visit some of our finest beaches, shopping and dining locations are just minutes away. Great home. (Check.) Great view. (Check.) Great community. (Check.) Great location. (Check.) This property checks all the right boxes for the time of your life in beautiful Naples, FL.

The most private homesite in Winding Cypress Resort community, this exceptional home offers views abundant with trees and lake, bordered by a lush preserve and expansive buffer zones. Breathtaking southwestern water views provide the ideal backdrop, rivaling the most stunning beach sunsets. Step outside to the largest covered lanai in the community, complete with a sparkling pool and spa, creating an idyllic space for relaxation and entertaining. Step inside to discover a home that has been expanded and meticulously designed, with raised ceilings and professionally finished interiors that exude sophistication. This home is equipped with premium features, including impact-resistant glass, natural gas and top-tier finishes throughout. The expansive layout offers views from every angle, ensuring that every room feels connected to the beautiful outdoor surroundings. Residents can indulge in the luxurious Winding Cypress Club, which features a state-of-the-art fitness center, catering kitchen, community room and activity room. Outdoor amenities abound, including pickleball, a resort-style pool with a lap section, spa, outdoor movement studio, barefoot bar, bocce ball courts, five Har-Tru tennis courts, a fire pit, a bird-watching overlook and a nature boardwalk with a picnic pavilion. At the center point between the pristine shores of Marco Island and the vibrant downtown Naples, this incredible resort location provides the ideal backdrop for an unparalleled lifestyle.

Welcome to a beautiful Pinnacle Model in the desirable, amenity rich community of Winding Cypress. This waterfront home is offered at an incredible value. Original owner care is apparent throughout. Builder and owner upgrades include; chef's kitchen with upgraded appliances, sink & faucet, soft close pull out cabinets including under-side lighting, custom quartz countertops, custom plank tile flooring, hurricane impact windows, slider, and entry door, upgraded & expansive lanai outdoor living area with Storm Smart Kevlar screen enclosure & ready for you to design your own outdoor kitchen, upgraded bathrooms with custom showers, faucets & fixtures, custom lighting & window treatments, 3 car garage with epoxy floor with additional refrigerator included. Winding Cypress is a guard gated natural gas community full of popular amenities including; a resident's only restaurant, amazing resort pool & spa, pickleball, tennis, & bocce courts, incredible fitness center loaded with all the training features including men' and women's locker rooms, a beautiful community center with conference rooms, a prep kitchen, library, lounge with fireplace, a dog park, nature trail boardwalk, and a community garden. The community is perfectly located just 10 minutes to the beaches and entertainment of Marco Island, and 15 minutes to the shoppes and restaurants of the renowned 5th Avenue in downtown Olde Naples. This home is perfect to start enjoying the lifestyle living of Winding Cypress!

Welcome to this stunning Summerwood floor plan with an extended great room. As you enter this 3 bedroom plus den home the quality of finishes is evident. The great room open plan concept allows for a great entertainment area with a large island kitchen and beautiful quartz countertops open to the dining and living area. Step out onto the large paver lanai area and enjoy the exceptional location of this lot looking across the lake to a preserve area with landscaping providing excellent privacy from adjoining homes. Relax in the heated pool or lounge on the spacious pool deck. This home offers Florida living at its best with a custom outdoor kitchen featuring a gas grill, fridge, vent hood and sink. The community offers natural gas for cooking, water heater and clothes dryer. The lanai is protected by electric rolling hurricane impact screens making preparation for storms easy. The community of Winding Cypress is nestled amongst 800 acres of natural preserve and 80 acres of serene lakes. This community offers residents a tranquil lifestyle surrounded by nature. Residents enjoy a wide array of amenities, including the Shady Palm Café, a spacious Clubhouse, and a luxurious resort-style pool and spa, fitness center, social program, movement room, pickle ball, tennis courts, bocce and the boardwalk walking trail. Surrounded by many restaurants and grocery stores and only a short drive to Downtown Naples this community checks all the boxes.

Welcome to this stunning Summerwood model in the desirable gated community of Winding Cypress. This 3 Bedroom + Den, 2 Bath home is loaded with upgrades and is sited on an oversized premier lot with stunningly gorgeous lake views. Enter home into a dramatic entry hallway which truly captures the incredible lake vistas. Light and bright open-concept living space with soaring 11.5 foot ceilings. Spacious living room with custom coffered ceiling, custom millwork accent wall and transom windows. Wall of sliding glass opens out to tranquil lanai blending indoor/outdoor living. Custom outdoor granite bar with seating for 7 and built-in KitchenAid grill plus lounge area is ideal for outdoor entertaining. A true chef's eat-in kitchen features stainless steel appliances, shaker cabinetry, contemporary quartz counters, oversized island and pantry. Lovely dining room with custom millwork accent wall with gorgeous lake vistas. Contemporary glass doors open to a den ideal for home office, media room or additional guest quarters. Master suite oasis boasting a spacious bedroom overlooking the lake opens to a spa-like en-suite bath including oversized walk-in shower, double vanity and separate water closet. 2 additional guest bedrooms with a shared full bath. Full-size laundry room with a side-by-side washer/dryer, custom counter and cabinetry is great for storage. Oversized 2-car attached garage Enjoy state of the art amenities including resort-style pool and spa, Shady Palm restaurant, Har-Tru tennis courts, pickleball courts, bocce, fitness center, club room and even a dog park. Convenient to downtown Naples renowned for its world class dining, shopping and beaches and also close to Marco Island. East access to I-75 and only 30 minutes to RSW airport. Truly exceptional paradise living!

Luxury living in this extraordinary Naples FL home and coveted community of Winding Cypress! Built in 2015 by Divosta homes this 3 bed, 3 bath, plus a den with a second story loft known as the Martin Ray flood plan. This home with over 2,600 sq feet under air, it's the perfect layout. Walk into a beautiful foyer entrance, that leads to the custom open layout kitchen, featuring premium granite countertops, Kenicto water system, custom cabinets, gas stove, and a butler pantry with beverage refrigerator and custom wine rack. The spacious living area with crown and base moldings, leads to the screened in lanai and custom 13X28 pool with 3 sunning shelf's. An east exposure for lots morning sun and with a lake and preserve view to enjoy. The screened in outdoor lanai area encompasses over 1,000 sq feet. The lush landscaping and pool is a tropical oasis to entertain and enjoy. Custom electric roll down hurricane shutters for maximum storm protection. Primary bedroom located on the 1st floor with beautiful tray ceiling and a view of the tropical back yard with a huge walk in closest with custom drawers and shelving.Primary bath has dual sinks and walk in shower. This split bedroom floor plan has so much privacy for guests with an upstairs loft that leads to the 3rd bedroom and en-suite bath. This home has 2 air conditioners with dual zone A/C system, plantation shutters through the home for the tropical feel, solid core doors with upgraded handles. Winding Cypress is a lifestyle community offering an array of amenities, including a resort-style pool and spa, pickleball and tennis courts, a residents-only restaurant, an expansive community center with an event room, library, outdoor fireplace, state-of-the-art fitness facilities, and a boardwalk nature trail for serene strolls. Sitting on 800 acres of preserved green space, this prime location is just 15 minutes from downtown Olde Naples and 10 minutes from Marco Island, offering the perfect blend of convenience and tranquility.

The Martin Ray floor plan is a breathtaking home located in the serene Winding Cypress community, overlooking a picturesque lake. This exquisite 2021 residence showcases the meticulous care of its single owner and boasts numerous upgrades throughout. It features a heated pool, three bedrooms, two bathrooms, and a den, providing ample space for living and entertaining. The heart of the home is a spacious, light-filled living area and a large kitchen with a generous island for seating. Culinary enthusiasts will appreciate the five-burner natural gas stove and the convenience of a butler's pantry. The exquisite quartz countertops complete the perfect setting for entertaining and everyday living. The home is adorned with impact windows and sliders, allowing natural light to flood in, and is accented with 8-foot doors and custom crown molding in the primary bedroom. The large primary bathroom features a walk-in shower, dual sinks, a dedicated toilet room, and access to the large walk-in closet with built in shelves, and enough room for a small crafts station. Additional highlights include two spacious guest bedrooms, elegant tile flooring throughout, and a two-car garage with a durable epoxy finish. Relax in your well-placed den with views of the natural preserve across the street or convert the space into a spacious home office. Outdoors, you can unwind in your private pool and enjoy the exquisite under-truss patio area. The electric roll-down screens and remote-controlled awning provide a perfect spot to relax poolside, savor the shade, and take in the tranquil lake views. The paver driveway has been widened and extended, while the pool deck pavers have recently been power washed and sealed for added appeal. The pie shaped lot is an added bonus giving you a large front yard and plenty of room between you and your neighbors. The conveniently situated lot location is not far from the resident's entrance, providing easy access in and out of the community. Winding Cypress is conveniently located near shopping and dining options and is enveloped by 800 acres of natural preserve and 80 acres of stunning lakes. Winding Cypress enhances the community experience with a wonderful dog park making it an ideal place for pet lovers This dedicated space allows residents and their furry friends to enjoy the outdoors socialize and stay active. Residents can avail themselves of various amenities, including the Shady Palm Café, a resort-style pool and spa, a fitness center, social programs, and sports facilities such as pickleball, tennis courts, and bocce ball. There is also a walking trail for those who love to explore nature. This home exemplifies the essence of Southwest Florida living at its finest. Schedule a showing today. BE SURE TO CLICK THE FULL VIRTUAL TOUR LINKS FOR DETAILS!