Winding Cypress Naples Real Estate - 37 Homes For Sale

The Crown Jewel of Winding Cypress! This RARELY available Stonewater floor plan with a TRUE 3-CAR GARAGE is a standout, offering an exceptional blend of luxury, privacy, and breathtaking views. A custom pool with picture-screen enclosure takes full advantage of the highly desirable SOUTHEASTERN EXPOSURE, showcasing fabulous long lake views. Designed for seamless indoor-outdoor living, this home features a stunning custom outdoor kitchen and a convenient half-pool bath upgrade. Inside, every detail has been thoughtfully enhanced with designer upgrades, including 18” x 36” tile throughout and a custom wall unit with a heat-generating fireplace. The split floor plan maximizes privacy, with all three bedrooms in separate areas of the home. Guest areas can be closed off with pocket doors, creating a private suite-like feel with access to their own bathroom. For peace of mind, this home features a whole-house generator, IMPACT GLASS throughout, and push-button hurricane shutters make storm protection effortless for the lanai. Located in Winding Cypress, a natural gas, low-fee, resort-style community, this home sits on an oversized, private lot on a cul-de-sac street. Perfectly situated between Marco Island and downtown Naples, residents enjoy easy access to world-class dining, shopping, and beaches—all within a golf-cart-friendly community. World-class amenities include a heated resort-style pool with a unique walk-in entrance—allowing effortless access—plus lap lanes, a hot tub, poolside cabanas, and a gas fire pit area. The Shady Palm Café, a covered outdoor restaurant, bar, and grill, provides the perfect place to unwind—whether dining al fresco or gathering for a drink. The expansive clubhouse features a large fitness center, movement studio, library, card room, and event room—all managed by an on-site Activities Director and full time property management. Outdoor enthusiasts will love exploring this 1,100-acre community, where over 800 acres of preserve are woven with miles of scenic sidewalks and a picturesque boardwalk leading to a bird-wading overlook. Enjoy a game of pickleball, bocce, or tennis. Additional amenities include separate dog parks for small and large dogs and a members-only community garden for those who enjoy growing their own vegetables. Don’t miss this rare opportunity to own a home that blends luxury, privacy, and resort-style living—schedule your private tour today!

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!

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!

Discover one of the largest and most recently built homes in the highly sought-after Winding Cypress community! This stunning residence boasts a serene preserve view that enhances the peaceful, natural surroundings. Blending luxury and functionality, the home offers 4 bedrooms, a den/office, 4 full baths, and a spacious 2-car garage, with every detail thoughtfully curated to elevate your Florida lifestyle. The heart of the home is the chef-inspired open kitchen, featuring premium KitchenAid appliances, quartz countertops, custom cabinetry, a walk-in pantry, and a natural gas cooktop—perfect for everyday living and entertaining. The expansive living and dining spaces flow seamlessly, with floor-to-ceiling glass sliders opening to an impressive covered lanai. Outside, the large dining area is ideal for hosting guests, while the heated saltwater spa/pool with spillover waterfalls creates a serene retreat. The extended lanai offers plenty of room for lounging and relaxation in the Florida sunshine. Inside, the home's design impresses with high ceilings, custom light fixtures, ceiling fans, and upgraded tile plank-style flooring. The spacious primary suite features a custom walk-in closet, dual sinks, and an oversized walk-in shower. Additional highlights include volume coffered ceilings, plantation shutters, epoxy flooring in the garage, and a built-in surround sound system. Winding Cypress offers exceptional resort-style amenities, including a pool, on-site restaurant Shady Palm, tennis, bocce, pickleball, a state-of-the-art fitness center, a dog park, an internet café, and over 800 acres of lush natural preserves to explore. Whether you’re seeking relaxation or an active lifestyle, there’s something for everyone. Conveniently located near world-class dining, shopping, beaches, and boating, this home is just minutes from the best of Naples and Marco Island. Don’t miss the opportunity to make this luxurious haven your own and experience the ultimate Florida lifestyle in the heart of paradise.

Welcome to this exceptional Infinity Model home, a rare find in the prestigious Winding Cypress community of Naples, Florida. Built by the esteemed DiVosta Builders, this home is one of only three Infinity Models in a community of over 750 residences, making it a truly exclusive opportunity. Designed with elegance and comfort in mind, this property blends high-end finishes, thoughtful upgrades, and a sprawling open-concept layout that’s perfect for both entertaining and everyday living. Upon entering, you’ll be greeted by soaring tray ceilings over 11 feet high, beautifully complemented by custom faux painting and crown molding. The home’s expansive great room flows seamlessly into the gourmet kitchen, featuring a 6-burner Thermador gas cooktop and range, a premium Liebherr refrigerator, and an oversized quartzite leather-finish island. Custom-built cabinetry and designer window treatments—all tailor-made—add to the refined aesthetic, while custom bed coverlets bring a personal touch of luxury to the bedrooms. The master bath has been completely remodeled to exude modern sophistication, featuring sleek, high-end finishes that transform it into a spa-like retreat. A contemporary floating vanity, premium fixtures, and an expansive glass-enclosed shower with designer tilework create an ambiance of refined elegance. Every detail has been meticulously crafted to provide both style and comfort, making this space a true sanctuary within the home. Step outside to an entertainer’s dream: a full outdoor kitchen equipped for al fresco dining and gatherings, set against the backdrop of a lush and private lanai. The brick-paved driveway leads to a three-car garage, which features epoxy flooring, an insulated door, built-in storage, and a dedicated air conditioning unit for year-round comfort. This home is designed for ultimate convenience, boasting hurricane impact windows and doors, a zero-corner slider, custom closets, and a whole-house generator. A tankless water heater ensures efficiency, while a Kinetico water filtration system delivers the highest quality water throughout the home. The Sonos speaker sound system fills every space with rich, immersive audio. Located in one of the few natural gas communities in Naples, Winding Cypress offers an unparalleled lifestyle with resort-style amenities, including a residents-only restaurant, pool and spa, fitness center, and courts for pickleball, tennis, and bocce. Surrounded by over 800 acres of green space, this community provides a peaceful retreat just 10 minutes from Marco Island’s stunning beaches and 15 minutes from the vibrant shopping, dining, and entertainment of Olde Naples. This is more than a home—it’s a refined sanctuary where luxury meets convenience in one of Naples' most sought-after communities. Don’t miss your chance to make it yours!

This popular DiVosta Pinnacle Model is situated in the amenity rich community of Winding Cypress. It is possible to purchase this beauty 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 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.

Discover luxury living in this breathtaking Pinnacle estate home, situated on one of the most coveted lakefront sites in the south Naples resort community of Winding Cypress. Step inside to an open and spacious floor plan, enhanced by soaring tray ceilings, architecturally stunning alcoves and graceful arches. The home’s designer kitchen serves as the centerpiece, featuring every upgrade possible — soft-close cabinetry, quartz countertops, a fully vented natural gas range and hood and an all-premium KitchenAid appliance package with pull-outs in all lower cabinets. Adjacent is a large pantry complete with a water filter system for added convenience. The primary suite is a private oasis with towering ceilings and full walk-in shower and massive walk-in closet, while guest quarters include an expansive bay window en suite, ensuring comfort and privacy for family and friends. Additional living spaces include a versatile den or hobby room with upgraded French glass doors and foyer layout. Outdoor living is equally impressive. Relax by the saltwater pool and spa while enjoying serene wide-open lake views. Host gatherings with ease, thanks to a fully equipped outdoor kitchen featuring an integrated hood, all set within an expansive lanai with an upgraded oversized pocket slider door. The screened front porch, extended paver paths and custom landscaping further enhance the home’s curb appeal. Practical features include a 4-foot garage extension with custom flooring for three cars, all-impact glass windows, Storm Smart Kevlar shutters and energy-efficient LED lighting throughout. Additional upgrades include raised tray with crown-trimmed ceilings, a heated fireplace with customizable colors and custom state-of-the-art lighting systems that add a touch of sophistication to every room. Located in the resort-style community of Winding Cypress, residents enjoy exclusive access to a wealth of amenities, including a restaurant and bar, state-of-the-art fitness center, resort-style and lap pools, a spa and sports facilities for bocce, pickleball and tennis. The community also boasts a fire pit, bird-watching overlooks, a nature boardwalk and a picnic pavilion. Perfectly positioned between downtown Naples and Marco Island, this home offers the ultimate in luxurious Florida living. From its high-end finishes to its extraordinary location, it’s a property that truly has it all.

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!

Introducing a luxury estate site with landscaped privacy corner lot home in Winding Cypress with pool and spa. Step into elegance with this stunning Pinnacle model estate home, set in the prestigious, gated community of Winding Cypress. This home stands out with its soaring raised tray ceilings, rare privacy and spacious yard, impact glass for peace of mind, and an expansive open layout filled with natural light and outstanding upgrades. Designed for those who love to entertain, the chef-inspired gourmet kitchen features top-tier finishes, premium appliances, and a spacious expanded island, the ideal gathering space for family and friends. With three bedrooms, three baths, a versatile den and an upgraded oversized three-car garage, this home offers flexibility and space to suit your lifestyle. Outside, a private backyard oasis awaits, complete with lush landscaping, a serene water view and a sprawling grassy yard, a rare find in this community. Take a refreshing dip in your sparkling pool and spa, designed for ultimate relaxation in a peaceful setting. Beyond your doorstep, Winding Cypress offers resort-style living like no other. The nearly 18,000-square-foot clubhouse boasts a zero-entry infinity pool with a lap section, a poolside restaurant, beach cabanas and even a sandy beach. Stay active with numerous pickleball courts, clay tennis courts, bocce, an outdoor yoga movement studio, and a vibrant community hall managed by a full-time activity director. Winding Cypress is a resort gated community at the midpoint between Marco Island and downtown Naples, and this home delivers the ultimate combination of luxury, convenience and an unmatched lifestyle. Don’t miss your chance to own one of the desirable and private estate homes in Winding Cypress of Naples.

This home is an amazing value for Winding Cypress!! Once you compare, you'll agree. The Pinnacle model is clearly the most popular floorplan in The Community. The sought after "open area concept" footprint boasts 3 expansive bedrooms including a most impressive owner's suite, 3 full baths, a large den, desirable 3 car garage, and 2496 square feet of indoor living space under air. Builder and owner upgrades include an executive waterfront premium lot, kitchen appliance package, pool with new heater integral spa, quartz counters, upgraded cabinet package, den/office, zero corner sliding glass doors, plank tile flooring, plumbed for a summer kitchen, built-in ceiling speakers, upgraded laundry center with built-in cabinets and utility tub, inviting lead glass front entry door. Winding Cypress is the "hidden gem" of Naples. Community amenities include a resident's only private restaurant, pickleball, tennis, & bocce courts, resort style pool with spa and cabanas, state of the art fitness center & motion room, club house with events rooms, prep kitchen, internet cafe & library, dog park, nature trail boardwalk & a community garden. Winding Cypress offers activities for every interest coordinated by an onsite, full-time Activities Director. Located just 15 minutes to downtown Olde Naples and 10 minutes to Marco Island and I-75, Winding Cypress is perfectly located for you to enjoy all of what SWFL paradise has to offer.

Welcome to your new home in Winding Cypress, a vibrant community in the heart of Southeast Naples. Surrounded by 800 acres of lush preserves and 80 acres of peaceful lakes, this is the ideal setting to enjoy a serene, nature-filled lifestyle. Yet, with Downtown Naples and the iconic 5th Avenue—one of America’s most beautiful streets—just 20 minutes away, you’ll always be close to the best of city living. This tastefully furnished home offers a neutral palette, spacious enough for guests yet cozy enough for just you and your significant other. Triple sliders open to a stunning outdoor oasis, featuring a heated pool and spa, along with a spacious seating area perfect for unwinding in the evenings while taking in a breathtaking Southwest Florida sunset. Built to the highest standards, this home offers enhanced hurricane protection, including four electric Storm Smart Screens on the lanai, impact-resistant windows and doors throughout, and a 20KW whole-house generator for added peace of mind. The vibrant Winding Cypress community offers a wealth of amenities, including a luxurious clubhouse with a state-of-the-art fitness center, catering kitchen, activity room, and community room. Outdoor enthusiasts will love the bocce ball courts, five tennis courts, four pickleball courts, a fire pit, and a nature boardwalk with a bird-watching overlook and picnic pavilion. The community Dog Park is a spacious and secure area where residents can bring their furry friends to run, play, and socialize. Winding Cypress is mere minutes from the sandy beaches of Marco Island and Naples and is the ideal spot for both relaxation and recreation!

Imagine waking up each morning in your dream home,Nestled in one of Naples' most sought-after gated communities. As you walk into this beautiful home you are greeted with the open-concept floor plan that welcomes you, with the warmth of granite countertops and the added upgrades of a gas stove and wall oven in your chef-inspired kitchen. Your home is more than just a place to live, it’s a sanctuary. Impact-resistant doors and windows not only provide peace of mind but also frame the breathtaking views of the lake outside. Whether you're enjoying a quiet morning coffee or hosting friends and family, the large covered lanai, complete with a summer kitchen, offers the perfect setting for outdoor living at its finest. Picture yourself grilling dinner while enjoying the beautiful skys over the lake, or simply relaxing with the breeze. Inside, every detail has been laid out to elevate your life. The tile flooring throughout gives the home a fresh, modern feel. In your primary suite, the dual sinks, separate shower, and soaking tub invite you to unwind.The walk-in closets provide plenty of space for your wardrobe, and the built-in cabinets and sink in the laundry room ensure that chores are as effortless as possible. For those seeking an active lifestyle, this community offers bocce, tennis, pickleball, and a refreshing community pool, all just steps away from your front door. When you’re ready to explore beyond your home, you’re only seconds away from the exclusive community restaurant. Outside of the community Naples offers world-class shopping, dining, and beaches. Owning this home means more than just having a place to live – it means embracing a lifestyle of comfort, convenience, and luxury. Don’t miss out on the opportunity to make this exceptional property yours.