Winding Cypress Naples Real Estate : 31 Homes for Sale

Winding Cypress Naples 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 SOUTHWEST EXPOSURE, showcasing long lake views and spectacular sunsets. Designed for seamless indoor-outdoor living, this home features a 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!

Winding Cypress Naples Homes for Sale: 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.

Winding Cypress Naples Homes for Sale: 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!

Winding Cypress Naples 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!

Winding Cypress Naples Homes for Sale: 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!

Winding Cypress Naples Homes for Sale: 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!

Winding Cypress Naples Homes for Sale: 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.

Winding Cypress Naples Homes for Sale: 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!

Winding Cypress Naples Homes for Sale: Wow! This beautifully designed and meticulously maintained home checks all the right boxes. 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 enough 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. The driveway and side walkway are extended. There is over $100k in upgrades to this magnificent home. And it is offered fully furnished. Just pack your bags and head on down to enjoy our very special slice of tropical paradise. Worried about maintenance and insurance costs, and/or storms? Newer construction (2021) negates a large future roof replacement cost for some time. And a newer A/C system should provide many more years of solid service. Hurricane impact doors and windows are throughout providing for great energy efficiency and home protection. Also, the lot of this property is elevated. It is not in a mandatory flood insurance zone. And there is a whole home gas generator too should the need ever arise. All aforementioned should assist in obtaining lower insurance premiums and keep maintenance costs down. This home offers easy peasy and worry-free living by any measure. 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.

Winding Cypress Naples Homes for Sale: 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.

Winding Cypress Naples Homes for Sale: Welcome to this Winding Cypress beauty! Why wait months to build and spend twice as much to get less in a home and amenities. This 2022 built classic Summerwood Model has everything you'll ever need in a home and is located in Naples best hidden secret.....Winding Cypress! Located on a private, quiet, dead end cul-de-sac, this home has many builder options and owner upgrades. The home is impeccably decorated and boasts a Chef's kitchen with upgraded cabinets & lighting, an oversized island with optional quartz countertops, optional custom plank tile flooring, a zero corner sliding glass doors that open to an absolutely amazing outdoor living area that boasts a custom built-in pool, extended lighted lanai, and wonderful lake views. A whole house generator powered by natural gas and electric storm shutters will offer peace of mind for the new owner. Enjoy using the added space of the optional den for that special purpose that is optimal for your personal lifestyle. Custom Plantation Shutters on the windows provide an awesome convenience and added interior climate control. The laundry center has optional cabinets, extended counters & a built-in utility tub. Winding Cypress is an amenity filled community that includes a resident's only poolside restaurant, spectacular resort pool & spa with showers, pickleball, tennis & bocce courts, an amazing fitness center with locker rooms, library, dog park, nature trail boardwalk, a community garden, onsite property management, and dozens of regular events scheduled by a full-time Events Coordinator. At just 15 minutes to Olde Naples & 10 minutes to Marco Island, Winding Cypress homeowners are just a short drive to pristine beaches, the greatest restaurants, & all the wonderful entertainment and culture that Naples has to offer.

Winding Cypress Naples Homes for Sale: Set within the desirable Winding Cypress community, this exceptional 3-bedroom + den, 3-bathroom pool home combines upscale living with comfort. The primary suite offers a spacious layout, an opulent en-suite bath, and abundant closet space, while the well-appointed guest rooms provide privacy and relaxation. A private preserve view enhances the serene setting. The generous living area extends to the screened lanai, featuring a heated saltwater pool with a paver deck—perfect for outdoor gatherings or quiet retreats. Inside, an open-concept design showcases elegant tile flooring, soft neutral tones, and designer finishes, creating an inviting ambiance. The stylish two-tone kitchen boasts a large center island, breakfast bar, and an adjoining dining area, perfect for entertaining or everyday meals. Additional features include enhanced storm protection, a generously sized laundry room with ample storage, and a two-car garage featuring an epoxy-coated floor for added durability and style. Thoughtfully designed with both elegance and functionality, this home is move-in ready and ideal for those seeking a refined yet relaxed Florida lifestyle. Winding Cypress offers an unparalleled blend of luxury, convenience, and community living. Positioned near Marco Island’s pristine beaches, the vibrant 5th Avenue district, and with easy access to I-75, this master-planned, gated community provides an exceptional lifestyle. Residents enjoy low HOA fees and a wealth of amenities, including pickleball, bocce, tennis, and a state-of-the-art fitness center. The community features a stunning resort-style pool, an internet café, a community garden, and a dedicated dog park, ensuring there’s something for everyone. Social events and activities bring neighbors together, enhancing the sense of community. The Clubhouse at Winding Cypress is the heart of the community, offering an elegant and inviting space for residents to connect, socialize, and unwind. With its sophisticated design and comfortable lounge areas, the Clubhouse serves as the perfect backdrop for community events, casual gatherings, and personal relaxation. Just beyond, residents can enjoy the luxurious pool area, designed as a private oasis for sunbathing, swimming, and unwinding in a tranquil setting. Blending modern living with natural beauty, Winding Cypress is surrounded by 800 acres of preserves and 80 acres of serene lakes. Conveniently located near Tamiami Crossing, featuring a variety of shopping options, and Freedom Square, offering restaurants and retail stores, residents have everything they need within reach. Developed by DiVosta Homes, Winding Cypress consists of 766 beautifully designed residences, each offering a tranquil lifestyle in the heart of Southeast Naples. The Winding Cypress Homeowners Association ensures a well-maintained and welcoming environment.

Winding Cypress Naples Homes for Sale: From the moment you drive into the beautiful community of Winding Cypress you will feel welcomed. The stunning entry to this picturesque enclave will be a place you can truly call HOME! This is a natural gas, resort-style community, with over 2/3rds of the neighborhood remaining a preserve! You are surrounded by nature, yet close to wonderful dining options, gourmet grocers, and lots of fun shopping! There’s a serene boardwalk that meanders through Winding Cypress which takes you to a covered overlook, the perfect place for tranquility and bird-watching! The community also boasts the popular Shady Palm Café, a spacious clubhouse and a state-of-the-art fitness center. Did I mention Pickle-ball? Bocce? Tennis? Yes, even a dog park! The “Mystique” floor plan features 3 spacious bedrooms and 3 full baths plus a den. The primary suite has a luxurious bath with double sinks, a huge custom walk-in shower and an enormous walk-in closet! There are wonderful corner pocket doors that open to a tranquil lanai featuring a private below ground, heated pool with LED colored lighting. The home also features stainless appliances, including the gas range, quartz counters, white cabinets, a pantry and an island! There is luxury vinyl wood-look flooring throughout the main living areas. The Great room built-in cabinets have so much storage, and there are additional can-lights throughout, as well as ceiling fans in every room. Equipped with Vivent Security Cameras at the lanai and front windows and doors. The home also has an over-sized garage with a work shop wall of cabinets and a remote-control screen! I don’t think this seller has left anything out!

Winding Cypress Naples Homes for Sale: 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's 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!

Winding Cypress Naples Homes for Sale: 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!

Winding Cypress Naples Homes for Sale: Don't miss out on this stunning impeccably maintained Summerwood model in the highly coveted Winding Cypress community. This beautifully designed home offers 3 bedrooms, plus a dedicated home office, perfect for today’s lifestyle. Step onto the charming front porch, an inviting space to unwind with your morning coffee, and be greeted by a designer glass entry door. Inside, you’ll find a bright and open layout enhanced by crown moldings, luxury tile flooring, and classic plantation shutters, creating an atmosphere of elegance throughout. The gourmet kitchen is a chef’s dream, featuring gleaming Quartz countertops, upgraded 42-inch cabinetry with dovetail soft-close drawers and pullouts, and high-end stainless-steel appliances. The seamless flow from the kitchen into the spacious open living and dining areas makes it ideal for both everyday living and entertaining guests. Enjoy peace of mind with impact-resistant windows and electric storm shutters along the covered lanai. Take full advantage of the abundant space and natural light pouring in through the sunroom. Custom closets throughout offer exceptional storage, keeping everything neat and organized. The extended 2-car garage is more than just a place to park—it includes a mini-split A/C system and epoxy flooring, offering extra room for storage or hobbies. Relax or entertain on the expansive covered lanai, where you can enjoy breathtaking, unobstructed long water views through a panoramic screen. Whether you're sipping a drink by day or watching the sunset by night, this lanai is the ultimate retreat. Winding Cypress is an amenity rich community with 850 acres of green preserve space. Residents enjoy the full-scale restaurant, pickleball, tennis, & bocce courts, a spectacular community pool and clubhouse, awesome fitness center, dog parks, 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. This home blends comfort, luxury, and functionality in perfect harmony—you will want to experience it firsthand!

Winding Cypress Naples Homes for Sale: Welcome to the best kept secret in Naples, the community of Winding Cypress. Winding Cypress is a DiVosta neighborhood, loaded with resident amenities, and just minutes to Olde Naples and Marco Island. This beauty is the most popular model, The Pinnacle, and it is being offered at an amazing value in equity! An entertainer's dream home boasting an expansive open floorplan joining a huge great room with the Chef's kitchen and separate dining area, flowing into an extended outdoor living space. Complete with 3 bedrooms including an owner's suite, 3 full bathrooms, large den/office option, and a valuable 3 car garage with a 4-foot extension. Additional enhancements and upgrades include; hurricane impact windows, entry door, and slider, electric Storm Smart Kevlar hurricane rated screens, extended outdoor living area including a custom outdoor natural gas kitchen, upgraded maple kitchen cabinets with pull outs, granite countertops and backsplash, and extended center island, upgraded faucets, tile, and bath fixtures, laundry room with built-in cabinets, counter, and utility sink/tub, an epoxy painted floor and additional utility sink/tub in the garage, and a custom lighting package. The amenities of Winding Cypress are second to none. The community offers an awesome, resident's only restaurant, pickleball, tennis, and bocce courts, the most amazing resort pool with spa, sand beach private cabanas, and men's & women's locker room and shower facilities. The clubhouse boasts a best-in-class fitness center and motion room, conference rooms with a prep kitchen, resident's library, and an outdoor gathering area with a built-in fireplace. Winding Cypress offers onsite management and full-time actives director. Your pets will enjoy the 2 dog parks to run and play. Additionally, there is a community garden to grow your vegetables and flowers as well as a boardwalk nature trail. Winding Cypress is comprised of 1250 total acres, with 850 acres being greenspace and preserve, giving a wonderful feel of openness, privacy, and natural surroundings not found in other new communities. Why would you wait to build, and spend significantly more, and end up with less?

Winding Cypress Naples Homes for Sale: This beautifully upgraded 2-bedroom plus den, 2-bath Mystique floorplan home in Winding Cypress offers the perfect blend of style, comfort, and functionality. The open-concept design features a zero-corner slider, seamlessly connecting indoor and outdoor spaces, while impact windows and doors provide security and energy efficiency. A whole-home generator ensures uninterrupted comfort and peace of mind. Inside, thoughtful upgrades enhance every space. The gourmet kitchen boasts built-in appliances and a spacious island, perfect for entertaining. Additional highlights include crown molding, built-in speakers, a custom living room accent wall, and built-in drop zone cabinetry for added style and organization. The den features a Murphy bed, making it a flexible space for a home office or extra bedroom. The laundry room is equipped with built-in cabinets, offering ample storage. Outside, the private backyard is a true retreat, featuring a pool and spa for ultimate relaxation. The outdoor kitchen is perfect for entertaining, while lush landscaping enhances the home’s peaceful ambiance. A tandem garage has the ability to accommodate up to three cars, providing plenty of parking and storage. Winding Cypress is a natural gas community with resort-style amenities! Dine at Shady Palm, the onsite restaurant, or enjoy pickleball, bocce, tennis, a state-of-the-art fitness center, a resort-style pool, a community garden, and even a dog park for your furry friend. This pet-friendly community allows rentals, has low fees, and boasts a prime location—central to Marco Island, 5th Avenue, and I- 75.

Winding Cypress Naples Homes for Sale: Step into the lap of luxury with this stunning villa in Winding Cypress. This exquisite property is not just a home; it's an embodiment of sophistication and comfort, offering a lifestyle that is truly unparalleled. The villa is being offered fully furnished, ensuring that every inch of this residence reflects a tasteful and cohesive design. As you enter, you'll be captivated by the elegance that defines every detail. The gas-heated pool beckons, inviting you to relax and unwind in your private oasis. The outdoor kitchen adds a touch of opulence, making it an ideal space for entertaining guests or enjoying alfresco dining under the clear Florida skies. The chef's dream kitchen is a masterpiece in itself, featuring top-of the-line Samsung appliances and stunning quartz countertops. The list of updates is extensive, a testament to the commitment to maintaining this villa in peak condition. While it's impossible to detail every enhancement, rest assured that no expense has been spared in ensuring that this property remains at the pinnacle of luxury living.

Winding Cypress Naples Homes for Sale: Welcome to your dream home at 7370 Mockingbird Court in beautiful Naples, FL! This charming 2-bedroom, 2-bathroom residence, with a versatile den that can easily be converted into a third bedroom, offers a spacious 1,805 square feet of living space, perfectly nestled on an 8,276 square foot lot. Step inside to discover a welcoming interior featuring both carpet and tile floors, ideal for comfort and style. The open living area is enhanced by new ceiling fans and pendant lighting, creating a bright and airy atmosphere. The kitchen is a chef's delight with brand new quartz countertops, a new sink and faucet, and a suite of new appliances including a dishwasher, refrigerator, and garbage disposal. The master suite offers a serene retreat with a new toilet in the master bath, ensuring modern convenience. Enjoy the luxury of central AC and gas heat throughout the home. The attached garage, equipped with a new garage door opener, provides ample space for parking and storage. Outdoor enthusiasts will appreciate the common outdoor space, private outdoor areas, and stunning lakefront views. The community amenities are second to none, featuring a pool, hot tub, gym, tennis court, and pickleball facilities. For those who love the water, the property is waterfront with lake views, perfect for tranquil evenings. Plus, there is room to add a pool, allowing you to customize your outdoor oasis. Additional features include a new gas hot water heater, added landscape lights, and a recently cleaned roof. Plus, enjoy the convenience of laundry in the building and a washer/dryer in the unit. Conveniently situated just minutes from shopping, dining, and all the attractions Naples has to offer, this home combines tranquility with exceptional lifestyle opportunities. This home is a true gem, offering a blend of comfort, style, and community amenities that make it a perfect place to call home. Don't miss the opportunity to make it yours!

Winding Cypress Naples Homes for Sale: This beautiful villa in highly sought-after Winding Cypress offers two bedrooms, two baths plus a den along with a two-car air-conditioned garage. Step onto your lanai with the largest pool and hot tub available in a villa. Couple that with a spectacular long lake view and you truly have a one-of-a-kind home. Winding Cypress offers resort-style living with a large amenity center, gym, exercise room, library, internet cafe, event room and restaurant. The resort-style pool has a lap lane and waterfall. Other amenities include pickleball, tennis, bocce, community garden and dog park. The community boardwalk allows you to walk deep into the preserve. Winding Cypress boasts 800 acres of untouched preserve surrounding our one-of-a-kind community.

Winding Cypress Naples Homes for Sale: This move in ready furnished Winding Cypress Serenity 2 bedroom plus den Attached Villa with POOL & SPA is a unique quality find. This Serenity floor plan with the kitchen conveniently tucked away behind peninsula island allows for optimal entertaining space. Kitchen features Quartz countertops, natural gas range & SS appliances. Other high quality highlights include, plantation shutters, crown molding, Lutron shades at slider, recessed & under cabinet lighting, upgraded lighted mirrors in both baths, laundry room cabinets & sink, privacy door for guest suite, pull down attic stairs in garage, wide, driveway, pest control piping in the walls, Storm Smart electric hurricane shades on lanai and landscaped lighting around lanai. Slight pie shape lot and lush landscaping offers extra privacy for lanai and pool area. Located in sought after Winding Cypress Community with it's rich amenities including a resort style pool, restaurant/bar, fire pit, fitness center, outdoor yoga deck, pickle-ball, tennis, bocce ball, community garden, dog park, and a nature trail boardwalk that wanders through protected natural preserves. Centrally located between Marco Island and 5th Ave allows easy access to the surrounding areas beautiful beaches, restaurants and entertainment.

Winding Cypress Naples Homes for Sale: This home is a true single famly NOT an attached villa. PRICE RIGHT ALMOST $100000k UNDER NEXT SINGLE FAMILY FOR SALE. Wonderful community with over 800 acres giving room for custom homes and large back yards, nature trails and room to relax. So well cared for. Enjoy the private park like back yard. Extended screened patio with outdoor kitchen perfect for dining al fresco. Light bright home with all the goodies. Even gas kitchen. Open floor plan plenty of storage. 3rd Bedroom is being used as Den but Can easily be converted to 3rd bedroom. The community has a dog park for Fido. Amenity rich community with low HOA Look what the community offers Neighborhood Features Natural Gas Community 800+ Acres of Natural Preserves Heated Resort-Style Pool & Spa Poolside sugar-sand beach and cabanas 17,500 sq. ft. Clubhouse with Activity Room, Catering Kitchen & Library State of the Art Fitness Center & Movement Studio Outdoor Barefoot Bar and Grill Natural Gas Fire Pit Activity Director 4 Bocce Ball Courts Tennis Courts 4 Pickleball Courts Dog Park Community Garden Boardwalk with Pavilion and Bird Wading Overlook 80 Acres of Lakes Home Lawn Maintenance included Entry Gate with Guard House Less than 3 miles from US-41 10 Minutes to I-75 15 Minutes to Fifth Avenue and Third Street Shopping & Dining 20 Minutes to Naples Pier and magnificent area beaches 20 Minutes to Marco Island prepared with care but subject to errors and omissions Buyer to verify everything to their satisfaction

Winding Cypress Naples Homes for Sale: The Finest in Resort Style Living! You do not want to miss this opportunity to own a find like this in the Community of Winding Cypress. This Beautifully updated 2+Den/2 Bath Gem has 9' 4" ceilings with a two car garage is move in ready and it has everything you need to call this sought after Villa your Home. New refrigerator, new hot water tank, new pavers, plantation shutters and much more. Almost 2/3 of this Amazing Community is set aside just for a tranquil preserve/wooded area. Only 8 miles to Downtown Naples + 9 miles to Marco Island. Just a few Amenities include Pickleball, Bocce Court, Clubhouse, Community Park, Community Pool/Spa/Hot Tub + Community Room and much, much more! What are you waiting for.. Call Now to set up your showing cause this Unique Property won't be on the market long!

Winding Cypress Naples Homes for Sale: Don't miss your chance to own a Serenity Turnkey Pool Villa in the highly sought-after Winding Cypress community! This meticulously designed residence boasts 3 bedrooms, 2 bathrooms, and a 2-car garage, offering both comfort and style. Step outside to your private outdoor oasis, complete with a tranquil waterfall feature, electrically heated salt pool, built-in speakers, and serene preserve views—the perfect setting for relaxation or entertaining. For added peace of mind there are also electric hurricane screens on the lanai. Inside, the versatile third bedroom can function as a den or guest room, featuring French doors and a closet. Elegant interior upgrades include crown molding, tray ceilings, built-in speakers, a security system, custom closet systems, and stunning diagonal tile flooring—just to name a few! Winding Cypress is a natural gas community with resort-style amenities! Dine at Shady Palm, the onsite restaurant, or enjoy pickleball, bocce, tennis, a state-of-the-art fitness center, a resort-style pool, a community garden, and even a dog park for your furry friend. This pet-friendly community allows rentals, has low fees, and boasts a prime location—central to Marco Island, 5th Avenue, and I- 75.

Winding Cypress Naples Homes for Sale: Absolutely the best deal on a 2 bedroom plus den with French doors, 2 baths, 2 car garage attached villa with your own POOL in Winding Cypress. You better Hurry. Furniture negotiable too, move right in for season, nicely furnished. What's Special: *Open floor plan *Epoxy garage floor *Granite countertops *3 ft. bathroom countertops *Remote controlled garage screen *Remote controlled hurricane shutters on the lanai *California Closets in all bedrooms *Pool. Den can be converted to a 3rd bedroom too. Come see this beautifully designed pool home boasting of an inviting open floor plan, perfect for entertaining and family living. The kitchen highlights its elegant backsplash and granite countertops that provide both beauty and durability. Each bathroom has been designed with 3 ft. of countertops for added space and comfort. California Closet's custom-design can be found in each closet to maximize storage and organization throughout. The home has also been designed with 8' doors, adding to the modern, airy feel. The garage is finished with epoxy flooring and comes with remote controlled garage screen for added ventilation and convenience. Step out to the back lanai where you will find remote controlled weather/hurricane shutters for those rainy afternoons or storm seasons, giving you peace of mind. Enjoy the private pool. perfect for relaxation and entertainment. The home has been smoke-free and pet-free, ensuring a clean, fresh environment for the next owners. With thoughtful upgrades and premium features, this home is ready to welcome you. Winding Cypress includes: *Over 800 acres *Natural preserve *Nature trails *Dog park, *Low HOA *Clubhouse activity room *Fitness center *Heated resort-style pool *White sandy lounge area *Bar and grill *Library *Catering kitchen *Tennis and pickleball courts *Natural gas *15 minutes from 5th Ave. *20 minutes from Marco Island *Major shopping brands 5 minutes away.

Winding Cypress Naples Homes for Sale: This beautiful Winding Cypress Serenity Villa home offers 1,554 sq. ft. of comfort with 2 bedroom plus den, 2 bathrooms, screened lanai, and a 2-car garage. It features multiple quality upgrades including stainless appliances with both gas and electric connectivity for the stove, 22" porcelain tile on the diagonal throughout, plantation shutters, Quartz countertops in kitchen and bathrooms, den with French doors, and much more. The full list of upgrades is in supplements. Located near downtown Naples and Marco Island, the community features a clubhouse with a resort style pool, spa, state of the art fitness room, restaurant, tennis, bocce and pickleball. Shopping and restaurants are nearby. The 800+ acre preserve with a boardwalk adds to the outdoor appeal. Ideal for those seeking a stylish home in a prime location.

Winding Cypress Naples Homes for Sale: Introducing the incredibly rare Winding Cypress model, the Cressida villa, now available with expansive private yard and lanai space. This unique villa features a dedicated private front entrance and an expanded foyer, complemented by an open yet defined living concept. The home boasts a wealth of builder-installed upgrades, including granite finishes, high-end porcelain floors, a glass-tiled backsplash, top-of-the-line cabinetry and crown molding throughout. The spacious backyard provides ample room to add a pool or a large sundeck of your choice. Winding Cypress stands out as one of Naples' most distinctive resort communities, encompassing over 800 acres of pristine preserve in an ideal location between Marco Island and downtown Naples 5th Avenue. Community amenities include a dog park and a vegetable garden. The Club at Winding Cypress is must-see, featuring a resort-style pool, sunset sand cabanas, bocce ball, pickleball, clay tennis courts, a yoga deck, a large gym facility, fire pits, a nature trail, locker rooms and a dedicated activities director. Enjoy a vibrant lifestyle with a sand bar, restaurant and a professional activity director on staff!

Winding Cypress Naples Homes for Sale: MOTIVATED SELLER. Welcome to this stunning 2+Den, 2 Bath home in the preserve-like community of Winding Cypress. As its name suggests, you will be ushered away from the worries of the world as you are greeted by this serene and natural, resort-style community boasting a poolside restaurant, 5 tennis courts, 4 bocce courts, 4 pickle ball courts, an atteneded fitness center, and an engaging social event calendar. Enjoy leisurely strolls at the nature boardwalk or take your furry companions to the community’s dog park. The property boasts generous yard space, a relaxing screened-in lanai, and meticulously maintained landscaping. Inside, you'll find a modern kitchen equipped with stainless-steel Whirlpool appliances and a newer washer and dryer. Whether you're entertaining or seeking tranquility, this home offers the perfect balance of comfort and convenience in an unbeatable location. Optimally located to experience the best that Naples and Marco Island have to offer, you'll find yourself ideally positioned between the shores of Marco Island's white sandy beaches and Naples' 5th Avenue, featuring lavish and upscale dining and shopping. An elegant home in a vibrant tropical paradise, come and experience southwest Florida at its finest.

Winding Cypress Naples Homes for Sale: Don’t miss this exceptional opportunity to own an upgraded Cressida villa in the sought-after community of Winding Cypress! This front-entry home lives like a single-family residence, offering 2 bedrooms + den, 2 bathrooms, a 2-car garage, and a stunning expanded patio with extra covered space—more than most villas. Inside, enjoy luxury upgrades including white cabinetry, quartz countertops, crown molding, and more. The outdoor space is equally impressive, featuring a built-in hood for effortless grilling and gorgeous mature landscaping. Winding Cypress is a natural gas community with resort-style amenities! Dine at Shady Palm, the onsite restaurant, or enjoy pickleball, bocce, tennis, a state-of-the-art fitness center, a resort-style pool, a community garden, and even a dog park for your furry friend. This pet-friendly community allows rentals, has low fees, and boasts a prime location—central to Marco Island, 5th Avenue, and I-75.

Winding Cypress Naples Homes for Sale: Price Negotiable! Seller is highly motivated!! Discover your slice of paradise in this stunning 2-bedroom plus den villa, located in the resort-style community of Winding Cypress. With exquisite builder-installed upgrades, this home features a sleek open floor plan, granite countertops, and elegant porcelain tile throughout. The kitchen is outfitted with stainless appliances and gas stove complemented by a stylish backsplash. The spacious den, equipped with French doors, can easily transform into a third bedroom, while California Closets in every room provide exceptional storage and organization and Plantation Shutters. Your attached 2-car garage is enhanced with Monkey Bar storage for maximum efficiency! Step outside to enjoy a wealth of amenities, including a restaurant and bar, a state-of-the-art fitness center, resort-style pools, and vibrant sports facilities for bocce, pickleball, and tennis. Unwind by the fire pit or explore the nature boardwalk and bird-watching overlooks. Perfectly situated between downtown Naples and Marco Island, this beautifully upgraded home offers the ultimate Florida lifestyle. Don’t miss out on this incredible opportunity

Winding Cypress Naples Homes Under Contract: Discover luxury living in this modern and bright single-family Martin Ray home, located in the resort-style community of Winding Cypress. With 2,107 square feet of living space, this open concept 3-bedroom plus den, 2-bathroom home offers a harmonious blend of elegance and functionality. Natural light and coffered ceiling details create a bright and airy atmosphere while modern design and neutral colors provide a sense of elegance and refinement. The kitchen showcases stainless steel appliances, gorgeous quartz countertops, white cabinetry, 42” upper cabinets, a walk-in pantry, under cabinet lighting, tile backsplash, ample storage space, and a large center island which blends seamlessly into the family and dining room creating the highly sought after open concept, perfect for families and entertaining. The master suite, located in the back of the home, provides a serene retreat with a spacious bedroom, tray ceiling, walk-in closet and a well-appointed en-suite bathroom featuring dual sinks, separate water closet, modern tile, and a walk-in shower. Two additional bedrooms and an adjacent bathroom, offer ample space and privacy for the entire family. Beautiful impact, tuck away sliding glass doors lead to an expansive lanai complete with picture window screens, serene NW lake views, and a heated saltwater pool with sun shelf and spa, providing a seamless transition between indoor and outdoor living. Other enhancement that set this home apart from the rest include impact windows and doors, coffered ceiling in the living room, crown molding, 6-inch baseboards, 8-foot doors, screened in front entry, separate laundry room with a sink and cabinetry, window blinds/curtain panels, glass doors on the den, upgraded landscaping, outdoor kitchen, auto pool filler, decorative Bahama shutters, Sentinel Storm Shades on the back lanai, and an extended 2-car garage with utility sink and epoxy flooring. Winding Cypress is a gated, resort-style community featuring 766 homes located in Naples, FL. Nestled within over 1,100 acres of natural preserves and 80 acres of serene lakes, this community offers residents a laid-back lifestyle surrounded by nature. Residents enjoy a wide array of amenities, including the Shady Palm pool side café, a spacious Clubhouse, resort-style pool/spa, lap pool, pickleball, tennis, bocce, fitness center, movement room, nature boardwalk, and dog park. Centrally located near shopping, restaurants, and the pristine beaches of Naples and Marco Island, Winding Cypress seamlessly merges the elegance of modern living and the serene beauty of its natural surroundings.

Winding Cypress Naples Homes Under Contract: 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 whole house generator, reverse osmosis water system, 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.

Winding Cypress Naples Homes Under Contract: Live the Vacation Lifestyle Every Day in Winding Cypress Welcome to a home that feels like a never-ending vacation. This stunning Summerwood residence, nestled in the resort-style community of Winding Cypress, is more than a home—it’s a lifestyle. From the moment you step through the dramatic entry hall, you’re greeted by breathtaking lake views that set the tone for tranquility and relaxation. The zero-clearance sliding glass doors seamlessly blend indoor elegance with outdoor splendor, leading to an expansive lanai designed for ultimate leisure and entertainment. Imagine starting your mornings with serene sunrises over the lake, enjoying your coffee on the lanai surrounded by picturesque scenery. The fully equipped bar—complete with a KitchenAid grill, refrigerator, freezer, and ample seating for seven—makes hosting sunset cocktail parties a breeze. Whether you prefer lounging in the shaded comfort or basking in the sun, this home caters to your every mood. Winding Cypress offers an unparalleled array of resort-style amenities: • A tropical pool oasis with cascading waterfalls, a hot tub, and a poolside bar serving refreshing drinks and delicious meals. • Social activities for every interest, from pickleball, tennis, and bocce to art clubs, gardening, and game nights. • Themed parties, live music, and dancing that make every evening unforgettable. When you’re ready to explore beyond the gates, you’re just nine miles from Marco Island’s pristine beaches and downtown Naples’ vibrant dining, shopping, and cultural scenes. From galleries to holiday snowfall in December, there’s always something to enjoy. This home is move-in ready, fully furnished down to the dishes. All that’s left is for you to pack your suitcase and embrace the dream vacation lifestyle—every single day.

Winding Cypress Naples Homes Under Contract: A MOST INCREDIBLE OFFERING. WELCOME TO THIS EXCLUSIVE MARTIN RAY MODEL FOOTPRINT. THIS HOME HAS IT ALL INCLUDING THE FOLLOWING: WHOLE HOUSE GENERATOR, HURRICANE IMPACT WINDOWS & SLIDING GLASS DOOR, HURRICANE IMPACT MAIN ENTRANCE DOOR WITH LEADED GLASS, STORMSMART ELECTRIC HURRICANE SHADES, 11 FOOT CEILINGS WITH TRAYS, COFFERS, & WIDE MOLDINGS, OPTIONAL DEN/OFFICE WITH TRAY CEILING, UPGRADED OWNER’S SUITE WITH SITTING AREA AND OPTIONAL BATHROOM LAYOUT, CUSTOM SINK, SHOWER, & BATHROOM FIXTURES, OPTIONAL WHOLE HOUSE LIGHTING PACKAGE, OPTIONAL EXTERIOR LIGHTING PACKAGE, OPTIONAL 3RD BEDROOM, BUTLER’S PANTRY WITH BAR AREA, WINE RACK, & WINE/BEVERAGE REFIGERATOR, UPGRADED KITCHEN CABINET PACKAGE INCLUDING SOFT CLOSE DOORS, DECORATIVE DOOR-END PANELS, WIDE DENTIL TRIM, PULL OUT DRAWERS, & UNDER CABINET LIGHTING, UPGRADED QUARTZ COUNTERTOPS, CUSTOM BRICK MOSAIC BACKSPLASH, UPGRADED APPLIANCE PACKAGE INCLUDING BOSCH REFRIGERATOR & DISHWASHER, UPGRADED PLANK TILE FLOORING THROUGHOUT, CUSTOM LAUNDRY CENTER WITH BUILT-IN CABINETS & UTILITY SINK, VITEX SMART HOME SECURITY & FIRE PACKAGE MONITORED BY CENTRAL STATION, WHOLE HOUSE ALARMED LEAK DETECTION SYSTEM, ELECTRIC WINDOW SHADES, SMOOTH INTERIOR WALLS, PLANTATION SHUTTERS THROUGHOUT, TANKLESS WATER HEATER, WHOLE HOUSE WATER FILTRATION SYSTEM, UPGRADED 8 FOOT SOLID CORE DOORS WITH DECORATIVE ARCH, OPTIONAL DROP ZONE OFF OF THE GARAGE, 2 CAR GARAGE WITH 4 FOOT EXTENSION WITH UTILITY SINK & INSULATED OVERHEAD DOOR, IMPRESSIVE EXTENDED LANAI WITH CUSTOM PAVERS AND TURF ACCENT & WIDE LAKE VIEW, PICTURE WINDOW LANAI SCREEN, EXTENDED DRIVEWAY & MAIN ENTRANCE PAVERS, PAVER SIDEWALKS ON BOTH SIDES TO LANAI, PROFESSIONALLY LANDSCAPED AROUND ENTIRE RESIDENCE, HOME HAS BEEN PROFESSIONALLY DESIGNED & DECORATED BY ROBB & STUCKY – FURNISHINGS ARE NEGOTIABLE OUTSIDE OF LIST PRICE. WINDING CYPRESS IS AN AMENITY RICH COMMUNITY, INCREDIBLE VALUE, AND A NAPLES HIDDEN GEM. AMENITIES INCLUDE A PRIVATE RESIDENT'S ONLY RESTAURANT, RESORT POOL & SPA, PICKLEBALL, TENNIS & BOCCE COURTS, SPECTACULAR COMMUNITY CENTER W/FITNESS CENTER, LOCKER ROOMS, CONFERENCE ROOMS & LIBRARY, DOG PARK, COMMUNITY GARDEN, BOARDWALK NATURE TRAIL, ONSITE HOA MANAGEMENT WITH A FULL-TIME ACTIVITIES MANAGER. YOU'RE 10 MINUTES TO THE BEACHES OF MARCO ISLAND & 15 MINUTES TO THE RESTAURANTS, ENTERTAINMENT & SHOPPES OF OLDE NAPLES.

Winding Cypress Naples Homes Under Contract: Rare villa opportunity in Winding Cypress! For the first time in over a year, a villa with a private pool and spa on an extra-large lot is available. Enjoy unmatched privacy with huge space between neighbors and serene ultra-private preserve views. This turnkey, fully furnished home features impact windows, 8-foot doors, new bedroom flooring, fresh landscaping and more. This natural gas community offers all hookups for an outdoor kitchen on your lanai, with gas, water and drain ready. Plus, extra garage storage is built in, making organization a breeze. Step into your own backyard oasis with a heated pool and spa, ideal for relaxing or entertaining in the Florida sunshine. Whether hosting guests or unwinding solo, this home offers the ideal blend of comfort and luxury. In the sought-after Winding Cypress community, residents enjoy resort-style amenities without the high fees. Dive into the expansive resort pool, stay active in the state-of-the-art fitness center, or explore miles of scenic nature with recreational and biking trails. The full-service restaurant and bar provide a social hub, while the tennis and bocce courts, garden and pickleball courts offer endless recreation options. The clubhouse also features a stunning social hall, library, and event spaces to connect with neighbors and friends or hold special celebrations.

Winding Cypress Naples Homes Under Contract: BIG PRICE REDUCTION! THIS IS ONE OF THE LOWEST PRICED VILLA POOL HOME! Discover this stunning 3-bedroom, 2-bathroom villa with a 2-car garage and a luxurious gas heated pool that is ideally situated on a premium pie-shaped lot adjacent to nature preserve and near to the vibrant Winding Cypress Amenity Center is the perfect place to make your own paradise. The flex room offers endless possibilities as a third bedroom or as a home office/den. The Serenity Model offers the perfect blend of charm and sophistication, whether you seek a year-round haven or a seasonal escape to enjoy Florida's renowned lifestyle. Indulge in effortless entertaining as the seamless open floor plan leads you to a covered lanai and expansive brick paver pool deck that gazes out onto a serene nature preserve. Witness breathtaking sunsets that paint the sky in hues of warmth while serenaded by the harmonious symphony of nature within your private screened enclosure in the prestigious Winding Cypress community. This home has features including stainless-steel appliances, elegant granite countertops, a beautifully tiled backsplash in the kitchen, and 20" ceramic tile flooring throughout the main living spaces. Noteworthy accents such as plantation shutters, rich wood flooring in the den, accordion hurricane shutters, an electric rolldown hurricane shutter at the lanai, and a host of other upscale finishes. Nestled within a secure, amenity-rich enclave, residents enjoy access to a lavish Community Center, overseen by a full-time activities’ director, offering an array of recreational facilities from card/game rooms and a library to a poolside bar and restaurant. Stay active with a state-of-the-art gym, outdoor Yoga and movement studios, group exercise classes, a resort-style pool with a dedicated lap lane, inviting fire pits, dog parks for both large and small dogs, illuminated tennis courts, pickleball and bocce courts, and sprawling lakes and nature preserves spanning nearly 800 acres, providing boundless walking and riding trails for outdoor enthusiasts. Perfectly positioned in proximity to upscale shopping, dining venues, the sandy beaches of Naples and nearby Marco Island, the ambiance of downtown Naples along 5th Avenue & 3rd Street, as well as convenient access to medical facilities, educational institutions, places of worship, I-75, RSW International Airport, and the breathtaking wonders of the Florida Everglades.

Winding Cypress Naples Homes: A staggering mix of natural beauty and fabulous Naples living. This jewel box home is situated on one of the most desirable lots in Winding Cypress. Look at the aerial view, simply breathtaking. Lot location had a $125,000 premium.Coveted Southern exposure Peaceful and full of nature. Well-designed, expansive floor plan offering generous size rooms, an outstanding white kitchen that is perfect for the serious cook or entertaining. You will love the large island, wine cooler, massive pantry, and natural gas. Split living area with unique closets and storage everywhere. Soaring ceilings. The west wing encompasses an impressive size Owner suite complete with massive walk-in closet. More than 2 cars? No worries, there is garage parking for 3. For the enjoyment of nature spend time in your southern exposure, spacious salt water pool/spa or patio with outdoor kitchen or relax on your lounger in the pool. A patio you can use year round unlike west facing patios that are so hot . Additional peace of mind is offered with impact windows and a generator. Please note this is not the base Pinnacle floor plan, this is top of the line and highly upgraded. Located off the main road on a cul de sac street. You must see this home. Winding Cypress is a wonderful community. Amenity rich with a low HOA. Amenity rich with low HOA Look what the community offers: Neighborhood Features Natural Gas Community ,800+ Acres of Natural Preserves, Heated Resort-Style Pool & Spa Poolside. sugar-sand beach and cabanas ,17,500 sq. ft. Clubhouse with Activity Room, Catering Kitchen & Library, State of the Art Fitness Center & Movement Studio. Outdoor Barefoot Bar and Grill, Natural Gas Fire Pit , Activity Director, 4 Bocce Ball Courts ,Tennis Courts, 4 Pickleball Courts, Dog Park, Community Garden, Boardwalk with Pavilion and Bird Wading. Overlook 80 Acres of Lakes.Home Lawn Maintenance included. Entry Gate with Guard House. Less than 3 miles from US-41 ,10 Minutes to I-75 ,15 Minutes to Fifth Avenue and Third Street Shopping & Dining, 20 Minutes to Naples Pier and magnificent area beaches. 20 Minutes to Marco Island prepared with care but subject to errors and ommissions Buyer to verify everything to their satisfaction

Winding Cypress Naples Homes: 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.

Winding Cypress Naples Homes: HURRICANCE READY!!!! NEW PRICE Improvement.This home is truly a showstopper , priced below market value and offering a "wow" factor that is hard to beat. The Stonewater model is the largest home built in Winding Cypress built in 2020 and still looks and feels like brand new. With approx.3000 sq. ft. of grand open space you'll be captivated from the moment you walk through the double front doors into the gracious foyer. The home features 13ft. coffered ceiling in the great room , formal dining area or custom for your use, office with glass French doors , 3 bdrms , 3 baths three car garage The lanai boasts POOL BATH WITH STORAGE ,a relaxing backdrop of the lake and peaceful preserve complete with an outdoor kitchen and hurricane shutter. Lanai furniture included in sale. A FEELING OF LIGHT AND SPACIOUSNESS IS WHAT YOU FEEL WHEN YOU WALK IN THE FRONT DOOR WITH ITS SOARING 13FT CEILING IN FOYER AND AND GREATROOM. This home is impeccable maintained and in like new condition. HURRICANE READY WITH ITS BRAND NEW whole house generator for peace of mind. Winding Cypress offers a wealth of amenities including a beautiful resort pool and restaurant. Don't miss the opportunity to see and appreciate the beauty of this exceptional home. Winding Cypress is conveniently located just 15 min to Marco Island , 75 and Downtown Naples

Winding Cypress Naples Homes: Ready for immediate occupancy! home is now vacant and has a nice clean open slate to custom this home to your liking .Take a look at this Pinnacle style home located in the sought after community of Winding Cypress features 3 bdrms 3 baths, office and 3 car garage , hurricane protection measures include whole house generator , impact doors and windows and hurricane storm screen on lanai. Extended oversized Lanai facing the lake has plenty of room for entertaining , practice your putting , or custom a new pool or spa. come and take a look at this Pinnacle style home in Winding Cypress, use your vision to custom this home to your own personal taste, You can't beat the floor plan with almost 2500 soft of living space and is a great value compared to other Pinnacle models sold here in Winding Cypress. Home is located within walking distance to all the amenities Winding Cypress has to offer,, beautiful resort pool , pool side resturant and bar, gym, sports courts and more . Walk to to the dog park and community garden. P

Winding Cypress Naples Homes: Like new, two years old four bedroom, three-bathroom residence in Winding Cypress. House has been totally custom remodeled. This furnished home showcases new furniture and TVs, finished with 9’ ceilings, 8’ doors, pristine tile floors. The gourmet kitchen features high end appliances with gas cooking, pullout drawer cabinets, designer backsplash, pantry, and a large center island. Each bedroom has an in-suite bathroom. Outside, you’ll find a WiFi-controlled heated pool and screened lanai with build- in barbeque grill. Extended driveway, two-car garage , epoxy floor, and overhead storage. Winding Cypress residents have access to a clubhouse with a social room, library, fitness center, resort-style pool and spa, outdoor bar and grill, tennis, pickleball, bocce, dog park, and a full social calendar. Just 15 minutes to downtown Naples and Marco Island. CDD paid in full.

Winding Cypress Naples Homes: Winding Cypress is the ultimate Naples resort community, and this home serves as the ultimate poolside retreat. The long southwest water views seamlessly blend waterfront serenity, preserved nature, and privacy. Adorning the oversized covered lanai is a deluxe outdoor kitchen complete with every conceivable feature and top-grade finishes. This award-winning Summerwood floor plan boasts every builder upgrade, including a double oven gourmet kitchen, top-of-the-line cabinets, crown molding, tray ceilings, easy-glide retractable storm shutters, and more. The open concept layout is enhanced with strategically placed windows, optimizing natural light and facilitating flexible furniture arrangement, making this home an ideal canvas for any decor. Residents can indulge in the luxurious Winding Cypress clubhouse, featuring a state-of-the-art fitness center, catering kitchen, community room, and activity room. Outdoor amenities abound, encompassing pickleball courts, resort-style and lap pools, a spa, an outdoor movement studio, a barefoot bar, bocce ball courts, five Har-Tru tennis courts, a fire pit, bird-watching overlook, and a nature boardwalk with a picnic pavilion. Ideally situated near the pristine shores of Marco Island and the vibrant downtown Naples, this resort community offers an unparalleled lifestyle.

Winding Cypress Naples Homes: Welcome to the award-winning Martin Ray home in the prestigious and centrally located Winding Cypress resort community in Naples. This exceptional home features an expansive lanai set on a protected and private preserve, with room for a pool, providing the perfect space to enjoy the serene Florida sunshine. Inside, the bright and airy ambiance is enhanced by a newly enlarged center island with top-of-the-line quartz finishes throughout the kitchen, gourmet natural gas appliances, reverse osmosis water system, high-quality wood grain ceramic tile flooring and impact-resistant glass. Elegant design upgrades also include custom dining area millwork, crown molding, new lighting, plantation shutters, custom drapes and a professionally built closet system in the primary bedroom. Whether you’re hosting a lavish gathering or enjoying a quiet evening at home, this residence seamlessly blends elegance and comfort. A bonus loft offers a versatile space for guests or in-home entertainment, with ample room for a pool table or home theater. Residents of Winding Cypress enjoy an array of luxurious amenities, including a clubhouse with a state-of-the-art fitness center, catering kitchen, community room and activity space. Outdoor amenities abound, featuring pickleball courts, a lap pool, spa, outdoor movement studio, The Shady Palm Café poolside restaurant, bocce ball courts, five Har-Tru tennis courts, a fire pit, bird-watching overlook and a nature boardwalk with a picnic pavilion. Ideally located near the pristine shores of Marco Island and vibrant downtown Naples, this resort-style community provides the perfect backdrop for an unparalleled lifestyle.

Winding Cypress Naples Homes: This pristine Abbeyville home in Winding Cypress has it all and is not to be missed! Built in 2021, this property has a fresh neutral palate and features a spacious open split bedroom floor plan with 2 bedrooms + den + sunroom and 2 full bathrooms. The 2-car garage has upgraded features including AC, an insulated garage door, a 4' extension, and extra lighting. 10' ceilings add to the spaciousness of this home! Wood look plank tile flooring throughout, crown molding, tray & coffered ceilings, extra canned lighting throughout, and plantation shutters in the front bedrooms, den, and over the kitchen sink elevate this home. The contemporary kitchen offers white shaker cabinets, quartz countertops, subway tile backsplash, stainless steel appliances including a gas range & hood, dishwasher, built-in microwave, stainless steel sink, undercabinet lighting, and a large extended kitchen island with additional cabinets on one side. The primary bath features a walk-in shower, granite countertop with dual vanities & drawers, comfort height toilet, and a large walk in closet with a built-in organizer. The guest bath includes granite countertop, a comfort height toilet and an upgraded walk-in shower with glass enclosure. The spacious laundry room has plenty of storage with built-in cabinets and organizers. Relax and enjoy your own heated pool with its lovely serene preserve view. Extra clusia hedges on both sides of the pool cage provide ultimate privacy. Move in ready, the sellers have thought of it all including added features such as a widened driveway, a paved walkway from the driveway to the lanai, lush landscaping with solar outdoor lighting, whole house gutters, Ring doorbell, and even a Generac 18KW whole home generator with a warranty! Winding Cypress is a highly sought after natural gas community containing 800 acres of natural preserves and 80 acres of lakes. Top notch amenities include a resort style pool with lap lanes & spa, a screened in outdoor bar and grill The Shady Palm, fire pits & fireplace, 2 dog parks, community garden, tennis, bocce, pickleball courts, in addition to a beautiful clubhouse featuring a fitness center and community & event rooms. Conveniently located within close proximity to downtown Naples, several beaches, Marco Island, & US-41.

Winding Cypress Naples Homes: Welcome to Winding Cypress, where modern elegance meets comfort in this stunning Abbeyville model, Pulte home built in 2021. A beautiful lake view frames the backyard of this meticulously maintained, well designed residence featuring two spacious bedrooms plus a versatile den, perfect for a home office or additional guest space. Step inside to discover a thoughtfully laid out floor plan, highlighting an abundance of natural light, neutral colors, tile flooring and high-end finishes throughout. The heart of the home is the open-concept living area, seamlessly connecting the kitchen, dining, and 2 living spaces—ideal for entertaining family and friends. Enjoy the luxury of your gas heated salt water pool, perfect for soaking up the sun or hosting summer gatherings. The home is equipped with natural gas, ensuring efficient cooking and heating, while hurricane windows and doors provide peace of mind during storm season. The garage boasts abundant storage options and an epoxy floor, adding both durability and style, and there are countless upgrades including a widened driveway to accommodate 3 across parking, a screened entry, custom closet organizer system in main bedroom and chrome pullout shelving in all kitchen and bathroom cabinets that elevate its charm and functionality. In addition, Winding Cypress is a Luxury Community offering Resort style amenities such as a heated pool with zero entry and lap lanes, restaurant, tennis, pickleball, clubhouse, fitness center and so much more. Perfectly located only 8 miles to downtown Naples attractions and beaches and also convenient to shopping, dining and Marco Island. Don't miss the opportunity to make this exquisite property your own, where every detail has been carefully curated for a sophisticated lifestyle in a serene community. Note: This home is a great opportunity with $25,000 in upgrades and listed below appraised value! *Appraisal report available upon request

Winding Cypress Naples Homes: In the prestigious Naples community of Winding Cypress, this exceptional property stands out for its distinctive features, seamlessly blending nature and luxury with a resort lifestyle. Complemented by the rare convenience of direct natural gas, the award-winning Abbeyville floor plan boasts multiple builder upgrades. The unique custom pool and spa integration with bench seating offers a relaxing respite at the end of the day. Enjoy meticulous landscaping through your “picture window” lanai screen, effortlessly merging indoor and outdoor living spaces. A thoughtfully designed open concept optimizes natural light through an abundance of windows. Additional amenities include laundry area with utility sink, walk-in closet and cabinets. Built-in custom closets are throughout, including cabinetry and Murphy bed in your bonus flex room. Other amenities include diagonal tile flooring, crown molding and primary tray ceiling, wainscoting in the sunroom and a Lennox Fresh-Aire UV purifier. The epoxy-finished garage offers plenty of storage. For peace of mind, a natural gas-powered whole-house Generac generator ensures reliable power on demand. You’ll enjoy Winding Cypress’s luxurious amenity center, featuring a state-of-the-art fitness center, catering kitchen, community great room and activity room. Outdoor enthusiasts can take advantage of pickleball, tennis, bocce, resort-style waterfall pool, spa/cabana area, outdoor café with classically trained executive chef, fire pit and fireplace areas, dog park and nature boardwalk with picnic pavilion. Ideally just 20 minutes from the pristine shores of Marco Island and vibrant downtown Naples, this sought-after resort community offers an unparalleled lifestyle against a backdrop of natural beauty.

Winding Cypress Naples Homes: JUST REDUCED AND PRICED TO SELL! Welcome to one of the most desirable neighborhoods in Naples. Winding Cypress boasts resort style living with pickleball, tennis, bocci, large gym, movement room, library, internet cafe, banquet room with kitchen, restaurant, and resort style pool with waterfall and lap lane. Currently the only Summerwood model for sale with peaceful panoramic water and preserve views. This impeccably kept two bedrooms with a den that could easily be a third bedroom, 2 bath home with large laundry room with tons of custom cabinetry. The oversized garage with four-foot extension makes one side of the garage 37' which can accommodate a 21' boat and trailer or third car, custom storage gives you plenty of room for all your toys. A real must-see home!