Winding Cypress Naples Real Estate : 27 Homes for Sale

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, upgraded oversized garage, 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: 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.

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 all furniture is negotiable. 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: 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.

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: Beautiful like new mystique contemporary home. 24x24 gorgeous marble look tile floor, custom wood moldings featuring beams in trey ceiling in gathering room, upgraded kitchen back splash and faucet , custom wood hallway, decorative wood wall design in master bedroom with oversized shower and upgraded shower heads, custom master closet, design. laundry room with plenty of cabinets and storage space. Glass doors in den/office with custom office set up. Zero clearance doors that invite the outside in, outdoor kitchen with vented hood, sink and grill, pool and lake view with plenty of privacy completes this home. A/C mini split, in extended 4 ft Garage, epoxy floor and shelving and floor storage above. Home has impact windows and doors. This home is Stunning inside and out. Winding Cypress is a one of the few communities that offer Natural Gas, and a full restaurant, bocci courts, pickle ball, dog park, beautiful resort clubhouse, pool and gym. Just minutes 15 min. to downtown, Marco and 75.

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 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 Mystique 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 upgrades. The home is impeccably decorated and boasts a Chef's kitchen with upgraded cabinets & lighting, an oversized island with quartz countertops, custom plank tile flooring, 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 builder 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 upgraded 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: Located in the highly sought-after community of Winding Cypress, this beautifully updated 3-bedroom, 2-bath home offers a perfect blend of luxury, comfort, and breathtaking lake views. Surrounded by 800 acres of natural preserve and 80 acres of serene lakes, this home provides a tranquil lifestyle immersed in nature, with access to all the incredible amenities this community has to offer. Inside, the open-concept layout features coffered ceilings in the living room, adding architectural elegance and a sense of spaciousness. Plantation shutters throughout enhance the light-filled spaces, creating an inviting and sophisticated atmosphere. The chef-inspired kitchen is equipped with a large walk-in pantry, perfect for all your storage needs, and flows seamlessly into the extended great room—ideal for both casual living and entertaining. The home also boasts a den with elegant French doors, providing a private and versatile space for an office, study, or cozy retreat. The large laundry room adds practicality and convenience, while the epoxy floor in the garage combines style and durability, creating a clean and functional space. Step outside to your own private oasis with an outdoor kitchen perfect for grilling and entertaining. The sparkling pool and hot tub, surrounded by a "no-see-um" screened enclosure, offer the perfect retreat with panoramic lake views. The lanai is equipped with hurricane storm screens for added peace of mind, and a whole-house generator ensures you’ll never be without power, even during the most unpredictable weather. Winding Cypress is more than just a neighborhood; it’s a lifestyle. Residents enjoy access to the Shady Palm Café, a spacious clubhouse, and luxurious resort-style amenities such as a pool and spa, fitness center, social programs, pickleball, tennis courts, bocce, and a scenic boardwalk walking trail. Surrounded by top-tier restaurants and grocery stores, and just a short drive to Downtown Naples, this community offers everything you need for both relaxation and convenience. Don’t miss your chance to own this exceptional home in one of the most desirable communities in the area.

Winding Cypress Naples Homes for Sale: Welcome to your personal retreat in Winding Cypress, where resort-style living meets sophisticated comfort! This magnificent Summerville Extended model by Pulte is move-in ready and offers an unparalleled blend of privacy, elegance, and stunning lake views. Perfectly positioned on an oversized, pie-shaped lot with no homes behind, you’ll enjoy serene tranquility and an open vista. Entertain with ease in the spectacular gourmet kitchen, a chef's delight featuring a natural gas cooktop, premium stainless steel appliances, a wall oven, gorgeous granite countertops, and an expansive island – ideal for gatherings. A large walk-in pantry provides ample storage. The open-concept design seamlessly connects the kitchen to the great room and leads out to an extended screened lanai, creating a harmonious indoor-outdoor living experience.   Step into your private backyard oasis, complete with a sparkling saltwater pool surrounded by lush, enhanced tropical landscaping for maximum privacy. Imagine beginning and ending your days with peaceful lakefront views, coffee in hand or wine glass clinking. This home comes with an impressive list of recent upgrades for ultimate comfort and security: a new hot water heater, an upgraded A/C system (with Blue Light & HEPA filter), a new garbage disposal, updated washer and dryer, a fresh exterior paint job, a new mainspring on the garage door, full hurricane impact windows, Kevlar hurricane roll-down shutters on the lanai, AND a whole-house generator! The primary suite is a private sanctuary, offering tranquil views, a luxurious bathroom, and two large walk-in closets. The thoughtful split floor plan ensures privacy and comfort for all. Winding Cypress community amenities are second to none: a grand clubhouse with a catering kitchen, a spectacular zero-entry resort-style pool and spa, a full-service restaurant, a state-of-the-art fitness center, tennis, pickleball, bocce courts, extensive walking and biking trails, a playground, and a dog park. This idyllic setting is just minutes from the vibrant heart of downtown Naples, world-renowned beaches, exceptional dining, and upscale shopping.   Whether you're seeking a seasonal escape or the perfect place to call home year-round, this property offers an irresistible combination of luxury, prime location, and an extraordinary lifestyle. Your lakefront paradise awaits – schedule your private showing today!

Winding Cypress Naples Homes for Sale: The perfect move in ready home for sale! This Summerwood floorplan features 2 bedrooms, 2 baths+den, saltwater pool and spa, and a 2+car garage offering a blend of style, comfort, and functionality. The open-concept layout features a dramatic zero-corner slider, seamlessly connecting indoor and outdoor spaces, while the whole home generator, exterior cameras, and impact windows and doors provide peace of mind. Inside, extensive upgrades are everywhere. The kitchen boasts built-in appliances and a spacious island, perfect for entertaining. Additional highlights include built-in Sonos speakers, crown molding, hard flooring throughout, custom primary closet, and a Murphy bed in the den—ideal for guests or a home office. The thoughtful laundry room has an upgraded washer and dryer and custom cabinets with a dedicated spot for charging your vacuum. You will have tons of storage space in the air conditioned tandem garage which can accommodate up to three cars. Outside, the saltwater pool and spa are heated by both gas and solar (a smart money-saving combo), expansive outdoor kitchen, hurricane screens for a second layer of protection, privacy lanai screening, plenty of seating areas, gorgeous lush landscaping, and areas for storage. This home has been meticulously maintained, most recently the duct work was cleaned and pavers sealed. 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: 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: 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. Situated on a picturesque lake in the serene WINDING CYPRESS Community, this stunning home comes with a TRANSFERRABLE FLOOD POLICY. 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 GAS STOVE and the convenience of a BUTLER'S PANTRY. The exquisite QUARTZ COUTERTOPS complete the perfect setting for entertaining and everyday living. The home is adorned with IMPACT WINDOW 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: 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 activities 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: ** PRICE REDUCTION ** Stunning Abbeyville home in Winding Cypress is move-in ready! This immaculate residence is a must-see, featuring a fresh neutral palette, offering a spacious open split-bedroom floor plan with 2 bedrooms, a flex/den & 2 full bathrooms. Entertainment is elevated with flat-screen TVs mounted in both bedrooms & living area. Soaring ceilings enhanced by elegant molding, tray & coffered details, along with extra recessed lighting. Plantation shutters in the front bedroom, flex/den & over the kitchen sink add both privacy & style. Enjoy matching tile flooring throughout the main areas, with warm wooden plank flooring accentuating the flex/den room. A new HVAC unit, installed in December 2021 & serviced bi-annually ensures year-round comfort. The gourmet kitchen is a chef’s delight with upgraded white shaker cabinets, quartz countertops, a stylish subway tile backsplash & stainless steel appliances including a gas range & hood, dishwasher, built-in microwave, & a stainless steel sink with in-sink disposal. Exquisite cabinet lighting brightens the space, while a large extended kitchen island with additional cabinets provides ample storage. The primary suite features a luxurious walk-in shower with a glass enclosure, dual vanities with a quartz countertop, leading onto a fabulous walk-in closet with built-in organizers. The guest bathroom similarly boasts upgraded features with a tub & shower/glass enclosure, quartz countertop & spacious linen closet. The convenient laundry room is outfitted with upgraded front-load washer & dryer along with built-in cabinets & organizers. Outside, the stunning outdoor oasis beckons with a crystal-clear kidney-shaped pool offering serene lake views. Privacy hedges frame the pool cage, which features both covered & uncovered lanai areas - the perfect balance for year-round enjoyment. Upgrades include new pool cage screens & a pool heater (December 2022). Additional features include built-in easy-to-slide high-end accordion hurricane shutters & an extended 2-car garage with epoxy flooring. Located in the premier Winding Cypress community - A highly sought-after natural gas community set among 800 acres of natural preserves & 80 acres of lakes - this home offers resort-style amenities including a lap pool with spa, screened-in outdoor bar & grill (The Shady Palm), fire pits, fireplace, two dog parks, a community garden, tennis, bocce & pickleball courts, a state-of-the-art clubhouse with a fitness center plus event rooms. Ideally situated just minutes from Downtown Naples, several beaches, Marco Island & US-41/I-75, this property blends luxury & convenience effortlessly. Don’t miss out on this incredible opportunity!

Winding Cypress Naples Homes for Sale: Welcome to this beautifully appointed 3-bedroom, 2-bathroom + den home in the vibrant and sought-after community of Winding Cypress in Naples. Perfectly positioned on a prime lakefront lot, this residence offers serene, long water views that extend to the untouched beauty of the preserve beyond. Thoughtfully designed for both comfort and style, this home features tall interior doorways, an extended screened-in lanai, and a fully equipped outdoor kitchen—ideal for entertaining or enjoying peaceful evenings overlooking the lake. Storm shutters provide added security and peace of mind, while the open and versatile layout includes a den perfect for a home office or flex space. The well-appointed kitchen boasts a gas range, catering to culinary enthusiasts, and a natural gas whole-home generator ensures uninterrupted comfort during any weather event. Additional conveniences include an HOA that covers landscaping and irrigation water, allowing for low-maintenance living. Winding Cypress is a gated, resort-style community offering an exceptional array of amenities. Residents enjoy a luxurious clubhouse, a tropical pool with waterfall features, a soothing spa, and a state-of-the-art fitness center. Recreational and social opportunities abound with pickleball, tennis, bocce, and a full calendar of community events. The Shady Palm Café serves delicious food and drinks poolside, while a scenic boardwalk winds through the community’s pristine natural surroundings. A spacious, secure dog park makes this neighborhood perfect for pet lovers as well. Conveniently located just off US-41, Winding Cypress offers easy access to world-class dining, shopping, entertainment, and the white-sand beaches that define Naples living. Experience the perfect blend of privacy, luxury, and vibrant community life in this exceptional home.

Winding Cypress Naples Homes for Sale: Sophisticated living with serene views in this rarely available Abbeyville model built in 2021. This home provides a shining example of comfort, style, and thoughtful design. Ideally positioned to offer peaceful water and sunset views, has been meticulously maintained and invites you to enjoy the absolute best in a Florida lifestyle. Step inside through a welcoming entryway and discover an open-concept floor plan filled with natural light. The heart of the home is the great room with tray ceiling and crown moldings, the modern kitchen, beautifully appointed with granite countertops, sleek stainless-steel appliances, and a generous center island suited for both everyday living and effortless entertaining. The spacious primary suite offers a peaceful retreat with a walk-in closet, double vanity, walk-in shower. A guest suite features an adjoining full bath, offering privacy and convenience for visiting friends or family. A versatile den provides the ideal setting for a home office or can easily serve as a third bedroom. The consistent tile flooring flows throughout the home. Step out to the extended lanai, plumbed for you to design your own outdoor kitchen where you will enjoy quiet mornings or relaxing evenings with tranquil views. The large private lot provides plenty of space to envision your own custom pool. This beautifully cared-for home offers a rare opportunity to enjoy an elevated lifestyle in a sought-after Winding Cypress Community—where every detail speaks to comfort, elegance, and thoughtful living. Winding Cypress is one of Naples hidden gems. Of the total 1250+ acres in the development, over 800 acres are dedicated to green space and preserve areas along with 80 acres of stunning lakes. The community is filled with amenities that include a full-service, residents only private restaurant, Las Vegas inspired resort pool, pickleball, tennis, and bocce courts. The expansive community center boasts a world class fitness gym and movement room, his and hers locker rooms, conference rooms and a library. Winding Cypress is pet friendly with 2 separate fenced in areas for K9 to play. HOA management and friendly staff are onsite to assist and coordinate regular events for all to enjoy.

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: PRICE DRASTICALLY REDUCED FOR QUICK 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: 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: Set against private garden views with tranquil eastern exposure, this beautifully appointed villa in Winding Cypress offers a peaceful retreat and effortless indoor-outdoor living. Featuring two bedrooms plus a den, two baths, and a two-car garage, this thoughtfully designed residence combines quiet luxury with meticulous updates in one of Naples’ most dynamic lifestyle communities. The screened lanai is ideal for entertaining or unwinding, complete with brick paver flooring, a saltwater pool with waterfall feature, pool heater, and recent upgrades including a new salt generator and pool pump. A custom outdoor kitchen with a stainless steel gas grill with matching hood and sink further enhances the outdoor living experience. Electric hurricane shutters protect the lanai, while manual shutters cover the remainder of the home. Inside, tile flooring extends throughout, accented by crown molding, recessed lighting, and white plantation shutters. The living room opens to the lanai through expansive glass sliders, anchored by a modern ceiling fan. The kitchen features white Shaker-style cabinetry, quartz countertops, a tile backsplash, pantry, and stainless steel appliances including a gas range, refrigerator with icemaker, microwave, and dishwasher. A modern chandelier defines the dining area, which flows easily into the main living space. The primary suite is a private haven with a tray ceiling, garden views, custom closet, and a spa-inspired bath featuring dual quartz vanities, full-width mirrors, and a frameless glass walk-in shower. The second bedroom includes a walk-in closet and an adjacent bath with a shower-tub combination. A den with French doors offers flexible space for a home office or reading room. Additional highlights include a mini-split air conditioning system in the garage, a brand-new water heater, and recent property updates including a full exterior repaint (approximately two years ago) and interior paint touch-ups. Residents of Winding Cypress enjoy access to resort-style amenities including a pool, an attended fitness center, an on-site restaurant, five tennis courts, four bocce ball courts, four pickleball courts, a community garden, and a dog park. With a vibrant social calendar, low HOA fees, rental-friendly policies, and a prime location near Marco Island, downtown Naples, 5th Avenue, and I-75, this villa offers elevated living in a premier Naples community.

Winding Cypress Naples Homes for Sale: Sophisticated Villa Living in Winding Cypress – Priced to Sell/Fully Furnished. An extraordinary opportunity awaits in the highly sought-after Winding Cypress community—this impeccably upgraded 3-bedroom, 2-bathroom villa is set on the largest homesite in the neighborhood, offering both privacy and an expansive outdoor retreat. Thoughtfully enhanced with luxury upgrades and high-end finishes, this residence is a rare find, now priced competitively for discerning buyers seeking exceptional value. From the moment you step inside, you’ll appreciate the seamless open-concept design, accentuated by elegant crown molding and designer window treatments. The chef’s kitchen features stunning granite countertops, a specialty tile backsplash, and a well-appointed summer kitchen with a Paradise Grill, bar seating, refrigerator, and a 5-year transferable warranty—perfect for effortless entertaining. The home is designed for both comfort and peace of mind, featuring an integrated whole-house backup generator, carbon monoxide detectors, an advanced security system with perimeter cameras and video doorbell, electronic front door lock, and accordion shutters on all windows. The extended, screened-in lanai—complete with ceiling fans, lighting, and electronic roll-down hurricane/security shutters—invites you to unwind in a serene outdoor sanctuary. Additional premium upgrades include a brand-new state-of-the-art extra-large capacity washer/dryer (2024) with a 5-year transferable warranty, epoxy-coated garage flooring and custom storage system (2024), split-fin garage A/C (2024) for year-round climate control, garage door and attic insulation (2024) for enhanced energy efficiency, and lush upgraded landscaping and exterior lighting for impeccable curb appeal. Resort-style living is at your doorstep with access to Winding Cypress’ world-class amenities, including a 5-star clubhouse with dining, resort and lap pools, a jacuzzi, fitness center, tennis, pickleball, bocce courts, a dog park, and more. This is a rare chance to own a premier villa in one of the area’s most coveted communities—offered at an exceptional value for those ready to make it their own. Schedule your private tour today and experience the elegance, comfort, and convenience of this one-of-a-kind residence.

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.