Winding Cypress Naples Real Estate : 23 Homes for Sale

Winding Cypress Naples Homes for Sale: Welcome to this stunning Tangerly Oak model home, thoughtfully designed with space, style, and Florida living in mind. This expansive 4-bedroom residence with a generous loft offers a flexible floor plan ideal for both everyday living and hosting guests, all enhanced by beautiful designer upgrades throughout. Step outside to an exceptional outdoor living space featuring a large covered lanai, resort-style pool and spa, and a fully equipped outdoor kitchen, perfectly positioned to capture long, wide lake views that create a peaceful and picturesque backdrop. Inside, the home is filled with light and refined finishes, showcasing the elevated craftsmanship and attention to detail that make the Tangerly Oak so desirable. Every space feels open, comfortable, and inviting. The community offers an impressive array of amenities, including a clubhouse, resort-style pool, fitness center, tennis, pickleball, bocce courts, and a dog park. Ideally located in a highly convenient area with easy access to restaurants and shopping, and just about 15 minutes from downtown Naples, this home delivers both luxury and lifestyle in one exceptional package.

Winding Cypress Naples Homes for Sale: FINALLY, your own PRIVATE & SERENE OASIS, you’ll never get tired of. Not some angled or cropped view- just Actual Expansive Preserve Views! This exceptional setting provides a rare sense of seclusion and tranquility, creating an authentic Florida paradise lifestyle. This is a unique residence in Winding Cypress. This residence offers unmatched privacy and outdoor living, with exceptional standout features: an expansive screened lanai with custom multi-color accent lighting, saltwater, heated, multi-color lite pool, plus an outdoor dry bar with refrigerator and cabinetry—all designed to create your own private resort overlooking nature. Inside, every detail reflects model-quality craftsmanship and UPGRADES galore! The home showcases a chef’s kitchen with Alexa-linked gas 5 Burner stove/oven, upgraded cabinetry with pull-out drawers, upgraded appliances. A butler’s wine bar with under cabinet lighting cabinetry throughout, upgraded wine dual temp refrigerator, pantry shelving, all add elegance and convenience. Additional upgrades include custom wall features, garage hallway bench with storage unit, and abundant built-in closet storage. The primary suite is highlighted by a custom walk-in closet with cabinetry, blending function and style. Custom front and lanai accent lighting enhance both curb appeal and evening ambiance. Prewired for Vitex audio video home automation. Winding Cypress is one of Naples’ premier resort-style communities, surrounded by 800 acres of preserve and 80 acres of lakes. Residents enjoy a zero-entry resort pool and spa, the Shady Palm Café with full-service bar and grill, a state-of-the-art fitness center, pickleball and tennis courts, dog park, community garden, walking/biking trails, and a full social calendar curated by the on-site activities’ director. All of this is just minutes from downtown Naples, Marco Island, beaches, world-class golf, shopping, and dining—yet with the peace and seclusion of a preserve setting. This is more than a home; it is a rare lifestyle opportunity combining privacy, luxury, and nature in perfect harmony.

Winding Cypress Naples Homes for Sale: Spacious & Immaculate accurately describe this outstanding retreat in the sought-after community of Winding Cypress. This rare, two-story Mystique footprint boasts 4 bedrooms, 3 full baths, a large den/office, and over 3160 square feet of adjusted living space, 3036 square feet under air. This residence was one of the last built in the community, 3 years new, and shows like a model home. Located on a very private lot on a cul-de-sac, this salt water pool home with private spa is meticulously one-owner maintained, beautifully decorated, and loaded with builder upgrades. For peace of mind, the owners added a whole house generator as well. The expansive, upstairs addition includes a huge private bedroom, a full bathroom, and an incredible flex area that can accommodate a 5th bedroom, cinema room, office, or however this extra space can benefit your living wants and needs. Winding Cypress is an amenity rich and active community with on-site management and a full-time Activities Director. It's perfectly situated just 15 minutes away from the restaurants, shoppes, and beaches of downtown Olde Naples, and only 10 minutes to all the entertainment of Marco Island.

Winding Cypress Naples Homes for Sale: The View !!!!!!!! built in 2022 Move in Ready ! Like new Contemporary style mystique model 3 bdrm den 2bath in Winding Cypress. Location Location with this breathtaking long lake view , last home on street on long landscaped corner affords plenty of privacy.Some of the Upgraded features consist of a widened paved recently sealed driveway comfortably fitting 2 cars side by side, zero clearance corner doors that invites the outside in, 4ft extended garage for larger vehicles plus overhead storage with Mini a/c split . whole house generator, impact windows and doors, outdoor kitchen numerous designer interior upgrades. tile marble look floors customs walls and designer closet system . full office set up for those working from home or seller will remove and redo room if requested. Great opportunity to live in Winding Cypress and all that this community has to offer

Winding Cypress Naples Homes for Sale: Welcome to newest and last phase of homes built in 2020 in the vibrant well maintained community of Winding Cypress. Located just off Collier and 41 and minutes to 75 , Marco Island and downtown Naples This summer wood model is sure to please with 3 bdrms 2 baths with full showers , primary bath with custom mirrors. custom closet , plantation shutters mini a/c in garage, whole house water purifier, generator, storm screens on lanai ,outdoor kitchen , pool and spa. with private views to the preserve ,vaulted ceilings, ceiling fans in every room , and oversized neutral tile through out placed on the diagonal . some furniture can remain with the house . exlcuded dining light fixture

Winding Cypress Naples Homes for Sale: Welcome to this beautifully designed residence located within one of Naples’ most desirable gated communities. The open-concept floor plan is enhanced by volume and tray ceilings, crown molding, plantation shutters throughout, and an extended driveway, adding both elegance and curb appeal. The spacious kitchen features granite countertops, a gas cooktop, wall oven, and ample cabinetry—making it both functional and inviting for everyday living and entertaining. Hurricane-impact doors and windows, along with electric hurricane screens on the lanai, provide peace of mind while framing tranquil lake views. Step outside to the expansive covered lanai with a summer kitchen, ideal for outdoor dining, entertaining, or enjoying a quiet morning coffee. While perfectly suited for those who prefer low-maintenance living without a pool, the home is also pool-ready should you wish to add one in the future. Tile flooring throughout enhances the home’s clean, modern aesthetic. The primary suite serves as a private retreat, offering dual sinks, a soaking tub, a separate walk-in shower, and generous walk-in closets. A thoughtfully designed laundry room with built-in cabinetry and a sink adds everyday convenience. Residents enjoy access to outstanding community amenities including bocce, tennis, pickleball, a resort-style pool, and the popular on-site community restaurant, Shady Palm, all just a short walk from the home. Ideally located minutes from world-class shopping, dining, and Naples’ renowned beaches, this property truly delivers the best of Naples living.

Winding Cypress Naples Homes for Sale: Discover resort-style living in this rare three-bedroom plus den, three-bath natural gas home in the highly sought-after community of Winding Cypress. Designed for privacy and effortless indoor–outdoor living, it features an oversized fully custom pool with integrated seamless spa and a panoramic barless screen lanai, integrated home theater sound, all overlooking lush, tranquil landscaping. The great room opens with a dramatic zero-corner disappearing slider, and the home is nearly brand new with 2022 construction still under the renowned DiVosta builder warranty. Located on a private cul-de-sac, this home offers peaceful living while keeping you close to world-class amenities. Winding Cypress boasts private nature trails, community gardens, and an impressive 18,000-square-foot resort clubhouse with a poolside restaurant, full-time activities director, lap lanes, zero-edge resort pool with waterfall, fire pit, pickleball, tennis, and more. The community now features two grand entrances/exits on both Tamiami Trail (U.S. 41) and Collier Boulevard (951), offering exceptional convenience.

Winding Cypress Naples Homes for Sale: Stunning 3-Bedroom + Den Home in Sought-After Winding Cypress – Welcome to your dream home in the prestigious, resort-style community of Winding Cypress in Naples, FL. Built in 2022, this impeccably maintained 3-bedroom + den, 2-bathroom residence blends modern design with everyday comfort. Step inside to find an open-concept floor plan featuring, abundant natural light, and contemporary finishes throughout. The kitchen boasts quartz countertops, stainless steel appliances, a large center island, and a spacious pantry—perfect for entertaining or casual family meals. The flexible den space offers the ideal setup for a home office, media room, or guest overflow. The primary suite is a serene retreat with a large walk-in closet and a spa-like ensuite bathroom featuring dual vanities and a walk-in shower. Recently installed lights on the lanai make the area glow at night. Very private preserve views! Also recently installed are electric retractable hurricane screens for added safety. Enjoy Florida living at its best with a screened lanai, ideal for relaxing or dining alfresco, with a large heated pool. The home also includes a 2-car garage, impact windows, and smart home features for added peace of mind. Residents of Winding Cypress enjoy resort-caliber amenities including a large clubhouse, fitness center, resort pool & spa, on-site restaurant, tennis & pickleball courts, fire pit, dog park, and over 800 acres of preserved natural space with walking/biking trails. Conveniently located just minutes from downtown Naples, white sand beaches, shopping, and dining. Don’t miss this rare opportunity to own a move-in ready home in one of Naples’ most desirable communities!

Winding Cypress Naples Homes for Sale: This gorgeous Mystique floor plan features 3 bedrooms, a den, a rare 3 full bathrooms, heated pool, and a 2-car garage. Inside the home is loaded with upgrades, impact windows and doors, custom built-in cabinetry in the living & laundry room, crown molding, tray ceilings, recessed lighting, electric blinds, designer hardware and lighting, and abundant storage throughout. Embrace the Florida lifestyle with the open-concept zero-corner slider connecting the indoor and outdoor living spaces. The pool deck offers a spacious covered lanai, a modern pool, added privacy, and highly desirable southwest exposure. No detail has been spared in the garage, which features a built-in workbench and storage, an electric screen garage door, epoxy flooring, and plenty of room for bikes and more. 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 two dog parks for your furry friends. This pet-friendly community allows rentals, has low fees, and boasts a prime location—convenient to Marco Island, 5th Avenue, and I-75.

Winding Cypress Naples Homes for Sale: Over 2200 Sq ft complete with your own POOL this is a great opportunity! Don't wait Check out this impeccably maintained residence offers an exceptional living experience. The open floor plan features THREE spacious bedrooms, a versatile den or flex room, and two full bathroom. Elegant details include crown molding, tray ceilings, plantation shutters, Hunter Douglas blinds, and updated LVP flooring. The ADDED SUNROOM provides a tranquil space for relaxation or entertaining. The custom gourmet kitchen equipped with under-cabinet lighting, granite countertops, a wall oven with microwave, gas cooktop, matching range hood, soft-close drawers with pull outs, and a walk-in pantry for more than ample storge. This property sits on an OVERSIZED PRIVATE lot with tropical landscaping, a newly screened lanai, and a large pool. STORM SCREENS and IMPACT GLASS windows and doors ensure year-round comfort and security. Additional upgrades include a WHOLE HOUSE GAS GENERATOR, NEWER HVAC system with UV lighting and HEPA filter, a NEW HOT WATER HEATER and an insulated garage door with new main spring. The FRESHLY PAINTED EXTERIOR and professionally inspected and cleaned roof complete with new roof vents enhance curb appeal and reliability. Residents enjoy access to resort-style amenities, including a clubhouse with a full-service restaurant and bar, event room, library, heated zero-entry pool with waterfall, spa, beach cabanas, and fire pit. The fitness center, movement studio, pickleball and tennis courts, bocce ball, walking and biking trails, nature boardwalk, community garden, and dog parks promote an active lifestyle. The community is set within over 800 acres of natural preserves and 80 acres of lakes, offering a luxurious and tranquil environment with convenient access to downtown Naples in about 15 minutes and Marco Island beaches.

Winding Cypress Naples Homes for Sale: Discover your dream home in the prestigious Winding Cypress community! This newly constructed, pet-friendly residence boasts 3 spacious bedrooms plus a versatile den, perfect for guests or a home office. Designed for seamless entertaining, the open-concept floor plan flows effortlessly, with zero-corner sliders merging the indoor living area with a stylish outdoor kitchen and bar—ideal for hosting family and friends. The living room and kitchen showcase beautiful tile flooring, adding elegance and durability to these high-traffic spaces. As you enter through the gated Winding Cypress entrance, you’re greeted by lush, resort-style grounds that instantly evoke a vacation vibe. Enjoy unparalleled amenities, including a resort-style pool, restaurant/bar, fire pit, state-of-the-art fitness center, outdoor yoga deck, pickleball, tennis, bocce ball, community garden, dog park, and a serene nature trail boardwalk winding through protected preserves. Perfectly situated between Marco Island and Fifth Avenue South, this home offers unmatched convenience, just minutes from pristine sandy beaches, world-class shopping, dining, and entertainment. Don’t miss the opportunity to own this exquisite retreat in one of Naples’ most sought-after communities!

Winding Cypress Naples Homes for Sale: Discover refined living with this beautifully appointed villa in Winding Cypress, where luxury and comfort meet in perfect balance. Designed for those who appreciate both elegance and ease, this home offers an unparalleled lifestyle inside and out. Arriving fully furnished and enhanced by the sellers’ two-seater Club Car golf cart, this property delivers a true move-in ready experience. Every detail has been curated for effortless enjoyment, whether you’re entertaining guests or savoring quiet moments at home. The gas-heated pool invites you to relax in your own private oasis, while the outdoor kitchen transforms casual gatherings into memorable evenings under Florida’s open skies. Indoors, the chef’s kitchen makes a bold statement with sleek Samsung appliances and striking quartz countertops. A thoughtful list of updates and enhancements reflects the exceptional care invested in this residence, ensuring peace of mind for the next owner. With its combination of sophistication, style, and fully furnished convenience, this villa represents one of the finest offerings in Winding Cypress.

Winding Cypress Naples Homes for Sale: Winding Cypress – PRICE REDUCED TO SELL- Rare opportunity to purchase in this community at this price point. Welcome to your Florida dream home in the sought-after gated community of Winding Cypress! This immaculate residence built in 2016, offers the perfect blend of modern luxury and relaxed coastal living. Featuring 2,230’sq under air, 4 bedrooms or use the 4TH bedroom as a den. Two full baths, and an open-concept floor plan, this home is designed for comfort and entertaining. Step inside to find upgraded tile flooring, a gourmet kitchen with granite countertops, stainless steel appliances, and a large center island ideal for gathering with friends and family. The spacious great room opens through sliding glass doors to a screened lanai, creating seamless indoor-outdoor living. This home also features a "sunroom" addition and an oversized garage. Enjoy peaceful views of the lush landscaping and lake—the perfect backdrop for morning coffee or sunset cocktails. The primary suite offers a spa-like bath with dual sinks, walk-in shower, and large walk-in closet. Additional features include plantation shutters, crown molding, impact-resistant windows and doors, new electric hurricane screens, a "sunroom" addition not included in other floor plans, and an oversized garage and a 2-car extended garage with epoxy flooring. Located within minutes of downtown Naples and the Gulf beaches, Winding Cypress offers resort-style amenities including a lagoon-style pool, on-site restaurant, tennis, pickleball, fitness center, dog park, and miles of nature trails. Move-in ready, this is the best priced home of its size in Winding Cypress — this home combines style, value, and an unbeatable location.

Winding Cypress Naples Homes for Sale: This home has just been freshly painted inside and out. professionally painted kitchen and bath cabinets, nice private south west waterview , screened lanai able to enlarge or even add a pool. Previous owner had a great workshop in garage with 8 overhead lights, charging station for a Tesla , framed peg boards for hanging tools , custom storage cabinets and a pull down staircase for added storage. Home features 2 bedrooms 2 baths plus den a whole house generator and attached manual and electric storm shutters. Remaining furniture in home is staying. Live Oak is a beautiful mature tree lined street on cul de sac and just a short walk to the amenity center, dog park or community garden This home is ready for immediate occupancy Winding Cypress amenity center offers so much within its gates, its own Shady Palm restaurant, resort pool , gym , bocci and pickleball courts, dog park , walking trails and so much more. Winding Cypress is a gated community located just mins to 75, downtown and Marco Island. Photos to be uploaded on 1/24

Winding Cypress Naples Homes for Sale: Some of the most stunning sunset water views in all of Winding Cypress can be enjoyed right from your pool and spa overlooking the sparkling long lake, where a fully equipped natural gas outdoor kitchen with a vented hood creates the ultimate setting for entertaining or simply relaxing and taking in the view. Inside, the open floor plan feels light, bright, and inviting with updated flooring and beautiful quartz and granite surfaces throughout. The home includes two large bedrooms plus a flexible den with an alcove space for a closet, making it ideal for guests or a home office. The gourmet kitchen blends style and function with granite countertops, a tasteful tiled backsplash, staggered cabinetry with under and over cabinet lighting, and bar seating for casual gatherings. Ceiling-mounted garage storage racks add convenience, and natural gas service enhances the home and outdoor living experience. Gently lived in as a pet-free, smoke-free seasonal residence, the property shows like new. Residents of Winding Cypress enjoy more than 800 acres of natural preserves and resort style amenities including a clubhouse with a heated pool, on site restaurant, fitness center, white sand beach, tennis and pickleball courts, dog park and scenic nature trails, all with low HOA fees and an ideal location just 25 minutes to Fifth Avenue South, 20 minutes to Marco Island, and five minutes to major shopping, making this home a blend of luxury, lifestyle and unforgettable views.

Winding Cypress Naples Homes for Sale: Single Family home in Winding Cypress -Ready for the season!! This charming model is the perfect fit featuring an inviting open-floor concept where natural light streams through the windows. The kitchen boasts granite counters, stainless appliances and a center island and extra storage for everyday use and easy entertaining. The pantry closet has plenty of space for all of your staple goods. Tile floors are throughout much of the space. There's a den/flex room with french doors that can be used as an additional bedroom when needed or office, hobby or quiet sitting room. Additional guest bedroom and bathroom with combined tub and shower and granite topped vanity offers privacy for your family and guests. The laundry room features a spacious storage area with shelving for your all your supplies. There are storage racks in the two car garage to house your coolers for the beach. Be sure to take time to relax and enjoy your morning beverage and the beautiful sunsets on the screened lanai that overlooks the OVERSIZED lot with mature landscaping complete with an outdoor kitchen with grill, sink, and fridge for your convenience. Winding Cypress is a sought after, gated community and is appreciated for its active, social lifestyle and world class amenities. It’s nestled within 800 acres of natural preserve and 80 acres of serene lakes teeming with migratory wildlife. Head over to the clubhouse with state-of-the-art fitness center, locker rooms with showers, movement room for classes, internet café, event room, catering kitchen, resort-style pool with spa and cabanas, restaurant with bar, firepit, pickleball, tennis and bocce courts. Take the pups to play in the dog park. Walk or ride your bike on the many paths including the peaceful preserve boardwalk. If gardening is your passion, there is a community garden to grow your favorite vegetables. HOA management and friendly staff are onsite to assist and coordinate regular events for all to enjoy. Minutes from beaches, golfing, fishing, boating, shopping, and cultural activities. It's time to enjoy the Florida lifestyle!

Winding Cypress Naples Homes for Sale: Situated within the gated, amenity-rich community of Winding Cypress, this thoughtfully designed two-bedroom plus den, two-bath residence offers an exceptional blend of comfort, quality, and relaxed Florida living. The open floor plan is enhanced by wood flooring throughout the main living areas, along with crown molding, and a distinctive coffered ceiling in the living and dining area, creating a refined yet inviting atmosphere. The kitchen is both elegant and functional, featuring 42" white cabinetry, granite countertops, tile backsplash, undercabinet lighting, and stainless-steel appliances—ideal for everyday living and entertaining alike. A flexible den with French doors provides the option for a private home office, media room, or additional guest space. Seamless indoor-outdoor living is achieved through the expansive custom lanai, designed for entertaining with an outdoor kitchen complete with gas grill, refrigerator, and sink, an above-ground hot tub with ample seating, and picture-frame lanai screens that showcase peaceful preserve surroundings. Additional highlights include a whole-house generator, two-car garage, and plantation shutters. Winding Cypress is a natural gas community thoughtfully designed around preserved natural beauty and an active, social lifestyle. At its heart is an impressive clubhouse with a heated resort-style pool and spa, poolside dining at The Shady Palm, state-of-the-art fitness center, library, and community gathering rooms. Other amenities include pickleball and tennis courts, bocce courts, dog parks, a community garden, and scenic walking and nature trails. Known for its welcoming atmosphere and beautifully maintained grounds, Winding Cypress offers a true sense of community while remaining conveniently close to everything Naples has to offer. A golf cart is included for effortless access throughout the neighborhood.

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: Welcome to your own slice of paradise. This stunning home invites you to live the dream, with two spacious bedrooms—each boasting generous walk-in closets—and two full bathrooms designed for ultimate comfort. Picture hosting guests effortlessly: the guest bedroom hallway's pocket door creates a private en-suite retreat, while both showers gleam with porcelain tile reaching to the ceiling, framed by sleek glass doors. In the master bath, a custom full-wall mirror reflects your serene start to the day, enhanced by elegant drop-down lighting—a high-end designer flourish that adds a touch of luxury. Versatility awaits in the den, tucked behind beautiful glass doors, ready to serve as your cozy office, inspiring workspace, or even a third bedroom. The expansive Great Room, crowned by 9'4" ceilings that amplify the sense of openness—ideal for gathering with friends or simply relaxing after a delightful day exploring Naples. The kitchen and baths feature quartz countertops and premium solid wood cabinets with soft-close doors and drawers. Throughout, high-traffic-grade porcelain tile flows underfoot, paired with upgraded smooth-finish walls, creating a polished, modern canvas that enhance both style and everyday joy. Step outside to your premium lot, where spacing between villas is welcome, and the view over the community's second-largest lake promises endless tranquility—timeless waters mirroring the sky. With the rear facing west, evenings become magical with vibrant sunsets. The primary exterior wall, oriented south, floods the interior with natural light, infusing your days with energy and warmth. Rest easy knowing everything is meticulously maintained: appliances, A/C, and water heater have been problem-free since new. Embrace the convenience of natural gas for cooking, drying laundry, and heating water. Fiber optic service ensures seamless 4K streaming and lightning-fast web access. A revalidated FEMA Letter of Map Change places it in Zone X, outside 100- and 500-year floodplains, so no flood insurance is needed. Impact windows and doors throughout deliver energy efficiency, superior sound insulation, and zero maintenance—slashing insurance premiums while granting absolute reassurance. This is truly a minimal-risk sanctuary. Nestled in the coveted Winding Cypress community—a "best buy" gem with low HOA fees—you'll feel the vibrant pulse of neighborhood life. Stroll, bike, or golf-cart to the onsite restaurant for casual dinners, modern fitness center for workouts, sparkling community pool for lazy afternoons, or a full calendar of social gatherings that foster friendships. Positioned between downtown Naples and Marco Island, pristine beaches, upscale shopping, and exquisite dining are minutes away, making every outing an adventure. This is a spectacular home in a wonderful community and Naples location. Paradise awaits your attendance.

Winding Cypress Naples Homes for Sale: Rare villa opportunity in Winding Cypress! This turnkey, fully furnished villa sits on an extra-large, ultra-private lot with exceptional spacing between neighbors, creating a peaceful and open feel that is hard to find. The backyard is a retreat, featuring a saltwater private pool framed by mature cypress trees, colorful landscaping and wide natural preserve views. Inside, the home offers thoughtful upgrades including 8-foot interior doors, new bedroom flooring, refreshed landscaping and built-in garage storage that helps keep everything organized. As a natural gas home, it features gas cooking and provides flexibility for future enhancements, offering efficiency and convenience. Living in Winding Cypress means enjoying resort-style amenities without the high fees. Residents have access to an expansive resort pool with beach entry, a full-service restaurant and bar, a state-of-the-art fitness center, pickleball, tennis and bocce courts, a dog park, and miles of scenic walking and biking trails. The beautifully designed clubhouse includes a social hall, gathering spaces and a library, creating opportunities to connect and engage with neighbors. This home blends nature, privacy, comfort and community into one exceptional offering.

Winding Cypress Naples Homes for Sale: Welcome to this meticulous light and bright two bedroom plus den, two bathroom property located in the preserve style, amenity rich community of Winding Cypress. Featuring stainless steel appliances, roomy kitchen, in residence laundry room with newer washer and dryer, screened in lanai, and open floor plan this home has multiple indoor and outdoor spaces for entertaining guests and hosting family. MOTIVATED SELLERS with furnishings NEGOTIABLE! Pet parents rejoice as Winding Cypress offers a dog park and various walking paths for your fur babies to enjoy in addition to the manicured back yard. A plethora of amenities ensures there’s something for everyone, with a resort style pool, attended fitness center, restaurant, five tennis courts, four bocce ball courts, four pickleball courts, and a packed social calendar to name a few. Conveniently located between iconic Marco Island and historic downtown Naples, the dining and shopping opportunities at your fingertips are endless. SELLERS NOW OFFERING $5,000 CONCESSIONS TOWARDS BUYER'S CLOSING COSTS! Lanai rescreened with BRAND NEW SCREEN January 2026!

Winding Cypress Naples Homes for Sale: OPPORTUNITY AWAITS – LOWEST PRICE AVAILABLE! Welcome to the largest villa model in Winding Cypress, featuring a rare private front entrance and expanded foyer that sets the tone for this thoughtfully designed home. This spacious 2-bedrooms and massive den offers an open yet defined living concept with abundant natural light and seamless indoor-outdoor flow. Enjoy a long list of builder upgrades including granite countertops, high-end porcelain tile flooring, a glass-tiled backsplash, premium cabinetry and crown molding throughout. Step outside to your expansive private yard and lanai offering plenty of space to add a pool or design your dream sundeck. Winding Cypress is one of Naples’ most sought-after resort-style communities spanning over 800 acres of pristine preserve and ideally located between Marco Island and downtown Naples’ 5th Avenue. Residents enjoy exceptional amenities including a dog park, community garden and the stunning 18,000 square foot clubhouse featuring a resort-style pool with sand cabanas, on-site restaurant and bar, pickleball, bocce and clay tennis courts, yoga deck, nature trails, state-of-the-art fitness center, fire pits, social lounges and a full-time professional activities director creating a vibrant lifestyle where every day feels like a vacation.

Winding Cypress Naples Homes for Sale: Experience luxury living in this beautifully appointed Serenity villa, greats you with LED walkway lighting along the entrance pathway. This property is nestled in one of Naples’ most desirable communities. This home features two spacious bedrooms, two elegant baths, and a flexible den—perfect for a home office, hobby room or additional guest area. The upgraded kitchen is equipped with stainless steel appliances, quartz counter tops in kitchen and both bathrooms, and bright 42” cabinetry with under lighting, creating an inviting space for entertaining. Enjoy the open-concept living and dining area with stylish tile flooring on the diagonal throughout, plantation shutters on all windows, and 2 interior pocket doors that provide privacy to the owners and guest suite areas. The sliding doors lead to a private covered screened lanai ideal for relaxing or dining outdoors. A large rear lot where you can design your own pool area if so desired. This property provides ample space for both relaxation and functionality as a vacation home or easy full-time Florida living. As a resident of Winding Cypress, you’ll have access to premier amenities including tennis, pickleball, bocce, a state-of-the-art fitness center, an exclusive on-site restaurant, and a resort-style pool with lap lanes and a waterfall. Located just minutes from Marco Island and Naples’ iconic 5th Avenue, this villa offers the perfect blend of comfort, style, and convenience for vacation or year-round living.

Winding Cypress Naples Homes Under Contract: Motivated Seller! Luxurious Lakeside Living in Winding Cypress – Rare One Owner Pinnacle Model! Welcome to this stunning lake view home offering 3,656 sq. ft. of modern elegance in the prestigious, amenity-rich community of Winding Cypress. With 4 bedrooms, 4 bathrooms, a den, bonus room, and 2,5-car garage, this home is thoughtfully designed for both everyday living and entertaining on a grand scale. Step inside to discover a light-filled open floor plan accented with tile flooring in the main living areas, brand-new luxury vinyl plank flooring in all three downstairs bedrooms, and crown molding throughout the first floor. The chef’s kitchen is a showstopper, boasting quartz countertops, premium KitchenAid stainless steel appliances, a new natural gas cooktop, soft-close cabinetry, walk-in pantry, new dishwasher, and upgraded sink—all designed for style and function. Enjoy seamless indoor-outdoor living with zero-corner sliding doors that open to an expansive lanai featuring a picture screen enclosure, heated pool and spa, and a custom outdoor kitchen with built-in hub. With southwestern exposure overlooking the long lake and preserve, sunsets here are simply unforgettable. Retreat to the primary suite with a spa-like bathroom and custom walk-in closets, while guests enjoy privacy with an en suite bedroom on the main level. Upstairs, the bonus room offers endless flexibility for a game room, theater, or additional living space. This home is equipped with hurricane-impact windows, built-in Sonos surround sound system, smart home features, and abundant storage—ensuring comfort, safety, and convenience. As a resident of Winding Cypress, you’ll enjoy world-class amenities, including:Heated resort-style & lap pools, hot tub, and gas fire pit, covered outdoor restaurant bar & grill, expansive clubhouse with fitness center, library, and event space, pickle ball, bocce, and tennis courts, miles of scenic sidewalks & boardwalk trails, two dog parks for furry family members. Perfectly positioned on a premium lot, close to the community center and surrounded by excellent local infrastructure, this home is one of the rarely available larger homes in Winding Cypress—ideal for hosting family and friends in comfort and style. Experience the best of modern Naples living in this extraordinary home.