Winding Cypress Naples Real Estate - 7 Homes For Sale

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.

3 bedroom and 3 bath Stonewater Model home in Winding Cypress

BRING OFFERS! Welcome to this highly upgraded Infinity Model, a rare offering in the prestigious Winding Cypress community of Naples. Built by renowned DiVosta Builders, this residence is one of only three Infinity Models within a community of more than 750 homes, making it an exceptionally unique opportunity. Featuring an extra-wide three-car garage with a dedicated third bay ideal for a golf cart, hobby vehicle, or additional storage, this home has been significantly enhanced with premium upgrades throughout and offers a level of quality rarely found in today's market. Designed for both luxury and everyday comfort, the expansive open-concept floor plan showcases soaring tray ceilings exceeding 11 feet, custom faux painting, extensive crown molding, and elegant designer finishes throughout. The spacious great room seamlessly connects to the gourmet kitchen, highlighted by a six-burner Thermador gas range and cooktop, premium Liebherr refrigerator, custom cabinetry, and a massive leather-finished quartzite island perfect for entertaining. The seller's extensive investment in upgrades is evident in every detail. Designer window treatments, custom bed coverlets, built-in features, and custom closets throughout create a refined, move-in-ready environment. The completely remodeled primary bath offers a spa-inspired retreat featuring a curbless walk-in shower, floating vanity, premium fixtures, designer tilework, and stunning 48-inch porcelain tile flooring throughout. Outdoor living is equally impressive. The expansive lanai with desirable western exposure captures spectacular Naples sunsets and provides ample space for a custom pool, spa, and additional outdoor living areas. Pool plans and contractor quotes are available, making it easy for the next owner to create their ideal backyard oasis. The fully equipped outdoor kitchen provides the perfect setting for entertaining family and friends while enjoying the privacy and tropical surroundings. Additional upgrades include hurricane-impact windows and doors, a dramatic zero-corner sliding glass door, whole-house generator, tankless water heater, Kinetico water filtration system, Sonos surround sound system, epoxy-coated garage floors, insulated garage doors, built-in garage storage, and a dedicated air-conditioning system for the garage. As one of Naples' premier natural gas communities, Winding Cypress offers an unmatched lifestyle with a residents-only restaurant, resort-style pool and spa, fitness center, pickleball, tennis and bocce courts, and over 800 acres of protected preserve. Ideally located just 10 minutes from Marco Island's white sand beaches and approximately 15 minutes from Olde Naples, this exceptional residence combines rarity, luxury, and location in one extraordinary offering. This is more than a home—it's a statement of quality, craftsmanship, and lifestyle. One or more photos have been virtually staged, AI-generated, or rendered.

This home is an amazing value for Winding Cypress!! Once you compare, you'll agree. The Stonewater model is the largest one floor living within The Community. The sought after "open area concept" footprint boasts 3 expansive bedrooms including a most impressive owner's suite, 3 full baths PLUS and additional POOL BATH , a large den-flex room with glass French doors, desirable 3 car garage with additional storage racks overhead. Upgrades include an executive waterfront and private preserve view lot, pool with integral spa.

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

This beautifully designed and impeccably maintained home offers the perfect blend of elegance and comfortable Naples living. Featuring the highly sought-after Summerwood floor plan with a spacious Great Room extension, the open layout creates an impressive, light-filled space perfect for entertaining guests or relaxing with family after a day exploring beautiful Naples, FL. The gourmet kitchen shines with upgraded stainless appliances, elegant quartz countertops, an oversized island perfect for casual dining and hosting, and a generous walk-in pantry. This home features a generous primary Master bedroom plus three versatile guest bedrooms. Any of the three guest bedrooms can easily function as a bedroom, home office, den, or media room to suit your lifestyle. The fourth bedroom is a major advantage for leasing the home, providing extra flexibility that can help attract tenants, support higher rental rates, and appeal to a wider range of renters who need extra space for guests, etc. It also functions well as internal storage space or could be used to expand the Master closet. Interior finishes include high-grade porcelain tile flooring throughout, a practical laundry/utility room with storage and sink. And natural gas service is used for cooking, water heating, and efficient clothes drying. Step outside to your private resort-style lanai. This expansive space features custom pavers, a built-in outdoor kitchen, and plenty of room for outdoor gatherings or quiet relaxation. Enjoy a swim in the heated pool and spa, soak up the southern Florida sunshine, or simply take in the spectacular eastern water views framed by a large portrait “no-see” lanai screen. These serene vistas consistently draw “wows” from everyone who visits. For added peace of mind and year-round comfort, the home includes impact-resistant hurricane doors and windows throughout. These premium features provide excellent storm protection, improve energy efficiency, and help reduce insurance premiums while eliminating the hassle of traditional shutters. Elegant Bahama shutters offer additional beauty and protection. The elevated lot is also not in a mandatory flood insurance zone, adding to the worry-free lifestyle. Nestled in the prestigious gated community of Winding Cypress, residents enjoy an onsite restaurant, modern fitness center, community pool, tennis courts, pickleball courts, and a full calendar of social events—all just a walk, bike, or golf cart ride away. Conveniently located between downtown Naples and Marco Island, you’re minutes from pristine beaches, upscale shopping, and fine dining. Offered fully furnished and move-in ready, this exceptional home truly checks every box: Impressive Great Room. (Check.) Gourmet kitchen & flexible living spaces. (Check.) Resort-style outdoor living with water views. (Check.) Outstanding community & prime location. (Check.) Ready for the Naples lifestyle you’ve dreamed of? This beautiful home delivers it all.

This 2 Story Mystique Model, located in the desireable community of Winding Cypress, absolutely has to be seen to appreciate all that it offers. Instead of using AI to draft a lofty, fluffy, low information description of this home, we are just going to just list a few of the features and upgrades of this 3-year-new beauty! WHOLE HOUSE GENERATOR, HEATED SALTWATER POOL W/SPA & WATER FEATURE, HURRICANE IMPACT WINDOWS & DOORS, ELECTRIC LANAI SUNSHADES, EXTENDED 3 CAR GARAGE W/MINI SPLIT AC, INSULATED OVERHEAD DOOR, EPOXY FLOORS & ADDITIONAL BUILT-IN/UNDER STAIRS CUBBY STORAGE, UPGRADED 2-TONE KITCHEN CABINETS W/UNDER CABINET LIGHTING, QUARTZ COUNTERS, BLACK STAINLESS APPLIANCE PACKAGE, OUTDOOR SUMMER KITCHEN WITH GRANITE/LEATHER TOP COUNTER, 2 HVAC UNITS W/DOWNSTAIRS & UPSTAIRS ZONES, AMAZING GLASS WALL ENCLOSED FLEX ROOM, UPGRADED LAUNDRY CENTER W/BUILT-IN CABINETS/COUNTERS & 2ND REFRIGERATOR, HUGE 2ND FLOOR AREA W/LARGE BEDROOM & FULL BATH, MURPHY BED, 2ND FLOOR FLEX SPACE FOR THEATER/MEDIA ROOM & ADDITIONAL DEN/OFFICE, PLANK TILE FLOOR THROUGHOUT DOWNSTAIRS, ALL UPGRADED FAUCETS/FIXTURES/LIGHTING/HARDWARE, IN-FLOOR OUTLETS, TRAY CEILING, SMART HOME CAT-6 WIRED W/MONITORED ALARM SYSTEM, & ALL THIS ON A DEAD END CUL-DE-SAC. Winding Cypress is noted for it's incredible high value amenities that include a private, resident's only, full-service restaurant and bar, Las Vegas styled resort pool & spa, pickelball, tennis & bocce courts, an amazing fitness center, nature trail/boardwalk, community garden, a dog park, all surrounded by 1250 total community acres that includes 800+ acres of preserve, green space & lakes. You are just 15 minutes to downtown Olde Naples & 10 minutes to Marco Island & I75. This home, and the Winding Cypress Community are very special!

Rare opportunity in Winding Cypress this Marten Ray Floor Plan sits on a premium lot with unobstructed lake and protected preserve views. Experience, complete privacy and a resort-style outdoor setting in one of Naples’ most desirable communities. Experience one of the most desirable homes in Winding Cypress, offering a rare combination of premium lot, complete upgrades, and true move-in ready convenience. Perfectly situated on what is believed to be one of the only homes in the community with a full, unobstructed rear exposure, this property showcases sweeping views of a permanent lake and protected state/federal preserve, delivering exceptional privacy with no future development behind you. Designed for effortless Florida living, the home features a resort-style outdoor setting with a heated-saltwater pool, multi-color lighting, in pool and lanai, expansive lanai, dry bar with cabinetry & refrigerator, outdoor TV and audio—ideal for entertaining or relaxing in a private natural setting. Inside, the residence has been extensively upgraded beyond builder-grade, to deliver a “better than new” experience, with no projects or additional investment required. The designer kitchen includes gas cooking, enhanced cabinetry, under-cabinet lighting, and a built-in wine bar with dual-zone cooler. Additional highlights include tile flooring throughout, upgraded lighting, a high-efficiency air conditioning system, custom pantry and primary closet cabinetry, and a fully optimized garage with added storage and functionality. The flexible floor plan offers 2 additional bedrooms for versatile guest accommodations and workspace options, including a dedicated office and an additional guest space, ideal for visiting family, remote work, or multi-purpose use. This home is well suited for buyers seeking quality, privacy, and ease of ownership in one of Naples’ most sought-after communities.

This impeccable Martin Ray truly has it all. The home features 3 bedrooms + den, 2 bathrooms, a 2-car garage with a 4-foot extension, and a custom pool perfectly positioned on a premier lot surrounded by lake views. Structurally designed for both style and peace of mind, the home offers soaring 11+ foot ceilings, impact windows and doors throughout, a whole-house generator that powers the pool as well, and hurricane screens for added protection. Inside, the upgrades are endless, including crown molding, tray ceilings, under-cabinet lighting, handmade Forge lighting fixtures, custom drop-zone cabinetry, plantation shutters, a California Closet mini bar, and so much more. The outdoor living space is a true showstopper, offering privacy, water views while overlooking the preserve. Added in 2022, the 34-foot custom pool features a flush spa, salt system, auto fill, 4 waterfalls, 2 whisper-quiet high-end pumps, gorgeous wet-edge pebble finish with glass accents, and imported Turkish non-slip marble pool decking. Even the pool cage was thoughtfully upgraded, with vertical support beams filled with concrete for enhanced stability. The garage is equally impressive with epoxy flooring, electric vehicle charging, double whole-house surge protection, and keyless entry. Outside, the home continues to impress with a rare custom 5-car paver driveway, updated timed lighting, extensive landscaping, a paver walkway, and a screened front entry. 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 2 dog parks for your furry friend. This pet-friendly community allows rentals, has low fees, and boasts a prime location—convenient to Marco Island, 5th Avenue, and I-75.

This meticulously maintained Mystique features 3 bedrooms + den, 2 bathrooms, 2 car garage with a pool and spa overlooking a lake! This home is situated on a spacious corner lot making it ideal for privacy while maintaining a stunning lake view. The turnkey designer furnishings have hardly been used and it's a pet free home. Outside the private oasis features a spa with waterfall, plenty of covered seating areas, and a top of the line outdoor kitchen. Recent updates include an upgraded 400 BTU pool heater (heats up pool quicker), new pool pump, and updated outdoor grill components. While located in the newest section of Winding Cypress - it is in a quiet location with convenient access to both gates. 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 2 dog parks for your furry friend. This pet-friendly community allows rentals, has low fees, and boasts a prime location—convenient to Marco Island, 5th Avenue, and I-75.

This Summerwood floorplan is being offered turnkey furnished and features 4 bedrooms, 2 bathrooms, a gas heated pool, and an extended 2-car garage. The home includes valuable storm-ready features such as a whole-home generator and electric hurricane screens on the lanai. Inside, the home is loaded with upgrades such as a crown molding, plantation shutters, California Closets cabinetry in the laundry room, pantry and primary closet. Embrace the Florida lifestyle with the open-concept layout seamlessly connecting indoor and outdoor living spaces. The pool deck features a spacious covered lanai and an expansive outdoor kitchen. No detail has been spared in the garage as well, it features a mini split, cabinets, and an extra 4 feet of length, allowing room for tools, 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 2 dog parks for your furry friend. This pet-friendly community allows rentals, has low fees, and boasts a prime location—convenient to Marco Island, 5th Avenue, and I-75.

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 den and 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