Winding Cypress Naples Real Estate : 17 Homes for Sale

Winding Cypress Naples 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.

Winding Cypress Naples Homes for Sale: The Martin Ray Floor Plan is PRIVACY-PRIVACY-PRIVACY. An exceptional model styled home on a premium lot with rare, unobstructed views of the lake and the Preserve. This residence offers unmatched privacy and outdoor living, with two standout features: an expansive screened lanai with custom accent lighting, saltwater, heated 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. 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, upgraded wine dual temp refrigerator, pantry shelving, adds 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. Winding Cypress is one of Naples’ premier resort-style communities, surrounded by 800 acres of protected 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: 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.

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: Move in Ready 3 year old 3 bdrm den 2bath Mystic model at Winding Cypress. Here are some of the reasons we are we different from the rest . widened paved driveway comfortablly fitting 2 cars side by side, corner lot for privacy, beautiful long lake view on WC largest lakes, 4ft extended garage for larger vehicles plus overhead storage with Mini a/c split in garage. whole house generator, impact windows and doors, outdoor kitchen numerous designer interior upgrades. tile floors . office all set up for someone who is working from home in den or seller will remove office furniture and redo room if not needed. located on dead end street in Phase 3 . A must to see ... Why go new and spend all the money on upgrades when you can have it all here . Home is also available to rent $4200.00 year lease

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: Perfection is the only way to describe this home! It shows like a model as it has been rarely lived in since built barely three years ago. Welcome to the desirable Pulte/DiVosta Mystique Model located in the popular amenity rich community of Winding Cypress. This waterfront property sits on a dead-end cul-de-sac and is loaded with owner and builder upgrades. It's impeccably decorated and furnished and could come turnkey providing the new owner with everything you'll ever need to begin living in paradise! The Mystique’s footprint, a 3 bed, 2 bath plus optional den offers the sought after open kitchen, great room, and dining area concept with split bedrooms to ensure comfort and privacy. All the bedrooms are large with the primary suite being expansive. This home's upgrades include a whole-house generator, a hurricane impact zero-corner sliding glass door that provides a spectacular indoor/outdoor living area combining an expansive great room to the under roof lanai dining and and separate sitting section. That's just part of the lighted lanai. There's an extended paver area for you to soak in the sun while you admire the custom pool with a soothing water feature. Looking out over the beautiful lake is made easy with the option "picture window" lanai screen. Electric StormSmart metal shutters enclose the lanai providing additional peace of mind, safety and security. Additional enhancements include a chef's kitchen layout with quartz counters, a natural gas cooktop and range, upgraded cabinets with above and under lighting, expansive island with an overhang to sit three, an upgraded backsplash and a large walk-in pantry. This home also boasts upgraded tile plank flooring, custom 8' doors throughout, high-end interior plantation shutters on all windows, an expanded laundry area with cabinets, counters, a utility sink, and extra storage. The 2 car garage has an insulated overhead door. Winding Cypress is optimally located just 15 minutes to Olde Naples, 10 minutes to both Marco Island and I75, and 30 minutes to RSW Airport. For this price point, the amenities at Winding Cypress are second to none. A resident's only full service restaurant, resort pool with spa that rivals a Las Vegas hotel, pickleball, tennis, and bocce courts, the best fitness center around, an vibrant community center with onsite management and Activities Director, a dog park, community garden, and a boardwalk nature trail are just a few of the things that make Winding Cypress so special. With only 766 single-family homes spread out over 1250 total acres that includes 850+ acres of spectacular preserve and lakes, enjoy the peace, serenity and beautiful wildlife that few communities are able to offer.

Winding Cypress Naples Homes for Sale: Sense the comfort and beauty of this magnificent home the minute you enter the foyer and see the view out to the inviting pool and spa. This 3 bedroom, plus separate den, great room floor-plan is perfect for entertaining or just a lovely place to call home. These original owners have impeccably maintained the home making it feel brand new. Built in 2021 it boasts a chef's delight kitchen with stainless steel appliances, center island and breakfast bar, natural gas cooktop/range, pull-out drawers, quartz counter-tops, recessed and pendant lighting, and more! The cook of the house will love it! The great room and dining area are adjacent to the kitchen. An extra plus is the den with double raised paneled doors and a window for natural light. The main bedroom is approx 14' x 16' and sits on its own separate wing from the other bedrooms. You will love the main bathroom with its 9' x 3'3" tiled shower with multiple shower heads, dual sinks, quartz counter-tops, walk-in closet and separate toilet closet. It is very spacious! Another plus to this home is the zero corner doors off the great room extending your great room out to your covered lanai. The extended lanai is all plumbed for the outdoor kitchen of your liking. Enjoy the Florida sunshine in your pool and spa in the privacy of your own backyard which backs up to a preserve. Some of the other features of this lovely home are a 9' x 7' laundry room with cabinets, folding counters, sink, and storage closet, 2 car garage with a 4 foot extension and epoxy flooring, and impact resistant windows and sliders. The home boasts beautiful tile and light colors throughout. The white plantation shutters in many of the rooms add to the character of the home. Winding Cypress is a newer, well maintained community offering an abundance of amenities. You will find a resort-style pool and separate spa, cabanas, Shady Palm Cafe, pickleball, bocce, tennis, state-of-the-art fitness center, community garden and a dog park for your fur babies. Winding Cypress sits in a great location in Collier County, less than 30 minutes from beautiful 5th Avenue in Naples, and the white sand beaches of Marco Island. This home is a must see!

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: Winding Cypress – Resort-Style Living in Naples - Priced to sell! 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, 3 bedrooms plus a den, 2 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 and priced to sell quickly — this home combines style, value, and an unbeatable location.

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: Ready for New Owners to Enjoy -Welcome home to this charming Abbeyville model featuring its inviting open-floor concept where natural light streams through the windows. The kitchen boasts granite counters, stainless appliances and a center island with pendant lights and extra storage for everyday use and easy entertaining. The pantry closet has plenty of space for all of your staple goods. Low maintenance tile floors are throughout much of the space. There's a den/flex room with french doors that can be used as an office, hobby or quiet sitting room. It can also be used as a third bedroom if desired. A separate guest bedroom and bathroom with combined tub and shower and granite topped vanity offers privacy for your family and guests. The laundry room is complete with washer, dryer, sink and features a spacious storage area with shelving for your cleaning supplies and more. There are storage racks in the two car garage to house all of your toys. Be sure to take time to relax and enjoy your morning beverage and the beautiful sunsets on the screened, pavered lanai that overlooks the delightful 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: 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: 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: Sophisticated Villa Living in Winding Cypress – OVER 100K In SAFTEY AND SECURITY UPGRADES! Priced to Sell and 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: Now being offered FURNISHED! 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. 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. PRICED TO SELL!

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

Winding Cypress Naples Homes Under Contract: PRICED TO SELL!! This beautiful Cressida model villa in highly sought-after Winding Cypress is move-in-ready. Freshly painted inside and out. Roof and all pavers have been power washed and sealed This beautiful villa offers two bedrooms, two baths plus a den along with a two-car air-conditioned garage. The den can be easily converted into a third bedroom. 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 Under Contract: This extended Summerwood floorplan is situated on a private street and features 3 bedrooms, a den, 2 bathrooms, a gas heated pool and spa, and an extended 2-car garage. The home includes valuable storm-ready features such as a whole-home generator, impact-resistant windows and doors, and electric hurricane screens for added protection. The open-concept layout seamlessly connects indoor and outdoor living spaces. The pool deck features a large covered lanai ideal for enjoying sunset views over the lake and preplumb of electric, gas, and water providing the option to add a built-in outdoor kitchen. Additional upgrades include tile flooring throughout, plantation shutters, trey ceiling, custom screened entryway, widened walkway & driveway and generous storage space. Turnkey furnishings are available with the sale, some exclusions. 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.

Winding Cypress Naples Homes Under Contract: 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 Under Contract: Welcome to this charming 2-bedroom plus den, 2-bath beautiful villa in the highly desirable community of Winding Cypress. Built in 2017, this residence offers 1,544 square feet of thoughtfully designed living space. The interior is light and bright, featuring easy-care tile floors in the main living areas, a breakfast bar for casual dining, and carpet in the bedrooms for added comfort. The den with French doors provides the perfect space for a home office or flex room, while the primary suite offers a private retreat with dual sinks and a walk-in shower. For added peace of mind, the home is equipped with a built-in Taexx pest control system. Step outside to your private backyard oasis, complete with a sparkling inground pool — NEW Pentair 1.5 HP SuperFlo Variable Speed pool pump installed September 2025 — perfect for relaxing or entertaining guests year-round. Winding Cypress is known for its resort-style amenities, including a large clubhouse, community pool with cabanas, fitness center, tennis, pickleball, and bocce courts, plus walking and biking trails surrounded by natural preserves. Ideally located in East Naples, you’re just a short drive from Marco Island, Downtown Naples, shopping, dining, and world-famous Gulf beaches. This home is the perfect combination of comfort, convenience, and community living.

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

Winding Cypress Naples Homes: This Pinnacle floorplan is situated on the largest lake in the neighborhood and features 3 bedrooms, a den, 3 bathrooms, a pool and spa, and a 3-car garage. The open-concept layout includes a dramatic zero-corner slider that seamlessly connects indoor and outdoor living spaces. Peace of mind comes with a whole-home generator and impact-resistant windows and doors. Inside, you'll find extensive upgrades throughout. The kitchen boasts built-in appliances and a spacious island—perfect for entertaining. Additional highlights include soaring tray ceilings, crown molding in the den and entry, and tile flooring throughout. The air-conditioned 3-car (extended by 4 ft) garage offers ample storage with custom shelving and a built-in workbench. Outdoors, the heated pool and spa are powered by both gas and solar, a smart, energy-efficient combination. The expansive outdoor kitchen, hurricane screens for added protection, and generous deck space create an ideal setting for sunset views. Other exterior features include lush landscaping with low-voltage lighting, an extra-wide driveway (recently sealed), a custom designed screened-in entryway, and panoramic wide lake views. 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.

Winding Cypress Naples Homes: EXCEPIONAL in design and setting, this Pinnacle model commands southwest-facing LAKE AND PRESERVE VIEWS from one of the most private parcels within Winding Cypress. The residence is enhanced by an extended, Climate-Controlled 3 CAR GARAGE with a high-performance Polymer finish—offering utility and Esthetic. Interior features include 12’ ceilings, Tray Ceilings, tile flooring throughout, Plantation Shutters, and custom millwork. The open-concept floor plan includes a great room with Electric Sliding Doors leading to the lanai. The kitchen is equipped with Quartz countertops, a large island with built-in wine cooler, KitchenAid and Whirlpool appliances, and a natural gas cooktop. The primary suite includes custom closets and an en-suite bath. The home is equipped with a whole-house Generac Generator, whole-house Water Purification with Reverse Osmosis, and a Built-in Surround sound system in the great room, primary bedroom, and lanai. A full home security system is also installed. Outdoor living space features an extended lanai with a custom Aragon Pool and Spa and an Upgraded Outdoor Kitchen great for Entertaining... Winding Cypress amenities include a clubhouse, fitness center, resort-style pool, tennis courts, pickleball, bocce, dog park, and nature trails.