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Winding Cypress Naples Florida Homes for Sale

Naples Florida Real Estate

Winding Cypress Naples Real Estate

Homes For Sale34$475K - $1.6M
Sold ( Past 6 Months )19$550K - $1.6M
Last updated at 6:08am 05/02/2025

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$1,649,000
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$201K
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Winding Cypress

6823 Winding Cypress Dr, Naples, FL 34114

Homes - 2,515 ft² / 3,077 ft² - 3 Car Garage

3+Den / 3 Baths / Pool / Spa

Built 2021
Winding Cypress Naples Homes for Sale: Massive $200K price reduction!! STUNNING lake and sunset views await from the lanai of this Pinnacle model home situated on an oversized lot in Winding Cypress. At just over 2,500 square feet, you will notice the attention to detail from the moment you walk in the front door. Features of this gorgeous home include: 3 bedrooms and 3 full baths, 3 car garage, faux paint accents on walls & ceilings, custom light fixtures and ceiling fans, zero corner slider, impact resistant doors and windows, KitchenAid appliances, Quartz countertops, natural gas (cooktop, grill and pool equipment), dry bar with wine fridge, high-end carpeting in the bedrooms, plantation shutters throughout and SO MUCH MORE! This home is perfect for entertaining! The large, open kitchen & living room is ideal for family gatherings. Open the sliders to seamlessly bring the indoor living space, outdoors. The summer kitchen and large dining area is perfect after a day of relaxing by the pool & spa. The primary suite features a massive walk-in closet that will fit the needs of those with the largest of wardrobes. There are plenty of amenities in Winding Cypress for those looking to stay active outside of the residence, featuring a resort-style pool, on-site restaurant (Shady Palm), tennis, bocce, and the hottest new sport - pickleball. Additional amenities include a dog park, well-appointed fitness center, and internet cafe. All of this is just a short drive to some of the finest dining, shopping, beaches, boating and sunsets in all of Florida - Downtown Naples/5th Ave and Marco Island. Close to I-75 and 30 minutes to Southwest Florida International Airport. Come live in paradise!



$1,599,000
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$100K
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Winding Cypress

6851 Winding Cypress Dr, Naples, FL 34114

Homes - 2,789 ft² / 3,479 ft² - 3 Car Garage

3+Den / 3 Baths / Pool

Built 2020
Winding Cypress Naples Homes for Sale: Indulge in breathtaking lake and sunset views from this exquisite Stonewater model home, ideally on a premium lot in the prestigious guard-gated low HOA fee community of Winding Cypress. From the moment you step inside, the meticulous attention to detail and timeless elegance will captivate you. This sophisticated residence features three bedrooms plus a den, three full baths and a spacious three-car garage, blending luxury and functionality seamlessly. The chef-inspired open kitchen is the heart of the home, showcasing KitchenAid appliances, quartz countertops, white cabinetry, a walk-in pantry, and natural gas cooktop, designed for everyday comfort and entertaining. Step out onto the expansive covered lanai, equipped with an upgraded natural gas summer kitchen, ideal for hosting gatherings. The extended screened enclosure boasts a large heated saltwater pool with three spillover waterfall features, creating an entertainer’s dream space with ample room for dining, lounging and relaxation. Inside, the open-concept great room design offers an effortless flow between indoor and outdoor living spaces, making it ideal for family gatherings and celebrations. The luxurious spacious primary suite features a custom-designed walk-in closet system, dual sinks and an oversized walk-in shower, embodying comfort and sophistication. Other exceptional highlights of the home include volume coffered ceilings, upgraded tile plank-style flooring, custom light fixtures and ceiling fans, a striking impact-resistant custom front door, landscape lighting, a whole home water filtration and softener system, and rolldown storm shades on the outdoor covered lanai for peace of mind and effortless living to name a few. Winding Cypress is renowned for its impressive amenities, offering an active and vibrant lifestyle. Enjoy the resort-style pool, on-site restaurant Shady Palm, tennis, bocce and pickleball, along with additional features like a dog park, state-of-the-art fitness center, internet café and over 800 acres of lush natural preserves to explore. Conveniently just minutes from world-class dining, shopping, pristine beaches, boating and spectacular sunsets, this home delivers the ultimate Florida lifestyle. Don’t miss the opportunity to make this piece of paradise your own!



$1,497,500
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$200K
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Winding Cypress

6878 Winding Cypress Dr, Naples, FL 34114

Homes - 2,989 ft² / 3,181 ft² - 2 Car Garage

4+Den / 4 Baths / Pool / Spa

Built 2022
Winding Cypress Naples Homes for Sale: Discover one of the largest and most recently built homes in the highly sought-after Winding Cypress community! This stunning residence boasts a serene preserve view that enhances the peaceful, natural surroundings. Blending luxury and functionality, the home offers 4 bedrooms, a den/office, 4 full baths, and a spacious 2-car garage, with every detail thoughtfully curated to elevate your Florida lifestyle. The heart of the home is the chef-inspired open kitchen, featuring premium KitchenAid appliances, quartz countertops, custom cabinetry, a walk-in pantry, and a natural gas cooktop—perfect for everyday living and entertaining. The expansive living and dining spaces flow seamlessly, with floor-to-ceiling glass sliders opening to an impressive covered lanai. Outside, the large dining area is ideal for hosting guests, while the heated saltwater spa/pool with spillover waterfalls creates a serene retreat. The extended lanai offers plenty of room for lounging and relaxation in the Florida sunshine. Inside, the home's design impresses with high ceilings, custom light fixtures, ceiling fans, and upgraded tile plank-style flooring. The spacious primary suite features a custom walk-in closet, dual sinks, and an oversized walk-in shower. Additional highlights include volume coffered ceilings, plantation shutters, epoxy flooring in the garage, and a built-in surround sound system. Winding Cypress offers exceptional resort-style amenities, including a pool, on-site restaurant Shady Palm, tennis, bocce, pickleball, a state-of-the-art fitness center, a dog park, an internet café, and over 800 acres of lush natural preserves to explore. Whether you’re seeking relaxation or an active lifestyle, there’s something for everyone. Conveniently located near world-class dining, shopping, beaches, and boating, this home is just minutes from the best of Naples and Marco Island. Don’t miss the opportunity to make this luxurious haven your own and experience the ultimate Florida lifestyle in the heart of paradise.



$1,497,500
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$100K
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Winding Cypress

7478 Winding Cypress Dr, Naples, FL 34114

Homes - 2,619 ft² / 3,097 ft² - 3 Car Garage

3+Den / 3 Baths

Built 2016
Winding Cypress Naples Homes for Sale: Welcome to this exceptional Infinity Model home, a rare find in the prestigious Winding Cypress community of Naples, Florida. Built by the esteemed DiVosta Builders, this home is one of only three Infinity Models in a community of over 750 residences, making it a truly exclusive opportunity. Designed with elegance and comfort in mind, this property blends high-end finishes, thoughtful upgrades, and a sprawling open-concept layout that’s perfect for both entertaining and everyday living. Upon entering, you’ll be greeted by soaring tray ceilings over 11 feet high, beautifully complemented by custom faux painting and crown molding. The home’s expansive great room flows seamlessly into the gourmet kitchen, featuring a 6-burner Thermador gas cooktop and range, a premium Liebherr refrigerator, and an oversized quartzite leather-finish island. Custom-built cabinetry and designer window treatments—all tailor-made—add to the refined aesthetic, while custom bed coverlets bring a personal touch of luxury to the bedrooms. The master bath has been completely remodeled to exude modern sophistication, featuring sleek, high-end finishes that transform it into a spa-like retreat. A contemporary floating vanity, premium fixtures, and an expansive glass-enclosed shower with designer tilework create an ambiance of refined elegance. Every detail has been meticulously crafted to provide both style and comfort, making this space a true sanctuary within the home. Step outside to an entertainer’s dream: a full outdoor kitchen equipped for al fresco dining and gatherings, set against the backdrop of a lush and private lanai. The brick-paved driveway leads to a three-car garage, which features epoxy flooring, an insulated door, built-in storage, and a dedicated air conditioning unit for year-round comfort. This home is designed for ultimate convenience, boasting hurricane impact windows and doors, a zero-corner slider, custom closets, and a whole-house generator. A tankless water heater ensures efficiency, while a Kinetico water filtration system delivers the highest quality water throughout the home. The Sonos speaker sound system fills every space with rich, immersive audio. Located in one of the few natural gas communities in Naples, Winding Cypress offers an unparalleled lifestyle with resort-style amenities, including a residents-only restaurant, pool and spa, fitness center, and courts for pickleball, tennis, and bocce. Surrounded by over 800 acres of green space, this community provides a peaceful retreat just 10 minutes from Marco Island’s stunning beaches and 15 minutes from the vibrant shopping, dining, and entertainment of Olde Naples. This is more than a home—it’s a refined sanctuary where luxury meets convenience in one of Naples' most sought-after communities. Don’t miss your chance to make it yours!



$1,399,000
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$100K
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Winding Cypress

7675 Winding Cypress Dr, Naples, FL 34114

Homes - 2,496 ft² / 3,061 ft² - 3 Car Garage

3+Den / 3 Baths / Pool / Spa

Built 2020
Winding Cypress Naples Homes for Sale: Discover luxury living in this breathtaking Pinnacle estate home, situated on one of the most coveted lakefront sites in the south Naples resort community of Winding Cypress. Step inside to an open and spacious floor plan, enhanced by soaring tray ceilings, architecturally stunning alcoves and graceful arches. The home’s designer kitchen serves as the centerpiece, featuring every upgrade possible — soft-close cabinetry, quartz countertops, a fully vented natural gas range and hood and an all-premium KitchenAid appliance package with pull-outs in all lower cabinets. Adjacent is a large pantry complete with a water filter system for added convenience. The primary suite is a private oasis with towering ceilings and full walk-in shower and massive walk-in closet, while guest quarters include an expansive bay window en suite, ensuring comfort and privacy for family and friends. Additional living spaces include a versatile den or hobby room with upgraded French glass doors and foyer layout. Outdoor living is equally impressive. Relax by the saltwater pool and spa while enjoying serene wide-open lake views. Host gatherings with ease, thanks to a fully equipped outdoor kitchen featuring an integrated hood, all set within an expansive lanai with an upgraded oversized pocket slider door. The screened front porch, extended paver paths and custom landscaping further enhance the home’s curb appeal. Practical features include a 4-foot garage extension with custom flooring for three cars, all-impact glass windows, Storm Smart Kevlar shutters and energy-efficient LED lighting throughout. Additional upgrades include raised tray with crown-trimmed ceilings, a heated fireplace with customizable colors and custom state-of-the-art lighting systems that add a touch of sophistication to every room. Located in the resort-style community of Winding Cypress, residents enjoy exclusive access to a wealth of amenities, including a restaurant and bar, state-of-the-art fitness center, resort-style and lap pools, a spa and sports facilities for bocce, pickleball and tennis. The community also boasts a fire pit, bird-watching overlooks, a nature boardwalk and a picnic pavilion. Perfectly positioned between downtown Naples and Marco Island, this home offers the ultimate in luxurious Florida living. From its high-end finishes to its extraordinary location, it’s a property that truly has it all.



$1,395,000
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$155K
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Winding Cypress

7788 Winding Cypress Dr, Naples, FL 34114

Homes - 2,496 ft² / 4,768 ft² - 3 Car Garage

3+Den / 3 Baths / Pool / Spa

Built 2019
Winding Cypress Naples Homes for Sale: Nestled within an exclusive gated community and surrounded by a serene nature preserve, this elegant 3-bedroom, 3-bathroom home with a spacious den/office is the epitome of refined Florida living. The open, airy floor plan flows seamlessly, with high ceilings and large windows that capture abundant natural light and offer unobstructed views of the lush preserve behind the home. This home has natural gas, generator, upgraded oversized garage, Sentricon system, central vac system, and many more upgrades. Step into the gourmet kitchen, complete with premium appliances, custom cabinetry, and an expansive island that's perfect for entertaining or family gatherings. Each bedroom is generously sized, featuring high-end finishes and ample storage, while the den/office provides an ideal, private space for working from home or additional relaxation. The master suite is a tranquil retreat with a luxurious en-suite bathroom featuring dual vanities, and a walk-in shower. Outdoors, your private paradise awaits, with a sparkling gas heated salt water pool and spa surrounded by a spacious patio, perfect for sunbathing, al fresco dining, or evening cocktails under the stars. The 3-car garage offers plenty of room for vehicles, storage, and hobbies. Living in this community comes with exceptional amenities that rival a luxury resort. Enjoy an on-site restaurant, a spectacular resort-style pool, tennis courts, pickleball, bocce, and a dog park, all thoughtfully designed to elevate your lifestyle. The well-appointed fitness center, internet café, and an engaging calendar of year-round social events ensure that there's always something to do. Centrally located between the pristine beaches of Marco Island and Naples, this home places you just moments away from world-class shopping, dining, and entertainment, yet offers a peaceful, nature-filled escape in your own backyard. Don't miss the opportunity to make this luxurious haven yours!



$1,299,000
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Winding Cypress

7520 Blackberry Dr, Naples, FL 34114

Homes - 2,496 ft² / 3,061 ft² - 3 Car Garage

3+Den / 3 Baths / Pool / Spa

Built 2017
Winding Cypress Naples Homes for Sale: Introducing a luxury estate site with landscaped privacy corner lot home in Winding Cypress with pool and spa. Step into elegance with this stunning Pinnacle model estate home, set in the prestigious, gated community of Winding Cypress. This home stands out with its soaring raised tray ceilings, rare privacy and spacious yard, impact glass for peace of mind, and an expansive open layout filled with natural light and outstanding upgrades. Designed for those who love to entertain, the chef-inspired gourmet kitchen features top-tier finishes, premium appliances, and a spacious expanded island, the ideal gathering space for family and friends. With three bedrooms, three baths, a versatile den and an upgraded oversized three-car garage, this home offers flexibility and space to suit your lifestyle. Outside, a private backyard oasis awaits, complete with lush landscaping, a serene water view and a sprawling grassy yard, a rare find in this community. Take a refreshing dip in your sparkling pool and spa, designed for ultimate relaxation in a peaceful setting. Beyond your doorstep, Winding Cypress offers resort-style living like no other. The nearly 18,000-square-foot clubhouse boasts a zero-entry infinity pool with a lap section, a poolside restaurant, beach cabanas and even a sandy beach. Stay active with numerous pickleball courts, clay tennis courts, bocce, an outdoor yoga movement studio, and a vibrant community hall managed by a full-time activity director. Winding Cypress is a resort gated community at the midpoint between Marco Island and downtown Naples, and this home delivers the ultimate combination of luxury, convenience and an unmatched lifestyle. Don’t miss your chance to own one of the desirable and private estate homes in Winding Cypress of Naples.



$1,100,000
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$50K
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Winding Cypress

7355 Mockingbird Ct, Naples, FL 34114

Homes - 2,198 ft² / 2,640 ft² - 2 Car Garage

3+Den / 2 Baths / Pool / Spa

Built 2016
Winding Cypress Naples Homes for Sale: Welcome to your new home in Winding Cypress, a vibrant community in the heart of Southeast Naples. Surrounded by 800 acres of lush preserves and 80 acres of peaceful lakes, this is the ideal setting to enjoy a serene, nature-filled lifestyle. Yet, with Downtown Naples and the iconic 5th Avenue—one of America’s most beautiful streets—just 20 minutes away, you’ll always be close to the best of city living. This tastefully furnished home offers a neutral palette, spacious enough for guests yet cozy enough for just you and your significant other. Triple sliders open to a stunning outdoor oasis, featuring a heated pool and spa, along with a spacious seating area perfect for unwinding in the evenings while taking in a breathtaking Southwest Florida sunset. Built to the highest standards, this home offers enhanced hurricane protection, including four electric Storm Smart Screens on the lanai, impact-resistant windows and doors throughout, and a 20KW whole-house generator for added peace of mind. The vibrant Winding Cypress community offers a wealth of amenities, including a luxurious clubhouse with a state-of-the-art fitness center, catering kitchen, activity room, and community room. Outdoor enthusiasts will love the bocce ball courts, five tennis courts, four pickleball courts, a fire pit, and a nature boardwalk with a bird-watching overlook and picnic pavilion. The community Dog Park is a spacious and secure area where residents can bring their furry friends to run, play, and socialize. Winding Cypress is mere minutes from the sandy beaches of Marco Island and Naples and is the ideal spot for both relaxation and recreation!



$1,099,000
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$200K
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Winding Cypress

6767 Pennyroyal Dr, Naples, FL 34114

Homes - 2,185 ft² / 2,895 ft² - 2 Car Garage

3+Den / 2 Baths / Pool

Built 2021
Winding Cypress Naples Homes for Sale: Wow! This beautifully designed and meticulously maintained home checks all the right boxes. Featuring the highly desirable Summerwood floor plan with Great Room extension, it is perfect for entertaining or simply relaxing at home after a nice day out in beautiful Naples, FL. The kitchen features upgraded appliances, quartz countertops, an oversized island and walk-in pantry. The two guest bedrooms provide enough room for guests. The office/den can easily serve as a 4th bedroom if desired. Other interior features include high-grade porcelain tile throughout, a laundry/utility room with plenty of storage and natural gas for cooking, heated water and clothes drying. Exterior upgrades abound with a one-of-a-kind extended lanai with custom pavers and a built-in outdoor kitchen. There is plenty of space for outdoor gatherings, cookouts, an afternoon nap, a dip in the pool or just taking in some Florida sunshine. Looking through the huge portrait "no-see" lanai screen is one of the very best long water views in the entire community. The view is simply gorgeous, inspiring "wows" from all. The driveway and side walkway are extended. There is over $100k in upgrades to this magnificent home. And all furniture is negotiable. Just pack your bags and head on down to enjoy our very special slice of tropical paradise. Worried about maintenance and insurance costs, and/or storms? Newer construction (2021) negates a large future roof replacement cost for some time. And a newer A/C system should provide many more years of solid service. Hurricane impact doors and windows are throughout providing for great energy efficiency and home protection. Also, the lot of this property is elevated. It is not in a mandatory flood insurance zone. And there is a whole home gas generator too should the need ever arise. All aforementioned should assist in obtaining lower insurance premiums and keep maintenance costs down. This home offers easy peasy and worry-free living by any measure. To top it all off, this sensational home resides in the highly prized community of Winding Cypress. An onsite restaurant, modern fitness center, community pool and a full calendar of social gatherings with some of the best Naples residents around are a nice walk, bike or golf cart ride away. Also, located conveniently between downtown Naples and Marco Island, opportunities to visit some of our finest beaches, shopping and dining locations are just minutes away. Great home. (Check.) Great view. (Check.) Great community. (Check.) Great location. (Check.) This property checks all the right boxes for the time of your life in beautiful Naples, FL.



$1,049,000
Decrease*
$51K
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Winding Cypress

7679 Winding Cypress Dr, Naples, FL 34114

Homes - 2,186 ft² / 2,591 ft² - 2 Car Garage

3 Bed / 2 Baths

Built 2019
Winding Cypress Naples Homes for Sale: Imagine waking up each morning in your dream home,Nestled in one of Naples' most sought-after gated communities. As you walk into this beautiful home you are greeted with the open-concept floor plan that welcomes you, with the warmth of granite countertops and the added upgrades of a gas stove and wall oven in your chef-inspired kitchen. Your home is more than just a place to live, it’s a sanctuary. Impact-resistant doors and windows not only provide peace of mind but also frame the breathtaking views of the lake outside. Whether you're enjoying a quiet morning coffee or hosting friends and family, the large covered lanai, complete with a summer kitchen, offers the perfect setting for outdoor living at its finest. Picture yourself grilling dinner while enjoying the beautiful skys over the lake, or simply relaxing with the breeze. Inside, every detail has been laid out to elevate your life. The tile flooring throughout gives the home a fresh, modern feel. In your primary suite, the dual sinks, separate shower, and soaking tub invite you to unwind.The walk-in closets provide plenty of space for your wardrobe, and the built-in cabinets and sink in the laundry room ensure that chores are as effortless as possible. For those seeking an active lifestyle, this community offers bocce, tennis, pickleball, and a refreshing community pool, all just steps away from your front door. When you’re ready to explore beyond your home, you’re only seconds away from the exclusive community restaurant. Outside of the community Naples offers world-class shopping, dining, and beaches. Owning this home means more than just having a place to live – it means embracing a lifestyle of comfort, convenience, and luxury. Don’t miss out on the opportunity to make this exceptional property yours.



$999,900
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$175K
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Winding Cypress

7530 Geranium Way, Naples, FL 34114

Homes - 2,496 ft² / 2,982 ft² - 3 Car Garage

3+Den / 3 Baths / Pool / Spa

Built 2018
Winding Cypress Naples Homes for Sale: This home is an amazing value for Winding Cypress!! Once you compare, you'll agree. The Pinnacle model is clearly the most popular floorplan in The Community. The sought after "open area concept" footprint boasts 3 expansive bedrooms including a most impressive owner's suite, 3 full baths, a large den, desirable 3 car garage, and 2496 square feet of indoor living space under air. Builder and owner upgrades include an executive waterfront premium lot, kitchen appliance package, pool with new heater integral spa, quartz counters, upgraded cabinet package, den/office, zero corner sliding glass doors, plank tile flooring, plumbed for a summer kitchen, built-in ceiling speakers, upgraded laundry center with built-in cabinets and utility tub, inviting lead glass front entry door. Winding Cypress is the "hidden gem" of Naples. Community amenities include a resident's only private restaurant, pickleball, tennis, & bocce courts, resort style pool with spa and cabanas, state of the art fitness center & motion room, club house with events rooms, prep kitchen, internet cafe & library, dog park, nature trail boardwalk & a community garden. Winding Cypress offers activities for every interest coordinated by an onsite, full-time Activities Director. Located just 15 minutes to downtown Olde Naples and 10 minutes to Marco Island and I-75, Winding Cypress is perfectly located for you to enjoy all of what SWFL paradise has to offer.



$995,000
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$50K
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Winding Cypress

6949 Winding Cypress Dr, Naples, FL 34114

Homes - 2,185 ft² / 2,895 ft² - 2 Car Garage

3+Den / 2 Baths / Pool

Built 2020
Winding Cypress Naples Homes for Sale: Welcome to this stunning Summerwood floor plan with an extended great room. As you enter this 3 bedroom plus den home the quality of finishes is evident. The great room open plan concept allows for a great entertainment area with a large island kitchen and beautiful quartz countertops open to the dining and living area. Step out onto the large paver lanai area and enjoy the exceptional location of this lot looking across the lake to a preserve area with landscaping providing excellent privacy from adjoining homes. Relax in the heated pool or lounge on the spacious pool deck. This home offers Florida living at its best with a custom outdoor kitchen featuring a gas grill, fridge, vent hood and sink. The community offers natural gas for cooking, water heater and clothes dryer. The lanai is protected by electric rolling hurricane impact screens making preparation for storms easy. The community of Winding Cypress is nestled amongst 800 acres of natural preserve and 80 acres of serene lakes. This community offers residents a tranquil lifestyle surrounded by nature. Residents enjoy a wide array of amenities, including the Shady Palm Café, a spacious Clubhouse, and a luxurious resort-style pool and spa, fitness center, social program, movement room, pickle ball, tennis courts, bocce and the boardwalk walking trail. Surrounded by many restaurants and grocery stores and only a short drive to Downtown Naples this community checks all the boxes.



$995,000
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$55K
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Winding Cypress

6699 Pennyroyal Dr, Naples, FL 34114

Homes - 2,094 ft² / 2,505 ft² - 2 Car Garage

3+Den / 2 Baths / Pool

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



$985,000
Decrease*
$115K
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Winding Cypress

6754 Pennyroyal Dr, Naples, FL 34114

Homes - 2,158 ft² / 3,256 ft² - 2 Car Garage

3+Den / 3 Baths / Pool

Built 2021
Winding Cypress Naples Homes for Sale: From the moment you drive into the beautiful community of Winding Cypress you will feel welcomed. The stunning entry to this picturesque enclave will be a place you can truly call HOME! This is a natural gas, resort-style community, with over 2/3rds of the neighborhood remaining a preserve! You are surrounded by nature, yet close to wonderful dining options, gourmet grocers, and lots of fun shopping! There’s a serene boardwalk that meanders through Winding Cypress which takes you to a covered overlook, the perfect place for tranquility and bird-watching! The community also boasts the popular Shady Palm Café, a spacious clubhouse and a state-of-the-art fitness center. Did I mention Pickle-ball? Bocce? Tennis? Yes, even a dog park! The “Mystique” floor plan features 3 spacious bedrooms and 3 full baths plus a den. The primary suite has a luxurious bath with double sinks, a huge custom walk-in shower and an enormous walk-in closet! There are wonderful corner pocket doors that open to a tranquil lanai featuring a private below ground, heated pool with LED colored lighting. The home also features stainless appliances, including the gas range, quartz counters, white cabinets, a pantry and an island! There is luxury vinyl wood-look flooring throughout the main living areas. The Great room built-in cabinets have so much storage, and there are additional can-lights throughout, as well as ceiling fans in every room. Equipped with Vivent Security Cameras at the lanai and front windows and doors. The home also has an over-sized garage with a work shop wall of cabinets and a remote-control screen! I don’t think this seller has left anything out!



$950,000
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Winding CypressNEW

7211 Live Oak Dr, Naples, FL 34114

Homes - 2,230 ft² / 2,667 ft² - 2 Car Garage

3+Den / 2 Baths / Pool

Built 2015
Winding Cypress Naples Homes for Sale: Lakefront Paradise Awaits in Winding Cypress! Imagine waking up to serene lake views every day in this meticulously maintained 3-bedroom, 2-bathroom haven located in the highly sought-after Winding Cypress community of Naples. Situated on an oversized, pie-shaped lot, this stunning Summerville extended model by Pulte offers the ultimate in Florida living. Step inside and be greeted by a gourmet kitchen that will delight any chef. Featuring a gas stove with natural gas line, stainless steel appliances, wall oven, gleaming granite countertops, an extended kitchen island perfect for entertaining, and a convenient walk-in pantry, this space is both beautiful and functional. Relax and unwind in your private backyard oasis, complete with a sparkling saltwater pool overlooking the tranquil lake – with no homes directly across, your peace and privacy are assured. The added landscaping around the pool creates an even more secluded and inviting atmosphere. Enjoy seamless indoor-outdoor living on the lanai, now featuring a new lanai screens. This exceptional home boasts numerous updates for your comfort and peace of mind, including a new hot water heater, a fresh exterior house paint job, a new mainspring on the garage door, and an upgraded A/C system with Blue Light and HEPA filter. Hurricane preparedness is a breeze with hurricane impact windows, Kevlar hurricane roll downs on lanai, and you'll never be without power thanks to the included generator. Convenience is key with a new garbage disposal, washer, and dryer also included. Beyond the beauty of this home, Winding Cypress offers an impressive array of resort-style amenities, including stunning clubhouse with a gathering room and catering kitchen, zero-entry resort-style pool and spa, state-of-the-art fitness center, restaurant, Pickleball and bocce ball courts, Tennis courts, Walking and biking trails, Playground, Dog park and so much more! Don't miss this incredible opportunity to own a piece of paradise in Winding Cypress. This move-in ready home offers the perfect blend of luxury, privacy, and an active lifestyle. Schedule your showing today!



$949,000
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Winding Cypress

7451 Blackberry Dr, Naples, FL 34114

Homes - 2,188 ft² / 2,629 ft² - 2 Car Garage

3+Den / 2 Baths / Pool / Spa

Built 2017
Winding Cypress Naples Homes for Sale: Located in the highly sought-after community of Winding Cypress, this beautifully updated 3-bedroom, 2-bath home offers a perfect blend of luxury, comfort, and breathtaking lake views. Surrounded by 800 acres of natural preserve and 80 acres of serene lakes, this home provides a tranquil lifestyle immersed in nature, with access to all the incredible amenities this community has to offer. Inside, the open-concept layout features coffered ceilings in the living room, adding architectural elegance and a sense of spaciousness. Plantation shutters throughout enhance the light-filled spaces, creating an inviting and sophisticated atmosphere. The chef-inspired kitchen is equipped with a large walk-in pantry, perfect for all your storage needs, and flows seamlessly into the extended great room—ideal for both casual living and entertaining. The home also boasts a den with elegant French doors, providing a private and versatile space for an office, study, or cozy retreat. The large laundry room adds practicality and convenience, while the epoxy floor in the garage combines style and durability, creating a clean and functional space. Step outside to your own private oasis with an outdoor kitchen perfect for grilling and entertaining. The sparkling pool and hot tub, surrounded by a "no-see-um" screened enclosure, offer the perfect retreat with panoramic lake views. The lanai is equipped with hurricane storm screens for added peace of mind, and a whole-house generator ensures you’ll never be without power, even during the most unpredictable weather. Winding Cypress is more than just a neighborhood; it’s a lifestyle. Residents enjoy access to the Shady Palm Café, a spacious clubhouse, and luxurious resort-style amenities such as a pool and spa, fitness center, social programs, pickleball, tennis courts, bocce, and a scenic boardwalk walking trail. Surrounded by top-tier restaurants and grocery stores, and just a short drive to Downtown Naples, this community offers everything you need for both relaxation and convenience. Don’t miss your chance to own this exceptional home in one of the most desirable communities in the area.



$899,900
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Winding Cypress

7128 Lily Way, Naples, FL 34114

Homes - 1,685 ft² / 2,086 ft² - 2 Car Garage

2+Den / 2 Baths / Pool

Built 2015
Winding Cypress Naples Homes for Sale: Stunning Abbeyville home in Winding Cypress is move-in ready! This immaculate residence is a must-see, featuring a fresh neutral palette, offering a spacious open split-bedroom floor plan with 2 bedrooms, a flex/den & 2 full bathrooms. Entertainment is elevated with flat-screen TVs mounted in both bedrooms & living area. Soaring ceilings enhanced by elegant molding, tray & coffered details, along with extra recessed lighting. Plantation shutters in the front bedroom, flex/den & over the kitchen sink add both privacy & style. Enjoy matching tile flooring throughout the main areas, with warm wooden plank flooring accentuating the flex/den room. A new HVAC unit, installed in December 2021 & serviced bi-annually ensures year-round comfort. The gourmet kitchen is a chef’s delight with upgraded white shaker cabinets, quartz countertops, a stylish subway tile backsplash & stainless steel appliances including a gas range & hood, dishwasher, built-in microwave, & a stainless steel sink with in-sink disposal. Exquisite cabinet lighting brightens the space, while a large extended kitchen island with additional cabinets provides ample storage. The primary suite features a luxurious walk-in shower with a glass enclosure, dual vanities with a quartz countertop, leading onto a fabulous walk-in closet with built-in organizers. The guest bathroom similarly boasts upgraded features with a tub & shower/glass enclosure, quartz countertop & spacious linen closet. The convenient laundry room is outfitted with upgraded front-load washer & dryer along with built-in cabinets & organizers. Outside, the stunning outdoor oasis beckons with a crystal-clear kidney-shaped pool offering serene lake views. Privacy hedges frame the pool cage, which features both covered & uncovered lanai areas - the perfect balance for year-round enjoyment. Upgrades include new pool cage screens & a pool heater (December 2022). Additional features include built-in easy-to-slide high-end accordion hurricane shutters & an extended 2-car garage with epoxy flooring. Located in the premier Winding Cypress community - A highly sought-after natural gas community set among 800 acres of natural preserves & 80 acres of lakes - this home offers resort-style amenities including a lap pool with spa, screened-in outdoor bar & grill (The Shady Palm), fire pits, fireplace, two dog parks, a community garden, tennis, bocce & pickleball courts, a state-of-the-art clubhouse with a fitness center plus event rooms. Ideally situated just minutes from Downtown Naples, several beaches, Marco Island & US-41/I-75, this property blends luxury & convenience effortlessly. Don’t miss out on this incredible opportunity!



$899,900
Decrease*
$250K
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Winding Cypress

7544 Winding Cypress Dr, Naples, FL 34114

Homes - 2,532 ft² / 3,518 ft² - 3 Car Garage

3+Den / 3 Baths

Built 2018
Winding Cypress Naples Homes for Sale: Welcome to a beautiful Pinnacle Model in the desirable, amenity rich community of Winding Cypress. This waterfront home is offered at an incredible value. Original owner care is apparent throughout. Builder and owner upgrades include; chef's kitchen with upgraded appliances, sink & faucet, soft close pull out cabinets including under-side lighting, custom quartz countertops, custom plank tile flooring, hurricane impact windows, slider, and entry door, upgraded & expansive lanai outdoor living area with Storm Smart Kevlar screen enclosure & ready for you to design your own outdoor kitchen, upgraded bathrooms with custom showers, faucets & fixtures, custom lighting & window treatments, 3 car garage with epoxy floor with additional refrigerator included. Winding Cypress is a guard gated natural gas community full of popular amenities including; a resident's only restaurant, amazing resort pool & spa, pickleball, tennis, & bocce courts, incredible fitness center loaded with all the training features including men's and women's locker rooms, a beautiful community center with conference rooms, a prep kitchen, library, lounge with fireplace, a dog park, nature trail boardwalk, and a community garden. The community is perfectly located just 10 minutes to the beaches and entertainment of Marco Island, and 15 minutes to the shoppes and restaurants of the renowned 5th Avenue in downtown Olde Naples. This home is perfect to start enjoying the lifestyle living of Winding Cypress!



$899,000
Decrease*
$71K
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Winding Cypress

6763 Winding Cypress Dr, Naples, FL 34114

Homes - 2,107 ft² / 2,390 ft² - 2 Car Garage

3+Den / 2 Baths / Pool

Built 2021
Winding Cypress Naples Homes for Sale: The Martin Ray floor plan is a breathtaking home located in the serene Winding Cypress community, overlooking a picturesque lake. This exquisite 2021 residence showcases the meticulous care of its single owner and boasts numerous upgrades throughout. It features a heated pool, three bedrooms, two bathrooms, and a den, providing ample space for living and entertaining. The heart of the home is a spacious, light-filled living area and a large kitchen with a generous island for seating. Culinary enthusiasts will appreciate the five-burner natural gas stove and the convenience of a butler's pantry. The exquisite quartz countertops complete the perfect setting for entertaining and everyday living. The home is adorned with impact windows and sliders, allowing natural light to flood in, and is accented with 8-foot doors and custom crown molding in the primary bedroom. The large primary bathroom features a walk-in shower, dual sinks, a dedicated toilet room, and access to the large walk-in closet with built in shelves, and enough room for a small crafts station. Additional highlights include two spacious guest bedrooms, elegant tile flooring throughout, and a two-car garage with a durable epoxy finish. Relax in your well-placed den with views of the natural preserve across the street or convert the space into a spacious home office. Outdoors, you can unwind in your private pool and enjoy the exquisite under-truss patio area. The electric roll-down screens and remote-controlled awning provide a perfect spot to relax poolside, savor the shade, and take in the tranquil lake views. The paver driveway has been widened and extended, while the pool deck pavers have recently been power washed and sealed for added appeal. The pie shaped lot is an added bonus giving you a large front yard and plenty of room between you and your neighbors. The conveniently situated lot location is not far from the resident's entrance, providing easy access in and out of the community. Winding Cypress is conveniently located near shopping and dining options and is enveloped by 800 acres of natural preserve and 80 acres of stunning lakes. Winding Cypress enhances the community experience with a wonderful dog park making it an ideal place for pet lovers This dedicated space allows residents and their furry friends to enjoy the outdoors socialize and stay active. Residents can avail themselves of various amenities, including the Shady Palm Café, a resort-style pool and spa, a fitness center, social programs, and sports facilities such as pickleball, tennis courts, and bocce ball. There is also a walking trail for those who love to explore nature. This home exemplifies the essence of Southwest Florida living at its finest. Schedule a showing today. BE SURE TO CLICK THE FULL VIRTUAL TOUR LINKS FOR DETAILS!



$895,000
Decrease*
$100K
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Winding Cypress

6906 Winding Cypress Dr, Naples, FL 34114

Homes - 2,124 ft² / 2,961 ft² - 2 Car Garage

3+Den / 3 Baths / Pool

Built 2022
Winding Cypress Naples Homes for Sale: This magnificent Mystique model by DiVosta, located in the prestigious Winding Cypress community, offers a perfect blend of elegance and luxury. Featuring 3 bedrooms plus a den, and 3 bathrooms, this spacious pool home offers comfortable living with all the amenities you'd expect in a high-end property. The primary suite is a true retreat, complete with a lavish en-suite bath and an expansive walk-in closet. The guest rooms are equally well-appointed, offering privacy and relaxation for visitors. A serene preserve view enhances the home's peaceful atmosphere, allowing you to unwind in complete tranquility. The open-concept living area transitions smoothly to the screened lanai, where a heated saltwater pool and paver deck set the stage for ideal outdoor entertaining or quiet relaxation. Inside, the home is upgraded with elegant tile flooring, neutral tones, and upscale finishes throughout, creating a warm and inviting environment. The stylish two-tone kitchen features a large center island, breakfast bar, and an adjoining dining space—perfect for family meals or casual gatherings. Additional features of this move-in-ready home include enhanced storm protection, a spacious laundry room with ample storage, and a two-car garage with an epoxy-coated floor for durability and style. Whether you're seeking luxury or comfort, this property offers both in abundance. Winding Cypress provides an exclusive living experience, combining luxurious amenities and a close-knit community. Ideally located near Marco Island’s pristine beaches, the vibrant 5th Avenue district, and with easy access to I-75, this gated community is perfectly positioned for convenience. Residents enjoy low HOA fees and an abundance of premium amenities including pickleball, bocce, tennis, and a state-of-the-art fitness center. The community also offers a resort-style pool, an internet café, a community garden, and a dedicated dog park, ensuring something for everyone. The centerpiece of Winding Cypress is its beautifully designed Clubhouse, a social hub where residents can relax and connect. Just steps away, the luxurious pool area offers a serene oasis for sunbathing, swimming, and unwinding. The community is surrounded by 800 acres of preserves and 80 acres of lakes, creating a unique connection to nature. Nearby shopping and dining options abound at Tamiami Crossing and Freedom Square, both within easy reach. Winding Cypress, developed by DiVosta Homes, features 766 meticulously crafted residences, offering an unparalleled lifestyle in the heart of Southeast Naples. The Homeowners Association ensures the community is beautifully maintained, making Winding Cypress one of Southwest Florida’s premier luxury neighborhoods. This is an exceptional opportunity to own a piece of paradise in a highly sought-after community. With its combination of luxury, comfort, and location, this property is sure to sell quickly.



$830,000
Decrease*
$165K
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Winding Cypress

7045 Live Oak Dr, Naples, FL 34114

Homes - 2,496 ft² / 3,061 ft² - 3 Car Garage

3+Den / 3 Baths

Built 2016
Winding Cypress Naples Homes for Sale: Welcome to the best kept secret in Naples, the community of Winding Cypress. Winding Cypress is a DiVosta neighborhood, loaded with resident amenities, and just minutes to Olde Naples and Marco Island. This beauty is the most popular model, The Pinnacle, and it is being offered at an amazing value in equity! An entertainer's dream home boasting an expansive open floorplan joining a huge great room with the Chef's kitchen and separate dining area, flowing into an extended outdoor living space. Complete with 3 bedrooms including an owner's suite, 3 full bathrooms, large den/office option, and a valuable 3 car garage with a 4-foot extension. Additional enhancements and upgrades include; hurricane impact windows, entry door, and slider, electric Storm Smart Kevlar hurricane rated screens, extended outdoor living area including a custom outdoor natural gas kitchen, upgraded maple kitchen cabinets with pull outs, granite countertops and backsplash, and extended center island, upgraded faucets, tile, and bath fixtures, laundry room with built-in cabinets, counter, and utility sink/tub, an epoxy painted floor and additional utility sink/tub in the garage, and a custom lighting package. The amenities of Winding Cypress are second to none. The community offers an awesome, resident's only restaurant, pickleball, tennis, and bocce courts, the most amazing resort pool with spa, sand beach private cabanas, and men's & women's locker room and shower facilities. The clubhouse boasts a best-in-class fitness center and motion room, conference rooms with a prep kitchen, resident's library, and an outdoor gathering area with a built-in fireplace. Winding Cypress offers onsite management and full-time activities director. Your pets will enjoy the 2 dog parks to run and play. Additionally, there is a community garden to grow your vegetables and flowers as well as a boardwalk nature trail. Winding Cypress is comprised of 1250 total acres, with 850 acres being greenspace and preserve, giving a wonderful feel of openness, privacy, and natural surroundings not found in other new communities. Why would you wait to build, and spend significantly more, and end up with less?



$730,000
Decrease*
$65.9K
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Winding Cypress

7370 Mockingbird Ct, Naples, FL 34114

Homes - 1,805 ft² / 2,222 ft² - 2 Car Garage

2+Den / 2 Baths

Built 2016
Winding Cypress Naples Homes for Sale: Welcome to your dream home at 7370 Mockingbird Court in beautiful Naples, FL! This charming 2-bedroom, 2-bathroom residence, with a versatile den that can easily be converted into a third bedroom, offers a spacious 1,805 square feet of living space, perfectly nestled on an 8,276 square foot lot. Step inside to discover a welcoming interior featuring both carpet and tile floors, ideal for comfort and style. The open living area is enhanced by new ceiling fans and pendant lighting, creating a bright and airy atmosphere. The kitchen is a chef's delight with brand new quartz countertops, a new sink and faucet, and a suite of new appliances including a dishwasher, refrigerator, and garbage disposal. The master suite offers a serene retreat with a new toilet in the master bath, ensuring modern convenience. Enjoy the luxury of central AC and gas heat throughout the home. The attached garage, equipped with a new garage door opener, provides ample space for parking and storage. Outdoor enthusiasts will appreciate the common outdoor space, private outdoor areas, and stunning lakefront views. The community amenities are second to none, featuring a pool, hot tub, gym, tennis court, and pickleball facilities. For those who love the water, the property is waterfront with lake views, perfect for tranquil evenings. Plus, there is room to add a pool, allowing you to customize your outdoor oasis. Additional features include a new gas hot water heater, added landscape lights, and a recently cleaned roof. Plus, enjoy the convenience of laundry in the building and a washer/dryer in the unit. Conveniently situated just minutes from shopping, dining, and all the attractions Naples has to offer, this home combines tranquility with exceptional lifestyle opportunities. This home is a true gem, offering a blend of comfort, style, and community amenities that make it a perfect place to call home. Don't miss the opportunity to make it yours!



$675,000
Decrease*
$74.9K
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Winding Cypress

7815 Jacaranda Ln, Naples, FL 34114

Homes - 1,574 ft² / 1,960 ft² - 2 Car Garage

2+Den / 2 Baths / Pool / Spa

Built 2019
Winding Cypress Naples Homes for Sale: PRICE DRASTICALLY REDUCED FOR QUICK SALE!! This beautiful villa in highly sought-after Winding Cypress offers two bedrooms, two baths plus a den along with a two-car air-conditioned garage. Step onto your lanai with the largest pool and hot tub available in a villa. Couple that with a spectacular long lake view and you truly have a one-of-a-kind home. Winding Cypress offers resort-style living with a large amenity center, gym, exercise room, library, internet cafe, event room and restaurant. The resort-style pool has a lap lane and waterfall. Other amenities include pickleball, tennis, bocce, community garden and dog park. The community boardwalk allows you to walk deep into the preserve. Winding Cypress boasts 800 acres of untouched preserve surrounding our one-of-a-kind community.



$669,900
Decrease*
$20K
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Winding Cypress

7248 Live Oak Dr, Naples, FL 34114

Homes - 1,685 ft² / 2,300 ft² - 2 Car Garage

2+Den / 2 Baths

Built 2016
Winding Cypress Naples Homes for Sale: This home is a true single famly NOT an attached villa. PRICED RIGHT ALMOST $230k UNDER THE NEXT ABBEY VILLE FLOOR PLAN FOR SALE IN COMMUNITY. BUILT AS AND COUNTY APPROVED AS A 3 BEDROOM HOME THIS FAMILY SELECTED THE FLEX ROOM OPTION HOWEVER WILL ADD THE CLOSET IF NEW OWNER WANTS Wonderful community with over 800 acres giving room for custom homes and large back yards, nature trails and room to relax. So well cared for. Enjoy the private park like back yard. Extended screened patio with outdoor kitchen perfect for dining al fresco. Light bright home with all the goodies. Even gas kitchen. Open floor plan plenty of storage. The community has a dog park for Fido. Amenity rich community with low HOA Look what the community offers Neighborhood Features Natural Gas Community 800+ Acres of Natural Preserves Heated Resort-Style Pool & Spa Poolside sugar-sand beach and cabanas 17,500 sq. ft. Clubhouse with Activity Room, Catering Kitchen & Library State of the Art Fitness Center & Movement Studio Outdoor Barefoot Bar and Grill Natural Gas Fire Pit Activity Director 4 Bocce Ball Courts Tennis Courts 4 Pickleball Courts Dog Park Community Garden Boardwalk with Pavilion and Bird Wading Overlook 80 Acres of Lakes Home Lawn Maintenance included Entry Gate with Guard House Less than 3 miles from US-41 10 Minutes to I-75 15 Minutes to Fifth Avenue and Third Street Shopping & Dining 20 Minutes to Naples Pier and magnificent area beaches 20 Minutes to Marco Island prepared with care but subject to errors and omissions Buyer to verify everything to their satisfaction



$650,000
Decrease*
$35K
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Winding Cypress

7666 Jacaranda Ln, Naples, FL 34114

Homes - 1,574 ft² / 1,574 ft² - 2 Car Garage

2+Den / 2 Baths

Built 2018
Winding Cypress Naples Homes for Sale: The Finest in Resort Style Living! You do not want to miss this opportunity to own a find like this in the Community of Winding Cypress. This Beautifully updated 2+Den/2 Bath Gem has 9' 4" ceilings with a two car garage is move in ready and it has everything you need to call this sought after Villa your Home. New refrigerator, new hot water tank, new pavers, plantation shutters and much more. Almost 2/3 of this Amazing Community is set aside just for a tranquil preserve/wooded area. Only 8 miles to Downtown Naples + 9 miles to Marco Island. Just a few Amenities include Pickleball, Bocce Court, Clubhouse, Community Park, Community Pool/Spa/Hot Tub + Community Room and much, much more! What are you waiting for.. Call Now to set up your showing cause this Unique Property won't be on the market long!



$640,000
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Winding Cypress

7167 Live Oak Dr, Naples, FL 34114

Homes - 1,544 ft² / 1,898 ft² - 2 Car Garage

3 Bed / 2 Baths / Pool

Built 2016
Winding Cypress Naples Homes for Sale: Don't miss your chance to own a Serenity Turnkey Pool Villa in the highly sought-after Winding Cypress community! This meticulously designed residence boasts 3 bedrooms, 2 bathrooms, and a 2-car garage, offering both comfort and style. Step outside to your private outdoor oasis, complete with a tranquil waterfall feature, electrically heated salt pool, built-in speakers, and serene preserve views—the perfect setting for relaxation or entertaining. For added peace of mind there are also electric hurricane screens on the lanai. Inside, the versatile third bedroom can function as a den or guest room, featuring French doors and a closet. Elegant interior upgrades include crown molding, tray ceilings, built-in speakers, a security system, custom closet systems, and stunning diagonal tile flooring—just to name a few! Winding Cypress is a natural gas community with resort-style amenities! Dine at Shady Palm, the onsite restaurant, or enjoy pickleball, bocce, tennis, a state-of-the-art fitness center, a resort-style pool, a community garden, and even a dog park for your furry friend. This pet-friendly community allows rentals, has low fees, and boasts a prime location—central to Marco Island, 5th Avenue, and I- 75.



$585,000
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Winding Cypress

7176 Live Oak Dr, Naples, FL 34114

Homes - 1,554 ft² / 1,934 ft² - 2 Car Garage

3 Bed / 2 Baths

Built 2015
Winding Cypress Naples Homes for Sale: Sophisticated Villa Living in Winding Cypress – Priced to Sell/Fully Furnished. An extraordinary opportunity awaits in the highly sought-after Winding Cypress community—this impeccably upgraded 3-bedroom, 2-bathroom villa is set on the largest homesite in the neighborhood, offering both privacy and an expansive outdoor retreat. Thoughtfully enhanced with luxury upgrades and high-end finishes, this residence is a rare find, now priced competitively for discerning buyers seeking exceptional value. From the moment you step inside, you’ll appreciate the seamless open-concept design, accentuated by elegant crown molding and designer window treatments. The chef’s kitchen features stunning granite countertops, a specialty tile backsplash, and a well-appointed summer kitchen with a Paradise Grill, bar seating, refrigerator, and a 5-year transferable warranty—perfect for effortless entertaining. The home is designed for both comfort and peace of mind, featuring an integrated whole-house backup generator, carbon monoxide detectors, an advanced security system with perimeter cameras and video doorbell, electronic front door lock, and accordion shutters on all windows. The extended, screened-in lanai—complete with ceiling fans, lighting, and electronic roll-down hurricane/security shutters—invites you to unwind in a serene outdoor sanctuary. Additional premium upgrades include a brand-new state-of-the-art extra-large capacity washer/dryer (2024) with a 5-year transferable warranty, epoxy-coated garage flooring and custom storage system (2024), split-fin garage A/C (2024) for year-round climate control, garage door and attic insulation (2024) for enhanced energy efficiency, and lush upgraded landscaping and exterior lighting for impeccable curb appeal. Resort-style living is at your doorstep with access to Winding Cypress’ world-class amenities, including a 5-star clubhouse with dining, resort and lap pools, a jacuzzi, fitness center, tennis, pickleball, bocce courts, a dog park, and more. This is a rare chance to own a premier villa in one of the area’s most coveted communities—offered at an exceptional value for those ready to make it their own. Schedule your private tour today and experience the elegance, comfort, and convenience of this one-of-a-kind residence.



$579,500
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Winding Cypress

7658 Jacaranda Ln, Naples, FL 34114

Homes - 1,554 ft² / 1,914 ft² - 2 Car Garage

2+Den / 2 Baths

Built 2018
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.



$554,900
Decrease*
$144K
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Winding Cypress

7702 Jacaranda Ln, Naples, FL 34114

Homes - 1,554 ft² / 1,898 ft² - 2 Car Garage

2+Den / 2 Baths / Pool

Built 2019
Winding Cypress Naples Homes for Sale: Absolutely the best deal on a 2 bedroom plus den with French doors, 2 baths, 2 car garage attached villa with your own POOL in Winding Cypress. You better Hurry. Furniture negotiable too, move right in for season, nicely furnished. What's Special: *Open floor plan *Epoxy garage floor *Granite countertops *3 ft. bathroom countertops *Remote controlled garage screen *Remote controlled hurricane shutters on the lanai *California Closets in all bedrooms *Pool. Den can be converted to a 3rd bedroom too. Come see this beautifully designed pool home boasting of an inviting open floor plan, perfect for entertaining and family living. The kitchen highlights its elegant backsplash and granite countertops that provide both beauty and durability. Each bathroom has been designed with 3 ft. of countertops for added space and comfort. California Closet's custom-design can be found in each closet to maximize storage and organization throughout. The home has also been designed with 8' doors, adding to the modern, airy feel. The garage is finished with epoxy flooring and comes with remote controlled garage screen for added ventilation and convenience. Step out to the back lanai where you will find remote controlled weather/hurricane shutters for those rainy afternoons or storm seasons, giving you peace of mind. Enjoy the private pool. perfect for relaxation and entertainment. The home has been smoke-free and pet-free, ensuring a clean, fresh environment for the next owners. With thoughtful upgrades and premium features, this home is ready to welcome you. Winding Cypress includes: *Over 800 acres *Natural preserve *Nature trails *Dog park, *Low HOA *Clubhouse activity room *Fitness center *Heated resort-style pool *White sandy lounge area *Bar and grill *Library *Catering kitchen *Tennis and pickleball courts *Natural gas *15 minutes from 5th Ave. *20 minutes from Marco Island *Major shopping brands 5 minutes away.



$549,900
Decrease*
$49.1K
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Winding Cypress

7602 Jacaranda Ln, Naples, FL 34114

Homes - 1,554 ft² / 1,914 ft² - 2 Car Garage

2+Den / 2 Baths

Built 2017
Winding Cypress Naples Homes for Sale: MOTIVATED SELLER. Welcome to this stunning 2+Den, 2 Bath home in the preserve-like community of Winding Cypress. As its name suggests, you will be ushered away from the worries of the world as you are greeted by this serene and natural, resort-style community boasting a poolside restaurant, 5 tennis courts, 4 bocce courts, 4 pickle ball courts, an atteneded fitness center, and an engaging social event calendar. Enjoy leisurely strolls at the nature boardwalk or take your furry companions to the community’s dog park. The property boasts generous yard space, a relaxing screened-in lanai, and meticulously maintained landscaping. Inside, you'll find a modern kitchen equipped with stainless-steel Whirlpool appliances and a newer washer and dryer. Whether you're entertaining or seeking tranquility, this home offers the perfect balance of comfort and convenience in an unbeatable location. Optimally located to experience the best that Naples and Marco Island have to offer, you'll find yourself ideally positioned between the shores of Marco Island's white sandy beaches and Naples' 5th Avenue, featuring lavish and upscale dining and shopping. An elegant home in a vibrant tropical paradise, come and experience southwest Florida at its finest.



$549,000
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Winding Cypress

7650 Jacaranda Ln, Naples, FL 34114

Homes - 1,579 ft² / 1,980 ft² - 2 Car Garage

2+Den / 2 Baths

Built 2018
Winding Cypress Naples Homes for Sale: Welcome to your dream home in the heart of one of Naples' most sought-after communities! This stunning FRONT entrance Cressida villa offers the perfect blend of comfort, style, and convenience. Featuring two spacious bedrooms, two full baths, and a versatile den/flex room that can be used as an in-home office or guest area, this home is designed to meet all your needs. The updated kitchen is a chef's delight, boasting stainless steel appliances, quartz countertops, bright white cabinetry with under-cabinet lighting, and a stunning backsplash. The open concept living/dining space includes a custom-built dry bar/coffee station, light tile flooring, and sliders that open to a private screened lanai. The covered lanai area is plumbed for an outdoor kitchen, allowing you to create the perfect space for entertaining. This property provides ample space for both relaxation and functionality, making it ideal for a vacation home or full-time Florida living. Winding Cypress offers a plethora of activities to enjoy the Florida lifestyle, including tennis, pickleball, bocce, a state-of-the-art fitness center, a resident-only on-site restaurant, a resort pool with lap lanes and a picturesque waterfall, and much more. Plus, you're just within 10 minutes from Marco Island and the iconic Naples 5th Avenue boutique shopping and 5-star dining pleasures.



$537,000
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Winding Cypress

7642 Jacaranda Ln, Naples, FL 34114

Homes - 1,554 ft² / 1,914 ft² - 2 Car Garage

2 Bed / 2 Baths

Built 2017
Winding Cypress Naples Homes for Sale: Tucked Away Treasure in Winding Cypress- Step into a slice of serenity with this charming attached villa, nestled in one of the most peaceful corners of Naples. Unlike the typical coastal designs so common in the area, this home offers a more rustic warmth—perfect for those who appreciate natural textures, cozy finishes, and a relaxed, grounded lifestyle. With 2 bedrooms, a versatile den, 2 full bathrooms, and a 2-car garage, this villa checks all the boxes for comfort and functionality. The open layout is inviting yet intimate, ideal for both quiet evenings and casual entertaining. The kitchen is equipped with natural gas—a rare find that’s perfect for those who love to cook and value energy efficiency. Step outside to the screened-in lanai where mornings are best spent with coffee in hand, surrounded by the sounds of nature and a view of your private backyard oasis. An extended outdoor patio provides the perfect space to unwind under the stars. Located within the gated, master-planned community of Winding Cypress, this home offers so much more than just a beautiful space—it’s part of a vibrant lifestyle. Developed by Divosta Homes and surrounded by over 800 acres of natural preserves and 80 acres of lakes, Winding Cypress is a nature lover’s dream, tucked beside the Picayune Strand Forest. Residents enjoy top-tier amenities including the Shady Palm Café, a stunning resort-style waterfall pool, clubhouse, fitness center, tennis, bocce, and pickleball courts, and scenic walking trails. Plus, you’re just minutes from shopping and dining at Tamiami Crossing and Freedom Square. If you’ve been waiting for a home that feels like a true escape—but still close to it all—7642 Jacaranda Ln is calling.



$529,000
Decrease*
$100K
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Winding Cypress

7638 Jacaranda Ln, Naples, FL 34114

Homes - 1,574 ft² / 1,977 ft² - 2 Car Garage

2+Den / 2 Baths

Built 2017
Winding Cypress Naples Homes for Sale: Introducing the incredibly rare Winding Cypress model, the Cressida villa, now available with expansive private yard and lanai space. This unique villa features a dedicated private front entrance and an expanded foyer, complemented by an open yet defined living concept. The home boasts a wealth of builder-installed upgrades, including granite finishes, high-end porcelain floors, a glass-tiled backsplash, top-of-the-line cabinetry and crown molding throughout. The spacious backyard provides ample room to add a pool or a large sundeck of your choice. Winding Cypress stands out as one of Naples' most distinctive resort communities, encompassing over 800 acres of pristine preserve in an ideal location between Marco Island and downtown Naples 5th Avenue. Community amenities include a dog park and a vegetable garden. The Club at Winding Cypress is must-see, featuring a resort-style pool, sunset sand cabanas, bocce ball, pickleball, clay tennis courts, a yoga deck, a large gym facility, fire pits, a nature trail, locker rooms and a dedicated activities director. Enjoy a vibrant lifestyle with a sand bar, restaurant and a professional activity director on staff!



$475,000
Decrease*
$100K
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Winding Cypress

7686 Jacaranda Ln, Naples, FL 34114

Homes - 1,574 ft² / 1,987 ft² - 2 Car Garage

2+Den / 2 Baths

Built 2018
Winding Cypress Naples Homes for Sale: Don’t miss this exceptional opportunity to own an upgraded Cressida villa in the sought-after community of Winding Cypress! This front-entry home lives like a single-family residence, offering 2 bedrooms + den, 2 bathrooms, a 2-car garage, and a stunning expanded patio with extra covered space—more than most villas. Inside, enjoy luxury upgrades including white cabinetry, quartz countertops, crown molding, and more. The outdoor space is equally impressive, featuring a built-in hood for effortless grilling and gorgeous mature landscaping. Winding Cypress is a natural gas community with resort-style amenities! Dine at Shady Palm, the onsite restaurant, or enjoy pickleball, bocce, tennis, a state-of-the-art fitness center, a resort-style pool, a community garden, and even a dog park for your furry friend. This pet-friendly community allows rentals, has low fees, and boasts a prime location—central to Marco Island, 5th Avenue, and I-75.



$925,000
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Winding Cypress

6854 Greenbriar Ct, Naples, FL 34114

Homes - 2,118 ft² / 2,545 ft² - 2 Car Garage

3+Den / 2 Baths

Built 2020
Winding Cypress Naples Homes Under Contract: A MOST INCREDIBLE OFFERING. WELCOME TO THIS EXCLUSIVE MARTIN RAY MODEL FOOTPRINT. THIS HOME HAS IT ALL INCLUDING THE FOLLOWING: WHOLE HOUSE GENERATOR, HURRICANE IMPACT WINDOWS & SLIDING GLASS DOOR, HURRICANE IMPACT MAIN ENTRANCE DOOR WITH LEADED GLASS, STORMSMART ELECTRIC HURRICANE SHADES, 11 FOOT CEILINGS WITH TRAYS, COFFERS, & WIDE MOLDINGS, OPTIONAL DEN/OFFICE WITH TRAY CEILING, UPGRADED OWNER’S SUITE WITH SITTING AREA AND OPTIONAL BATHROOM LAYOUT, CUSTOM SINK, SHOWER, & BATHROOM FIXTURES, OPTIONAL WHOLE HOUSE LIGHTING PACKAGE, OPTIONAL EXTERIOR LIGHTING PACKAGE, OPTIONAL 3RD BEDROOM, BUTLER’S PANTRY WITH BAR AREA, WINE RACK, & WINE/BEVERAGE REFIGERATOR, UPGRADED KITCHEN CABINET PACKAGE INCLUDING SOFT CLOSE DOORS, DECORATIVE DOOR-END PANELS, WIDE DENTIL TRIM, PULL OUT DRAWERS, & UNDER CABINET LIGHTING, UPGRADED QUARTZ COUNTERTOPS, CUSTOM BRICK MOSAIC BACKSPLASH, UPGRADED APPLIANCE PACKAGE INCLUDING BOSCH REFRIGERATOR & DISHWASHER, UPGRADED PLANK TILE FLOORING THROUGHOUT, CUSTOM LAUNDRY CENTER WITH BUILT-IN CABINETS & UTILITY SINK, VITEX SMART HOME SECURITY & FIRE PACKAGE MONITORED BY CENTRAL STATION, WHOLE HOUSE ALARMED LEAK DETECTION SYSTEM, ELECTRIC WINDOW SHADES, SMOOTH INTERIOR WALLS, PLANTATION SHUTTERS THROUGHOUT, TANKLESS WATER HEATER, WHOLE HOUSE WATER FILTRATION SYSTEM, UPGRADED 8 FOOT SOLID CORE DOORS WITH DECORATIVE ARCH, OPTIONAL DROP ZONE OFF OF THE GARAGE, 2 CAR GARAGE WITH 4 FOOT EXTENSION WITH UTILITY SINK & INSULATED OVERHEAD DOOR, IMPRESSIVE EXTENDED LANAI WITH CUSTOM PAVERS AND TURF ACCENT & WIDE LAKE VIEW, PICTURE WINDOW LANAI SCREEN, EXTENDED DRIVEWAY & MAIN ENTRANCE PAVERS, PAVER SIDEWALKS ON BOTH SIDES TO LANAI, PROFESSIONALLY LANDSCAPED AROUND ENTIRE RESIDENCE, HOME HAS BEEN PROFESSIONALLY DESIGNED & DECORATED BY ROBB & STUCKY – FURNISHINGS ARE NEGOTIABLE OUTSIDE OF LIST PRICE. WINDING CYPRESS IS AN AMENITY RICH COMMUNITY, INCREDIBLE VALUE, AND A NAPLES HIDDEN GEM. AMENITIES INCLUDE A PRIVATE RESIDENT'S ONLY RESTAURANT, RESORT POOL & SPA, PICKLEBALL, TENNIS & BOCCE COURTS, SPECTACULAR COMMUNITY CENTER W/FITNESS CENTER, LOCKER ROOMS, CONFERENCE ROOMS & LIBRARY, DOG PARK, COMMUNITY GARDEN, BOARDWALK NATURE TRAIL, ONSITE HOA MANAGEMENT WITH A FULL-TIME ACTIVITIES MANAGER. YOU'RE 10 MINUTES TO THE BEACHES OF MARCO ISLAND & 15 MINUTES TO THE RESTAURANTS, ENTERTAINMENT & SHOPPES OF OLDE NAPLES.



$899,000
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Winding Cypress

6763 Pennyroyal Dr, Naples, FL 34114

Homes - 2,208 ft² / 2,892 ft² - 2 Car Garage

3+Den / 2 Baths

Built 2020
Winding Cypress Naples Homes Under Contract: Don't miss out on this stunning impeccably maintained Summerwood model in the highly coveted Winding Cypress community. This beautifully designed home offers 3 bedrooms, plus a dedicated home office, perfect for today’s lifestyle. Step onto the charming front porch, an inviting space to unwind with your morning coffee, and be greeted by a designer glass entry door. Inside, you’ll find a bright and open layout enhanced by crown moldings, luxury tile flooring, and classic plantation shutters, creating an atmosphere of elegance throughout. The gourmet kitchen is a chef’s dream, featuring gleaming Quartz countertops, upgraded 42-inch cabinetry with dovetail soft-close drawers and pullouts, and high-end stainless-steel appliances. The seamless flow from the kitchen into the spacious open living and dining areas makes it ideal for both everyday living and entertaining guests. Enjoy peace of mind with impact-resistant windows and electric storm shutters along the covered lanai. Take full advantage of the abundant space and natural light pouring in through the sunroom. Custom closets throughout offer exceptional storage, keeping everything neat and organized. The extended 2-car garage is more than just a place to park—it includes a mini-split A/C system and epoxy flooring, offering extra room for storage or hobbies. Relax or entertain on the expansive covered lanai, where you can enjoy breathtaking, unobstructed long water views through a panoramic screen. Whether you're sipping a drink by day or watching the sunset by night, this lanai is the ultimate retreat. Winding Cypress is an amenity rich community with 850 acres of green preserve space. Residents enjoy the full-scale restaurant, pickleball, tennis, & bocce courts, a spectacular community pool and clubhouse, awesome fitness center, dog parks, community garden, boardwalk nature trail, and a full-time activities program that offers something for everyone on a weekly, regular basis. Located just 15 minutes to the beaches of Marco Island and 20 minutes to restaurants and shoppes in Olde Naples. This home blends comfort, luxury, and functionality in perfect harmony—you will want to experience it firsthand!



$799,000
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Winding Cypress

6758 Pennyroyal Dr, Naples, FL 34114

Homes - 1,921 ft² / 2,512 ft² - 2 Car Garage

2+Den / 2 Baths / Pool / Spa

Built 2021
Winding Cypress Naples Homes Under Contract: This beautifully upgraded 2-bedroom plus den, 2-bath Mystique floorplan home in Winding Cypress offers the perfect blend of style, comfort, and functionality. The open-concept design features a zero-corner slider, seamlessly connecting indoor and outdoor spaces, while impact windows and doors provide security and energy efficiency. A whole-home generator ensures uninterrupted comfort and peace of mind. Inside, thoughtful upgrades enhance every space. The gourmet kitchen boasts built-in appliances and a spacious island, perfect for entertaining. Additional highlights include crown molding, built-in speakers, a custom living room accent wall, and built-in drop zone cabinetry for added style and organization. The den features a Murphy bed, making it a flexible space for a home office or extra bedroom. The laundry room is equipped with built-in cabinets, offering ample storage. Outside, the private backyard is a true retreat, featuring a pool and spa for ultimate relaxation. The outdoor kitchen is perfect for entertaining, while lush landscaping enhances the home’s peaceful ambiance. A tandem garage has the ability to accommodate up to three cars, providing plenty of parking and storage. Winding Cypress is a natural gas community with resort-style amenities! Dine at Shady Palm, the onsite restaurant, or enjoy pickleball, bocce, tennis, a state-of-the-art fitness center, a resort-style pool, a community garden, and even a dog park for your furry friend. This pet-friendly community allows rentals, has low fees, and boasts a prime location—central to Marco Island, 5th Avenue, and I- 75.



$549,999
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Winding Cypress

7591 Jacaranda Ln, Naples, FL 34114

Homes - 1,554 ft² / 8,872 ft² - 2 Car Garage

2+Den / 2 Baths

Built 2016
Winding Cypress Naples Homes Under Contract: Price Negotiable! Seller is highly motivated!! Discover your slice of paradise in this stunning 2-bedroom plus den villa, located in the resort-style community of Winding Cypress. With exquisite builder-installed upgrades, this home features a sleek open floor plan, granite countertops, and elegant porcelain tile throughout. The kitchen is outfitted with stainless appliances and gas stove complemented by a stylish backsplash. The spacious den, equipped with French doors, can easily transform into a third bedroom, while California Closets in every room provide exceptional storage and organization and Plantation Shutters. Your attached 2-car garage is enhanced with Monkey Bar storage for maximum efficiency! Step outside to enjoy a wealth of amenities, including a restaurant and bar, a state-of-the-art fitness center, resort-style pools, and vibrant sports facilities for bocce, pickleball, and tennis. Unwind by the fire pit or explore the nature boardwalk and bird-watching overlooks. Perfectly situated between downtown Naples and Marco Island, this beautifully upgraded home offers the ultimate Florida lifestyle. Don’t miss out on this incredible opportunity



$720,000
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Winding Cypress

7742 Jacaranda Ln, Naples, FL 34114

Homes - 1,554 ft² / 1,894 ft² - 2 Car Garage

2+Den / 2 Baths / Pool / Spa

Built 2019
Winding Cypress Naples Homes Under Contract: This move in ready furnished Winding Cypress Serenity 2 bedroom plus den Attached Villa with POOL & SPA is a unique quality find. This Serenity floor plan with the kitchen conveniently tucked away behind peninsula island allows for optimal entertaining space. Kitchen features Quartz countertops, natural gas range & SS appliances. Other high quality highlights include, plantation shutters, crown molding, Lutron shades at slider, recessed & under cabinet lighting, upgraded lighted mirrors in both baths, laundry room cabinets & sink, privacy door for guest suite, pull down attic stairs in garage, wide, driveway, pest control piping in the walls, Storm Smart electric hurricane shades on lanai and landscaped lighting around lanai. Slight pie shape lot and lush landscaping offers extra privacy for lanai and pool area. Located in sought after Winding Cypress Community with it's rich amenities including a resort style pool, restaurant/bar, fire pit, fitness center, outdoor yoga deck, pickle-ball, tennis, bocce ball, community garden, dog park, and a nature trail boardwalk that wanders through protected natural preserves. Centrally located between Marco Island and 5th Ave allows easy access to the surrounding areas beautiful beaches, restaurants and entertainment.



$1,550,000
Sold Price:
$1,495,000
Sold Date:
01/21/2025
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Winding Cypress

6883 Cocoplum St, Naples, FL 34114

Homes - 2,519 ft² / 3,510 ft² - 3 Car Garage

3+Den / 3 Baths / Pool / Spa

Built 2021
Winding Cypress Naples Homes: This popular DiVosta Pinnacle Model is situated in the amenity rich community of Winding Cypress. It is possible to purchase this beauty furnished or turnkey furnished as negotiated and agreed upon. This property is a one owner home that's loaded with builder and owner upgrades to include: custom tile plank flooring throughout, 12'+ coffered/tray ceilings with crown molding and custom detail wall, saltwater pool w/integral spa, whole house generator, hurricane impact windows, zero corner slider with impact glass, Storm Smart Kevlar screen across lanai, leaded glass front door, upgraded kitchen appliance package, upgraded kitchen & bath cabinet package, plantation shutters throughout, home security system, extended 3 car garage w/epoxy floor, additional refrigerator/freezer & built in cabinets, custom closet and pantry storage systems, upgraded laundry room w/built in cabinets and utility sink, den complete with built in desk & storage system, upgraded electrical include custom fixtures, ceiling fans and dimmer switches. The exterior has beautiful Bohemian shutters along with a paver walkaround. This gorgeous home sits on an oversized private lot at the end of a dead-end cul-de-sac. Winding Cypress boasts one of the most outstanding community amenities anywhere in Naples and at an incredible value. They include a private, residents only restaurant, spectacular resort pool, spa & beach cabana, expansive clubhouse w/an amazing fitness center w/men's/women's locker rooms, conference & meeting rooms, library, community kitchen, pickleball, tennis, & bocce courts, dog park, nature boardwalk, and a community garden. Winding Cypress is perfectly located 10 minutes from Marco Island & 15 minutes from downtown Olde Naples.



$1,075,000
Sold Price:
$995,000
Sold Date:
11/15/2024
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Winding Cypress

7063 Winding Cypress Dr, Naples, FL 34114

Homes - 2,496 ft² / 3,656 ft² - 3 Car Garage

3+Den / 3 Baths

Built 2016
Winding Cypress Naples Homes: Ready for immediate occupancy! home is now vacant and has a nice clean open slate to custom this home to your liking .Take a look at this Pinnacle style home located in the sought after community of Winding Cypress features 3 bdrms 3 baths, office and 3 car garage , hurricane protection measures include whole house generator , impact doors and windows and hurricane storm screen on lanai. Extended oversized Lanai facing the lake has plenty of room for entertaining , practice your putting , or custom a new pool or spa. come and take a look at this Pinnacle style home in Winding Cypress, use your vision to custom this home to your own personal taste, You can't beat the floor plan with almost 2500 soft of living space and is a great value compared to other Pinnacle models sold here in Winding Cypress. Home is located within walking distance to all the amenities Winding Cypress has to offer,, beautiful resort pool , pool side resturant and bar, gym, sports courts and more . Walk to to the dog park and community garden. P



$1,050,000
Sold Price:
$992,500
Sold Date:
04/17/2025
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Winding Cypress

7404 Winding Cypress Dr, Naples, FL 34114

Homes - 2,062 ft² / 2,493 ft² - 2 Car Garage

2+Den / 2 Baths / Pool / Spa

Built 2016
Winding Cypress Naples Homes: The most private homesite in Winding Cypress Resort community, this exceptional home offers views abundant with trees and lake, bordered by a lush preserve and expansive buffer zones. Breathtaking southwestern water views provide the ideal backdrop, rivaling the most stunning beach sunsets. Step outside to the largest covered lanai in the community, complete with a sparkling pool and spa, creating an idyllic space for relaxation and entertaining. Step inside to discover a home that has been expanded and meticulously designed, with raised ceilings and professionally finished interiors that exude sophistication. This home is equipped with premium features, including whole house generator, reverse osmosis water system, impact-resistant glass, natural gas and top-tier finishes throughout. The expansive layout offers views from every angle, ensuring that every room feels connected to the beautiful outdoor surroundings. Residents can indulge in the luxurious Winding Cypress Club, which features a state-of-the-art fitness center, catering kitchen, community room and activity room. Outdoor amenities abound, including pickleball, a resort-style pool with a lap section, spa, outdoor movement studio, barefoot bar, bocce ball courts, five Har-Tru tennis courts, a fire pit, a bird-watching overlook and a nature boardwalk with a picnic pavilion. At the center point between the pristine shores of Marco Island and the vibrant downtown Naples, this incredible resort location provides the ideal backdrop for an unparalleled lifestyle.



$969,000
Sold Price:
$935,000
Sold Date:
04/01/2025
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Winding Cypress

7683 Winding Cypress Dr, Naples, FL 34114

Homes - 2,018 ft² / 2,502 ft² - 2 Car Garage

3+Den / 2 Baths

Built 2018
Winding Cypress Naples Homes: Live the Vacation Lifestyle Every Day in Winding Cypress Welcome to a home that feels like a never-ending vacation. This stunning Summerwood residence, nestled in the resort-style community of Winding Cypress, is more than a home—it’s a lifestyle. From the moment you step through the dramatic entry hall, you’re greeted by breathtaking lake views that set the tone for tranquility and relaxation. The zero-clearance sliding glass doors seamlessly blend indoor elegance with outdoor splendor, leading to an expansive lanai designed for ultimate leisure and entertainment. Imagine starting your mornings with serene sunrises over the lake, enjoying your coffee on the lanai surrounded by picturesque scenery. The fully equipped bar—complete with a KitchenAid grill, refrigerator, freezer, and ample seating for seven—makes hosting sunset cocktail parties a breeze. Whether you prefer lounging in the shaded comfort or basking in the sun, this home caters to your every mood. Winding Cypress offers an unparalleled array of resort-style amenities: • A tropical pool oasis with cascading waterfalls, a hot tub, and a poolside bar serving refreshing drinks and delicious meals. • Social activities for every interest, from pickleball, tennis, and bocce to art clubs, gardening, and game nights. • Themed parties, live music, and dancing that make every evening unforgettable. When you’re ready to explore beyond the gates, you’re just nine miles from Marco Island’s pristine beaches and downtown Naples’ vibrant dining, shopping, and cultural scenes. From galleries to holiday snowfall in December, there’s always something to enjoy. This home is move-in ready, fully furnished down to the dishes. All that’s left is for you to pack your suitcase and embrace the dream vacation lifestyle—every single day.



$899,000
Sold Price:
$850,000
Sold Date:
02/27/2025
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Winding Cypress

7073 Live Oak Dr, Naples, FL 34114

Homes - 2,867 ft² / 3,202 ft² - 2 Car Garage

3+Den / 3 Baths

Built 2016
Winding Cypress Naples Homes: Welcome to the award-winning Martin Ray home in the prestigious and centrally located Winding Cypress resort community in Naples. This exceptional home features an expansive lanai set on a protected and private preserve, with room for a pool, providing the perfect space to enjoy the serene Florida sunshine. Inside, the bright and airy ambiance is enhanced by a newly enlarged center island with top-of-the-line quartz finishes throughout the kitchen, gourmet natural gas appliances, reverse osmosis water system, high-quality wood grain ceramic tile flooring and impact-resistant glass. Elegant design upgrades also include custom dining area millwork, crown molding, new lighting, plantation shutters, custom drapes and a professionally built closet system in the primary bedroom. Whether you’re hosting a lavish gathering or enjoying a quiet evening at home, this residence seamlessly blends elegance and comfort. A bonus loft offers a versatile space for guests or in-home entertainment, with ample room for a pool table or home theater. Residents of Winding Cypress enjoy an array of luxurious amenities, including a clubhouse with a state-of-the-art fitness center, catering kitchen, community room and activity space. Outdoor amenities abound, featuring pickleball courts, a lap pool, spa, outdoor movement studio, The Shady Palm Café poolside restaurant, bocce ball courts, five Har-Tru tennis courts, a fire pit, bird-watching overlook and a nature boardwalk with a picnic pavilion. Ideally located near the pristine shores of Marco Island and vibrant downtown Naples, this resort-style community provides the perfect backdrop for an unparalleled lifestyle.



$899,000
Sold Price:
$890,000
Sold Date:
03/28/2025
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Winding Cypress

7556 Winding Cypress Dr, Naples, FL 34114

Homes - 2,107 ft² / 2,500 ft² - 2 Car Garage

3+Den / 2 Baths / Pool / Spa

Built 2018
Winding Cypress Naples Homes: Discover luxury living in this modern and bright single-family Martin Ray home, located in the resort-style community of Winding Cypress. With 2,107 square feet of living space, this open concept 3-bedroom plus den, 2-bathroom home offers a harmonious blend of elegance and functionality. Natural light and coffered ceiling details create a bright and airy atmosphere while modern design and neutral colors provide a sense of elegance and refinement. The kitchen showcases stainless steel appliances, gorgeous quartz countertops, white cabinetry, 42” upper cabinets, a walk-in pantry, under cabinet lighting, tile backsplash, ample storage space, and a large center island which blends seamlessly into the family and dining room creating the highly sought after open concept, perfect for families and entertaining. The master suite, located in the back of the home, provides a serene retreat with a spacious bedroom, tray ceiling, walk-in closet and a well-appointed en-suite bathroom featuring dual sinks, separate water closet, modern tile, and a walk-in shower. Two additional bedrooms and an adjacent bathroom, offer ample space and privacy for the entire family. Beautiful impact, tuck away sliding glass doors lead to an expansive lanai complete with picture window screens, serene NW lake views, and a heated saltwater pool with sun shelf and spa, providing a seamless transition between indoor and outdoor living. Other enhancement that set this home apart from the rest include impact windows and doors, coffered ceiling in the living room, crown molding, 6-inch baseboards, 8-foot doors, screened in front entry, separate laundry room with a sink and cabinetry, window blinds/curtain panels, glass doors on the den, upgraded landscaping, outdoor kitchen, auto pool filler, decorative Bahama shutters, Sentinel Storm Shades on the back lanai, and an extended 2-car garage with utility sink and epoxy flooring. Winding Cypress is a gated, resort-style community featuring 766 homes located in Naples, FL. Nestled within over 1,100 acres of natural preserves and 80 acres of serene lakes, this community offers residents a laid-back lifestyle surrounded by nature. Residents enjoy a wide array of amenities, including the Shady Palm pool side café, a spacious Clubhouse, resort-style pool/spa, lap pool, pickleball, tennis, bocce, fitness center, movement room, nature boardwalk, and dog park. Centrally located near shopping, restaurants, and the pristine beaches of Naples and Marco Island, Winding Cypress seamlessly merges the elegance of modern living and the serene beauty of its natural surroundings.



$799,900
Sold Price:
$775,000
Sold Date:
03/11/2025
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Winding Cypress

6852 Winding Cypress Dr, Naples, FL 34114

Homes - 1,804 ft² / 2,237 ft² - 2 Car Garage

2+Den / 2 Baths / Pool

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



$799,000
Sold Price:
$785,000
Sold Date:
12/18/2024
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Winding Cypress

6792 Bromeliad Dr, Naples, FL 34114

Homes - 1,774 ft² / 2,433 ft² - 2 Car Garage

2+Den / 2 Baths / Pool

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



$769,900
Sold Price:
$720,000
Sold Date:
02/13/2025
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Winding Cypress

7247 Live Oak Dr, Naples, FL 34114

Homes - 1,910 ft² / 2,435 ft² - 2 Car Garage

2+Den / 2 Baths

Built 2015
Winding Cypress Naples Homes: JUST REDUCED AND PRICED TO SELL! Welcome to one of the most desirable neighborhoods in Naples. Winding Cypress boasts resort style living with pickleball, tennis, bocci, large gym, movement room, library, internet cafe, banquet room with kitchen, restaurant, and resort style pool with waterfall and lap lane. Currently the only Summerwood model for sale with peaceful panoramic water and preserve views. This impeccably kept two bedrooms with a den that could easily be a third bedroom, 2 bath home with large laundry room with tons of custom cabinetry. The oversized garage with four-foot extension makes one side of the garage 37' which can accommodate a 21' boat and trailer or third car, custom storage gives you plenty of room for all your toys. A real must-see home!




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