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Winding Cypress Naples Florida Homes for Sale

Naples Florida Real Estate

Winding Cypress Naples Real Estate

Homes For Sale28$575K - $1.7M
Sold21$521K - $1.6M
Last updated at 7:30pm 02/10/2025

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$1,697,500
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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.



$1,649,000
Decrease*
$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
Decrease*
$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!



$1,550,000
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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, 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!



$1,499,000
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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.



$1,274,900
Decrease*
$24.1K
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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: Motivated Seller! 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 it is offered fully furnished. 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.



$1,150,000
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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!



$1,149,000
Decrease*
$101K
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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 for Sale: 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.



$1,100,000
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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!



$1,050,000
Decrease*
$150K
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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 exquisite 3-bedroom + den, 3-bathroom pool home offers a perfect blend of luxury and comfort in the prestigious gated community of Winding Cypress. As you step inside, you'll be greeted by a spacious open floor plan with elegant tile flooring, neutral tones, and designer fixtures that create a warm and inviting atmosphere. The beautifully designed two-toned kitchen is a chef's dream, featuring a large center island, breakfast bar, and an adjoining dining room, making it ideal for both casual family meals and entertaining guests. The expansive living area flows seamlessly to the screened lanai, where you'll find a pavered patio and a heated saltwater pool, providing the perfect setting for relaxation and outdoor gatherings. Enjoy the serene views of the private preserve, offering a peaceful backdrop to your daily life. The master suite is a true retreat, with ample space, a luxurious en-suite bathroom, and plenty of closet space. The additional guest rooms are equally spacious, ensuring comfort and privacy for family and friends. Winding Cypress offers a wealth of amenities, including dining at the onsite Shady Palm restaurant, multiple sports options like pickleball, bocce, and tennis, and a state-of-the-art fitness center. Residents can also relax by the resort-style pool, enjoy the internet café, participate in community social events, or explore the community garden. For pet lovers, there's even a dedicated dog park for fido to exercise and play. With low HOA fees and a central location between the pristine beaches of Marco Island, the vibrant 5th Avenue, and convenient access to I-75, this home is a rare find that perfectly balances luxury, convenience, and community living.



$1,049,000
Decrease*
$101K
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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!



$1,045,000
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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.



$998,000
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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 for Sale: 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.



$995,000
Decrease*
$130K
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Winding Cypress

7235 Live Oak Dr, Naples, FL 34114

Homes - 2,640 ft² / 4,444 ft² - 2 Car Garage

3+Den / 3 Baths / Pool

Built 2015
Winding Cypress Naples Homes for Sale: Luxury living in this extraordinary Naples FL home and coveted community of Winding Cypress! Built in 2015 by Divosta homes this 3 bed, 3 bath, plus a den with a second story loft known as the Martin Ray flood plan. This home with over 2,600 sq feet under air, it's the perfect layout. Walk into a beautiful foyer entrance, that leads to the custom open layout kitchen, featuring premium granite countertops, Kenicto water system, custom cabinets, gas stove, and a butler pantry with beverage refrigerator and custom wine rack. The spacious living area with crown and base moldings, leads to the screened in lanai and custom 13X28 pool with 3 sunning shelf's. An east exposure for lots morning sun and with a lake and preserve view to enjoy. The screened in outdoor lanai area encompasses over 1,000 sq feet. The lush landscaping and pool is a tropical oasis to entertain and enjoy. Custom electric roll down hurricane shutters for maximum storm protection. Primary bedroom located on the 1st floor with beautiful tray ceiling and a view of the tropical back yard with a huge walk in closest with custom drawers and shelving.Primary bath has dual sinks and walk in shower. This split bedroom floor plan has so much privacy for guests with an upstairs loft that leads to the 3rd bedroom and en-suite bath. This home has 2 air conditioners with dual zone A/C system, plantation shutters through the home for the tropical feel, solid core doors with upgraded handles. Winding Cypress is a lifestyle community offering an array of amenities, including a resort-style pool and spa, pickleball and tennis courts, a residents-only restaurant, an expansive community center with an event room, library, outdoor fireplace, state-of-the-art fitness facilities, and a boardwalk nature trail for serene strolls. Sitting on 800 acres of preserved green space, this prime location is just 15 minutes from downtown Olde Naples and 10 minutes from Marco Island, offering the perfect blend of convenience and tranquility.



$995,000
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Winding CypressNEW

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. 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 actives 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?



$970,000
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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!



$939,000
Decrease*
$56K
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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 for Sale: Welcome to this stunning 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!



$789,900
Decrease*
$10K
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Winding Cypress

7670 Jacaranda Ln, Naples, FL 34114

Homes - 1,594 ft² / 1,964 ft² - 2 Car Garage

3 Bed / 2 Baths / Pool

Built 2018
Winding Cypress Naples Homes for Sale: Step into the lap of luxury with this stunning villa in Winding Cypress. This exquisite property is not just a home; it's an embodiment of sophistication and comfort, offering a lifestyle that is truly unparalleled. The villa is being offered fully furnished, ensuring that every inch of this residence reflects a tasteful and cohesive design. As you enter, you'll be captivated by the elegance that defines every detail. The gas-heated pool beckons, inviting you to relax and unwind in your private oasis. The outdoor kitchen adds a touch of opulence, making it an ideal space for entertaining guests or enjoying alfresco dining under the clear Florida skies. The chef's dream kitchen is a masterpiece in itself, featuring top-of the-line Samsung appliances and stunning quartz countertops. The list of updates is extensive, a testament to the commitment to maintaining this villa in peak condition. While it's impossible to detail every enhancement, rest assured that no expense has been spared in ensuring that this property remains at the pinnacle of luxury living.



$765,000
Decrease*
$30.9K
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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!



$689,900
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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. 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. 3rd Bedroom is being used as Den but Can easily be converted to 3rd bedroom. 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



$685,000
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Winding CypressNEW

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!



$659,000
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Winding Cypress

7199 Live Oak Dr, Naples, FL 34114

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

2+Den / 2 Baths / Pool / Spa

Built 2015
Winding Cypress Naples Homes for Sale: Rare villa opportunity in Winding Cypress! For the first time in over a year, a villa with a private pool and spa on an extra-large lot is available. Enjoy unmatched privacy with huge space between neighbors and serene ultra-private preserve views. This turnkey, fully furnished home features impact windows, 8-foot doors, new bedroom flooring, fresh landscaping and more. This natural gas community offers all hookups for an outdoor kitchen on your lanai, with gas, water and drain ready. Plus, extra garage storage is built in, making organization a breeze. Step into your own backyard oasis with a heated pool and spa, ideal for relaxing or entertaining in the Florida sunshine. Whether hosting guests or unwinding solo, this home offers the ideal blend of comfort and luxury. In the sought-after Winding Cypress community, residents enjoy resort-style amenities without the high fees. Dive into the expansive resort pool, stay active in the state-of-the-art fitness center, or explore miles of scenic nature with recreational and biking trails. The full-service restaurant and bar provide a social hub, while the tennis and bocce courts, garden and pickleball courts offer endless recreation options. The clubhouse also features a stunning social hall, library, and event spaces to connect with neighbors and friends or hold special celebrations.



$629,000
Decrease*
$70K
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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 price, the best deal on a 2 bedroom plus den with French doors, 2 bath, 2 car garage attached villa with your own pool in Winding Cypress. You better Hurry. 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.



$595,000
Decrease*
$39.5K
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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.



$592,499
Decrease*
$0K
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Winding Cypress

7619 Jacaranda Ln, Naples, FL 34114

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

2+Den / 2 Baths

Built 2016
Winding Cypress Naples Homes for Sale: This impeccably maintained residence, boasting serene lake vistas, presents an array of desirable features. Comprising two bedrooms, two bathrooms, a den complete with a Murphy bed, a two-car garage, and a utility-equipped laundry room, this property epitomizes comfort and functionality. Nestled within the highly coveted and rapidly flourishing community of Winding Cypress in Naples, the home has been thoughtfully enhanced to offer an elevated living experience. Highlights include a meticulously designed kitchen outfitted with a gas range, shaker cabinets, quartz countertops, a breakfast bar, pantry, and stainless steel appliances. The owner has upgraded the windows to impact glass and installed an electric hurricane shade for the lanai area, prioritizing safety and convenience. Winding Cypress stands out as one of Naples' premier residential developments, boasting top-tier resort-style amenities such as a poolside bar and grill, outdoor yoga deck, fire pit, dog parks, community garden, and extensive nature trails traversing an 800-acre natural preserve. Offering an unparalleled lifestyle, now is the opportune moment to seize the chance to reside on Jacaranda Lane in Winding Cypress.



$589,000
Decrease*
$10K
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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: 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.



$579,000
Decrease*
$50K
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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!



$575,000
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Winding CypressNEW

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.



$769,900
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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 Under Contract: 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!



$899,000
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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 Under Contract: 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.



$799,900
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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 Under Contract: 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.



$650,000
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Winding Cypress

7267 Live Oak Dr, Naples, FL 34114

Homes - 2,230 ft² / 2,634 ft² - 2 Car Garage

3+Den / 2 Baths

Built 2015
Winding Cypress Naples Homes Under Contract: Best-Valued Single-Family Home with Quality Finishes and Resort-Style Amenities in Winding Cypress! This beautifully crafted 3-bedroom, 2-bathroom home, complete with a private office, is the best-valued single-family residence in the desirable Winding Cypress community. Thoughtfully designed with quality finishes, this home features tile flooring throughout, plantation shutters, crown molding, high-end granite countertops and stainless-steel appliances with huge island/breakfast bar in a gourmet kitchen, equipped with natural gas cooking. The separate dining area offers an inviting space for meals and entertaining. Outside, enjoy the private, screened-in lanai surrounded by lush tropical gardens and a raised herb garden. This home is equipped with full hurricane protection on all windows and doors, including Storm Smart hurricane screens on the lanai, ensuring peace of mind in stormy weather. The Sellers have shared that their home has never incurred damage from any of the recent storms. Pre-inspected and move-in ready, with low HOA fees, this home is a true value. Winding Cypress is an amenity-rich, pet-friendly community, featuring a resort-style pool and spa, outdoor bar and grill, tennis, pickleball, bocce courts, and two gated, off-leash dog parks. With a vibrant social calendar, there are endless ways to connect and enjoy the neighborhood. Conveniently located near downtown Naples, with its beautiful beaches, dining, and entertainment, as well as the scenic Marco Island coastline, this home blends luxury, security, and community lifestyle. Don’t miss your chance to make this tropical retreat your own!



$635,000
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Winding Cypress

7113 Live Oak Dr, Naples, FL 34114

Homes - 1,554 ft² / 2,748 ft² - 2 Car Garage

2+Den / 2 Baths / Pool

Built 2016
Winding Cypress Naples Homes Under Contract: BIG PRICE REDUCTION! THIS IS ONE OF THE LOWEST PRICED VILLA POOL HOME! Discover this stunning 3-bedroom, 2-bathroom villa with a 2-car garage and a luxurious gas heated pool that is ideally situated on a premium pie-shaped lot adjacent to nature preserve and near to the vibrant Winding Cypress Amenity Center is the perfect place to make your own paradise. The flex room offers endless possibilities as a third bedroom or as a home office/den. The Serenity Model offers the perfect blend of charm and sophistication, whether you seek a year-round haven or a seasonal escape to enjoy Florida's renowned lifestyle. Indulge in effortless entertaining as the seamless open floor plan leads you to a covered lanai and expansive brick paver pool deck that gazes out onto a serene nature preserve. Witness breathtaking sunsets that paint the sky in hues of warmth while serenaded by the harmonious symphony of nature within your private screened enclosure in the prestigious Winding Cypress community. This home has features including stainless-steel appliances, elegant granite countertops, a beautifully tiled backsplash in the kitchen, and 20" ceramic tile flooring throughout the main living spaces. Noteworthy accents such as plantation shutters, rich wood flooring in the den, accordion hurricane shutters, an electric rolldown hurricane shutter at the lanai, and a host of other upscale finishes. Nestled within a secure, amenity-rich enclave, residents enjoy access to a lavish Community Center, overseen by a full-time activities’ director, offering an array of recreational facilities from card/game rooms and a library to a poolside bar and restaurant. Stay active with a state-of-the-art gym, outdoor Yoga and movement studios, group exercise classes, a resort-style pool with a dedicated lap lane, inviting fire pits, dog parks for both large and small dogs, illuminated tennis courts, pickleball and bocce courts, and sprawling lakes and nature preserves spanning nearly 800 acres, providing boundless walking and riding trails for outdoor enthusiasts. Perfectly positioned in proximity to upscale shopping, dining venues, the sandy beaches of Naples and nearby Marco Island, the ambiance of downtown Naples along 5th Avenue & 3rd Street, as well as convenient access to medical facilities, educational institutions, places of worship, I-75, RSW International Airport, and the breathtaking wonders of the Florida Everglades.



$1,579,000
Sold Price:
$1,450,000
Sold Date:
09/17/2024
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Winding Cypress

6903 Cocoplum St, Naples, FL 34114

Homes - 3,656 ft² / 5,000 ft² - 3 Car Garage

4+Den / 4 Baths / Pool / Spa

Built 2021
Winding Cypress Naples Homes: Welcome to an unparalleled blend of luxury and comfort in the prestigious Winding Cypress community. This exquisite 2-story furnished Pinnacle model home, boasting over 3,600 square feet of meticulously designed living space, offers an extraordinary lifestyle experience. As you enter this breathtaking residence, you'll be captivated by the open floor plan that seamlessly connects the living room and kitchen, perfect for both everyday living and entertaining. The kitchen is a chef’s dream, featuring a premium gas cooktop, quartz countertops, soft-close cabinets, and a generous island that serves as a focal point for gatherings. The zero corner impact glass sliders create the perfect Florida indoor/outdoor lifestyle by extending the living space into the private outdoor oasis. Here, you’ll find an incredible pool with a raised spa featuring an infinity edge, a sun shelf, and fountains. The premier outdoor kitchen makes alfresco dining a pleasure, set against the backdrop of a panoramic screen that offers unobstructed views of the serene estuary. Retreat to the opulent owner's suite, where luxury meets tranquility. The spa-like ensuite bathroom is designed to pamper, with dual vanities, a spacious shower, and a walk-in custom closet that provides ample storage. Two additional well-appointed bedrooms on the first floor offer comfort and privacy; one with its own en-suite bath, and the other with a bathroom conveniently located just outside the door. The second floor adds an impressive 1,168 square feet of living space, featuring an additional bedroom and full bathroom. This area is an entertainer’s dream, offering a flexible space that can be tailored to your specific needs—be it a guest suite, home office, or media room. Practicality is not forgotten in this luxurious setting. A whole-house on-demand natural gas generator ensures you’re never without power, adding peace of mind to the comfort and elegance of your home. The extended 3-car garage with epoxy floor has Wi-fi enabled garage door openers, a large utility sink, and plywood decking in the attic for extra storage. Winding Cypress is more than just a neighborhood; it’s a community designed to enhance your lifestyle. Enjoy the resort-style clubhouse with its expansive swimming pool, state-of-the-art fitness center, community garden, boardwalk trail, and poolside restaurant and bar. Relax by the fire pits or take advantage of the various recreational facilities. Pet owners will be delighted with the special park dedicated to dogs, ensuring every member of the family feels at home. Discover the epitome of modern living in this resort-style, amenity-rich community. Embrace a lifestyle of luxury and leisure in your new home at Winding Cypress, where every detail is designed with your utmost comfort and enjoyment in mind. Welcome home.



$1,550,000
Sold Price:
$1,525,000
Sold Date:
09/20/2024
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Winding Cypress

6932 Cocoplum St, Naples, FL 34114

Homes - 2,515 ft² / 3,400 ft² - 3 Car Garage

3+Den / 3 Baths / Pool / Spa

Built 2019
Winding Cypress Naples Homes: A staggering mix of natural beauty and fabulous Naples living. This jewel box home is situated on one of the most desirable lots in Winding Cypress. Look at the aerial view, simply breathtaking. Lot location had a $125,000 premium.Coveted Southern exposure Peaceful and full of nature. Well-designed, expansive floor plan offering generous size rooms, an outstanding white kitchen that is perfect for the serious cook or entertaining. You will love the large island, wine cooler, massive pantry, and natural gas. Split living area with unique closets and storage everywhere. Soaring ceilings. The west wing encompasses an impressive size Owner suite complete with massive walk-in closet. More than 2 cars? No worries, there is garage parking for 3. For the enjoyment of nature spend time in your southern exposure, spacious salt water pool/spa or patio with outdoor kitchen or relax on your lounger in the pool. A patio you can use year round unlike west facing patios that are so hot . Additional peace of mind is offered with impact windows and a generator. Please note this is not the base Pinnacle floor plan, this is top of the line and highly upgraded. Located off the main road on a cul de sac street. You must see this home. Winding Cypress is a wonderful community. Amenity rich with a low HOA. Amenity rich 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 ommissions Buyer to verify everything to their satisfaction



$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.



$1,500,000
Sold Price:
$1,400,000
Sold Date:
09/10/2024
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Winding Cypress

6909 Winding Cypress Dr, Naples, FL 34114

Homes - 2,522 ft² / 3,501 ft² - 3 Car Garage

3+Den / 3 Baths / Pool / Spa

Built 2019
Winding Cypress Naples Homes: Welcome to your dream home in Winding Cypress. This stunning residence epitomizes luxury living in paradise. As you step through the door into a haven of elegance and comfort. This meticulously crafted residence features an array of upgrades.



$1,495,000
Sold Price:
$1,495,000
Sold Date:
10/08/2024
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Winding Cypress

6962 Winding Cypress Dr, Naples, FL 34114

Homes - 2,952 ft² / 4,247 ft² - 3 Car Garage

3+Den / 3 Baths / 1 Half / Pool

Built 2020
Winding Cypress Naples Homes: HURRICANCE READY!!!! NEW PRICE Improvement.This home is truly a showstopper , priced below market value and offering a "wow" factor that is hard to beat. The Stonewater model is the largest home built in Winding Cypress built in 2020 and still looks and feels like brand new. With approx.3000 sq. ft. of grand open space you'll be captivated from the moment you walk through the double front doors into the gracious foyer. The home features 13ft. coffered ceiling in the great room , formal dining area or custom for your use, office with glass French doors , 3 bdrms , 3 baths three car garage The lanai boasts POOL BATH WITH STORAGE ,a relaxing backdrop of the lake and peaceful preserve complete with an outdoor kitchen and hurricane shutter. Lanai furniture included in sale. A FEELING OF LIGHT AND SPACIOUSNESS IS WHAT YOU FEEL WHEN YOU WALK IN THE FRONT DOOR WITH ITS SOARING 13FT CEILING IN FOYER AND AND GREATROOM. This home is impeccable maintained and in like new condition. HURRICANE READY WITH ITS BRAND NEW whole house generator for peace of mind. Winding Cypress offers a wealth of amenities including a beautiful resort pool and restaurant. Don't miss the opportunity to see and appreciate the beauty of this exceptional home. Winding Cypress is conveniently located just 15 min to Marco Island , 75 and Downtown Naples



$1,100,000
Sold Price:
$1,000,000
Sold Date:
08/20/2024
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Winding Cypress

7554 Blackberry Dr, Naples, FL 34114

Homes - 2,867 ft² / 3,648 ft² - 2 Car Garage

3+Den / 3 Baths / Pool

Built 2017
Winding Cypress Naples Homes: Welcome to the award-winning Martin Ray home in the prestigious and central Winding Cypress resort community in Naples. This exceptional home boasts a stunning custom pool and lanai, complete with an in-water sundeck, ideal for soaking the Florida sunshine. Relax and unwind as you enjoy the picturesque views of the private waterfront. Inside, you'll find a bright and airy ambiance, highlighted by top-of-the-line quartz finishes and gourmet appliances powered by natural gas. Whether you're hosting a lavish gathering or enjoying a quiet evening in, this home offers the ideal blend of elegance and comfort. A bonus loft offers a cool option for guests or in-home entertainment with plenty of room for a pool table or even a home theater! Residents will enjoy the luxurious Winding Cypress clubhouse, offering a state-of-the-art fitness center, catering kitchen, community room and activity room. Outdoor amenities abound, from pickleball, resort-style and lap pools to a spa, outdoor movement studio, barefoot bar, bocce ball courts, five Har-Tru tennis courts, fire pit, bird-watching overlook and a nature boardwalk with a picnic pavilion. In ideal proximity to the pristine shores of Marco Island and vibrant downtown Naples, this amazing resort location provides the ideal backdrop for an unparalleled lifestyle.



$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



$999,000
Sold Price:
$945,000
Sold Date:
09/30/2024
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Winding Cypress

6801 Greenbriar Ct, Naples, FL 34114

Homes - 2,152 ft² / 2,582 ft² - 2 Car Garage

4 Bed / 3 Baths / Pool

Built 2022
Winding Cypress Naples Homes: Like new, two years old four bedroom, three-bathroom residence in Winding Cypress. House has been totally custom remodeled. This furnished home showcases new furniture and TVs, finished with 9’ ceilings, 8’ doors, pristine tile floors. The gourmet kitchen features high end appliances with gas cooking, pullout drawer cabinets, designer backsplash, pantry, and a large center island. Each bedroom has an in-suite bathroom. Outside, you’ll find a WiFi-controlled heated pool and screened lanai with build- in barbeque grill. Extended driveway, two-car garage , epoxy floor, and overhead storage. Winding Cypress residents have access to a clubhouse with a social room, library, fitness center, resort-style pool and spa, outdoor bar and grill, tennis, pickleball, bocce, dog park, and a full social calendar. Just 15 minutes to downtown Naples and Marco Island. CDD paid in full.



$899,000
Sold Price:
$860,000
Sold Date:
11/01/2024
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Winding Cypress

7420 Winding Cypress Dr, Naples, FL 34114

Homes - 2,198 ft² / 2,626 ft² - 2 Car Garage

4 Bed / 2 Baths / Pool / Spa

Built 2017
Winding Cypress Naples Homes: Winding Cypress is the ultimate Naples resort community, and this home serves as the ultimate poolside retreat. The long southwest water views seamlessly blend waterfront serenity, preserved nature, and privacy. Adorning the oversized covered lanai is a deluxe outdoor kitchen complete with every conceivable feature and top-grade finishes. This award-winning Summerwood floor plan boasts every builder upgrade, including a double oven gourmet kitchen, top-of-the-line cabinets, crown molding, tray ceilings, easy-glide retractable storm shutters, and more. The open concept layout is enhanced with strategically placed windows, optimizing natural light and facilitating flexible furniture arrangement, making this home an ideal canvas for any decor. Residents can indulge in the luxurious Winding Cypress clubhouse, featuring a state-of-the-art fitness center, catering kitchen, community room, and activity room. Outdoor amenities abound, encompassing pickleball courts, resort-style and lap pools, a spa, an outdoor movement studio, a barefoot bar, bocce ball courts, five Har-Tru tennis courts, a fire pit, bird-watching overlook, and a nature boardwalk with a picnic pavilion. Ideally situated near the pristine shores of Marco Island and the vibrant downtown Naples, this resort community offers an unparalleled lifestyle.



$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



$795,000
Sold Price:
$775,000
Sold Date:
10/15/2024
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Winding Cypress

7507 Blackberry Dr, Naples, FL 34114

Homes - 1,805 ft² / 2,160 ft² - 2 Car Garage

2+Den / 2 Baths / Pool / Spa

Built 2017
Winding Cypress Naples Homes: In the prestigious Naples community of Winding Cypress, this exceptional property stands out for its distinctive features, seamlessly blending nature and luxury with a resort lifestyle. Complemented by the rare convenience of direct natural gas, the award-winning Abbeyville floor plan boasts multiple builder upgrades. The unique custom pool and spa integration with bench seating offers a relaxing respite at the end of the day. Enjoy meticulous landscaping through your “picture window” lanai screen, effortlessly merging indoor and outdoor living spaces. A thoughtfully designed open concept optimizes natural light through an abundance of windows. Additional amenities include laundry area with utility sink, walk-in closet and cabinets. Built-in custom closets are throughout, including cabinetry and Murphy bed in your bonus flex room. Other amenities include diagonal tile flooring, crown molding and primary tray ceiling, wainscoting in the sunroom and a Lennox Fresh-Aire UV purifier. The epoxy-finished garage offers plenty of storage. For peace of mind, a natural gas-powered whole-house Generac generator ensures reliable power on demand. You’ll enjoy Winding Cypress’s luxurious amenity center, featuring a state-of-the-art fitness center, catering kitchen, community great room and activity room. Outdoor enthusiasts can take advantage of pickleball, tennis, bocce, resort-style waterfall pool, spa/cabana area, outdoor café with classically trained executive chef, fire pit and fireplace areas, dog park and nature boardwalk with picnic pavilion. Ideally just 20 minutes from the pristine shores of Marco Island and vibrant downtown Naples, this sought-after resort community offers an unparalleled lifestyle against a backdrop of natural beauty.



$725,000
Sold Price:
$690,000
Sold Date:
09/30/2024
View Details

Winding Cypress

7793 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: Rare opportunity to own the crème de la crème villa in Winding Cypress. This pool home features 2 bedrooms, plus den, 2 bathrooms and a 2 car garage and is being offered turnkey furnished! The property boasts exceptional upgrades, including impact windows, a whole-house generator, crown molding, tile throughout, electric hurricane screens, upgraded appliances, closet systems throughout and so much more. The outdoor oasis features a gorgeous outdoor kitchen, remote control awning for additional shade, and arguably one of the best lake views in all of Winding Cypress! Winding Cypress has amenities galore! Enjoy dining at Shady Palm, the onsite restaurant, play pickleball, bocce, tennis, workout in the state of the art fitness center or lounge by the resort style pool, garden at the community garden, or take fido to the dog park! Winding Cypress is pet friendly, allows rentals, has low fees and is centrally located between Marco Island, 5th Ave, & I75 making it an ideal location!



$725,000
Sold Price:
$710,000
Sold Date:
01/21/2025
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Winding Cypress

7263 Live Oak Dr, Naples, FL 34114

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

2+Den / 2 Baths / Pool

Built 2017
Winding Cypress Naples Homes: WOW! HERE IS A GORGEOUS RESIDENCE THAT WAS PROFESSIONALLY DECORATED AND IS IN PRISTINE CONDITION. THE HOME HAS A RESORT STYLE LARGE PAVER DECK SALT WATER POOL WITH A PICTURE FRAME SCREENED LANAI. ENJOY AN EXPANSIVE DECK AREA TO RELAX, SOAK UP THE SUN, OR JUST TAKE IN THE STUNNING LAKE VIEW. THE GOURMET KITCHEN HAS STATE OF THE ART APPLIANCES, QUARTZ COUNTERS, TILE BACK SPLASH WITH HAND CRAFTED WOOD CABINETRY. THE LUXURIOUS PRIMARY SUITE HAS A VIEW OF THE POOL AND LAKE WITH CUSTOM WOOD FLOORING AND A HUGE WALK IN CLOSET. THE HOTEL INSPIRED OWNERS BATH IS SURE TO IMPRESS. ON THE FRONT END OF THE HOME IS A GUEST BEDROOM WITH LOTS OF NATURAL LIGHT, AND A IMPRESSIVE GUEST BATH. ADDITIONALLY THE RESIDENCE HAS A NICE SIZED DEN, OR POSSIBLE THIRD BEDROOM. ADDITIONAL UPGRADES INCLUDE, WHOLE HOUSE GENERATOR, ACCORDION SHUTTERS, EXTENDED GARAGE, HARD WOOD AND TILE FLOORS THROUGHOUT, DESIGNER FIXTURES AND MORE. WINDING CYPRESS IS A GATED COMMUNITY RICH IN AMENITIES, WITH A RESTAURANT AND POOL BAR RIGHT ON SITE.



$689,000
Sold Price:
$690,000
Sold Date:
11/08/2024
View Details

Winding Cypress

7256 Live Oak Dr, Naples, FL 34114

Homes - 1,685 ft² / 2,081 ft² - 2 Car Garage

3 Bed / 2 Baths / Pool / Spa

Built 2015
Winding Cypress Naples Homes: Welcome to this stunning 3-bedroom, 2-bathroom oasis, perfectly designed for both relaxation and entertaining. Step inside to find a beautifully appointed open floor plan featuring elegant crown molding, recessed lighting, and gleaming tile laid on the diagonal, creating a seamless flow throughout the home. The heart of the house is the gourmet kitchen, where you'll be inspired to cook and gather. It boasts sleek granite countertops, a stylish tile backsplash, stainless steel appliances, and a spacious island with extra storage and a convenient breakfast bar. Retreat to your private backyard paradise with a sparkling screened-in heated salt-water pool and spa, perfect for year-round enjoyment. The large laundry room was completely built out with cabinets and utility sink. Located in the beautiful gated community of Winding Cypress with world-class amenities. Featuring an on-site restaurant, the Shady Palm, a resort-style pool, tennis, pickleball & bocce courts, outdoor yoga deck, a dog park, fitness center, community garden and nature trails, internet café and an array of social events. Centrally located and just a short drive to Naples pristine beaches, shops and dining.



$610,000
Sold Price:
$600,000
Sold Date:
09/30/2024
View Details

Winding Cypress

7574 Jacaranda Ln, Naples, FL 34114

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

2+Den / 2 Baths / Pool

Built 2016
Winding Cypress Naples Homes: Villa w/ PEACEFUL view! Attached villa Serenity floor plan that lives like a single family home w/ luxury features throughout- tray ceilings, 18" tile flooring, quartz countertops, custom tile backsplash in kitchen, convection double oven, designer light fixtures, high-end cabinetry, crown molding, French door entry to den, frameless glass enclosure in master shower, custom built heated pool, & a built-in Generac generator system & transferrable home warranty. The outdoor living space is the GEM of the home- massive pool deck, solar & gas heated pool, large covered area w/ enough room for dining set & lounging area, & having a serene lake view. Meticulously maintained & updated w/ new accordion hurricane shutters, whole home water filtration system for optimum water quality, & freshly painted exterior. The roof was just power washed this past summer. This natural gas community has over 800 acres of lakes & preserve, resort- style pool, fire pit, community rm, restaurant, tennis, bocce ball, pickleball, cabanas, yoga deck, fitness facility, locker rooms, full time activities director, catering room, catering kitchen, activity room, nature board walk, garden, small & large dog parks.




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Need professional assistance selling your property at Winding Cypress Naples? Find out how an Area Specialist can help to generate more property exposure in order to get the most money for your investment in the least amount of time.Contact Us.
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