Winding Cypress, Naples, FL Real Estate Search

Winding Cypress, Naples, FL Homes for Sale

Winding Cypress is a gated, master-planned community in Naples FL known for its pockets of luxury homes connected by meandering roads, all tucked within mature forests. Developed by DiVosta Homes, the community was constructed with the committment to preserve the ecological integrity of the area. Winding Cypress encompasses over 800 acres of natural preserves and 80 acres of sparkling lakes. The community is located adjacent to Piscayune Strand Forest. Winding Cypress offers a fabulous amenity center with resort style pool, poolside bar and grill, state of the art fitness center, outdoor fireplace, tennis, pickleball, dog park and miles of beautiful walking paths.

There are 828 homes in Winding Cypress - both single family homes and attached villas - ranging in size from 1542 square feet to over 3500 square feet. There are 7 floor plans for single family homes and 2 floor plans for attached villas. Almost all of the homes have private views of water or preserve.

Winding Cypress is perfectly situated between downtown Naples and Marco Island. Shopping, restaurants and the sugar sand gulf beaches are just a short drive away.

Our website features the best Winding Cypress, Naples, FL real estate search for homes available. It is the only site you will ever need! It is easy-to-use and updated by the official REALTOR®’s database every 15 minutes. 

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Winding Cypress, Naples, FL Homes for Sale

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Newest Winding Cypress, Naples, FL Homes for Sale

$799,000
2 Beds 2 Baths 224051672 MLS
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.

7507 Blackberry DR, Naples

$1,125,000
3 Beds 3 Baths 224052130 MLS
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.

7235 Live Oak DR, Naples

$1,589,999
4 Beds 4 Baths 224050943 MLS
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.

6903 Cocoplum ST, Naples

$1,175,000
3 Beds 2 Baths 224048891 MLS
Experience luxury living in this spectacular residence, on oversized, corner lot with SW exposure,  nestled in  the coveted Winding Cypress community in Naples. This spacious 3-bedroom, 2-bathroom home with a den boasts an open layout kitchen featuring premium granite countertops, custom cabinets with roll-out trays, gas stove, and a butler pantry with beverage refrigerator. The bright living area offers incredible views of the pool and opens onto a lanai with shutters to shield from the sun. Relax and unwind by the oversized saltwater pool custom built pool (34’ long) with flush spa and luxurious waterfall features, while enjoying the private views of the lake, preserve and abundant wildlife.  A dedicated home office provides a quiet workspace for productivity. The large master bedroom serves as a serene retreat. Extra driveway area for parking of  5 cars and extended garage  offering plenty of room for multiple cars and guests.  Enjoy peace of mind with Generac whole house generator.   Winding Cypress is a vibrant community offering an unparalleled 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. Nestled 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.

7343 Mockingbird CT, Naples

$1,850,000
3 Beds 3 Baths 224045959 MLS
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!

6823 Winding Cypress DR, Naples

$1,500,000
3 Beds 3 Baths 224039811 MLS
Welcome to your dream home in the coveted natural gas community of Winding Cypress. This stunning residence epitomizes luxury living in paradise. As you step through the leaded glass door into a haven of elegance and comfort. This meticulously crafted Pinnacle Model features an array of upgrades, ensuring a lifestyle of sophistication, convenience and peace of mind. You're secure with the hurricane impact windows, zero corner slider, and whole house generator. From the moment you enter, the attention to detail is evident with the expansive 11-foot ceilings with coffered trays, crown molding, LED lighting and wood flooring throughout. The open-concept layout seamlessly blends indoor and outdoor living, creating a space perfect for both relaxation and entertaining. The chef's kitchen, include Quartz countertops, 42-inch luxury cabinets with soft closures and pull-out drawers, under-cabinet lighting, top-of-the-line appliances , natural gas cooktop and separate wall oven. A built in entertainment area with wine or beverage cooler is perfect for hosting gatherings with friends and family. The spacious owner's suite, with custom California Closets and luxurious ensuite bathroom with enlarged shower, upgraded fixtures and faucets. Two additional large bedrooms, including a second ensuite, offer ample space for guests or family members. Step outside to your own private oasis, where breathtaking long lake sunset views are unobstructed through the panoramic screen, custom heated saltwater pool with water features, a custom gas summer kitchen, and expansive dining and sitting areas. Electric Storm Smart Kevlar Screens provide added comfort and protection. Winding Cypress offers a wealth of community features, including a residents-only restaurant, resort-style pool with spa and cabanas, pickleball, tennis, and bocce courts, an event room with catering kitchen, library, internet cafe, awesome fitness center, and lounge areas with gas fireplaces. Nature enthusiasts will appreciate the boardwalk nature trail, providing a serene escape into the preserve. Conveniently located just minutes from the pristine beaches of Marco Island and the vibrant dining, shopping, and entertainment of downtown Olde Naples. Enjoy plenty of golf options just around the corner. Don't miss this opportunity to make this exquisite home your own. With all the features and upgrades already in place and no wait to move in, this property represents an exceptional value compared to new construction.

6909 Winding Cypress DR, Naples

$595,000
2 Beds 2 Baths 224036315 MLS
Welcome to your serene and private retreat in Naples! This charming lake view and corner villa with 2 Bedrooms PLUS DEN and 2 Bathrooms is nestled within a gated community, offering both privacy and security and lots of natural light. Inside, you'll find sophisticated touches such as an upgraded kitchen with Stainless Steel appliances, 9" x 40" wood plank style porcelain tiles throughout the entire home in a neutral tone, modern plantation shutters, and crown moulding throughout the home. The entire villa has been freshly painted, both inside and out and fresh, new landscaping has been installed. There is plenty of storage available with custom closet organization in the master bedroom, second bedroom and the garage with heavy duty shelving. Enjoy purified drinking water from a Reverse Osmosis System from Kinetico. The paved and screened lanai was extended and has been pre-plumbed for your future outdoor kitchen and ready for your outdoor TV. The Winding Cypress community offers a range of amenities to enrich your lifestyle. Stay active with access to a fitness center, tennis courts, and pickleball courts. There is a beautiful resort style pool, hot tub, and the Shady Palm Cafe serving delicious food and refreshing drinks. The Clubhouse has a wonderful library and can be rented out for events with a full kitchen. There is dog park and community garden that all residents can enjoy. Winding Cypress is centrally located near Marco Island, Downtown Naples, I-75, and plenty of shopping options.

7561 Jacaranda LN, Naples

$650,000
3 Beds 2 Baths 224032420 MLS
Welcome to your new home, a rare opportunity to own a unique three-bedroom Serenity model with a newly added whole-home generator powered by direct natural gas and motorized retractable lanai storm shutter screens. Enjoy the outstanding ample space inside and out, with a fully expanded screened and paver lanai with beautiful, lush landscaping for privacy. The layout inside includes an extremely spacious owner's suite, along with a modern, open natural gas cook's kitchen and convenient breakfast bar setup. Guests’ privacy is ensured with a split floor plan bedroom with en suite and bath. This nearly new home boasts builder-installed upgrades, including quartz finishes throughout, tray and volume ceilings, high-end porcelain floors, a glass-tiled kitchen backsplash, double vanity, huge walk-in closet and French doors. The Club at Winding Cypress is a must-see, offering a massive resort pool, sunset sand cabanas, bocce ball, eight pickleball courts, clay tennis courts, a yoga deck, a massive gym facility, fire pits, a boardwalk nature trail, locker rooms, a full-time activities director, a poolside restaurant/bar and more. This is the ultimate villa in Winding Cypress. This incredible community stands out as one of Naples' most unique, resort-style, non-golf communities, encompassing over 800 acres of pristine preserve, ensuring an ideal location. Ideally in the center point between Marco Island and 5th Avenue in downtown Naples, this community offers a lifestyle of unparalleled luxury and convenience.

7663 Jacaranda LN, Naples

$687,000
3 Beds 2 Baths 224025546 MLS
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.

7113 Live Oak DR, Naples

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The data relating to real estate for sale on this web site comes in part from the Broker Reciprocity Program (BR Program) of M.L.S. of Naples, Inc. Properties listed with brokerage firms other than this company are marked with the BR Program Icon or the BR House Icon and detailed information about them includes the name of the listing brokers. The properties displayed may not be all the properties available through the BR Program. The information provided is for consumers’ personal, non-commercial use and may not be used for any other purpose.