Winding Cypress Real Estate

Recently Sold Listings in Winding Cypress, Naples, FL

< Back to all Homes for Sale in Winding Cypress, Naples, FL

Be the First to Know About New Winding Cypress Homes

Stay ahead with real-time updates — no searching required.

See Homes Before Everyone Else

Winding Cypress Real Estate Map Search

Search by Lifestyle
  Advanced Search   Market Reports   Home Value   Connect

All Sold in Winding Cypress, Naples, FL

$1,895,000
3 Beds ⋅ 3.5 Baths ⋅ 223084084 MLS
A world of sophistication & style awaits in this Winding Cypress masterpiece w/lake views. As you navigate the open-concept home, the marriage of textures, materials & high-end furnishings creates a sensory experience, where each turn reveals a new awe-inspiring surprise. Stunning coffered ceilings w/tongue & groove designs & shiplap accent walls grace the living spaces, while designer lighting fixtures serve as works of art, casting a warm & inviting glow throughout. For the culinary enthusiast, a natural gas kitchen awaits. The expansive lanai is a destination in itself, where luxury & nature seamlessly converge w/a saltwater pool/spa, outdoor kitchen w/built-in gas grill & al fresco dining. Whether it's a quiet dinner under the stars or a lively celebration w/friends & family, the peaceful outdoor ambiance enhances every moment. The master suite is a testament to the designer's vision, with a blend of textures & colors that create a harmonious retreat. The master bath, w/its gorgeous tile work, becomes a spa-like sanctuary, inviting relaxation & indulgence. Discover the epitome of high-end living in this one of a kind home in the amenity-rich community of Winding Cypress.

7513 Winding Cypress DR, Naples
$1,690,000
3 Beds ⋅ 3.5 Baths ⋅ 223039927 MLS
Spectacular Stonewater Well Appointed Home. Located in Winding Cypress a Premier Community with 800 Acres of Natural Preserves. Coffered Volume Ceilings. Gourmet Kitchen with Wolf Steam Oven + Additional Full Oven & Warming Drawer. Luxurious Primary Suite. Guest Bedrooms with Ensuite's. Outdoor Living at it's Best. Panoramic Sunsets over a Tropical Lake & Preserve View from Your Lanai. Large Heated Pool with Swim Platform, Spa & Fountain. Impact Windows & Doors. Tankless Gas Water Heater & Generac Natural Gas Whole House Generator. And More...Amenities Include Community Center, Shady Palm Bar & Grille, Fitness Center, Heated Pool & Spa. Pickle Ball, Tennis, Bocce Ball, Nature Trail & Bird Sanctuary. Dog Park. Short Distance from Marco Island & Naples Beaches & Restaurants. MUST SEE!!!

6919 Cocoplum ST, Naples
$1,565,000
3 Beds ⋅ 3 Baths ⋅ 224025231 MLS
An amazing opportunity to purchase a Pinnacle estate home in Winding Cypress! This home features 3 bedrooms, den, 3 bathrooms, pool & spa with a 3 car garage! No expense has been spared in this meticulously maintained home with tons of upgrades including built in appliances, hard flooring throughout, zero corner slider, crown molding, trey ceilings, electric hurricane shutters on lanai, natural gas, and so much more! The outdoor oasis features a large pool and spa with water features, huge backyard, built-in outdoor kitchen and a gorgeous lake view. 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!

6880 Cocoplum ST, Naples
$1,550,000
3 Beds ⋅ 3.5 Baths ⋅ 223072512 MLS
Discover luxury living in this exquisite Stonewater resort home in one of the most outstanding communities in South Naples on one of the best lakefront land sites imaginable. Boasting nearly 3,000 square feet of living space, this residence offers a spacious and open floor plan with high tray ceilings, architecturally stunning alcoves and arches, and top-level finishes throughout adorned in high-end, custom-designed light fixtures. Enjoy the tranquility of southern exposure and breathtaking lake views from the oversized covered lanai. The interior features a designer kitchen with soft-close cabinets, quartz countertops and natural gas cooking. Residents enjoy exclusive access to the Winding Cypress Club, complete with restaurant and bar, full-time activity director, a state-of-the-art fitness center, resort-style pool, lap pool, spa, outdoor movement studio, bocce ball courts, pickleball and tennis courts, fire pit, bird-watching overlook and nature boardwalk with a picnic pavilion. This home showcases the best in Florida living and is conveniently located at an ideal counterpoint between downtown Naples and Marco Island.

6920 Cocoplum ST, Naples
$1,550,000
3 Beds ⋅ 3 Baths ⋅ 223064337 MLS
Welcome to your DREAM HOME in the prestigious and highly sought after Naples lifestyle community of WINDING CYPRESS. Located on an oversized preserve lot with a pond view, this stunning  ''Pinnacle floor plan'' boasts over 2,500 sq feet under air with 3 large bedrooms 3 bathrooms plus a spacious den. This beautiful and well cared for home was built in 2020 and has everything already anyone could possibly want including a large ''picture window'' screened in gas heated saltwater pool and spa, custom outdoor kitchen, brick paver large lanai with a perfect covered area for entertaining. Hurricane shutters on the entire home for protection and newly installed electric hurricane screen for the covered lanai. Park all of your vehicles in the oversized and epoxy 3 car garage with hurricane rated/insulated garage doors with additional insulation in the attic to accommodate the separate garage A/C for optional cooling.  Brand new whole house generator that was recently installed which also accommodates additional power for the pool and spa. Plenty of space in your custom designed closet in the master bedroom and pantry done by one of the finest in the industry, California Closets. Stunning white quartz countertop kitchen with high end stainless steel KitchenAid appliances including an additional beverage refrigerator and gas cooktop. Located in an X flood zone with no flood insurance required.

6907 Cocoplum ST, Naples
$1,525,000
3 Beds ⋅ 3 Baths ⋅ 224028845 MLS
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

6932 Cocoplum ST, Naples
$1,500,000
4 Beds ⋅ 4 Baths ⋅ 223065846 MLS
Impressive 4bed/4 bath Home in the highly sought after community of Winding Cypress! Pinnacle, two-story model w/ many upgrades. End lot provides great privacy. Outdoor living space offers extended lanai area, outdoor gas kitchen, beautiful pool/spa & premium LONG lake views. Storm Smart electric lanai screens, wood-like tile flooring throughout & expanded kitchen island with bar seating for 5 or more. Kitchen includes: wine fridge and custom cabinetry w/ soft-close, & stainless steel appliance package. Sizable Master Suite with walk-in closet and large Master bathroom. Upstairs loft has a massive living area featuring a sitting area, bathroom, and separate bedroom. Big garage where you can park three cars. Winding Cypress features: An AMAZING active lifestyle community with something for everyone. Beach entry pool, waterfalls, poolside bar and grill, state-of-the-art fitness center, tennis, bocce, pickleball, social activities (off-site events, clubs, groups, classes) & miles of walking paths and boardwalks. Act fast this property is sure not to last!

7383 Mockingbird CT, Naples
$1,495,000
4 Beds ⋅ 4 Baths ⋅ 225067265 MLS
Motivated Seller! Luxurious Lakeside Living in Winding Cypress – Rare One Owner Pinnacle Model! Welcome to this stunning lake view home offering 3,656 sq. ft. of modern elegance in the prestigious, amenity-rich community of Winding Cypress. With 4 bedrooms, 4 bathrooms, a den, bonus room, and 2,5-car garage, this home is thoughtfully designed for both everyday living and entertaining on a grand scale. Step inside to discover a light-filled open floor plan accented with tile flooring in the main living areas, brand-new luxury vinyl plank flooring in all three downstairs bedrooms, and crown molding throughout the first floor. The chef’s kitchen is a showstopper, boasting quartz countertops, premium KitchenAid stainless steel appliances, a new natural gas cooktop, soft-close cabinetry, walk-in pantry, new dishwasher, and upgraded sink—all designed for style and function. Enjoy seamless indoor-outdoor living with zero-corner sliding doors that open to an expansive lanai featuring a picture screen enclosure, heated pool and spa, and a custom outdoor kitchen with built-in hub. With southwestern exposure overlooking the long lake and preserve, sunsets here are simply unforgettable. Retreat to the primary suite with a spa-like bathroom and custom walk-in closets, while guests enjoy privacy with an en suite bedroom on the main level. Upstairs, the bonus room offers endless flexibility for a game room, theater, or additional living space. This home is equipped with hurricane-impact windows, built-in Sonos surround sound system, smart home features, and abundant storage—ensuring comfort, safety, and convenience. As a resident of Winding Cypress, you’ll enjoy world-class amenities, including:Heated resort-style & lap pools, hot tub, and gas fire pit, covered outdoor restaurant bar & grill, expansive clubhouse with fitness center, library, and event space, pickle ball, bocce, and tennis courts, miles of scenic sidewalks & boardwalk trails, two dog parks for furry family members. Perfectly positioned on a premium lot, close to the community center and surrounded by excellent local infrastructure, this home is one of the rarely available larger homes in Winding Cypress—ideal for hosting family and friends in comfort and style. Experience the best of modern Naples living in this extraordinary home.

7412 Winding Cypress DR, Naples
$1,495,000
3 Beds ⋅ 3 Baths ⋅ 224083615 MLS
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.

6883 Cocoplum ST, Naples
$1,495,000
3 Beds ⋅ 3.5 Baths ⋅ 224034128 MLS
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

6962 Winding Cypress DR, Naples
$1,475,000
3 Beds ⋅ 3.5 Baths ⋅ 225016804 MLS
3 bedroom and 3 bath Stonewater Model home in Winding Cypress

6912 Cocoplum ST, Naples
$1,450,000
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
Start Your Search

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.