Winding Cypress Naples Florida - 18 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!

Welcome to the rare opportunity to own the prestigious Stonewater model home in the desirable, amenity filled community of Winding Cypress. This property sits on one of the most beautiful and private waterfront lots. View spectacular sunsets over a big water lake with a wildlife-rich preserve as a private backdrop. As soon as you walk through the double-door front entrance, your breath will be taken away as you marvel at the grandeur of the open living space highlighted by a 12 foot ceiling accented with built-in trays. The split bedrooms and open living area floorplan is most popular and sought after as it is perfect for large gatherings and entertaining with family and friends while offering a quiet and separate space for guests during the overnights. The primary suite is expansive, big enough for king bed furniture and additional sitting area. The bath area boasts a beautiful walk-in tiled shower, large dual sink vanity, and oversized walk-in closet. The entrance to the two other bedrooms and baths can be closed off from the main living area by pocket doors giving a private feel of additional suites. The chef's kitchen boasts a beautiful quartz center island with sink, upgraded appliances that include a natural gas cook top, double built-in oven, custom cabinets with underside lighting and a huge walk-in pantry. There's also a formal dining area adjacent to kitchen and great room gathering space. Open up the French doors and enjoy the quaintness of your added den, study or office. This is an extra large space perfect to be set up with your personal wants and needs in mind. Nothing helps out a homeowner more than a three car garage. This one has a ton of built-in ceiling and wall storage racks for everything imaginable including bicycles. The garage doors are insulated as well as the attic above. As you step outside onto the custom upgraded pavers and look out over the big water lake, you can't help but admire the beautiful salt water pool with optional integral infinity spa. On the far side of the lake is a stunning and private preserve that speaks to tranquility, relaxation, and peacefulness as you sit in your lanai, swim in your pool, or unwind in your spa. Winding Cypress is a well designed community of over 1200 acres total with 850 acres of green space. It is amenity rich to include a resident's only full-scale restaurant, pickleball, tennis, & bocce courts, a spectacular community pool and clubhouse, awesome fitness center, dog park, 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.

Wow! This beautifully designed and meticulously maintained home is absolutely spectacular. 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 ample 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. Construction is top-notch with hurricane impact doors and windows throughout and there is a whole home gas generator too should the need arise. The driveway and side walkway are extended. There is over $100k in upgrades to this magnificent home. It is offered fully furnished. Just pack your bags and head on down to enjoy our very special slice of tropical paradise. 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.

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.

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.

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.

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

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!

This pre-inspected, intelligently-priced single family home is located in a stunning natural gas community and perfectly situated between Marco Island and downtown Naples. Among other amenities, this community has TWO dog parks! Stunning landscaping greets you at the front door, and you can step outdoors and savor a sanctuary of comfort and tranquility from the botanical plantings on your paver-lined outdoor patio with a raised herb garden. And not to worry…you will find hurricane protection on the windows as well as motorized Storm Smart screens on the lanai. Finishes in this lovely home include plantation shutters, wainscoting, crown moldings and tiled floors throughout. The Great Room floor plan includes a gourmet kitchen complete with granite countertops, abundant cabinetry, stainless steel appliances with gas cooking, and a large center island with breakfast bar and an attached Dining area. Relax or entertain in the bright and spacious Gathering room with an added “Sunroom” which leads to the screened-in lanai. In addition to the generously sized Owners’ Suite, there is ample room for your guests with two more bedrooms. French doors lead to a private office or den. Pet-friendly Winding Cypress Community offers two dog parks, tennis, pickleball, bocce, outdoor bar and grill room, and a resort-style pool. Residents also have access to a clubhouse with a social room, library, fitness center and a full social calendar. This is the one you’ve waiting for!!

Time to enjoy life. 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

What's Special: *Open floor plan *Epoxy garage floor *Granite countertops *3 feet bathroom countertops *Remote controlled garage screen *Remote controlled hurricane shutters on the lanai *California Closets in all bedrooms *Pool. 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. Whether you prefer a fully furnished home or want to bring your own personal touch, this property is available with or without furniture. 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.

Welcome to your dream home in the highly sought-after Winding Cypress community! This beautifully maintained 2-bedroom plus den, 2-bathroom pool home features an inviting open floor plan, perfect for modern living and entertaining. The kitchen is a chef's delight, boasting a breakfast bar and sleek stainless steel appliances. The generous primary bedroom offers a serene retreat with an ensuite bathroom that includes dual vanities and a spacious shower. An additional bedroom and a full bathroom provide ample space for guests or a home office. Enjoy the Florida lifestyle year-round in the enclosed lanai with a heated pool. Recent updates include Storm Smart Shutters, an upgraded shower door in the primary bathroom, a rescreened lanai (March 2024), and new carpet in the bedrooms. Winding Cypress offers an array of amenities, including tennis and pickleball courts, a state-of-the-art fitness center, a clubhouse, and more. Don't miss the opportunity to own this stunning home in a vibrant community!