Winding Cypress Homes with Main Level Primary Interior

Winding Cypress Homes with Main Level Primary Interior

Welcome to Winding Cypress, an exquisite community nestled in the heart of Naples, Florida, within the beautiful Collier County. This stunning development offers a perfect blend of luxury and comfort, with homes designed to cater to the needs of modern living. One of the standout features of Winding Cypress is its thoughtfully designed residences that boast main-level primary suites, providing both convenience and elegance for homeowners.

Imagine waking up in your spacious primary bedroom, bathed in natural light, with easy access to your private outdoor oasis. The main-level primary interiors are a hallmark of Winding Cypress, offering a seamless flow between indoor and outdoor living spaces. These homes are meticulously crafted to ensure that every square foot is utilized efficiently, creating an inviting atmosphere perfect for both relaxation and entertaining.

The community itself is surrounded by lush landscapes and serene waterways, providing a tranquil backdrop for a vibrant lifestyle. Residents at Winding Cypress enjoy an array of amenities, including a resort-style pool, state-of-the-art fitness center, and a lively clubhouse, making it easy to connect with neighbors and build lasting friendships.

Located just minutes from Naples’ stunning beaches, world-class dining, and upscale shopping, Winding Cypress is not just a place to live; it’s a lifestyle choice. Whether you’re looking for a seasonal retreat or a year-round residence, this community offers the ideal setting to embrace the Florida sunshine and create cherished memories. Come discover the charm of Winding Cypress, where luxurious living meets the beauty of nature.

Newest Winding Cypress Homes with Main Level Primary Interior

7775 Winding Cypress Drive, Naples
$990,000
4 Beds ⋅ 3 Baths ⋅ 226037594 MLS
Thank you for taking a look at the best value in sought after Winding Cypress! This pristine, 2-Story Summerwood Model, is loaded with options and is located on one of the nicest, private, and quiet lots in the entire community. This amazing home is perfectly situated on a lake's edge with a preserve backdrop. It's on a cul-de-sac with no thru traffic, and miles off of major roadways so it's incredibly quiet, private, with no road noise. If you are looking for a luxurious and functional space to entertain guests, or have them spend some overnights visiting, this is the property for you. Pride of original ownership is clear. With over 3200 square feet there's incredible room to entertain while also providing privacy for visitors. This home boasts 4 bedrooms, 3 full baths, and a large office or flex room that can be used as the new owner desires. The upstairs area is expansive with a huge gathering space that can be used as a theater room, craft area, media room, or office. The upstairs has it's own large bedroom and full bathroom. The 2nd floor also has it's own zoned climate control with a dedicated additional HVAC unit. The upgrades and amenities that this property offers are impressive. These features include: an upgraded kitchen package that adds optional cabinets, quartz counters & premium appliances, plank tile flooring, an incredible extended great room gathering space, built-in saltwater pool w/integral spa, a whole house generator, easy-use accordion shutters, hurricane rated electric shades enclosing the lanai, an outdoor summer kitchen, surround sound ceiling speakers, an upgraded, private owner's suite, built-in closet organizers, convenient interior plantation shutters, and a deep 2 car garage with epoxy flooring and a must have 2nd refrigerator. Winding Cypress is an amenity rich, natural gas community and a hidden gem of Naples. Meet friends and neighbors at the resident's only, full-service restaurant and bar that's conveniently located at the edge of the incredible resort pool. Play pickleball, tennis, or bocce on the premium lighted courts. Take advantage of the world-class fitness center. Enjoy the nature trail boardwalk, dog parks, and community garden. Participate in any of the huge selection of activities that the community and HOA offers. Speaking of the HOA, you will not find a better value for cost anywhere in Naples. It's not even close. The HOA General Manager, Assistant Manager, Activities Director, and Support Staff are all full-time and on site to better assist the residents. Winding Cypress is conveniently located just 10 minutes to the beaches and entertainment on Marco Island, 15 minutes to all that downtown Olde Naples has to offer, 10 minutes to I75, and just 35 minutes to RSW Airport.

7775 Winding Cypress Drive, Naples
7247 Clamshell Lane, Naples
$1,549,000
4 Beds ⋅ 4 Baths ⋅ 226035902 MLS
A MUST-SEE HOME IN A MUST SEE COMMUNITY Extensive upgrades and designer elements elevate this home, based on an award winning model. Gorgeous water/preserve views are seen both back and front. This quiet, lush green street is just a short walk to the recreation center where several activities, amenities and social events can be enjoyed. Winding Cypress has low HOA fees, numerous inclusions and is full of natural beauty. Motivated seller. All of which make this a must-see home and community. Inside, beautiful design blends elegance with functionality. The roomy open floor plan is ideal for easy mingling but has plenty of private spaces for everyday life. Enter a spacious foyer leading to the great room. Here, defined living and dining areas border a showpiece kitchen with a huge 10-foot island, gas cooking and a walk-in pantry, enhanced by several upgrades such as premium cabinetry and appliances, quartz countertops, generous crown molding and wainscoting, upgraded porcelain tile flooring, custom lighting and other designer finishes. Zero-corner doors enable fabulous indoor-outdoor entertaining, opening up the house to a beautiful lanai which has uncommon, high-impact, structural upgrades. It is oversized/extended to create a wide open feel and multiple spaces for relaxing and entertaining. The pool with spa and Baja shelf is also oversized for daytime full family fun and a dramatic lit atmosphere at night. The picture-frame screen enclosure is yet another upgrade for best showcasing the stunning views of water, preserve and large flocks of birds in winter. The ground floor primary suite offers a private retreat with a poolside bedroom, spa-like bathroom, coastal design enhancements and large walk-in closet. This floor also has two more bedrooms, each with a walk-in closet, and a den that can be used as a study, sitting room, TV room, or flex space. Upstairs is a large bedroom that comfortably sleeps up to 6 people; a full bath and a huge 34X21 loft that can be used as a quiet home office, fitness room, media room or play area for example. The floor plan has lots of storage and works well for a variety of lifestyles/needs like hosting large family gatherings, working from home, or multigenerational living. Other upgrades include full impact glass, an oversized, shelved, three vehicle garage with epoxy flooring. This home is situated on one of the most desirable, tranquil lots and is a one owner home. Winding Cypress has a guard-gate, all landscaping and a wow amenity center included in the low HOA, as are pickleball, tennis, bocce, fitness center, resort-style pool, on-site restaurant and bar, dog park, scenic walking trails and a full schedule of entertainment and social activities—providing a resort style country club lifestyle without country club fees. It is just minutes to Marco Island, downtown Naples, beaches, boating, golf, shopping, restaurants, hospitals, I-75.

7247 Clamshell Lane, Naples
7602 Jacaranda Lane, Naples
$564,900
2 Beds ⋅ 2 Baths ⋅ 226035971 MLS
**Motivated sellers!! Seller concession of $5k!!!This freshly painted, light-filled attached villa in Winding Cypress features two bedrooms plus a den with easy conversion to a third bedroom, two full bathrooms, and a two-car garage. An open floor plan, bright kitchen with stainless-steel Whirlpool appliances, granite counters and an in-residence laundry room with a newer washer and dryer make everyday living comfortable. A newly screened lanai overlooks a very private backyard, creating a relaxing setting.Winding Cypress offers an exceptional collection of resort amenities, including a resort-style pool and spa, poolside restaurant, attended fitness center, yoga lawn, outdoor fireplace, five tennis courts, eight pickleball courts, and four bocce courts. Explore the nature boardwalk and walking paths, community garden,visit the covered dog park, or enjoy an active calendar of social events. This home has 100% hurricane coverage. Conveniently located between downtown Naples and Marco Island, this home provides easy access to white-sand beaches, Fifth Avenue shopping and dining, and I-75. Make the Southwest Florida lifestyle your own. Furnishings negotiable!

7602 Jacaranda Lane, Naples
7670 Jacaranda Lane, Naples
$615,000
3 Beds ⋅ 2 Baths ⋅ 226034452 MLS
Escape cookie-cutter living at 7670 Jacaranda, where custom millwork, extensive built-ins and thoughtful upgrades give this 2018-built home a character all its own. The open kitchen anchors the main living area with upgraded Samsung smart appliances, natural gas range, custom built-in coffee bar, sleek cabinetry and quartz counters, flowing naturally into the dining and living spaces. High ceilings with crown molding and transom windows create a light and bright interior with the utmost in privacy. The living room features a custom entertainment wall with fireplace and built-in cabinetry for a striking focal point. The attention to detail continues into the primary suite, where a dramatic ceiling treatment adds architectural interest and a spacious bath with dual vanities and an oversized glass-enclosed shower. The custom walk-in closet is beautifully finished with extensive cabinetry, drawers, shelving and hanging space. Additional bedrooms are sunny and inviting, while a dedicated laundry room adds excellent storage and everyday functionality. Handcrafted storage options have been thoughtfully tucked in throughout the residence, allowing the square footage to live large. Outside, the home shifts seamlessly into Florida living. The expansive screened lanai surrounds a sparkling gas-heated saltwater pool with a cascading water feature and generous space for lounging and entertaining, while the covered outdoor living area with built-in outdoor kitchen creates a true extension of the interior. Beyond the enclosure, find a lush and private yard with mature landscaping for additional green space and privacy. The attached two car-garage is fully insulated with built-in shelving and an expanded attic space for even more storage, plus two 15-amp circuits, making it a breeze to add EV charging. Winding Cypress is a unique guarded and gated community with an emphasis on natural spaces, thanks to over 800 acres of natural preserves alongside 80 acres of lakes, all adjacent to the Picayune Strand State Forest. The community's wooden boardwalk is perfect for morning walks and birdwatching or visit the extensive amenities center anchoring the neighborhood. There you'll find a resort-style pool and spa, state-of-the-art fitness center, tennis, pickleball and bocce courts, dog park, walking and biking opportunities and the popular Shady Palm Cafe for casual dining and drinks close to home. An active social calendar and inviting gathering spaces create plenty of opportunities to connect, while the community’s preserve setting gives it a peaceful, distinctly Florida feel. Thoughtfully customized, impeccably maintained and surrounded by the natural beauty of Winding Cypress, 7670 Jacaranda offers a distinctly different take on Naples living.

7670 Jacaranda Lane, Naples
6825 Greenbriar Court, Naples
$965,000
4 Beds ⋅ 3 Baths ⋅ 226034030 MLS
Preserve views on a quiet cul-de-sac street define this two-story Mystique residence in Winding Cypress, where a saltwater pool with spillover spa, expansive outdoor living and flexible interior spaces create a home designed for relaxation and entertaining. With four bedrooms, a den, an upstairs flex room, three baths and a two-car garage, the floor plan offers exceptional versatility while maintaining an open, connected feel throughout the main living areas. A whole-house generator is on-site, providing added peace of mind during storm-related power outages. A brick paver driveway, tile roof and professional landscaping establish a polished arrival. Inside, wood-look tile flooring, recessed lighting and white plantation shutters carry a clean, cohesive aesthetic throughout the home. The living room is filled with natural light from five windows and anchored by a modern ceiling fan, while the adjacent dining area draws additional light through its windows and sliding glass door, creating an easy transition between indoor and outdoor spaces. Open to the living and dining areas, the kitchen serves as the center of the main level with white shaker-style cabinetry, quartz countertops and a designer marble tile backsplash. A three-seat island provides a natural gathering place, complemented by stainless steel gas cooking appliances and a pantry. Positioned just off the kitchen, the primary suite offers a private retreat with a tray ceiling, walk-in closet and well-appointed en-suite bath. A dual-sink white vanity provides generous preparation space, while the floor-to-ceiling tiled walk-in shower features a built-in bench. A dedicated linen closet adds further storage. Additional guest bedrooms and baths provide comfortable accommodations, while a downstairs den with French doors creates a quiet setting for work or study. Upstairs, the carpeted flex room expands the home’s versatility and can readily serve as a media room, fitness space, office, playroom or secondary lounge. The upstairs bedroom and full bath create a private retreat that is especially well suited for extended family or out-of-town guests, offering added separation and privacy from the main living areas. Outdoors, a covered living area with paver flooring overlooks the screened saltwater pool and spillover spa, both framed by brick pavers. Beyond the pool enclosure, the home backs to a preserve and small creek, providing a natural backdrop and an added sense of privacy. Residents of Winding Cypress enjoy access to a private clubhouse with year-round gatherings, live music, holiday events and community activities. Ideally between downtown Naples and beaches of Marco Island, this residence combines preserve-side privacy, substantial indoor-outdoor living, flexible accommodations and the added security of a whole-house generator in one of Southwest Florida’s well-established communities.

6825 Greenbriar Court, Naples
7700 Winding Cypress Drive, Naples
$1,250,000
5 Beds ⋅ 3 Baths ⋅ 226032436 MLS
BEAUTIFUL AND METICULOUSLY MAINTAINED 5 BEDROOM, 3 BATH HOME IN DIVOSTA’S GATED WINDING CYPRESS COMMUNITY, ONE OF NAPLES MOST DESIRABLE LOCATIONS, CONVENIENT TO DOWNTOWN NAPLES, MARCO ISLAND’S PRISTINE BEACHES AS WELL AS NEARBY SHOPPING AND RESTAURANTS, THIS SUMMERWOOD FLOORPLAN FEATURES A MASTER ON MAIN LIVING FLOOR WITH LARGE BATH AND WALK-IN CLOSET, A LARGE LOFT SPACE UPSTAIRS WITH A SEPARATE BEDROOM AND FULL BATH, AND 3 OTHER BEDROOMS AND BATH ON THE MAIN LIVING LEVEL. NUMEROUS UPGRADES INCLUDE OVERSIZED POOL AND SPA, EXTENDED LANAI AND GARAGE, ZERO CORNER SLIDING DOORS LEADING TO LANAI, FRAMED DROP SOFFIT IN MASTER, FLOOR OUTLET, DECORATIVE GLASS FRONT DOOR, OVERSIZED KITCHEN ISLAND, OUTDOOR KITCHEN WITH BUILT-IN GRILL AND COOLER, TANKLESS WATER HEATER, AND CUSTOM CABINETRY AND TILE. WINDING CYPRESS FEATURES A GATED ENTRANCE WITH GUARD, DOG PARK, COMMUNITY GARDEN, TENNIS, PICKLEBALL, BEAUTIFUL CLUBHOUSE WITH BAR AND GRILL, LARGE RESORT POOL AND DECKS…TRULY A GEM IN SOUTH NAPLES! AND NO FLOOD INSURANCE REQUIRED!!

7700 Winding Cypress Drive, Naples
6907 Cocoplum Street, Naples
$1,295,000
3 Beds ⋅ 3 Baths ⋅ 226027501 MLS
PRICED TO SELL! Discover exceptional value in one of Naples’ most desirable lifestyle communities, Winding Cypress. Ideally situated on an oversized preserve lot with peaceful pond views, this beautifully maintained Pinnacle floor plan offers over 2,500 square feet of living space with 3 spacious bedrooms, 3 full bathrooms, and a versatile den. Built in 2020, this move-in-ready residence combines elegant finishes, thoughtful upgrades, and outstanding indoor-outdoor living. The expansive outdoor area features a large picture-window screened lanai, gas-heated saltwater pool and spa, custom outdoor kitchen, and generous brick-paver lanai with a covered entertaining area—perfect for enjoying the Naples lifestyle year-round. A newly installed electric hurricane screen provides additional protection and convenience. The home is equipped with whole-house hurricane shutters, a whole-house generator capable of supporting the pool and spa, and an oversized 3-car garage with epoxy flooring and hurricane-rated, insulated garage doors. Additional attic insulation and a separate garage A/C system provide the option for climate-controlled storage or workspace. The beautifully appointed kitchen features white quartz countertops, premium stainless steel appliances, a gas cooktop, and a beverage refrigerator. The spacious primary suite offers exceptional organization with a custom California Closets design, while the custom pantry provides additional storage and functionality. Beyond the residence, Winding Cypress offers an exceptional resort-style lifestyle. The impressive clubhouse features a heated resort pool and spa, poolside dining at The Shady Palm, state-of-the-art fitness center, library, and elegant gathering rooms. Residents also enjoy tennis and pickleball courts, bocce, dog parks, a community garden, and scenic walking and nature trails. Beautifully maintained grounds and a welcoming atmosphere create a true sense of community, all while being conveniently located near the best of Naples. Located in an X flood zone, with no flood insurance required, this exceptional home offers the perfect combination of luxury, privacy, recreation, and peace of mind. Priced to sell and offering tremendous value, this is an opportunity to own a beautifully upgraded home in one of Naples’ premier communities.

6907 Cocoplum Street, Naples
7156 Live Oak Drive, Naples
$590,000
3 Beds ⋅ 2 Baths ⋅ 226024508 MLS
PRICE ALERT- This is the LOWEST TRUE 3-BEDROOM complete with your own private pool located in the amenity rich community of Winding Cypress!!! The ultimate blend of luxury, comfort, and effortless living is TURNKEY READY for your immediate enjoyment. The 2-car attached garage—complete with convenient overhead storage racks and additional utility sink—offer great convenience. Discover a bright, open-concept living space featuring seamless tile flooring throughout. The spacious great room flows effortlessly into your own private outdoor oasis. The enlarged screened lanai offers you enjoyment of a private pool and outdoor grill kitchen, located on a exceptionally private lot that offers a serene, peaceful retreat for relaxation or entertaining. The owner’s suite serves as a tranquil escape, boasting elegant tray ceilings and an ensuite bath complete with a dual-sink vanity, a walk-in shower, a linen closet, and a generous walk-in closet. Two additional bedrooms provide ample space and privacy for visitors and guests. Key upgrades and features include: NEW HVAC Unit for year-round comfort and energy efficiency. Storm Smart ELECTRIC STORM SHUTTERS on the rear lanai. ACCORDION SHUTTERS on all exterior windows for ultimate peace of mind and storm protection. Winding Cypress is renowned for its world-class amenities, including a resort-style pool, a resident-only restaurant, pickleball, tennis, bocce, a state-of-the-art fitness center, two dog parks, and a vibrant social calendar. Perfectly positioned just minutes from the award-winning beaches of both Naples and Marco Island, as well as shopping, dining, and entertainment, this property is an ideal choice for a full-time residence, a seasonal retreat, or a savvy investment option. Don't miss this rare opportunity to live the Florida dream!

7156 Live Oak Drive, Naples
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