Winding Cypress Homes with Street Lights Community Type

Winding Cypress Homes with Street Lights Community Type

Welcome to Winding Cypress, a stunning new development nestled in the heart of Naples, Florida. This vibrant community in Collier County offers the perfect blend of luxury and comfort, making it an ideal place to call home. Winding Cypress is designed for those who appreciate the beauty of nature while enjoying the conveniences of modern living.

As you enter this picturesque neighborhood, you’ll be greeted by beautifully landscaped streets adorned with charming street lights that illuminate the paths for evening strolls. The community boasts a variety of meticulously crafted homes, each designed with an eye for detail and a commitment to quality. Whether you’re seeking a cozy villa or a spacious single-family home, Winding Cypress has something for everyone.

One of the standout features of Winding Cypress is its commitment to an active lifestyle. Residents can enjoy a wealth of amenities, including a resort-style pool, fitness center, and walking trails that wind through lush greenery. The community also fosters a sense of connection with its neighbors, encouraging social interactions through planned events and activities.

Located just minutes from Naples’ stunning beaches, world-class dining, and shopping, Winding Cypress offers the perfect balance of tranquility and convenience. With its welcoming atmosphere, beautiful homes, and vibrant community spirit, Winding Cypress is more than just a place to live; it’s a lifestyle waiting to be embraced. Come discover the charm of Winding Cypress, where your dream home awaits!

Newest Winding Cypress Homes with Street Lights Community Type

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
7098 Live Oak Drive, Naples
$520,000
3 Beds ⋅ 2 Baths ⋅ 226038340 MLS
Enjoy the ease of Florida living in this beautifully maintained, Serenity floor plan single family villa, ideally situated on a corner lot in the gated, amenity-rich community of Winding Cypress. Being offered turnkey furnished, this thoughtfully designed residence has three bedrooms, two baths, and an inviting open-concept design, while combining comfortable living with effortless indoor-outdoor enjoyment. Tile flooring throughout, granite countertops, tile backsplash, and stainless-steel appliances create a timeless, welcoming kitchen. New AC in 2021. Plantation shutters throughout and a freshly painted interior add to the appeal, while the extended screened lanai provides a relaxing outdoor retreat overlooking a peaceful, landscaped view. A newly added privacy hedge (2025) enhances the setting, creating an ideal space to enjoy morning coffee or unwind at the end of the day. Impact-resistant doors and windows, hurricane fabric screens for the lanai, and an attached two-car garage offer added convenience and peace of mind. Winding Cypress, a natural gas community carefully designed around preserved natural beauty, is known for its active, social lifestyle and impressive amenities. Residents enjoy a welcoming clubhouse, heated resort-style pool and spa, poolside dining at the Shady Palm, fitness center, library, and community gathering rooms. Pickleball, tennis, and bocce courts offer opportunities to stay active, while two dog parks, a community garden, and scenic walking and nature trails invite residents to enjoy the outdoors. Whether seeking a seasonal retreat or a year-round residence, this residence offers an appealing combination of comfort, convenience, and the vibrant Winding Cypress lifestyle, conveniently close to everything Naples has to offer.

7098 Live Oak 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
7072 Live Oak Drive, Naples
$1,450,000
4 Beds ⋅ 4 Baths ⋅ 226031553 MLS
Welcome to this beautifully appointed 4-bedroom, 4-bath residence offering approximately 3,350 square feet and a custom, one-of-a-kind floor plan not found elsewhere in the community. Designed for effortless Florida living, the spacious interior features multiple living and dining areas, a private office, elegant architectural details and an impressive kitchen with white cabinetry, a large island and abundant workspace. A built-in wine bar adds the perfect touch for entertaining. Expansive sliders open to a screened lanai with an outdoor kitchen, private pool and spa, fire pit and peaceful water views. Additional highlights include generously sized bedrooms, well-appointed baths, a walk-in closet, separate laundry room and attached garage. Located in a sought-after natural gas community with beautiful surroundings and resort-style amenities, this exceptional home combines custom design, comfort and the indoor-outdoor lifestyle Southwest Florida is known for.

7072 Live Oak Drive, Naples
7230 Live Oak Drive, Naples
$1,100,000
3 Beds ⋅ 3 Baths ⋅ 226034017 MLS
Beautiful home inside and out Pinnacle style home in Winding Cypress. This home features 3 generous size bedrooms, 3 full bath , 2 car plus golf cart garage . Custom oversized salt water heated pool with stairs , sunshelf, 3 waterfall features and oversized hot tub all surrounded by beautiful landscaping on an oversized lot with plenty of privacy. All impact resistance doors and windows, zero corner slider and a transfer switch with portable generator which handles lights, refrigerator and tv. Located close to the amenity center , dog park etc and all that Winding Cypress community offers, The Shady Palm restaurant, resort pool and spa, incredible gym and motion room for active classes, library , event room . Winding Cypress can be as active as you wish to be or to chill , either way you will fall in love with this community

7230 Live Oak Drive, 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
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
7478 Winding Cypress Drive, Naples
$1,349,500
3 Beds ⋅ 3 Baths ⋅ 226021460 MLS
BRING OFFERS! Welcome to this highly upgraded Infinity Model, a rare offering in the prestigious Winding Cypress community of Naples. Built by renowned DiVosta Builders, this residence is one of only three Infinity Models within a community of more than 750 homes, making it an exceptionally unique opportunity. Featuring an extra-wide three-car garage with a dedicated third bay ideal for a golf cart, hobby vehicle, or additional storage, this home has been significantly enhanced with premium upgrades throughout and offers a level of quality rarely found in today's market. Designed for both luxury and everyday comfort, the expansive open-concept floor plan showcases soaring tray ceilings exceeding 11 feet, custom faux painting, extensive crown molding, and elegant designer finishes throughout. The spacious great room seamlessly connects to the gourmet kitchen, highlighted by a six-burner Thermador gas range and cooktop, premium Liebherr refrigerator, custom cabinetry, and a massive leather-finished quartzite island perfect for entertaining. The seller's extensive investment in upgrades is evident in every detail. Designer window treatments, custom bed coverlets, built-in features, and custom closets throughout create a refined, move-in-ready environment. The completely remodeled primary bath offers a spa-inspired retreat featuring a curbless walk-in shower, floating vanity, premium fixtures, designer tilework, and stunning 48-inch porcelain tile flooring throughout. Outdoor living is equally impressive. The expansive lanai with desirable western exposure captures spectacular Naples sunsets and provides ample space for a custom pool, spa, and additional outdoor living areas. Pool plans and contractor quotes are available, making it easy for the next owner to create their ideal backyard oasis. The fully equipped outdoor kitchen provides the perfect setting for entertaining family and friends while enjoying the privacy and tropical surroundings. Additional upgrades include hurricane-impact windows and doors, a dramatic zero-corner sliding glass door, whole-house generator, tankless water heater, Kinetico water filtration system, Sonos surround sound system, epoxy-coated garage floors, insulated garage doors, built-in garage storage, and a dedicated air-conditioning system for the garage. As one of Naples' premier natural gas communities, Winding Cypress offers an unmatched lifestyle with a residents-only restaurant, resort-style pool and spa, fitness center, pickleball, tennis and bocce courts, and over 800 acres of protected preserve. Ideally located just 10 minutes from Marco Island's white sand beaches and approximately 15 minutes from Olde Naples, this exceptional residence combines rarity, luxury, and location in one extraordinary offering. This is more than a home—it's a statement of quality, craftsmanship, and lifestyle. One or more photos have been virtually staged, AI-generated, or rendered.

7478 Winding Cypress Drive, Naples
7666 Jacaranda Lane, Naples
$575,000
2 Beds ⋅ 2 Baths ⋅ 226008768 MLS
Experience elevated resort-style living in the highly desirable community of Winding Cypress. This impeccably maintained and tastefully updated 2-bedroom plus den, 2-bath villa offers soaring 9’4” ceilings and an attached two-car garage, delivering both comfort and functionality in a truly move-in-ready residence. Thoughtful upgrades include a newer refrigerator and hot water heater, upgraded pavers, plantation shutters, and additional enhancements that add both style and peace of mind. The flexible den provides the perfect space for a home office, guest retreat, or additional lounge area. Winding Cypress is designed for those who value lifestyle. Nearly two-thirds of the community is preserved as tranquil natural landscape and wooded conservation, creating a serene, private atmosphere rarely found this close to everything. Ideally located just 8 miles from Downtown Naples and 9 miles from Marco Island, you are moments from world-class dining, shopping, and Gulf beaches. Residents enjoy an impressive amenity package featuring pickleball, bocce, clubhouse, resort-style pool and spa, community park, social rooms, and more. Opportunities like this are rare. Schedule your private showing today.

7666 Jacaranda Lane, Naples
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