Winding Cypress Homes with Pickleball Amenities

Welcome to Winding Cypress, a picturesque subdivision nestled in the heart of Naples, Florida, within the vibrant Collier County. This charming community offers a perfect blend of serene living and modern conveniences, making it an ideal choice for families, retirees, and anyone seeking a slice of paradise.

Winding Cypress is not just a neighborhood; it’s a lifestyle. With its lush landscapes and beautifully designed homes, residents enjoy the tranquility of nature while being just moments away from Naples' stunning beaches, upscale shopping, and gourmet dining. The community is thoughtfully planned, featuring a variety of home styles that cater to diverse tastes and preferences, ensuring you find the perfect place to call home.

One of the standout features of Winding Cypress is its commitment to an active lifestyle, prominently showcased by its pickleball amenities. For enthusiasts of all ages, the community boasts state-of-the-art pickleball courts that foster camaraderie and friendly competition among neighbors. Whether you're a seasoned player or a newcomer eager to learn, these facilities provide a fantastic opportunity to stay active while building lasting friendships.

Additionally, Winding Cypress offers an array of amenities designed to enhance your lifestyle, including a resort-style pool, fitness center, and walking trails that weave through the scenic landscape. With a focus on community engagement and wellness, residents can partake in various social events and activities year-round.

Discover the charm of Winding Cypress, where elegant homes meet an active lifestyle in one of Florida's most sought-after locations. Embrace the beauty of Naples living—your dream home awaits!

Newest Winding Cypress Homes with Pickleball Amenities

$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, 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 gracious open floor plan is ideal for easy mingling but has plenty of private spaces for everyday life. Enter the spacious foyer to a great room. Defined living and dining areas border a showpiece kitchen with a huge 10-foot island, gas cooking, and a spacious walk-in pantry, enhanced by several upgrades such as premium cabinetry, quartz countertops, upgraded appliances, generous crown molding and wainscoting upgraded porcelain tile flooring, custom lighting, and other designer finishes. Zero-corner doors (another upgrade) enable fabulous indoor-outdoor entertaining and open to the stunning lanai which also boasts several upgrades. The lanai is extended/oversized for a spacious open feel and multiple spaces for relaxing and entertaining. The pool with spa and Baja shelf is oversized for full family fun during the day and a dramatic lit atmosphere at night. The premium picture-frame screen enclosure is yet another upgrade that showcases the stunning views overlooking water, preserve - and occasionally, wildlife. The primary suite offers a private retreat with a poolside bedroom, spa-like bathroom, coastal design enhancements and large walk-in closet. On the other side of the house are two 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 huge bedroom that comfortably sleeps up to 6 people; a full bath, and a huge loft area 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 and needs, including hosting large family gatherings, working from home, or multigenerational living. Other upgrades include full impact glass, an oversized, fully shelved three-car garage with epoxy flooring. This home is situated on one of the most desirable, tranquil, lots in the community and is a single owner home. Winding Cypress has guard-gated security, landscaping and a wow amenity center included in the HOA, as are pickleball, tennis, bocce, a state-of-the-art fitness center, a resort-style pool, an on-site restaurant and bar, a dog park, scenic walking trails and a full calendar of entertainment and social activities—providing a resort style country club lifestyle without country club fees. Just minutes from Marco Island, downtown Naples, beaches, boating, golf, shopping, restaurants, hospitals, I-75.

7247 Clamshell LN, Naples

$579,000

2 Beds ⋅ 2 Baths ⋅ 226035971 MLS

**Motivated sellers!! 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 LN, 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 DR, Naples

$1,195,000

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 DR, 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 CT, Naples

$1,030,000

4 Beds ⋅ 2 Baths ⋅ 2026039825 MLS

Most lake lots give you water. This one gives you the sunset. The western exposure at 7564 Winding Cypress Drive turns the back of the house into the best seat in the community every evening, and the extended lanai is built with no-see-um mesh in picture-window construction, so the horizon comes through without a frame across it. Behind that view is a one-owner 2018 DiVosta Summerwood, offered for the first time since it was built and expanded well past the standard plan: 2,230 square feet, four bedrooms, ten-foot ceilings, eight-foot doors, and an extended great room under a coffered ceiling with crown molding carried through every room. Arched openings, plantation shutters on every window, and porcelain plank floors give the interior a finished, architectural quality that reads as both coastal and modern. The kitchen was renovated after purchase and it shows: white shaker cabinetry, salt-and-pepper granite, a counter-to-ceiling white subway backsplash, an externally vented stainless chimney hood over a natural gas range, under-cabinet lighting, a wine fridge, a walk-in pantry, and an extended island with seating under glass pendants. The dining area sits beneath its own cluster chandelier, and the great room holds a full sectional, a game table, and a bar cabinet with room to spare. Outside, the lanai is a true second living room. A resort-style saltwater pool with an in-water sundeck, a spa placed on the sight line so the water reads as one composition from inside the house, a Silver River travertine deck, and a covered section deep enough for an outdoor sectional and a six-seat dining table. Natural gas outdoor is included as well. Foxtail and Christmas palms frame the lake beyond. New pool motor in 2024. Then the part that separates a Florida house from a Florida headache. Impact windows, custom window treatments and impact doors are installed throughout. StormSmart electric screens on the lanai and front vestibule. A whole-house and pool Generac generator. A flat concrete tile roof, tankless water heater, and centrally wired alarm. Close the house in May, fly north, and stop watching the tropics. The extended garage has its own split-system A/C; the attic has pull-down stairs and added insulation. The owner's suite carries a California Closets build-out, and every closet in the house has extra shelving. Dimmer switches throughout. The designer furnishings shown, indoors and out, are available under separate negotiation. Bring a suitcase if you like. Winding Cypress is a gated, natural-gas community of 766 homes set inside 800 acres of protected preserve and 80 acres of lakes. Residents have an on-site restaurant and bar, resort and lap pools with a spa and fire pit, an oversized fitness center, tennis, pickleball, bocce, two dog parks, a full activities calendar, and miles of boardwalk and preserve trail. Lawn care is included in the dues. Marco Island's beaches are ten minutes out; Fifth Avenue South is about fifteen.

7564 Winding Cypress DR, 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 DR, 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 ST, Naples

$599,900

3 Beds ⋅ 2 Baths ⋅ 226024508 MLS

This TURNKEY FURNISHED TRUE 3-BEDROOM , 2-bathroom villa offers the ultimate blend of luxury, comfort, and effortless living is move-in ready for your immediate enjoyment. LOWEST 3 BEDROOM WITH A POOL IN THIS COMMUNITY. 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: Brand-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 DR, Naples

$920,000

3 Beds ⋅ 2 Baths ⋅ 226022635 MLS

This meticulously maintained Mystique features 3 bedrooms + den, 2 bathrooms, 2 car garage with a pool and spa overlooking a lake! This home is situated on a spacious corner lot making it ideal for privacy while maintaining a stunning lake view. The turnkey designer furnishings have hardly been used and it's a pet free home. Outside the private oasis features a spa with waterfall, plenty of covered seating areas, and a top of the line outdoor kitchen. Recent updates include an upgraded 400 BTU pool heater (heats up pool quicker), new pool pump, and updated outdoor grill components. While located in the newest section of Winding Cypress - it is in a quiet location with convenient access to both gates. Winding Cypress is a natural gas community with resort-style amenities! Dine at Shady Palm, the onsite restaurant, or enjoy pickleball, bocce, tennis, a state-of-the-art fitness center, a resort-style pool, a community garden, and even 2 dog parks for your furry friend. This pet-friendly community allows rentals, has low fees, and boasts a prime location—convenient to Marco Island, 5th Avenue, and I-75.

6727 Pennyroyal DR, 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 DR, 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 LN, 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.