Winding Cypress Homes with Clubhouse Amenities

Welcome to Winding Cypress, a picturesque subdivision nestled in the heart of Naples, Florida, within the vibrant Collier County. This charming community seamlessly blends natural beauty with modern living, offering residents a serene lifestyle that is both luxurious and inviting.

Winding Cypress is renowned for its stunning homes that exemplify Florida's architectural elegance. Each residence is designed with meticulous attention to detail, featuring open floor plans, gourmet kitchens, and expansive outdoor spaces perfect for entertaining. With a variety of styles and sizes, there’s a perfect home for everyone, whether you’re a growing family or looking to downsize.

One of the standout features of Winding Cypress is its impressive clubhouse amenities. The community clubhouse serves as a social hub, offering a wealth of activities and facilities that cater to an active lifestyle. Residents can enjoy a sparkling resort-style pool, state-of-the-art fitness center, and engaging social events that foster a strong sense of community. The clubhouse is ideal for gatherings, whether you’re hosting a family event or mingling with neighbors over coffee.

Surrounded by lush landscapes and serene lakes, Winding Cypress provides ample opportunities for outdoor recreation. Residents can explore miles of scenic walking and biking trails, ensuring that nature is always just a step away.

Living in Winding Cypress means embracing a lifestyle of comfort, convenience, and camaraderie. Experience the beauty of Naples living in a community that truly feels like home. Come discover your dream home in Winding Cypress today!

Newest Winding Cypress Homes with Clubhouse Amenities

$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

$1,300,000

4 Beds ⋅ 4.5 Baths ⋅ 226024563 MLS

PRICE IMPROVEMENT _Ready for New Owners- Look at all the upgrades in this prestigious, stately, and expansive Stonewater offering everything option possible located in the highly-desirable natural gas community of Winding Cypress. The open concept main living area plus a 2nd floor for guest, media, home office, craft or game room of your choice. This is DiVosta Builder's flagship luxury home and a very rare find. This property sits on the most exceptional 1/4 acre lot with a spectacular large LAKE AND PRESEVE from your rear covered lanai. Quiet, serene privacy is what you should expect all day long, especially as you witness the incredible early morning sunrises. As soon as you enter the home's grand foyer via the front double doors, you can't help but notice the opulent main gathering area highlighted by soaring 13 foot tray ceilings, luxury detail, convenience features, and ownership peace of mind everywhere you look, this property has it all. The waterfront, 4+ bedroom, 4 1/2 bath, and 3 car garage with 4 foot extension residence is loaded with upgrades. Builder and owner added features include: HURRICANE RESISTANT/IMPACT WINDOWS DOORS & SLIDERS, WHOLE HOUSE GENERATOR, HEATED BUILT-IN POOL W/INTEGRAL SPA, CUSTOM KITCHEN CABINETS W/ABOVE & UNDER CABINET LIGHTING, QUARTZ COUNTERTOPS, UPGRADED APPLIANCE PACKAGE, WALK-IN PANTRY, UPGRADED LANAI W/PICTURE WINDOW SCREEN, HURRICANE RESISTANT ELECTRIC SHADES, POOL BATH, POOL STORAGE ROOM & SUMMER KITCHEN, CUSTOM PLANK TILE THROUGHOUT ENTIRE 1ST FLOOR, EXPANSIVE OWNER'S SUITE W/SITTING AREA, TRAY CEILING, FRENCH DOORS TO HUGE OWNER'S BATH W/DUAL VANITY, EXTENDED WALK-IN SHOWER, MAKEUP VANITY, LARGE WALK-IN CLOSET, BREAKFAST AREA W/CABINETS & BEVERAGE COOLER, DESIREABLE OPEN FIRST FLOOR GATHERING SPACE W/SPECTACULAR HIGH CEILINGS ENCOMPASSING GREAT ROOM, DINING AREA, KITCHEN & BREAKFAST NOOK, GLASS WALL OF DOUBLE SLIDERS THAT OPENS OUT TO LANAI & OUTDOOR LIVING SPACE, UPGRADED LIGHTING AND PLUMBING FIXTURES, 2 OTHER DOWNSTAIRS BEDROOMS CONVERT TO ENSUITES, LAUNDRY CENTER W/CABINETS & CUSTOM TUB, EXPANSIVE 2ND FLOOR LIVING SPACE INCLUDING THE 4TH BEDROOM & FULL BATHROOM, HUGE THEATER/MEDIA ROOM SPACE W/ ADDITIONAL SITTING AREA & WALK-IN CLOSET, BONUS ADDED DEN/OFFICE W/FRENCH DOORS, DUAL ZONED COOLING/HEATING W/2 HVAC UNITS, DESIRABLE 3 CAR EXTENDED GARAGE WITH RUBBER TILE FLOORING & 6 CEILING MOUNTED STORAGE RACKS. Winding Cypress is a most sought after, newer gated community renowned for it's amazing amenities at a great value. Of the total 1250 acres making up the community, Winding Cypress boasts over 825 acres of green space, mature landscape, lakes and preserve. Conveniently located just 15 minutes to downtown Olde Naples, 10 minutes to Marco Island, and 10 minutes to I75, you are close to the best beaches, dining, and boutique shopping that Southwest Florida has to offer.

7759 Winding Cypress DR, 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

$940,000

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

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