Winding Cypress Homes with Waterfront

Winding Cypress Homes with Waterfront

Welcome to Winding Cypress, a picturesque subdivision nestled in the heart of Naples, Florida, within the stunning Collier County. This charming community is renowned for its serene atmosphere, lush landscapes, and an abundance of natural beauty that captures the essence of Florida living.

Winding Cypress boasts an array of exquisite homes, many of which feature breathtaking waterfront views. Imagine waking up to the gentle sounds of nature, with tranquil waters just outside your window. These waterfront properties not only offer stunning vistas but also provide a unique lifestyle that includes opportunities for fishing, kayaking, and serene evening strolls along the water's edge.

The community is designed with a focus on outdoor living, featuring walking trails, scenic parks, and gathering spaces that encourage a sense of camaraderie among residents. Whether you’re hosting a barbecue with friends or enjoying a quiet evening watching the sunset over the water, Winding Cypress provides the perfect backdrop for your everyday life.

In addition to its natural beauty, Winding Cypress is conveniently located near Naples' vibrant downtown area, where you'll find an array of dining, shopping, and entertainment options. The pristine beaches of the Gulf Coast are just a short drive away, making it easy to indulge in sun-soaked days by the shore.

If you're searching for a home that combines luxury, nature, and a welcoming community, Winding Cypress in Naples, Florida, is the perfect place to call home. Experience the magic of waterfront living and discover the lifestyle you've always dreamed of!

Newest Winding Cypress Homes with Waterfront

4 Beds ⋅ 5 Baths ⋅ Winding Cypress SubDv.

Welcome to one of the most prestigious, stately, and expansive offerings throughout the entire, always-desirable community of Winding Cypress. This exclusive Stonewater Model, with a full 2nd floor of living space, is a 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 view and full preserve backdrop across the water. 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 2 story foyer via the front double doors, you can't help but notice the opulent main gathering area highlighted by soaring 13 foot ceilings with stylish tray surrounds. With 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 custom 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 Drive, Naples

3 Beds ⋅ 2 Baths ⋅ Winding Cypress SubDv.

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 Drive, Naples

3 Beds ⋅ 3 Baths ⋅ Winding Cypress SubDv.

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

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