Winding Cypress Homes with Single Family Residence Building Design

Welcome to Winding Cypress, a serene and picturesque subdivision nestled in the heart of Naples, Florida, within the beautiful Collier County. This charming community offers an idyllic blend of natural beauty and modern living, making it the perfect place to call home.

Winding Cypress is renowned for its stunning single-family residences, each meticulously designed to embody the essence of Florida living. These homes feature open floor plans, spacious interiors, and an array of upscale finishes, ensuring that every family can find their perfect sanctuary. With an emphasis on outdoor living, many residences boast private backyards, perfect for entertaining or simply enjoying the warm Florida sun.

The community is surrounded by lush landscapes, tranquil lakes, and scenic walking trails, providing residents with ample opportunities to connect with nature. Winding Cypress is not just a neighborhood; it’s a lifestyle. The community offers a wealth of amenities, including a resort-style pool, clubhouse, fitness center, and social activities that foster a strong sense of community among residents.

Located just a short drive from Naples' pristine beaches, world-class dining, and shopping, Winding Cypress combines the tranquility of suburban living with the vibrancy of city life. Families will appreciate the top-rated schools and proximity to parks, making it an ideal choice for those looking to settle down in a welcoming environment.

Experience the charm and beauty of Winding Cypress, where your dream home awaits in one of Florida’s most sought-after locations. Discover the perfect blend of comfort, style, and community in this enchanting Naples subdivision.

Newest Winding Cypress Homes with Single Family Residence Building Design

$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

$799,900

3 Beds ⋅ 2 Baths ⋅ 226027255 MLS

Beautifully upgraded 2021 Mystique model in desirable Phase 3 of Winding Cypress! this 3-bedroom =den home features a custom built in entertainment center with designer gas fireplace ,built in bar, whole-house generator, storm screens, decorative stone exterior, landscape uplighting, and more. the open floor plan with zero corner sliding doors is perfect for entertaining while the private preserve-view lanai offers a peaceful outdoor retreat. This lot will not accomidate a pool. A truly move-in-ready home that combines luxury comfort and Florida living at its finest. Enjoy all the rich filled amenities that Winding Cypress has to offer and all a short drive to beaches and downtown Naples

6820 Winding Cypress DR, Naples

$1,400,000

4 Beds ⋅ 4.5 Baths ⋅ 226024563 MLS

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 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

$949,900

3 Beds ⋅ 2 Baths ⋅ 226005365 MLS

Welcome to newest and last phase of homes built in 2020 in the vibrant well maintained community of Winding Cypress. Located just off Collier and 41 and minutes to 75 , Marco Island and downtown Naples This summer wood model is sure to please with 3 bdrms den and 2 baths with full showers , primary bath with custom mirrors. custom closet , plantation shutters mini a/c in garage, whole house water purifier, generator, storm screens on lanai ,outdoor kitchen , pool and spa. with private views to the preserve ,vaulted ceilings, ceiling fans in every room , and oversized neutral tile through out placed on the diagonal . some furniture can remain with the house . exlcuded dining light fixture

6844 Winding Cypress DR, Naples

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