Winding Cypress Homes with Tennis Court(s) Community Type

Winding Cypress Homes with Tennis Court(s) Community Type

Welcome to Winding Cypress, an exquisite community nestled in the heart of Naples, Florida, within the vibrant Collier County. This stunning development embodies the essence of luxurious living, offering a harmonious blend of nature, modern amenities, and an active lifestyle that caters to residents of all ages.

At Winding Cypress, you’ll discover a collection of beautifully designed homes that reflect the spirit of Florida living. Each residence is meticulously crafted with high-end finishes and spacious layouts, providing an inviting atmosphere for family gatherings or entertaining friends. Many homes feature private outdoor spaces, perfect for soaking up the sun or enjoying the serene views of the surrounding landscape.

One of the standout features of Winding Cypress is its dedication to an active lifestyle, highlighted by the community’s exceptional tennis courts. Whether you’re a seasoned player or just starting, the well-maintained courts provide the perfect setting for friendly matches or competitive play. The community fosters a sense of camaraderie, with numerous social events centered around tennis, allowing residents to connect and build lasting friendships.

Beyond the courts, Winding Cypress offers a wealth of amenities, including a resort-style pool, fitness center, and walking trails that meander through lush natural preserves. The community is also conveniently located near Naples’ pristine beaches, upscale shopping, and gourmet dining, ensuring that you are never far from the best that Southwest Florida has to offer.

Experience the charm and elegance of Winding Cypress, where your dream home awaits in a community designed for both relaxation and recreation. Embrace the Naples lifestyle today!

Newest Winding Cypress Homes with Tennis Court(s) Community Type

$1,200,000
3 Beds ⋅ 3 Baths ⋅ 226029565 MLS
Positioned on a premier waterfront lot with sweeping western sunset views, this pristine Stonewater home combines modern sophistication with effortless Florida outdoor living in one of Naples’ premier resort communities. This Home highlights include a spacious layout of 3 bedrooms all ensuite by pocket doors, plus a private den/ flex room with French doors, 3 full custom baths, and an oversized 3-car garage with storage racks. The gourmet kitchen is outfitted with Stainless steel appliances package, natural gas cooktop, quartz counters, under cabinet lighting, walk-in pantry with plenty of storage, and expansive central island for entertaining guest. Upscale Details include: Coffered ceilings, plank tile flooring in the main living area, designer lighting, lead glass front door, and primary suite with large walk-in closet. Integrated water filtration/softener system, custom landscape lighting, and motorized roll-down storm shades on the rear lanai. The resort outdoor living includes a breathtaking saltwater pool with waterfall feature set against panoramic lake views, extended covered sitting and dining areas complete with a custom built in natural gas summer kitchen ideal for alfresco dining and sunset cocktails with year round Florida hosting. Enjoy the exceptionally low HOA fees paired with world-class amenities: on-site dining at The Shady Palm, resort pool with lap swimming, spa, active pickleball, tennis, and bocce, fitness center, dog parks, and over 800 acres of natural preserves —just minutes from 5th Ave South, Marco Island, and Gulf beaches. Don't miss out on the chance to enjoy all that Winding Cypress has to offer with plenty of room for family and guest to visit.

6851 Winding Cypress Drive, 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
$599,900
3 Beds ⋅ 2 Baths ⋅ 226024508 MLS
Welcome to your private paradise in the highly sought-after, resort-style community of Winding Cypress! 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. 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 Drive, 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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