Winding Cypress Homes with Tennis Community Type

Welcome to Winding Cypress, a picturesque neighborhood nestled in the heart of Naples, Florida, in the vibrant Collier County. This charming community is not just a place to live; it's a lifestyle that embraces the best of Florida living, combining natural beauty with modern amenities.

Winding Cypress is renowned for its stunning homes that reflect a blend of contemporary design and classic elegance. Many of these residences feature spacious layouts, high-end finishes, and inviting outdoor spaces that encourage relaxation and entertainment. The community is particularly appealing to tennis enthusiasts, boasting a robust tennis program that caters to players of all skill levels. With well-maintained courts and a welcoming atmosphere, residents can enjoy friendly matches or participate in organized events throughout the year.

Beyond tennis, Winding Cypress offers an array of amenities that enhance the community experience. Residents can take advantage of the resort-style pool, state-of-the-art fitness center, and scenic walking trails that wind through lush landscapes. The clubhouse serves as a social hub, where neighbors gather for events, activities, and casual get-togethers, fostering a strong sense of community.

Nature lovers will appreciate the proximity to beautiful parks and preserves, offering opportunities for hiking, birdwatching, and enjoying the vibrant Florida wildlife. Plus, with Naples' stunning beaches and upscale shopping and dining just a short drive away, Winding Cypress truly offers the perfect blend of tranquility and convenience.

Discover your dream home in Winding Cypress, where every day feels like a vacation, and a thriving community awaits you!

Newest Winding Cypress Homes with Tennis Community Type

$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 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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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.