Winding Cypress Homes under $800,000

Winding Cypress Homes under $800,000

Welcome to Winding Cypress, a picturesque subdivision nestled in the heart of Naples, Florida, within the vibrant Collier County. This charming community offers a unique blend of serene landscapes and modern living, making it an ideal choice for families, retirees, and anyone seeking a tranquil yet active lifestyle.

Winding Cypress is designed with nature in mind, featuring stunning lakes, lush preserves, and walking trails that encourage residents to embrace the great outdoors. The community is not just about beautiful scenery; it fosters a sense of belonging with its friendly atmosphere and numerous social events throughout the year. Residents can enjoy amenities such as a resort-style pool, fitness center, and clubhouse, perfect for gatherings and relaxation.

One of the most appealing aspects of Winding Cypress is the availability of homes priced under $800,000. This makes it an attractive option for first-time homebuyers and those looking to downsize without compromising on quality or comfort. The homes in this subdivision boast open floor plans, modern finishes, and energy-efficient designs, ensuring that you find a perfect fit for your lifestyle.

Living in Winding Cypress means you're just a short drive away from the stunning beaches of Naples, world-class dining, and vibrant shopping districts. With its convenient location and affordable housing options, Winding Cypress is not just a place to live—it's a community where you can truly thrive. Discover your dream home in this enchanting neighborhood and experience the best of Naples living!

Newest Winding Cypress Homes under $800,000

7602 Jacaranda Lane, Naples
$579,000
2 Beds ⋅ 2 Baths ⋅ Winding Cypress SubDv.
**Motivated sellers!! This freshly painted, light-filled attached villa in Winding Cypress features two bedrooms plus a den with easy conversion to a third bedroom, two full bathrooms, and a two-car garage. An open floor plan, bright kitchen with stainless-steel Whirlpool appliances, granite counters and an in-residence laundry room with a newer washer and dryer make everyday living comfortable. A newly screened lanai overlooks a very private backyard, creating a relaxing setting.Winding Cypress offers an exceptional collection of resort amenities, including a resort-style pool and spa, poolside restaurant, attended fitness center, yoga lawn, outdoor fireplace, five tennis courts, eight pickleball courts, and four bocce courts. Explore the nature boardwalk and walking paths, community garden,visit the covered dog park, or enjoy an active calendar of social events. This home has 100% hurricane coverage. Conveniently located between downtown Naples and Marco Island, this home provides easy access to white-sand beaches, Fifth Avenue shopping and dining, and I-75. Make the Southwest Florida lifestyle your own. Furnishings negotiable!

7602 Jacaranda Lane, Naples
7156 Live Oak Drive, Naples
$599,900
3 Beds ⋅ 2 Baths ⋅ Winding Cypress SubDv.
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 Drive, Naples
7666 Jacaranda Lane, Naples
$575,000
2 Beds ⋅ 2 Baths ⋅ Winding Cypress SubDv.
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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