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 enchanting community is designed for those who appreciate a harmonious blend of natural beauty and modern living. With its lush landscapes and serene waterways, Winding Cypress offers a tranquil retreat just minutes away from the stunning Gulf Coast beaches and the vibrant culture of downtown Naples.

Homes in Winding Cypress are crafted with care and attention to detail, showcasing a variety of architectural styles that cater to diverse tastes. One of the most appealing aspects of this community is the availability of homes priced under $800,000, making it an attractive option for first-time buyers, families, and retirees alike. These thoughtfully designed residences feature open floor plans, gourmet kitchens, and private outdoor spaces, perfect for enjoying Florida's year-round sunshine.

Residents of Winding Cypress enjoy access to a wealth of amenities, including a resort-style clubhouse, a sparkling pool, and well-maintained walking trails that wind through the community. The neighborhood fosters a strong sense of community, encouraging social gatherings and activities that bring neighbors together.

With its ideal location, beautiful homes, and a welcoming atmosphere, Winding Cypress is not just a place to live; it's a lifestyle. Experience the charm of Naples living in this delightful community, where your dream home awaits at an accessible price point. Come explore all that Winding Cypress has to offer, and discover why so many have chosen to call this vibrant neighborhood home!

Newest Winding Cypress Homes under $800,000

7602 Jacaranda Lane, Naples
$564,900
2 Beds ⋅ 2 Baths ⋅ Winding Cypress SubDv.
**Motivated sellers!! Seller concession of $5k!!!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
7670 Jacaranda Lane, Naples
$615,000
3 Beds ⋅ 2 Baths ⋅ Winding Cypress SubDv.
Escape cookie-cutter living at 7670 Jacaranda, where custom millwork, extensive built-ins and thoughtful upgrades give this 2018-built home a character all its own. The open kitchen anchors the main living area with upgraded Samsung smart appliances, natural gas range, custom built-in coffee bar, sleek cabinetry and quartz counters, flowing naturally into the dining and living spaces. High ceilings with crown molding and transom windows create a light and bright interior with the utmost in privacy. The living room features a custom entertainment wall with fireplace and built-in cabinetry for a striking focal point. The attention to detail continues into the primary suite, where a dramatic ceiling treatment adds architectural interest and a spacious bath with dual vanities and an oversized glass-enclosed shower. The custom walk-in closet is beautifully finished with extensive cabinetry, drawers, shelving and hanging space. Additional bedrooms are sunny and inviting, while a dedicated laundry room adds excellent storage and everyday functionality. Handcrafted storage options have been thoughtfully tucked in throughout the residence, allowing the square footage to live large. Outside, the home shifts seamlessly into Florida living. The expansive screened lanai surrounds a sparkling gas-heated saltwater pool with a cascading water feature and generous space for lounging and entertaining, while the covered outdoor living area with built-in outdoor kitchen creates a true extension of the interior. Beyond the enclosure, find a lush and private yard with mature landscaping for additional green space and privacy. The attached two car-garage is fully insulated with built-in shelving and an expanded attic space for even more storage, plus two 15-amp circuits, making it a breeze to add EV charging. Winding Cypress is a unique guarded and gated community with an emphasis on natural spaces, thanks to over 800 acres of natural preserves alongside 80 acres of lakes, all adjacent to the Picayune Strand State Forest. The community's wooden boardwalk is perfect for morning walks and birdwatching or visit the extensive amenities center anchoring the neighborhood. There you'll find a resort-style pool and spa, state-of-the-art fitness center, tennis, pickleball and bocce courts, dog park, walking and biking opportunities and the popular Shady Palm Cafe for casual dining and drinks close to home. An active social calendar and inviting gathering spaces create plenty of opportunities to connect, while the community’s preserve setting gives it a peaceful, distinctly Florida feel. Thoughtfully customized, impeccably maintained and surrounded by the natural beauty of Winding Cypress, 7670 Jacaranda offers a distinctly different take on Naples living.

7670 Jacaranda Lane, Naples
7156 Live Oak Drive, Naples
$590,000
3 Beds ⋅ 2 Baths ⋅ Winding Cypress SubDv.
PRICE ALERT- This is the LOWEST TRUE 3-BEDROOM complete with your own private pool located in the amenity rich community of Winding Cypress!!! The ultimate blend of luxury, comfort, and effortless living is TURNKEY 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: 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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