Winding Cypress Homes under $1.25 million

Winding Cypress Homes under $1.25 million

Welcome to Winding Cypress, a breathtaking community nestled in the heart of Naples, Florida, within the picturesque Collier County. This vibrant neighborhood is designed for those who appreciate the perfect blend of luxury and nature, offering a serene lifestyle amidst stunning landscapes and modern amenities.

Winding Cypress features an impressive selection of homes priced under $1.25 million, making it an ideal choice for families, retirees, and anyone seeking a tranquil retreat in one of Florida's most sought-after locations. Each residence is thoughtfully designed with open floor plans, high ceilings, and premium finishes, ensuring comfort and elegance in every detail. With various styles and layouts available, you’re sure to find the perfect home that suits your unique lifestyle.

Beyond the beautiful homes, Winding Cypress boasts a wealth of community amenities designed to enhance your living experience. Residents can enjoy a resort-style pool, state-of-the-art fitness center, and miles of walking and biking trails that wind through lush landscapes. The community is also home to a vibrant clubhouse, where neighbors can gather for social events, activities, and relaxation.

Located just minutes from Naples' pristine beaches, world-class shopping, and exquisite dining options, Winding Cypress offers the ideal balance of tranquility and convenience. Whether you’re looking to embrace an active lifestyle or simply unwind in a beautiful setting, this community is the perfect place to call home. Discover your dream home in Winding Cypress today and experience the best of Naples living!

Newest Winding Cypress Homes under $1.25 million

7602 Jacaranda Lane, Naples
$579,000
2 Beds ⋅ 2 Baths ⋅ 226035971 MLS
**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
7670 Jacaranda Lane, Naples
$625,000
3 Beds ⋅ 2 Baths ⋅ 226034452 MLS
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
7230 Live Oak Drive, Naples
$1,195,000
3 Beds ⋅ 3 Baths ⋅ 226034017 MLS
Beautiful home inside and out Pinnacle style home in Winding Cypress. This home features 3 generous size bedrooms, 3 full bath , 2 car plus golf cart garage . Custom oversized salt water heated pool with stairs , sunshelf, 3 waterfall features and oversized hot tub all surrounded by beautiful landscaping on an oversized lot with plenty of privacy. All impact resistance doors and windows, zero corner slider and a transfer switch with portable generator which handles lights, refrigerator and tv. Located close to the amenity center , dog park etc and all that Winding Cypress community offers, The Shady Palm restaurant, resort pool and spa, incredible gym and motion room for active classes, library , event room . Winding Cypress can be as active as you wish to be or to chill , either way you will fall in love with this community

7230 Live Oak Drive, Naples
6825 Greenbriar Court, Naples
$965,000
4 Beds ⋅ 3 Baths ⋅ 226034030 MLS
Preserve views on a quiet cul-de-sac street define this two-story Mystique residence in Winding Cypress, where a saltwater pool with spillover spa, expansive outdoor living and flexible interior spaces create a home designed for relaxation and entertaining. With four bedrooms, a den, an upstairs flex room, three baths and a two-car garage, the floor plan offers exceptional versatility while maintaining an open, connected feel throughout the main living areas. A whole-house generator is on-site, providing added peace of mind during storm-related power outages. A brick paver driveway, tile roof and professional landscaping establish a polished arrival. Inside, wood-look tile flooring, recessed lighting and white plantation shutters carry a clean, cohesive aesthetic throughout the home. The living room is filled with natural light from five windows and anchored by a modern ceiling fan, while the adjacent dining area draws additional light through its windows and sliding glass door, creating an easy transition between indoor and outdoor spaces. Open to the living and dining areas, the kitchen serves as the center of the main level with white shaker-style cabinetry, quartz countertops and a designer marble tile backsplash. A three-seat island provides a natural gathering place, complemented by stainless steel gas cooking appliances and a pantry. Positioned just off the kitchen, the primary suite offers a private retreat with a tray ceiling, walk-in closet and well-appointed en-suite bath. A dual-sink white vanity provides generous preparation space, while the floor-to-ceiling tiled walk-in shower features a built-in bench. A dedicated linen closet adds further storage. Additional guest bedrooms and baths provide comfortable accommodations, while a downstairs den with French doors creates a quiet setting for work or study. Upstairs, the carpeted flex room expands the home’s versatility and can readily serve as a media room, fitness space, office, playroom or secondary lounge. The upstairs bedroom and full bath create a private retreat that is especially well suited for extended family or out-of-town guests, offering added separation and privacy from the main living areas. Outdoors, a covered living area with paver flooring overlooks the screened saltwater pool and spillover spa, both framed by brick pavers. Beyond the pool enclosure, the home backs to a preserve and small creek, providing a natural backdrop and an added sense of privacy. Residents of Winding Cypress enjoy access to a private clubhouse with year-round gatherings, live music, holiday events and community activities. Ideally between downtown Naples and beaches of Marco Island, this residence combines preserve-side privacy, substantial indoor-outdoor living, flexible accommodations and the added security of a whole-house generator in one of Southwest Florida’s well-established communities.

6825 Greenbriar Court, Naples
7564 Winding Cypress Drive, Naples
$1,030,000
4 Beds ⋅ 2 Baths ⋅ 2026039825 MLS
Most lake lots give you water. This one gives you the sunset. The western exposure at 7564 Winding Cypress Drive turns the back of the house into the best seat in the community every evening, and the extended lanai is built with no-see-um mesh in picture-window construction, so the horizon comes through without a frame across it. Behind that view is a one-owner 2018 DiVosta Summerwood, offered for the first time since it was built and expanded well past the standard plan: 2,230 square feet, four bedrooms, ten-foot ceilings, eight-foot doors, and an extended great room under a coffered ceiling with crown molding carried through every room. Arched openings, plantation shutters on every window, and porcelain plank floors give the interior a finished, architectural quality that reads as both coastal and modern. The kitchen was renovated after purchase and it shows: white shaker cabinetry, salt-and-pepper granite, a counter-to-ceiling white subway backsplash, an externally vented stainless chimney hood over a natural gas range, under-cabinet lighting, a wine fridge, a walk-in pantry, and an extended island with seating under glass pendants. The dining area sits beneath its own cluster chandelier, and the great room holds a full sectional, a game table, and a bar cabinet with room to spare. Outside, the lanai is a true second living room. A resort-style saltwater pool with an in-water sundeck, a spa placed on the sight line so the water reads as one composition from inside the house, a Silver River travertine deck, and a covered section deep enough for an outdoor sectional and a six-seat dining table. Natural gas outdoor is included as well. Foxtail and Christmas palms frame the lake beyond. New pool motor in 2024. Then the part that separates a Florida house from a Florida headache. Impact windows, custom window treatments and impact doors are installed throughout. StormSmart electric screens on the lanai and front vestibule. A whole-house and pool Generac generator. A flat concrete tile roof, tankless water heater, and centrally wired alarm. Close the house in May, fly north, and stop watching the tropics. The extended garage has its own split-system A/C; the attic has pull-down stairs and added insulation. The owner's suite carries a California Closets build-out, and every closet in the house has extra shelving. Dimmer switches throughout. The designer furnishings shown, indoors and out, are available under separate negotiation. Bring a suitcase if you like. Winding Cypress is a gated, natural-gas community of 766 homes set inside 800 acres of protected preserve and 80 acres of lakes. Residents have an on-site restaurant and bar, resort and lap pools with a spa and fire pit, an oversized fitness center, tennis, pickleball, bocce, two dog parks, a full activities calendar, and miles of boardwalk and preserve trail. Lawn care is included in the dues. Marco Island's beaches are ten minutes out; Fifth Avenue South is about fifteen.

7564 Winding Cypress Drive, Naples
7700 Winding Cypress Drive, Naples
$1,250,000
5 Beds ⋅ 3 Baths ⋅ 226032436 MLS
BEAUTIFUL AND METICULOUSLY MAINTAINED 5 BEDROOM, 3 BATH HOME IN DIVOSTA’S GATED WINDING CYPRESS COMMUNITY, ONE OF NAPLES MOST DESIRABLE LOCATIONS, CONVENIENT TO DOWNTOWN NAPLES, MARCO ISLAND’S PRISTINE BEACHES AS WELL AS NEARBY SHOPPING AND RESTAURANTS, THIS SUMMERWOOD FLOORPLAN FEATURES A MASTER ON MAIN LIVING FLOOR WITH LARGE BATH AND WALK-IN CLOSET, A LARGE LOFT SPACE UPSTAIRS WITH A SEPARATE BEDROOM AND FULL BATH, AND 3 OTHER BEDROOMS AND BATH ON THE MAIN LIVING LEVEL. NUMEROUS UPGRADES INCLUDE OVERSIZED POOL AND SPA, EXTENDED LANAI AND GARAGE, ZERO CORNER SLIDING DOORS LEADING TO LANAI, FRAMED DROP SOFFIT IN MASTER, FLOOR OUTLET, DECORATIVE GLASS FRONT DOOR, OVERSIZED KITCHEN ISLAND, OUTDOOR KITCHEN WITH BUILT-IN GRILL AND COOLER, TANKLESS WATER HEATER, AND CUSTOM CABINETRY AND TILE. WINDING CYPRESS FEATURES A GATED ENTRANCE WITH GUARD, DOG PARK, COMMUNITY GARDEN, TENNIS, PICKLEBALL, BEAUTIFUL CLUBHOUSE WITH BAR AND GRILL, LARGE RESORT POOL AND DECKS…TRULY A GEM IN SOUTH NAPLES! AND NO FLOOD INSURANCE REQUIRED!!

7700 Winding Cypress Drive, Naples
7156 Live Oak Drive, Naples
$590,000
3 Beds ⋅ 2 Baths ⋅ 226024508 MLS
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
6727 Pennyroyal Drive, Naples
$920,000
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 Drive, Naples
7666 Jacaranda Lane, 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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