Winding Cypress Real Estate

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All Sold in Winding Cypress, Naples, FL

$1,400,000
3 Beds ⋅ 3 Baths ⋅ 224039811 MLS
Welcome to your dream home in Winding Cypress. This stunning residence epitomizes luxury living in paradise. As you step through the door into a haven of elegance and comfort. This meticulously crafted residence features an array of upgrades.

6909 Winding Cypress DR, Naples
$1,260,000
3 Beds ⋅ 3 Baths ⋅ 225060759 MLS
This Pinnacle floorplan is situated on the largest lake in the neighborhood and features 3 bedrooms, a den, 3 bathrooms, a pool and spa, and a 3-car garage. The open-concept layout includes a dramatic zero-corner slider that seamlessly connects indoor and outdoor living spaces. Peace of mind comes with a whole-home generator and impact-resistant windows and doors. Inside, you'll find extensive upgrades throughout. The kitchen boasts built-in appliances and a spacious island—perfect for entertaining. Additional highlights include soaring tray ceilings, crown molding in the den and entry, and tile flooring throughout. The air-conditioned 3-car (extended by 4 ft) garage offers ample storage with custom shelving and a built-in workbench. Outdoors, the heated pool and spa are powered by both gas and solar, a smart, energy-efficient combination. The expansive outdoor kitchen, hurricane screens for added protection, and generous deck space create an ideal setting for sunset views. Other exterior features include lush landscaping with low-voltage lighting, an extra-wide driveway (recently sealed), a custom designed screened-in entryway, and panoramic wide lake views. 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.

6839 Winding Cypress DR, Naples
$1,255,000
3 Beds ⋅ 3 Baths ⋅ 225001834 MLS
Discover luxury living in this breathtaking Pinnacle estate home, situated on one of the most coveted lakefront sites in the south Naples resort community of Winding Cypress. Step inside to an open and spacious floor plan, enhanced by soaring tray ceilings, architecturally stunning alcoves and graceful arches. The home’s designer kitchen serves as the centerpiece, featuring every upgrade possible — soft-close cabinetry, quartz countertops, a fully vented natural gas range and hood and an all-premium KitchenAid appliance package with pull-outs in all lower cabinets. Adjacent is a large pantry complete with a water filter system for added convenience. The primary suite is a private oasis with towering ceilings and full walk-in shower and massive walk-in closet, while guest quarters include an expansive bay window en suite, ensuring comfort and privacy for family and friends. Additional living spaces include a versatile den or hobby room with upgraded French glass doors and foyer layout. Outdoor living is equally impressive. Relax by the saltwater pool and spa while enjoying serene wide-open lake views. Host gatherings with ease, thanks to a fully equipped outdoor kitchen featuring an integrated hood, all set within an expansive lanai with an upgraded oversized pocket slider door. The screened front porch, extended paver paths and custom landscaping further enhance the home’s curb appeal. Practical features include a 4-foot garage extension with custom flooring for three cars, all-impact glass windows, Storm Smart Kevlar shutters and energy-efficient LED lighting throughout. Additional upgrades include raised tray with crown-trimmed ceilings, a heated fireplace with customizable colors and custom state-of-the-art lighting systems that add a touch of sophistication to every room. Located in the resort-style community of Winding Cypress, residents enjoy exclusive access to a wealth of amenities, including a restaurant and bar, state-of-the-art fitness center, resort-style and lap pools, a spa and sports facilities for bocce, pickleball and tennis. The community also boasts a fire pit, bird-watching overlooks, a nature boardwalk and a picnic pavilion. Perfectly positioned between downtown Naples and Marco Island, this home offers the ultimate in luxurious Florida living. From its high-end finishes to its extraordinary location, it’s a property that truly has it all.

7675 Winding Cypress DR, Naples
$1,200,000
3 Beds ⋅ 3 Baths ⋅ 223094938 MLS
Located in the highly sought after and amenity rich community of Winding Cypress, this 3 Bedroom + Den, 3 Bath Summerwood boasts a hard to find spacious loft that adds an additional 900+ sq ft of living area. The meticulously maintained home has numerous upgrades that include an extended finished garage with utility sink and space for a golf cart, upgraded flooring, cabinetry, countertops and appliances, extended kitchen island, crown molding, built in speaker system, outdoor kitchen and much, much more. The beautifully appointed lanai is a haven with a covered living area next to the heated pool and spa with gorgeous views of the preserve. Residents enjoy access to an exceptional Amenity Center complete with a state-of-the-art fitness center, resort style pool and spa, restaurant, bocce ball, tennis and pickleball courts, and full time activity director. It is a pet friendly neighborhood with 2 off-leash dog runs. This home is conveniently located between Marco Island and downtown Naples and is in the perfect location to enjoy all that Southwest Florida has to offer. Why wait for a new home when you can make this yours now!

7565 Blackberry DR, Naples
$1,200,000
3 Beds ⋅ 3 Baths ⋅ 223078079 MLS
Beautifully appointed TURNKEY FURNISHED 3 bedroom plus den, 3 full bath, single family pool home in sought after Winding Cypress. The home is finished with meticulously crafted upgrades including luxury designer furnishings and fixtures throughout. Chef's kitchen features quartz counters, Kitchen Aid SS appliance package, natural gas, large island & breakfast room. The extended gathering room leads to the covered lanai with summer kitchen, bar and pool/spa with water features. Zero corner sliding glass doors seamlessly integrate the living areas, creating an inviting atmosphere for relaxation & entertainment. Amenity rich Winding Cypress features a resort style pool, restaurant/bar, fire pit, fitness center, out door yoga deck, pickle-ball, tennis, bocce ball, community garden, dog park, and a nature trail boardwalk.

6695 Pennyroyal DR, Naples
$1,175,000
3 Beds ⋅ 3 Baths ⋅ 225046502 MLS
EXCEPIONAL in design and setting, this Pinnacle model commands southwest-facing LAKE AND PRESERVE VIEWS from one of the most private parcels within Winding Cypress. The residence is enhanced by an extended, Climate-Controlled 3 CAR GARAGE with a high-performance Polymer finish—offering utility and Esthetic. Interior features include 12’ ceilings, Tray Ceilings, tile flooring throughout, Plantation Shutters, and custom millwork. The open-concept floor plan includes a great room with Electric Sliding Doors leading to the lanai. The kitchen is equipped with Quartz countertops, a large island with built-in wine cooler, KitchenAid and Whirlpool appliances, and a natural gas cooktop. The primary suite includes custom closets and an en-suite bath. The home is equipped with a whole-house Generac Generator, whole-house Water Purification with Reverse Osmosis, and a Built-in Surround sound system in the great room, primary bedroom, and lanai. A full home security system is also installed. Outdoor living space features an extended lanai with a custom Aragon Pool and Spa and an Upgraded Outdoor Kitchen great for Entertaining... Winding Cypress amenities include a clubhouse, fitness center, resort-style pool, tennis courts, pickleball, bocce, dog park, and nature trails.

7597 BLACKBERRY DR, Naples
$1,175,000
3 Beds ⋅ 3 Baths ⋅ 224048727 MLS
Enjoy stunning peaceful views of the long lake and natural preserve from your spacious screened-in lanai with private pool and spa. This beautiful Pinnacle model home offers 3 bedrooms plus den/office, 3 full bathrooms and 3-car garage. Freshly painted inside and out and featuring luxury upgrades throughout, including Zero Corner sliders to lanai, wood-look tile in living areas and plush carpet in the bedrooms, plantation shutters, custom light fixtures, impact resistant windows & doors, natural gas (cooktop, pool, spa, water heater, full house generator) and more! The stunning chef’s kitchen includes upgraded stainless-steel appliances, center island with extra cabinet space, tile backsplash and crisp white cabinets. Enjoy your private backyard with brick pool deck, a large sitting area that has been pre plumbed for outdoor kitchen, heated pool and spa, and tranquil views. The large laundry room was completely built out with cabinets and utility sink. Located in the beautiful gated community of Winding Cypress with world-class amenities. Featuring an on-site restaurant, the Shady Palm, a resort-style pool, tennis, pickleball & bocce courts, a dog park, well-appointed fitness center, internet café and an array of social events. Centrally located and just a short drive to Naples pristine beaches, shops and dining.

7628 Winding Cypress DR, Naples
$1,150,000
3 Beds ⋅ 3.5 Baths ⋅ 225083620 MLS
This home is an amazing value for Winding Cypress!! Once you compare, you'll agree. The Stonewater model is the largest one floor living within The Community. The sought after "open area concept" footprint boasts 3 expansive bedrooms including a most impressive owner's suite, 3 full baths PLUS and additional POOL BATH , a large den-flex room with glass French doors, desirable 3 car garage with additional storage racks overhead. Upgrades include an executive waterfront and private preserve view lot, pool with integral spa.

7716 Winding Cypress DR, Naples
$1,150,000
3 Beds ⋅ 2 Baths ⋅ 224008485 MLS
Ideally located equidistant between Downtown Naples and Marco Island, Winding Cypress coexists with the natural flora and fauna of Southwest Florida. Enjoy bird songs along with deer and wild turkey sightings while walking or biking through the community. Get to know your neighbors while basking in the sun at the resort style community pool complete with gorgeous waterfall and cabana beach area or grabbing a bite to eat at the Shady Palm Cafe. There's never a dull moment with non-stop neighborhood activities and groups. And if tennis, pickleball, or bocce ball are your sport, we have you covered. Call this 3 bedroom plus a den, 2 bath, 2 car garage Summerwood model residence your home and you can enjoy all Winding Cypress has to offer. On quiet days relax on the ample lakefront lanai and swim or soak in the gas heated pool and spa. Delight in trying out new recipes in the well appointed kitchen with granite countertops, stainless steel appliances, and gas stove. With the ADT home security system and impact glass doors and windows this house will be your sanctuary.

7615 Winding Cypress DR, Naples
$1,145,000
3 Beds ⋅ 3 Baths ⋅ 224000268 MLS
Meticulously maintained three-bedroom plus den, three-bathroom residence in Winding Cypress with breathtaking lake views. You’ll be greeted by an open layout bathed in natural light from a corner pocketing impact glass slider. This furnished home showcases new furniture and TVs, finished with 9’ ceilings, 8’ doors, pristine tile floors, closet built-ins, and plantation shutters throughout. The gourmet kitchen features KitchenAid appliances with gas cooking, pullout drawer cabinets, designer backsplash, pantry, and a large center island. Each bedroom boasts an en-suite bathroom. Outside, you’ll find a WiFi-controlled heated pool and spa under a screened lanai with a stunning backdrop of the lake. Additional features include Vitex smart home, StormSmart electric shutters, 22kW whole home generator, water filtration system, extended driveway, and a two-car garage with AC, epoxy floor, and overhead storage. Winding Cypress residents have access to a clubhouse with a social room, library, fitness center, resort-style pool and spa, outdoor bar and grill, tennis, pickleball, bocce, dog park, and a full social calendar. Just 15 minutes to downtown Naples and Marco Island. CDD paid in full.

6818 Greenbriar CT, Naples
$1,120,000
4 Beds ⋅ 3 Baths ⋅ 224036182 MLS
Gorgeously appointed turnkey furnished 2 story Summerwood for sale featuring 4 bedrooms, 3 bathrooms, den, loft, extended 2 car garage, pool & spa! This home has it all when it comes to upgrades, from the zero corner sliders, built in appliances, plantation shutters, in ceiling Sonos speakers, crown molding, storm smart shutters all around, 2 separate living rooms with the loft and so much more. The outdoor oasis features an extended covered lanai, outdoor kitchen, mounted tv, pool and spa overlooking a gorgeous preserve for the utmost privacy! Winding Cypress has amenities galore...Enjoy dining at Shady Palm, the onsite restaurant, play pickleball, bocce, tennis, workout in the state of the art fitness center or lounge by the resort style pool, garden at the community garden, or take fido to the dog park! Winding Cypress is pet friendly, allows rentals, has low fees and is centrally located between Marco Island, 5th Ave, & I75 making it an ideal location!

7493 Winding Cypress DR, Naples
$1,100,000
3 Beds ⋅ 3 Baths ⋅ 225038123 MLS
Introducing a luxury estate with landscaped privacy corner lot home in Winding Cypress with pool and spa. Step into elegance with this stunning Pinnacle model estate home, set in the prestigious, gated community of Winding Cypress. This home stands out with its soaring raised tray ceilings, rare privacy and spacious yard, impact glass for peace of mind, and an expansive open layout filled with natural light and outstanding upgrades. Designed for those who love to entertain, the chef-inspired gourmet kitchen features top-tier finishes, premium appliances, and a spacious expanded island, the ideal gathering space for family and friends. With three bedrooms, three baths, a versatile den and an upgraded oversized three-car garage, this home offers flexibility and space to suit your lifestyle. Outside, a private backyard oasis awaits, complete with lush landscaping, a serene water view and a sprawling grassy yard, a rare find in this community. Take a refreshing dip in your sparkling pool and spa, designed for ultimate relaxation in a peaceful setting. Beyond your doorstep, Winding Cypress offers resort-style living like no other. The nearly 18,000-square-foot clubhouse boasts a zero-entry infinity pool with a lap section, a poolside restaurant, beach cabanas and even a sandy beach. Stay active with numerous pickleball courts, clay tennis courts, bocce, an outdoor yoga movement studio, and a vibrant community hall managed by a full-time activity director. Winding Cypress is a resort gated community at the midpoint between Marco Island and downtown Naples, and this home delivers the ultimate combination of luxury, convenience and an unmatched lifestyle. Don’t miss your chance to own one of the desirable and private estate homes in Winding Cypress of Naples.

7520 Blackberry DR, 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.