Winding Cypress Real Estate

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All Sold in Winding Cypress, Naples, FL

$975,000
3 Beds ⋅ 3 Baths ⋅ 225034039 MLS
This home is an amazing value for Winding Cypress!! Once you compare, you'll agree. The Pinnacle model is clearly the most popular floorplan in The Community. The sought after "open area concept" footprint boasts 3 expansive bedrooms including a most impressive owner's suite, 3 full baths, a large den, desirable 3 car garage, and 2496 square feet of indoor living space under air. Builder and owner upgrades include an executive waterfront premium lot, kitchen appliance package, pool with new heater integral spa, quartz counters, upgraded cabinet package, den/office, zero corner sliding glass doors, plank tile flooring, plumbed for a summer kitchen, inviting lead glass front entry door.

7530 Geranium WAY, Naples
$975,000
3 Beds ⋅ 3 Baths ⋅ 224088928 MLS
Nestled within an exclusive gated community and surrounded by a serene nature preserve, this elegant 3-bedroom, 3-bathroom home with a spacious den/office is the epitome of refined Florida living. The open, airy floor plan flows seamlessly, with high ceilings and large windows that capture abundant natural light and offer unobstructed views of the lush preserve behind the home. This home has natural gas, generator, upgraded oversized garage, Sentricon system, central vac system, and many more upgrades. Step into the gourmet kitchen, complete with premium appliances, custom cabinetry, and an expansive island that's perfect for entertaining or family gatherings. Each bedroom is generously sized, featuring high-end finishes and ample storage, while the den/office provides an ideal, private space for working from home or additional relaxation. The master suite is a tranquil retreat with a luxurious en-suite bathroom featuring dual vanities, and a walk-in shower. Outdoors, your private paradise awaits, with a sparkling gas heated salt water pool and spa surrounded by a spacious patio, perfect for sunbathing, al fresco dining, or evening cocktails under the stars. The 3-car garage offers plenty of room for vehicles, storage, and hobbies. Living in this community comes with exceptional amenities that rival a luxury resort. Enjoy an on-site restaurant, a spectacular resort-style pool, tennis courts, pickleball, bocce, and a dog park, all thoughtfully designed to elevate your lifestyle. The well-appointed fitness center, internet café, and an engaging calendar of year-round social events ensure that there's always something to do. Centrally located between the pristine beaches of Marco Island and Naples, this home places you just moments away from world-class shopping, dining, and entertainment, yet offers a peaceful, nature-filled escape in your own backyard. Don't miss the opportunity to make this luxurious haven yours!

7788 Winding Cypress DR, Naples
$965,000
3 Beds ⋅ 3 Baths ⋅ 223050442 MLS
H10980 Enter the brick paved driveway to this gorgeous three bedroom three bath plus den home in the prestigious community of Winding Cypress. This lake view home offers a large living area with Plantation shutters throughout, 90 degree corner sliders to bring the outside in, whole house water filtration and impact windows and sliders, open kitchen with island, stainless Kitchenaide appliances, include a gas stove and plentiful cabinetry with adjacent dining area. The bedrooms are spacious each with their own bath and a large den with built in Murphy bed. The master en-suite offers a large walk in shower and his and her sinks with an expansive walk in closet. Expansive lanai, also with brick pavers and under cover area for dining and lots of sunning spots around the pool and spa with beautiful waterfall feature. Oversized garage. Winding Cypress is conveniently located in South Naples, just a 15 minute ride to Marco Island or 5th Ave and the beaches. Offering a very active lifestyle with miles of walking paths, boardwalk, beautiful clubhouse with fitness, resort style pool, pickleball, tennis and plenty of social gatherings.

6818 Greenbriar CT, Naples
$963,000
3 Beds ⋅ 2 Baths ⋅ 225067825 MLS
Rare opportunity in Winding Cypress this Marten Ray Floor Plan sits on a premium lot with unobstructed lake and protected preserve views. Experience, complete privacy and a resort-style outdoor setting in one of Naples’ most desirable communities. Experience one of the most desirable homes in Winding Cypress, offering a rare combination of premium lot, complete upgrades, and true move-in ready convenience. Perfectly situated on what is believed to be one of the only homes in the community with a full, unobstructed rear exposure, this property showcases sweeping views of a permanent lake and protected state/federal preserve, delivering exceptional privacy with no future development behind you. Designed for effortless Florida living, the home features a resort-style outdoor setting with a heated-saltwater pool, multi-color lighting, in pool and lanai, expansive lanai, dry bar with cabinetry & refrigerator, outdoor TV and audio—ideal for entertaining or relaxing in a private natural setting. Inside, the residence has been extensively upgraded beyond builder-grade, to deliver a “better than new” experience, with no projects or additional investment required. The designer kitchen includes gas cooking, enhanced cabinetry, under-cabinet lighting, and a built-in wine bar with dual-zone cooler. Additional highlights include tile flooring throughout, upgraded lighting, a high-efficiency air conditioning system, custom pantry and primary closet cabinetry, and a fully optimized garage with added storage and functionality. The flexible floor plan offers 2 additional bedrooms for versatile guest accommodations and workspace options, including a dedicated office and an additional guest space, ideal for visiting family, remote work, or multi-purpose use. This home is well suited for buyers seeking quality, privacy, and ease of ownership in one of Naples’ most sought-after communities.

7457 Winding Cypress DR, Naples
$962,500
3 Beds ⋅ 2 Baths ⋅ 226019748 MLS
This impeccable Martin Ray truly has it all. The home features 3 bedrooms + den, 2 bathrooms, a 2-car garage with a 4-foot extension, and a custom pool perfectly positioned on a premier lot surrounded by lake views. Structurally designed for both style and peace of mind, the home offers soaring 11+ foot ceilings, impact windows and doors throughout, a whole-house generator that powers the pool as well, and hurricane screens for added protection. Inside, the upgrades are endless, including crown molding, tray ceilings, under-cabinet lighting, handmade Forge lighting fixtures, custom drop-zone cabinetry, plantation shutters, a California Closet mini bar, and so much more. The outdoor living space is a true showstopper, offering privacy, water views while overlooking the preserve. Added in 2022, the 34-foot custom pool features a flush spa, salt system, auto fill, 4 waterfalls, 2 whisper-quiet high-end pumps, gorgeous wet-edge pebble finish with glass accents, and imported Turkish non-slip marble pool decking. Even the pool cage was thoughtfully upgraded, with vertical support beams filled with concrete for enhanced stability. The garage is equally impressive with epoxy flooring, electric vehicle charging, double whole-house surge protection, and keyless entry. Outside, the home continues to impress with a rare custom 5-car paver driveway, updated timed lighting, extensive landscaping, a paver walkway, and a screened front entry. 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.

7343 Mockingbird CT, Naples
$950,000
4 Beds ⋅ 2 Baths ⋅ 224031113 MLS
This meticulously maintained residence presents a rare opportunity to indulge in modern elegance and comfort. Upon entering through the leaded glass front door, you're greeted by an inviting atmosphere accentuated by the spectacular open floor plan living. The heart of the home lies in its chef-inspired kitchen, you will be delighted with abundant storage, granite counters, gas cooking, while a breakfast bar offers a casual dining option. Whether preparing a gourmet meal or enjoying a quick snack, this kitchen is sure to inspire culinary creativity. A pristine heated saltwater pool offers a refreshing swim from the sun-drenched afternoons. Host gatherings with ease in the full outdoor kitchen, complete with a grill, and ample seating space. Covered sitting areas provide shade and tranquility, ideal for unwinding with a good book or enjoying alfresco dining under the stars.

7592 Winding Cypress DR, Naples
$945,000
4 Beds ⋅ 3 Baths ⋅ 224052264 MLS
Like new, two years old four bedroom, three-bathroom residence in Winding Cypress. House has been totally custom remodeled. This furnished home showcases new furniture and TVs, finished with 9’ ceilings, 8’ doors, pristine tile floors. The gourmet kitchen features high end appliances with gas cooking, pullout drawer cabinets, designer backsplash, pantry, and a large center island. Each bedroom has an in-suite bathroom. Outside, you’ll find a WiFi-controlled heated pool and screened lanai with build- in barbeque grill. Extended driveway, two-car garage , 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.

6801 Greenbriar CT, Naples
$935,000
3 Beds ⋅ 2 Baths ⋅ 224082513 MLS
Live the Vacation Lifestyle Every Day in Winding Cypress Welcome to a home that feels like a never-ending vacation. This stunning Summerwood residence, nestled in the resort-style community of Winding Cypress, is more than a home—it’s a lifestyle. From the moment you step through the dramatic entry hall, you’re greeted by breathtaking lake views that set the tone for tranquility and relaxation. The zero-clearance sliding glass doors seamlessly blend indoor elegance with outdoor splendor, leading to an expansive lanai designed for ultimate leisure and entertainment. Imagine starting your mornings with serene sunrises over the lake, enjoying your coffee on the lanai surrounded by picturesque scenery. The fully equipped bar—complete with a KitchenAid grill, refrigerator, freezer, and ample seating for seven—makes hosting sunset cocktail parties a breeze. Whether you prefer lounging in the shaded comfort or basking in the sun, this home caters to your every mood. Winding Cypress offers an unparalleled array of resort-style amenities: • A tropical pool oasis with cascading waterfalls, a hot tub, and a poolside bar serving refreshing drinks and delicious meals. • Social activities for every interest, from pickleball, tennis, and bocce to art clubs, gardening, and game nights. • Themed parties, live music, and dancing that make every evening unforgettable. When you’re ready to explore beyond the gates, you’re just nine miles from Marco Island’s pristine beaches and downtown Naples’ vibrant dining, shopping, and cultural scenes. From galleries to holiday snowfall in December, there’s always something to enjoy. This home is move-in ready, fully furnished down to the dishes. All that’s left is for you to pack your suitcase and embrace the dream vacation lifestyle—every single day.

7683 Winding Cypress DR, Naples
$925,000
3 Beds ⋅ 2 Baths ⋅ 225023660 MLS
A MOST INCREDIBLE OFFERING MARTIN RAY. THIS HOME HAS IT ALL. HURRICANE IMPACT WINDOWS & SLIDING GLASS DOOR, HURRICANE IMPACT MAIN ENTRANCE DOOR WITH LEADED GLASS, CEILINGS WITH TRAYS, COFFERS, & WIDE MOLDINGS, EXTERIOR LIGHTING PACKAGE, KITCHEN CABINET PACKAGE INCLUDING SOFT CLOSE DOORS, QUARTZ COUNTERTOPS,2 CAR GARAGE WITH UTILITY SINK, EXTENDED DRIVEWAY & MAIN ENTRANCE PAVERS, PAVER SIDEWALKS ON BOTH SIDES TO LANAI, PROFESSIONALLY LANDSCAPED AROUND ENTIRE RESIDENCE, HOME HAS BEEN PROFESSIONALLY DESIGNED & DECORATED.

6854 Greenbriar CT, Naples
$910,000
3 Beds ⋅ 2 Baths ⋅ 226000187 MLS
This Summerwood floorplan is situated on a gorgeous lake and features 3 bedrooms, a den, 2 bathrooms, a gas heated pool and spa, and an extended 2-car garage. The home includes valuable storm-ready features such as a whole-home generator, impact-resistant windows and doors, and electric hurricane screens for added protection. Inside, the home is loaded with upgrades such as a custom built-in bar, TV stand and vanity, custom cabinetry in the primary closet, pantry, and laundry room, crown molding, tray ceiling, and a modern curated accent wall. Upgraded kitchen appliances and abundant storage complete the space. Embrace the Florida lifestyle with the open-concept layout seamlessly connecting indoor and outdoor living spaces. The pool deck features a spacious covered lanai overlooking the lake with a highly desirable southwest exposure, along with an outdoor kitchen and a custom saltwater pool and spa complete with a sun ledge. No detail has been spared in the garage as well, it features a mini split, insulated door, and an extra 4 feet of length, allowing room for tools, bikes and more! 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.

6779 Winding Cypress DR, Naples
$905,000
2 Beds ⋅ 2 Baths ⋅ 226009304 MLS
Experience refined Naples living in this impeccably maintained, fully furnished residence in the prestigious gated community of Winding Cypress. Featuring two bedrooms plus a den, two baths, plus an extended additional den leading to the waterfront pool area, and an extended 2-car garage; this home has been thoughtfully designed and is move-in ready - blending comfort, elegance, and effortless luxury. Inside, tiled wood-plank flooring flows seamlessly throughout, complemented by plantation shutters throughout the home that add both timeless elegance and privacy. The beautifully curated furnishings enhance each space, delivering a polished, designer feel from the moment you enter. The gourmet kitchen serves as the heart of the home, featuring a large center island with seating, a pantry closet, gas stove, and abundant cabinetry. Ideal for both everyday living and entertaining, the kitchen opens to the spacious dining and living areas, allowing for easy gatherings and relaxed conversation. The versatile den provides the perfect setting for a private office, media room, or additional guest accommodations. The primary suite is a luxurious retreat, complete with a spa-inspired bath and a recently customized walk-in closet designed for optimal organization and style. The guest bedroom and bath provide comfort and privacy for visitors. Step outside to your private oasis—a covered lanai with comfortable seating that transitions seamlessly to the screened-in pool and spa area. The expansive pavered deck surrounds a sparkling pool and spa accented by a tranquil waterfall feature, all overlooking a peaceful lake view. Storm Smart lanai shutters offer added protection and convenience, while upgraded landscaping and lanai lighting create a stunning ambiance day and night. The beautifully landscaped lawn enhances the serene setting, delivering exceptional curb appeal and a tranquil outdoor backdrop. An underground gas generator provides an additional layer of security and peace of mind, ensuring uninterrupted comfort year-round. Winding Cypress elevates the lifestyle even further with an impressive array of resort-style amenities. Residents enjoy a stunning clubhouse, state-of-the-art fitness center, resort-style pool and spa, tennis and pickleball courts, bocce, an on-site restaurant, community garden, dog park, and miles of scenic walking and biking trails. A vibrant social calendar and beautifully maintained grounds make every day feel like a private resort experience. Ideally situated just minutes from the world-class dining, upscale shopping, art galleries, and white-sand beaches of downtown Naples, this home offers the perfect combination of luxury, location, and lifestyle. An exceptional opportunity to own a furnished, lakefront retreat in one of Naples’ most sought-after communities.

7545 Geranium WAY, Naples
$900,000
4 Beds ⋅ 2 Baths ⋅ 226023986 MLS
This Summerwood floorplan is being offered turnkey furnished and features 4 bedrooms, 2 bathrooms, a gas heated pool, and an extended 2-car garage. The home includes valuable storm-ready features such as a whole-home generator and electric hurricane screens on the lanai. Inside, the home is loaded with upgrades such as a crown molding, plantation shutters, California Closets cabinetry in the laundry room, pantry and primary closet. Embrace the Florida lifestyle with the open-concept layout seamlessly connecting indoor and outdoor living spaces. The pool deck features a spacious covered lanai and an expansive outdoor kitchen. No detail has been spared in the garage as well, it features a mini split, cabinets, and an extra 4 feet of length, allowing room for tools, bikes and more! 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.

7473 Winding Cypress 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.