Winding Cypress Houses For Sale

Spacious & immaculate accurately describe this outstanding retreat in the sought-after community of winding cypress. This rare, two-story mystique footprint boasts 4 bedrooms, 3 full baths, a large den/office, and over 3160 square feet of adjusted living space, 3036 square feet under air. This residence was one of the last built in the community, 3 years new, and shows like a model home. Located on a very private lot on a cul-de-sac, this salt water pool home with private spa is meticulously one-owner maintained, beautifully decorated, and loaded with builder upgrades. For peace of mind, the owners added a whole house generator as well. The expansive, upstairs addition includes a huge private bedroom, a full bathroom, and an incredible flex area that can accommodate a 5th bedroom, cinema room, office, or however this extra space can benefit your living wants and needs. Winding cypress is an amenity rich and active community with on-site management and a full-time activities director. It's perfectly situated just 15 minutes away from the restaurants, shoppes, and beaches of downtown olde naples, and only 10 minutes to all the entertainment of marco island.

Welcome to your beautiful summerwood floor plan home ... Enjoy florida living in this impeccably maintained stunning home featuring 3 bedrooms, den/sitting room, 2 full bathrooms. Enjoy a spacious living room which is open to the gourmet kitchen featuring a natural gas range, a large pantry and an island, with ample prep space, for gathering with friends and family. There is tile flooring throughout! Step outside to the a very sought after outdoor living life with the extended lanai!! On the lanai is a built in kitchen for all of your entertaining needs! The home has a full house generator & impact resistence windows. The window and sliding door to the lanai are storm protected with a storm smart screen!! The primary suite is a private retreat with a walk-in closet, dual-sink vanity, and a large step in with glass shower. The dining room offers tranquil views of the expansive lanai. A 2 car garage has a huge extra space for storage. The brick-paver driveway provides ample parking. Set on a beautiful homesite, this residence blends privacy with proximity to the best of south naples. The subdivision hosts an amazing club, with all residents enjoying access to the community’s restaurant, resort style pool, exercise room/gym, tennis, bocce, and pickleball courts. Experience unparalleled luxury, comfort, and location here, an absolute must-see!

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.

Paradise at your fingertips. This modern three-bedroom plus den residence in the prestigious resort style living gated community of winding cypress, offers a bright, expansive open floor plan, breathtaking lake views, ceramic tile throughout and a gorgeous and functional updated kitchen featuring solid maple shaker cabinetry, premium hardware, and spacious pantry. This residence is also equipped with gas stove, brand new lg studio refrigerator and stove to enjoy a fabulous culinary experience. The magnificent quartz island, ideal to entertain and savor your favor meals is illuminated by one of a kind showstopper custom abalone shell chandelier which mirrors the one in the dining room creating a one of kind ambiance. The large family room flows harmoniously to an inviting bar area to taste your favorite drink. The master bedroom provides high ceilings, custom made cabinetry and serene lake views. Both bathrooms feature aquadome led fog-free mirrored medicine cabinets adding a touch of functionality and elegance. Life al fresco is enjoyed to the fullest in the spectacular extended back patio, with outdoor kitchen and several sitting areas. This enclosed lanai with panoramic premium screens allows for breathtaking unobstructed water and sky views. Also available is an initial electrical connection to install a jacuzzi if desired. Ample storage and full hurricane protection plus generator to provide extra peace of mind. Additional traits are the wakaflex installed on all vents, openings and roof crown for maximum weather protection, the eufy home security system, recently painted inside and out, maytag washer and dryer, culligan reverse osmosis water filter, front entry screened enclosure and driveway expanded to accommodate 3 vehicles. The 2-car garage comes with overhead storage. Winding cypress offers world-class amenities, including a clubhouse, on-site restaurant, fitness center, resort pool, and tennis/pickleball courts. Positioned between the sun-drenched beaches of marco island and upscale dining, shops and galleries of downtown naples, this home offers the ultimate setting for relaxation, comfortable living and sophisticated entertaining.

Discover refined living with this beautifully appointed villa in winding cypress, where luxury and comfort meet in perfect balance. Designed for those who appreciate both elegance and ease, this home offers an unparalleled lifestyle inside and out. Arriving fully furnished and enhanced by the sellers’ two-seater club car golf cart, this property delivers a true move-in ready experience. Every detail has been curated for effortless enjoyment, whether you’re entertaining guests or savoring quiet moments at home. The gas-heated pool invites you to relax in your own private oasis, while the outdoor kitchen transforms casual gatherings into memorable evenings under florida’s open skies. Indoors, the chef’s kitchen makes a bold statement with sleek samsung appliances and striking quartz countertops. A thoughtful list of updates and enhancements reflects the exceptional care invested in this residence, ensuring peace of mind for the next owner. With its combination of sophistication, style, and fully furnished convenience, this villa represents one of the finest offerings in winding cypress.

A must-see opportunity—spacious, stunning views, showpiece home and resort style florida living. A rare opportunity to own a 4 bedroom estate home with breathtaking views in the sought-after community of winding cypress, offering top-tier amenities at surprisingly low hoa fees. This award-winning pinnacle model boasts numerous upgrades and interiors like the builder’s model home and is on one of the most desirable lots in the community. It overlooks serene lake and preserve views both front and back, uninterrupted by other homes. Tucked within a quiet 15-home enclave away from density—yet just steps to pickleball, tennis, fitness center, and on-site restaurant—this home offers a rare combination of peacefulness and convenience. Homes on this special street are rarely available. Virtual showings available on request. Designed to embody the best of florid living, the home is loaded with high value upgrades including full impact windows, a spectacular oversized lanai with multiple entertaining areas, a panoramic picture-frame screen enclosure for dramatic views, zero-corner sliding glass doors for seamless indoor-outdoor occasions and an oversized epoxy floored 3 car garage. The huge outdoor space includes an oversized pool and spa with water features, —perfect for hosting or relaxing while enjoying breathtaking views over the water and preserve. Inside, the beautifully design blends elegance with functionality. The light filled open-concept great room has defined living and dining areas and a showpiece chef’s kitchen featuring a 10-foot quartz island, natural gas cooking, premium cabinetry, high-end appliances, and a walk-in pantry. Rich molding, wainscoting, coastal ceilings, upgraded flooring and other designer finishes elevate the entire home beyond the ordinary. The main-level primary suite provides a private retreat overlooking the pool. This level also has two additional guest bedrooms and a versatile den. Upstairs, a spacious loft of almost 1200 sq ft has a huge additional bedroom, a huge flex area and a full bath ideal for guests, multigenerational living, a media room, fitness space, or home office. Residents of winding cypress enjoy a true resort lifestyle with guard-gated security and full landscaping maintenance included, along with a resort-style pool, clubhouse, on-site restaurant and bar, state-of-the-art fitness center, pickleball, tennis, bocce, a dog park, community garden, scenic boardwalk trails, and a vibrant social calendar—all at amazingly low hoa fees. Ideally located just minutes from marco island, downtown naples, 5th avenue, beaches, boating, golf, shopping, dining, hospitals, and i-75, this home offers the perfect balance of luxury, lifestyle, and location.

On a private corner homesite with breathtaking long lake views, this like-new contemporary residence built in 2022 offers an exceptional blend of style, comfort and modern functionality within the sought-after community of winding cypress. Designed with a great room and split-bedroom floor plan, this three-bedroom plus den, two-bath home with a two-car garage showcases light-filled interiors, neutral paint tones, recessed lighting, crown molding and elegant marble-look tile flooring throughout the main living areas. Move-in ready and thoughtfully upgraded, the home captures the essence of effortless florida living with a refined, modern aesthetic. Crown molding, expansive lake views and zero-corner sliding glass doors enhance the open and airy living room, seamlessly inviting the outdoors in to create an indoor-outdoor experience. Just beyond, the spacious screened lanai offers multiple seating areas, a ceiling fan, and a full outdoor kitchen, all overlooking a large heated pool and spa, perfect for entertaining or relaxing in complete privacy. The adjacent dining area features marble tile flooring, crown molding, an updated hanging light fixture and tranquil water views, ideally positioned off the kitchen for everyday living and hosting. The well-appointed kitchen is a standout, featuring white cabinetry, a tile backsplash, a large island with pendant lighting and a three-seater bar. Premium kitchenaid stainless steel appliances include a gas cooktop with a hood, a wall oven, a microwave, a dishwasher and a french door refrigerator, complemented by upgraded cabinetry and finishes. The den offers a functional workspace with a built-in desk and cabinetry, recessed lighting and a french double-door entry, ideal for working from home. The primary suite is a serene retreat with a tray ceiling, recessed lighting, a designer accent wall and a spacious walk-in closet with custom built-ins. The en-suite bath is thoughtfully designed with a double vanity, an expanded walk-in shower with additional sprayer, linen closet and private water closet. Guest bedrooms are equally inviting, each filled with natural light, including one with plantation shutters and custom moldings. Additional highlights include a widened and recently sealed driveway, impact windows and doors, a whole-house generator, custom wood backing for mounted televisions, upgraded molding throughout and a garage with overhead storage and a mini-split air conditioning system. The laundry room is equipped with a whirlpool front-load washer and dryer, utility sink and overhead cabinetry. Offering privacy as the last home on the street and showcasing extensive designer upgrades throughout, this residence presents a rare opportunity to enjoy luxurious lakefront living in one of naples desirable communities. Resort-style perks include the on-site shady palm café for casual dining and drinks, a state-of-the-art fitness center, a resort pool and spa, tennis, pickleball and bocce courts.

Welcome to newest and last phase of homes built in 2020 in the vibrant well maintained community of winding cypress. Located just off collier and 41 and minutes to 75 , marco island and downtown naples this summer wood model is sure to please with 3 bdrms den and 2 baths with full showers , primary bath with custom mirrors. Custom closet , plantation shutters mini a/c in garage, whole house water purifier, generator, storm screens on lanai , outdoor kitchen , pool and spa. With private views to the preserve , vaulted ceilings, ceiling fans in every room , and oversized neutral tile through out placed on the diagonal . Some furniture can remain with the house . Exlcuded dining light fixture

Welcome to this highly upgraded infinity model, a rare offering in the prestigious winding cypress community of naples. Built by renowned divosta builders, this residence is one of only three infinity models within a community of more than 750 homes, making it an exceptionally unique opportunity. Featuring an extra-wide three-car garage with a dedicated third bay ideal for a golf cart, hobby vehicle, or additional storage, this home has been significantly enhanced with premium upgrades throughout and offers a level of quality rarely found in today's market. Designed for both luxury and everyday comfort, the expansive open-concept floor plan showcases soaring tray ceilings exceeding 11 feet, custom faux painting, extensive crown molding, and elegant designer finishes throughout. The spacious great room seamlessly connects to the gourmet kitchen, highlighted by a six-burner thermador gas range and cooktop, premium liebherr refrigerator, custom cabinetry, and a massive leather-finished quartzite island perfect for entertaining. The seller's extensive investment in upgrades is evident in every detail. Designer window treatments, custom bed coverlets, built-in features, and custom closets throughout create a refined, move-in-ready environment. The completely remodeled primary bath offers a spa-inspired retreat featuring a curbless walk-in shower, floating vanity, premium fixtures, designer tilework, and stunning 48-inch porcelain tile flooring throughout. Outdoor living is equally impressive. The expansive lanai with desirable western exposure captures spectacular naples sunsets and provides ample space for a custom pool, spa, and additional outdoor living areas. Pool plans and contractor quotes are available, making it easy for the next owner to create their ideal backyard oasis. The fully equipped outdoor kitchen provides the perfect setting for entertaining family and friends while enjoying the privacy and tropical surroundings. Additional upgrades include hurricane-impact windows and doors, a dramatic zero-corner sliding glass door, whole-house generator, tankless water heater, kinetico water filtration system, sonos surround sound system, epoxy-coated garage floors, insulated garage doors, built-in garage storage, and a dedicated air-conditioning system for the garage. As one of naples' premier natural gas communities, winding cypress offers an unmatched lifestyle with a residents-only restaurant, resort-style pool and spa, fitness center, pickleball, tennis and bocce courts, and over 800 acres of protected preserve. Ideally located just 10 minutes from marco island's white sand beaches and approximately 15 minutes from olde naples, this exceptional residence combines rarity, luxury, and location in one extraordinary offering. This is more than a home—it's a statement of quality, craftsmanship, and lifestyle. One or more photos have been virtually staged, ai-generated, or rendered.