Winding Cypress Houses For Sale

Opportunity awaits – lowest price available! Welcome to the largest villa model in winding cypress, featuring a rare private front entrance and expanded foyer that sets the tone for this thoughtfully designed home. This spacious 2-bedrooms and massive den offers an open yet defined living concept with abundant natural light and seamless indoor-outdoor flow. Enjoy a long list of builder upgrades including granite countertops, high-end porcelain tile flooring, a glass-tiled backsplash, premium cabinetry and crown molding throughout. Step outside to your expansive private yard and lanai offering plenty of space to add a pool or design your dream sundeck. Winding cypress is one of naples’ most sought-after resort-style communities spanning over 800 acres of pristine preserve and ideally located between marco island and downtown naples’ 5th avenue. Residents enjoy exceptional amenities including a dog park, community garden and the stunning 18, 000 square foot clubhouse featuring a resort-style pool with sand cabanas, on-site restaurant and bar, pickleball, bocce and clay tennis courts, yoga deck, nature trails, state-of-the-art fitness center, fire pits, social lounges and a full-time professional activities director creating a vibrant lifestyle where every day feels like a vacation.

This 2 story mystique model, located in the desireable community of winding cypress, absolutely has to be seen to appreciate all that it offers. Instead of using ai to draft a lofty, fluffy, low information description of this home, we are just going to just list a few of the features and upgrades of this 3-year-new beauty! Whole house generator, heated saltwater pool w/spa & water feature, hurricane impact windows & doors, electric lanai sunshades, extended 3 car garage w/mini split ac, insulated overhead door, epoxy floors & additional built-in/under stairs cubby storage, upgraded 2-tone kitchen cabinets w/under cabinet lighting, quartz counters, black stainless appliance package, outdoor summer kitchen with granite/leather top counter, 2 hvac units w/downstairs & upstairs zones, amazing glass wall enclosed flex room, upgraded laundry center w/built-in cabinets/counters & 2nd refrigerator, huge 2nd floor area w/large bedroom & full bath, murphy bed, 2nd floor flex space for theater/media room & additional den/office, plank tile floor throughout downstairs, all upgraded faucets/fixtures/lighting/hardware, in-floor outlets, tray ceiling, smart home cat-6 wired w/monitored alarm system, & all this on a dead end cul-de-sac. Winding cypress is noted for it's incredible high value amenities that include a private, resident's only, full-service restaurant and bar, las vegas styled resort pool & spa, pickelball, tennis & bocce courts, an amazing fitness center, nature trail/boardwalk, community garden, a dog park, all surrounded by 1250 total community acres that includes 800+ acres of preserve, green space & lakes. You are just 15 minutes to downtown olde naples & 10 minutes to marco island & i75. This home, and the winding cypress community are very special!

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.

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.

Discover effortless luxury in this lovely villa—your private oasis in a premier gated naples community, winding cypress. This inviting 2-bedroom + den, 2-bath home delivers exceptional comfort and versatility with a bright, open layout designed for effortless living and entertaining. Step into the expansive great room with high ceilings, creating an open, airy vibe—perfect for gathering with friends or unwinding after a day out in naples. The chef's kitchen impresses with premium quartz countertops, solid wood soft-close cabinets, and natural gas cooking. High-traffic porcelain tile flooring flows seamlessly throughout the entire villa, paired with smooth-finish walls for a clean, modern, low-maintenance aesthetic. The flexible den, enclosed by beautiful glass panel doors, adapts effortlessly as a home office or third bedroom. Both bedrooms feature generous walk-in closets, and the bathrooms showcase floor-to-ceiling porcelain tile, glass showers, and spa-like sophistication. The master bath elevates your routine with a dramatic full-wall custom mirror and elegant drop-down designer lighting. Outside, this premium lot offers generous spacing between villas and captivating views over the community's second-largest lake—where serene water vistas create an unparalleled sense of tranquility and timeless appeal. The west-facing orientation captures breathtaking sunsets reflecting off the shimmering waters, while the south-facing exposure floods the interior with natural light. Plenty of space awaits an extended lanai or private pool, all enhanced by the soothing backdrop of the lake. Built for peace of mind: impact windows and doors boost energy efficiency, reduce noise, and lower insurance premiums—no flood insurance required in fema zone x. Appliances, a/c, and water heater have performed flawlessly since new. Fiber optic connectivity ensures ultra-fast internet and seamless 4k streaming. Natural gas powers cooking, drying, hot water, and preps for a whole-home generator. Nestled in gated winding cypress—praised as naples' best lifestyle value with remarkably low hoa fees that cover comprehensive maintenance (lawn care, irrigation, community upkeep) plus full access to extensive high-end amenities—you'll embrace the pet-friendly lifestyle with two dedicated dog parks, miles of scenic walking/biking trails across 800+ acres of preserved natural land, and a vibrant social calendar with events curated by the on-site activities director. Resort-style perks include the on-site shady palm café for casual dining and drinks, state-of-the-art fitness center with movement/yoga room, sparkling resort pool and spa, lighted tennis and pickleball courts, bocce courts, community garden, fire pit, and more—all accessible by foot, bike, or golf cart. Conveniently located between downtown naples and marco island, you're minutes from pristine beaches, upscale shopping, and fine dining. Paradise is calling.

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!

Nestled within the gated, amenity-rich community of winding cypress, this thoughtfully designed turnkey furnished two-bedroom plus den, two-bath residence offers an exceptional blend of comfort, quality, and relaxed florida living. The open floor plan is enhanced by wood flooring throughout the main living areas, along with crown molding, and a distinctive coffered ceiling in the living and dining area, creating a refined yet inviting atmosphere. The kitchen is both elegant and functional, featuring 42" white cabinetry, granite countertops, tile backsplash, undercabinet lighting, and stainless-steel appliances—ideal for everyday living and entertaining alike. A flexible den with french doors provides the option for a private home office, media room, or additional guest space. Seamless indoor-outdoor living is achieved through the expansive custom lanai, designed for entertaining with an outdoor kitchen complete with gas grill, refrigerator, and sink, an above-ground hotsprings hot tub with beautiful outdoor furnishings including a dining table for six, over-sized parasol umbrellas that provide shade, and picture-frame lanai screens that showcase peaceful preserve surroundings. Additional highlights include a whole-house gas generator, two-car garage, and plantation shutters. Winding cypress is a natural gas community thoughtfully designed around preserved natural beauty and an active, social lifestyle. At its heart is an impressive clubhouse with a heated resort-style pool and spa, poolside dining at the shady palm, state-of-the-art fitness center, library, and community gathering rooms. Other amenities include pickleball and tennis courts, bocce courts, dog parks, a community garden, and scenic walking and nature trails. Known for its welcoming atmosphere and beautifully maintained grounds, winding cypress offers a true sense of community while remaining conveniently close to everything naples has to offer. A six-passenger well-maintained golf cart is included for effortless access throughout the neighborhood.

Discover your dream home in the prestigious winding cypress community! This newly constructed, pet-friendly residence boasts 3 spacious bedrooms plus a versatile den, perfect for guests or a home office. Designed for seamless entertaining, the open-concept floor plan flows effortlessly, with zero-corner sliders merging the indoor living area with a stylish outdoor kitchen and bar—ideal for hosting family and friends. The living room and kitchen showcase beautiful tile flooring, adding elegance and durability to these high-traffic spaces. As you enter through the gated winding cypress entrance, you’re greeted by lush, resort-style grounds that instantly evoke a vacation vibe. Enjoy unparalleled amenities, including a resort-style pool, restaurant/bar, fire pit, state-of-the-art fitness center, outdoor yoga deck, pickleball, tennis, bocce ball, community garden, dog park, and a serene nature trail boardwalk winding through protected preserves. Perfectly situated between marco island and fifth avenue south, this home offers unmatched convenience, just minutes from pristine sandy beaches, world-class shopping, dining, and entertainment. Don’t miss the opportunity to own this exquisite retreat in one of naples’ most sought-after communities!

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.

Welcome to this beautifully designed residence located within one of naples’ most desirable gated communities. The open-concept floor plan is enhanced by volume and tray ceilings, crown molding, plantation shutters throughout, and an extended driveway, adding both elegance and curb appeal. The spacious kitchen features granite countertops, a gas cooktop, wall oven, and ample cabinetry—making it both functional and inviting for everyday living and entertaining. Hurricane-impact doors and windows, along with electric hurricane screens on the lanai, provide peace of mind while framing tranquil lake views. Step outside to the expansive covered lanai with a summer kitchen, ideal for outdoor dining, entertaining, or enjoying a quiet morning coffee. While perfectly suited for those who prefer low-maintenance living without a pool, the home is also pool-ready should you wish to add one in the future. Tile flooring throughout enhances the home’s clean, modern aesthetic. The primary suite serves as a private retreat, offering dual sinks, a soaking tub, a separate walk-in shower, and generous walk-in closets. A thoughtfully designed laundry room with built-in cabinetry and a sink adds everyday convenience. Residents enjoy access to outstanding community amenities including bocce, tennis, pickleball, a resort-style pool, and the popular on-site community restaurant, shady palm, all just a short walk from the home. Ideally located minutes from world-class shopping, dining, and naples’ renowned beaches, this property truly delivers the best of naples living.

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.

Rare to find, this light-filled 2-story stonewater model offering 4 bedrooms, den and 4.5 baths on a pie shaped waterfront lot in the highly desirable gated community of winding cypress in naples. This home has been upgraded to include all available options totaling over $650, 000 including 2nd floor loft, hurricane windows and doors, upgraded finishes throughout including smooth drywall, seamless porcelain floors, plantation shutters, california closets, lanai with outdoor gas grill, pool bath, in house water-purifying system, storm smart shutters, screened in saltwater lap pool and extended finished 3 car garage. The open-concept design features a spacious great room where the living, dining, kitchen and den/office areas flow together effortlessly. The gourmet kitchen is a true centerpiece with top-of-the-line appliances, ample cabinetry, and generous workspace and pantry to satisfy any home cook or entertainer. A comfortable primary suite on the main level and two flexible guest suites provide excellent privacy for owners and visitors alike. Upstairs loft offers flexible space for living, office, or hobbies, and includes a beverage center plus a fourth bedroom and bath. The expansive screened lanai with peaceful lake view creates an ideal setting for year-round indoor-outdoor living and entertaining. Located in one of naples’ most sought-after resort-style communities, residents of winding cypress enjoy a clubhouse, restaurant, resort pool, fitness center, tennis, pickle ball, bocce, dog park, and miles of walking trails. Just a short drive to beaches, boating, dining, and shopping, this home is perfect for full-time living or a luxurious seasonal retreat.

Welcome to this stunning tangerly oak model home, thoughtfully designed with space, style, and florida living in mind. This expansive 4-bedroom residence with a generous loft offers a flexible floor plan ideal for both everyday living and hosting guests, all enhanced by beautiful designer upgrades throughout. Step outside to an exceptional outdoor living space featuring a large covered lanai, resort-style pool and spa, and a fully equipped outdoor kitchen, perfectly positioned to capture long, wide lake views that create a peaceful and picturesque backdrop. Inside, the home is filled with light and refined finishes, showcasing the elevated craftsmanship and attention to detail that make the tangerly oak so desirable. Every space feels open, comfortable, and inviting. The community offers an impressive array of amenities, including a clubhouse, resort-style pool, fitness center, tennis, pickleball, bocce courts, and a dog park. Ideally located in a highly convenient area with easy access to restaurants and shopping, and just about 15 minutes from downtown naples, this home delivers both luxury and lifestyle in one exceptional package.

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.

This beautifully designed and impeccably maintained home offers the perfect blend of elegance and comfortable naples living. Featuring the highly sought-after summerwood floor plan with a spacious great room extension, the open layout creates an impressive, light-filled space perfect for entertaining guests or relaxing with family after a day exploring beautiful naples, fl. The gourmet kitchen shines with upgraded stainless appliances, elegant quartz countertops, an oversized island perfect for casual dining and hosting, and a generous walk-in pantry. This home features a generous primary master bedroom plus three versatile guest bedrooms. Any of the three guest bedrooms can easily function as a bedroom, home office, den, or media room to suit your lifestyle. The fourth bedroom is a major advantage for leasing the home, providing extra flexibility that can help attract tenants, support higher rental rates, and appeal to a wider range of renters who need extra space for guests, etc. It also functions well as internal storage space or could be used to expand the master closet. Interior finishes include high-grade porcelain tile flooring throughout, a practical laundry/utility room with storage and sink. And natural gas service is used for cooking, water heating, and efficient clothes drying. Step outside to your private resort-style lanai. This expansive space features custom pavers, a built-in outdoor kitchen, and plenty of room for outdoor gatherings or quiet relaxation. Enjoy a swim in the heated pool and spa, soak up the southern florida sunshine, or simply take in the spectacular eastern water views framed by a large portrait “no-see” lanai screen. These serene vistas consistently draw “wows” from everyone who visits. For added peace of mind and year-round comfort, the home includes impact-resistant hurricane doors and windows throughout. These premium features provide excellent storm protection, improve energy efficiency, and help reduce insurance premiums while eliminating the hassle of traditional shutters. Elegant bahama shutters offer additional beauty and protection. The elevated lot is also not in a mandatory flood insurance zone, adding to the worry-free lifestyle. Nestled in the prestigious gated community of winding cypress, residents enjoy an onsite restaurant, modern fitness center, community pool, tennis courts, pickleball courts, and a full calendar of social events—all just a walk, bike, or golf cart ride away. Conveniently located between downtown naples and marco island, you’re minutes from pristine beaches, upscale shopping, and fine dining. Offered fully furnished and move-in ready, this exceptional home truly checks every box: impressive great room. (check.) gourmet kitchen & flexible living spaces. (check.) resort-style outdoor living with water views. (check.) outstanding community & prime location. (check.) ready for the naples lifestyle you’ve dreamed of? This beautiful home delivers it all.

Rare opportunity in winding cypress this marten ray model home, turnkey home fully upgraded, move-in ready home 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. Furnishings are available, offering a turnkey opportunity for those seeking a seamless seasonal or full-time transition, or immediate move-in experience.