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.

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!

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.

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

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.