Winding Cypress

List Price:  $1,099,000

Wow! This beautifully designed and meticulously maintained home checks all the right boxes. Featuring the highly desirable Summerwood floor plan with Great Room extension, it is perfect for entertaining or simply relaxing at home after a nice day out in beautiful Naples, FL. The kitchen features upgraded appliances, quartz countertops, an oversized island and walk-in…

List Price:  $3,800

Attached villa in the highly sought after community of Winding Cypress. This home boasts 2 bedrooms plus a en which can be used as a 3rd bedroom, 2 full bathrooms and a 2 car garage. Well maintained and fully furnished including household items (kitchen, linens, etc.) The community is situated off of Collier…

List Price:  $1,294,000

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…

List Price:  $575,000

The Finest in Resort Style Living! You do not want to miss this opportunity to own a find like this in the Community of Winding Cypress. This Beautifully updated 2+Den/2 Bath Gem has 9' 4" ceilings with a two car garage is move in ready and it has everything you need to call this sought…

List Price:  $6,000

Wow! This beautifully designed and meticulously maintained home in the highly desirable Naples community of Winding Cypress is now available to rent! And it checks all the right boxes. It's turnkey and ready for occupancy. And the layout, as well as lanai make it perfect for entertaining or simply relaxing at home after a nice…

List Price:  $950,000

This move-in ready Summerville Extended model by Pulte offers the perfect blend of privacy, elegance, and resort-style living in one of Naples' most desirable communities. Perfectly situated on an oversized pie-shaped lot with no homes behind you, this 3-bedroom, 2-bathroom home delivers serene lake views and a true sense of tranquility. Step into the gourmet kitchen,…

List Price:  $1,100,000

Welcome to your new home in Winding Cypress, a vibrant community in the heart of Southeast Naples. Surrounded by 800 acres of lush preserves and 80 acres of peaceful lakes, this is the ideal setting to enjoy a serene, nature-filled lifestyle. Yet, with Downtown Naples and the iconic 5th Avenue—one of America’s most beautiful streets—just…

List Price:  $1,299,000

Introducing a luxury estate site 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…

List Price:  $537,000

Tucked Away Treasure in Winding Cypress- Step into a slice of serenity with this charming attached villa, nestled in one of the most peaceful corners of Naples. Unlike the typical coastal designs so common in the area, this home offers a more rustic warmth—perfect for those who appreciate natural textures, cozy finishes, and a…

List Price:  $7,000

Home away from home! Enjoy a newly built, barely lived in home, in one of the most amenity rich communities in all of Naples. Featuring 2 Bedrooms + Den, 2 Full Bathrooms, screened-in lanai, 10' foot ceilings, and a large open floor plan, this property has everything one needs in order to ensure a relaxing,…

List Price:  $949,000

Located in the highly sought-after community of Winding Cypress, this beautifully updated 3-bedroom, 2-bath home offers a perfect blend of luxury, comfort, and breathtaking lake views. Surrounded by 800 acres of natural preserve and 80 acres of serene lakes, this home provides a tranquil lifestyle immersed in nature, with access to all the incredible amenities…

List Price:  $549,000

Welcome to your dream home in the heart of one of Naples' most sought-after communities! This stunning FRONT entrance Cressida villa offers the perfect blend of comfort, style, and convenience. Featuring two spacious bedrooms, two full baths, and a versatile den/flex room that can be used as an in-home office or guest area, this home…

List Price:  $849,000

Stunning Abbeyville home in Winding Cypress is move-in ready! This immaculate residence is a must-see, featuring a fresh neutral palette, offering a spacious open split-bedroom floor plan with 2 bedrooms, a flex/den & 2 full bathrooms. Entertainment is elevated with flat-screen TVs mounted in both bedrooms & living area. Soaring ceilings enhanced by elegant molding,…

List Price:  $1,049,000

Imagine waking up each morning in your dream home,Nestled in one of Naples' most sought-after gated communities. As you walk into this beautiful home you are greeted with the open-concept floor plan that welcomes you, with the warmth of granite countertops and the added upgrades of a gas stove and wall oven in your chef-inspired…

List Price:  $585,000

Sophisticated Villa Living in Winding Cypress – Priced to Sell/Fully Furnished. An extraordinary opportunity awaits in the highly sought-after Winding Cypress community—this impeccably upgraded 3-bedroom, 2-bathroom villa is set on the largest homesite in the neighborhood, offering both privacy and an expansive outdoor retreat. Thoughtfully enhanced with luxury upgrades and high-end finishes, this residence is…

List Price:  $5,950

Gorgeous kitchen with an oversized island is open to the bright and airy great room as well as your very own private pool and spa! Sliding doors fold all the way back allowing for fabulous inside/outside entertaining. The chef's dream kitchen offers GAS cooking, a huge pantry and counter island seating. Your private pool and…

List Price:  $5,900

Built in 2021, this spacious floor plan offers 3 bedrooms, 3 full baths plus a den. The primary suite has a luxurious bath with double sinks, a huge custom walk-in shower and an enormous walk-in closet! There are wonderful corner pocket doors that open to a tranquil lanai featuring a private below ground, heated pool…

List Price:  $549,000

This beautiful Winding Cypress Serenity Villa home offers 1,554 sq. ft. of comfort with 2 bedroom plus den, 2 bathrooms, screened lanai, and a 2-car garage. It features multiple quality upgrades including stainless appliances with both gas and electric connectivity for the stove, 22" porcelain tile on the diagonal throughout, plantation shutters, Quartz countertops in…

List Price:  $899,900

Welcome to a beautiful Pinnacle Model in the desirable, amenity rich community of Winding Cypress. This waterfront home is offered at an incredible value. Original owner care is apparent throughout. Builder and owner upgrades include; chef's kitchen with upgraded appliances, sink & faucet, soft close pull out cabinets including under-side lighting, custom quartz countertops, custom…

List Price:  $875,000

Built in 2022, this 2,124-square-foot Mystique model by DiVosta offers a rare turnkey opportunity, fully furnished with over $100,000 in luxury personal property, including indoor and outdoor furniture, artwork, decor, cookware, bedding, and more. Virtually everything photographed is included, ensuring effortless move-in-ready elegance. The residence blends sophisticated design with functionality, featuring porcelain tile flooring, premium…

List Price:  $675,000

PRICE DRASTICALLY REDUCED FOR QUICK SALE!! This beautiful villa in highly sought-after Winding Cypress offers two bedrooms, two baths plus a den along with a two-car air-conditioned garage. Step onto your lanai with the largest pool and hot tub available in a villa. Couple that with a spectacular long lake view and you truly have…

List Price:  $640,000

Don't miss your chance to own a Serenity Turnkey Pool Villa in the highly sought-after Winding Cypress community! This meticulously designed residence boasts 3 bedrooms, 2 bathrooms, and a 2-car garage, offering both comfort and style. Step outside to your private outdoor oasis, complete with a tranquil waterfall feature, electrically heated salt pool, built-in speakers, and…

List Price:  $1,497,500

Welcome to this exceptional Infinity Model home, a rare find in the prestigious Winding Cypress community of Naples, Florida. Built by the esteemed DiVosta Builders, this home is one of only three Infinity Models in a community of over 750 residences, making it a truly exclusive opportunity. Designed with elegance and comfort in mind, this…

List Price:  $995,000

Welcome to this Winding Cypress beauty! Why wait months to build and spend twice as much to get less in a home and amenities. This 2022 built classic Summerwood Model has everything you'll ever need in a home and is located in Naples best hidden secret.....Winding Cypress! Located on a private, quiet, dead-end cul-de-sac, this…

List Price:  $6,500

Annual Rental available for immediate occupancy. Turnkey Furnished, and ready for you to enjoy. This 2 story Summerwood model home with Breathtaking Pool and Spa offers a spectacular open floor plan. This home has a very large, beautiful Gourmet kitchen with Dining area, generous Great room with baby Grand Piano, 3 Bedrooms, 3 bathrooms on…

List Price:  $830,000

Welcome to the best kept secret in Naples, the community of Winding Cypress. Winding Cypress is a DiVosta neighborhood, loaded with resident amenities, and just minutes to Olde Naples and Marco Island. This beauty is the most popular model, The Pinnacle, and it is being offered at an amazing value in equity! An entertainer's dream…

List Price:  $1,399,000

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,…

List Price:  $985,000

From the moment you drive into the beautiful community of Winding Cypress you will feel welcomed. The stunning entry to this picturesque enclave will be a place you can truly call HOME! This is a natural gas, resort-style community, with over 2/3rds of the neighborhood remaining a preserve! You are surrounded by nature, yet close…

List Price:  $730,000

Welcome to your dream home at 7370 Mockingbird Court in beautiful Naples, FL! This charming 2-bedroom, 2-bathroom residence, with a versatile den that can easily be converted into a third bedroom, offers a spacious 1,805 square feet of living space, perfectly nestled on an 8,276 square foot lot. Step inside to discover a welcoming interior featuring…

List Price:  $669,900

This home is a true single famly NOT an attached villa. PRICED RIGHT ALMOST $230k UNDER THE NEXT ABBEY VILLE FLOOR PLAN FOR SALE IN COMMUNITY. BUILT AS AND COUNTY APPROVED AS A 3 BEDROOM HOME THIS FAMILY SELECTED THE FLEX ROOM OPTION HOWEVER WILL ADD THE CLOSET IF NEW OWNER WANTS Wonderful…

List Price:  $9,500

A stunning new pool and outdoor lanai, complement this exquisitely designed home, which offers tranquil views of the lake. This property features three bedrooms plus a den and three bathrooms, making it ideal for vacationing. The interior boasts a bright and airy coastal contemporary style with an open floor plan. This is a perfect vacation…

List Price:  $899,000

The Martin Ray floor plan is a breathtaking home located in the serene Winding Cypress community, overlooking a picturesque lake. This exquisite 2021 residence showcases the meticulous care of its single owner and boasts numerous upgrades throughout. It features a heated pool, three bedrooms, two bathrooms, and a den, providing ample space for living and…

List Price:  $995,000

Welcome to this stunning Summerwood floor plan with an extended great room. As you enter this 3 bedroom plus den home the quality of finishes is evident. The great room open plan concept allows for a great entertainment area with a large island kitchen and beautiful quartz countertops open to the dining and living area.…

List Price:  $12,000

From the moment you arrive at the stunning entry, Winding Cypress invites you into this wonderful community. This natural gas, resort-style community, remaining almost 2/3 preserve, welcomes you with a streetscape of superb views and new homes designed for the way you live. This premier Naples location offers highly attractive fees for the variety of…

List Price:  $1,395,000

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…

List Price:  $8,500

Unwind in this brand new, pristine vacation rental. Revel in the allure of a splendid pet-friendly home with a dazzling outdoor lanai, designed for the ultimate outdoor living experience. This residence boasts abundant natural light, a refreshing coastal contemporary interior, and an inviting open floor plan. With three bedrooms plus a versatile office you'll have ample…

List Price:  $529,000

Introducing the incredibly rare Winding Cypress model, the Cressida villa, now available with expansive private yard and lanai space. This unique villa features a dedicated private front entrance and an expanded foyer, complemented by an open yet defined living concept. The home boasts a wealth of builder-installed upgrades, including granite finishes, high-end porcelain floors, a…

List Price:  $1,649,000

Massive $200K price reduction!! STUNNING lake and sunset views await from the lanai of this Pinnacle model home situated on an oversized lot in Winding Cypress. At just over 2,500 square feet, you will notice the attention to detail from the moment you walk in the front door. Features of this gorgeous home include: 3…

List Price:  $7,000

Beautiful two bedroom plus den, two bath attached villa pool home in the amenity rich gated community of Winding Cypress. Main bedroom has a king bed, second bedroom has a queen bed and den has a full size pullout couch that sleeps 2 and includes a full wardrobe armor for clothing . Spacious attached 2-car…

List Price:  $12,000

This newly completed and spacious PET FRIENDLY home offers 3 bedrooms (King, King & 2 Twins) plus a den that is equipped with a queen-size murphy bed. This home is full of entertaining options that allow you to bring the extended family along. With its open floor plan as well as zero-corner sliders that…

List Price:  $7,000

Available for season 2025. Light, bright and beautifully updated two bedroom plus den, two bath attached villa pool home in the amenity rich gated community of Winding Cypress. Main bedroom has a king bed, second bedroom has a queen size bed and den has a queen size Murphy bed. Spacious attached 2-car garage. Water filter…