128 properties for sale in Winding Cypress

This is a Real Estate-Owned (REO)/post-foreclosure home owned or managed by a bank. All offers are considered; however, the highest and best will most likely be accepted

This is a Real Estate-Owned (REO)/post-foreclosure home owned or managed by a bank. All offers are considered; however, the highest and best will most likely be accepted

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

Nestled in the heart of the highly sought after community of Avalon, this exceptional Keswick model first floor end-unit residence offers a truly unique living experience. The west-facing lanai provides breathtaking sunset views over the lake, complemented by two beautifully lit fountains. Enjoy convenient access to the community's heated pool, spa, clubhouse, and mailboxes, all just a short walk away. Upon entering, you'll appreciate the sun-filled open floor plan, complete with designer finishes including top-of-the-line fixtures, lighting, and fans throughout. Additional features include electric sheer sunshades over triple and double sliding glass doors, electric sunshades on the lanai, plantation shutter, stainless steel appliances, Carrara-like granite countertops, and recently updated dishwasher in kitchen. Built to withstand Florida's weather, this home boasts impact glass windows and doors, ensuring safety and security. The HOA covers landscaping, irrigation, water, sewer, int

Nestled in the heart of the highly sought after community of Avalon, this exceptional Keswick model first floor end-unit residence offers a truly unique living experience. The west-facing lanai provides breathtaking sunset views over the lake, complemented by two beautifully lit fountains. Enjoy convenient access to the community's heated pool, spa, clubhouse, and mailboxes, all just a short walk away. Upon entering, you'll appreciate the sun-filled open floor plan, complete with designer finishes including top-of-the-line fixtures, lighting, and fans throughout. Additional features include electric sheer sunshades over triple and double sliding glass doors, electric sunshades on the lanai, plantation shutter, stainless steel appliances, Carrara-like granite countertops, and recently updated dishwasher in kitchen. Built to withstand Florida's weather, this home boasts impact glass windows and doors, ensuring safety and security. The HOA covers landscaping, irrigation, water, sewer, int

Positioned in the desirable community of Pepperwood and lovingly maintained by its original owner, this beautifully updated residence enjoys southern exposure and tranquil garden views, creating a light-filled and inviting atmosphere. Thoughtfully renovated and impeccably maintained, this two-bedroom, two-bath condominium offers an excellent Naples location, paired with comfortable indoor-outdoor living. Whether you are seeking a seasonal retreat, investment opportunity or full-time residence, this property presents exceptional value in a serene yet convenient setting. A screened lanai with tiled flooring and a ceiling fan provides covered outdoor living space overlooking lush, peaceful garden views, ideal for morning coffee or relaxing afternoons. Impact sliding doors and windows offer storm protection and added peace of mind. The residence includes one assigned carport space and extra storage for added convenience. Inside, porcelain tile flooring flows seamlessly throughout the main

Welcome to this conveniently located Mainsail IV community nestled between Marco Island and Naples. This impeccably maintained second floor condo features 2 bedroom and 2 full baths, It is turnkey furnished with a Tommy Bahama decor that offers comfort, style and reflects the coastal vibe of this area. Enjoy the serene view of the adjacent waterway from the well appointed lanai which offers the comfort and security of roll down shutters, New 2025 Au002FC, water heater, washeru002Fdryer and upgraded plumbing fixtures make this turnkey Mainsail unit very desirable whether fulltime or part-time occupancy is desired, Listing is an owner of this property and has a current Florida Real Estate License

Experience elevated Florida living in this meticulously upgraded 2020 Stock Development Siesta model, where luxury and functionality come together seamlessly. The backyard is designed for true indoor-outdoor living, featuring a custom heated saltwater pool, expansive entertaining area, and a fully equipped outdoor kitchen—set within an exceptionally quiet and private setting that creates the perfect retreat. Inside, the home showcases a beautifully appointed chef’s kitchen with quartz countertops, glass tile backsplash, and designer lighting, all flowing into refined living spaces highlighted by crown molding, custom wainscoting, plantation shutters, and striking cypress ceiling beams. The primary suite offers a private retreat with a spa-like bath, including dual vanities, a soaking tub, and a frameless walk-in shower, complemented by a spacious walk-in closet. Built with comfort and peace of mind, this home includes impact-resistant windows, Storm Smart hurricane screens, a whole-hou

BRAND-NEW ROOF to be installed before closing! LARGEST Oakmont model in Verona Walk with 200+ extra square feet of living space! Beautiful 3-bedroom + officeu002Fden, 2.5-bath home in the premier 24-hour guard-gated community of Verona Walk. Offering nearly 2,200 square feet of living space, this spacious floor plan is designed for privacy and effortless flow. The expansive interior is highlighted by impressive 12+ foot ceilings and large sliding glass doors that frame serene water views while filling the home with abundant natural light. The sliders open to a huge covered lanai, seamlessly blending indoor and outdoor living and creating the perfect space to relax or entertain overlooking the tranquil waterfront. Completely move-in ready, the home features fresh interior paint (2024) and upgraded recessed lighting throughout, creating a bright, clean, and modern feel. Verona Walk delivers an unparalleled resort-style lifestyle with amenities designed for ultimate convenience. The vibra

The spacious residence in Classics Plantation Estates at Lely Resort has been thoughtfully renovated and offers a refined blend of comfort, scale and relaxed Naples living. With over 3,200 sq. Ft. under air, four bedrooms plus a den and a seamless indoor-outdoor flow, the home is well suited for both everyday living and entertaining with family and friends. A grand double door entry opens to light-filled living spaces with volume ceilings, wide plank flooring, designer lighting and expansive sliding glass doors overlooking the lanai, pool and golf course beyond. The kitchen serves as a natural gathering space in the heart of the home with custom cabinetry, stainless steel appliances, statement vent hood, waterfall island and breakfast nook overlooking the outdoor living area with summer kitchen. The home's primary suite offers a peaceful private retreat with dual vanities, soaking tub, walk-in shower, and elegant architectural detailing. The guest suites provide comfort and flexibility

Located in the upscale and highly sought-after community of The Classics Plantation Estates, this residence perfectly embodies the Florida lifestyle. From the moment you drive through the gates, you’ll notice lush landscaping, tree-lined sidewalks ideal for morning walks, and architecturally distinct homes. This property stands out—situated on a large corner lot with a rare side yard that can be fenced, perfect for a spacious dog run. The exterior has been freshly painted, enhancing its curb appeal against the vibrant green landscape. A three-car side-entry garage and an oversized paved driveway create an impressive front elevation. Step inside this stunning courtyard-style home, offering approximately 600 sq. Ft. of outdoor living space. The custom pool with cascading waterfalls serves as the centerpiece, surrounded by multiple seating areas ideal for relaxing or entertaining. Featuring 4 bedrooms and 3 en-suite baths, this home ensures comfort and privacy for family and guests. The o

Extremely motivated seller, bring all offers Welcome to this GORGEOUS picture-perfect home in the award-winning community of Fiddler's Creek! This move-in ready 2,247-square-foot beauty is a must-see as it has the BEST UNOBSTRUCTED WATER VIEWS in the entire community! This 4-bedroom, 2-bath home provides abundant space and natural light. The bright interior is beautifully decorated with neutral décor and features tray and volume ceilings, wainscoting, arched doorways, crown molding, and tile throughout. The great room layout seamlessly connects the open living area, dining area and gourmet kitchen which boasts granite countertops, gas cooking, pantry, stainless steel appliances and breakfast bar. The master suite has walk-in closets and en suite with dual sinks and vanities, walk in tile shower, separate soaking tub and enclosed water closet. Enjoy the sun filled days in your gas-heated pool with a BRAND NEW HEATER AND PUMP with a spa and entertain with ease on the screened lanai with

Welcome to this stunning, newly built villa 2023 in Azure at Hacienda Lakes! This home has 2 bedrooms, 2 baths, plus den where modern design meets exceptional quality. Hardly used and meticulously maintained, this home features many builder's upgrades. As you step inside, you’ll immediately be impressed by the open-concept layout featuring 10’ to 10’6 ceilings and impact glass windows and doors. The gourmet kitchen features high-end appliances, a large island, ample cabinetry, and a pantry. The den provides a versatile space ideal for a home office or cozy reading nook. The master suite offers a peaceful retreat, complete with a luxurious en-suite bath featuring upgraded finishes, a large walk-in shower, and a stylish double sink vanity. The second bedroom is spacious and can easily accommodate family or guests. Both bathrooms have been beautifully designed with modern touches that reflect the home's upscale upgrades. Step outside to the premium lakeview extended screened-in lanai, a p

Enjoy tranquil golf course views from this well-maintained, beautifully furnished first-floor end residence in the desirable Cherry Oaks village of Fiddler’s Creek, ideally on The Lane, a quiet, private enclave with no through traffic and a serene lake in front, offering exceptional privacy and a peaceful setting. With sought-after southwestern exposure, this spacious home is filled with plentiful natural light, enhancing its warm and inviting ambiance throughout. Thoughtfully designed with popular Blossom floor plan, this coach home features three spacious bedrooms plus a den, two full baths and a two-car garage, all complemented by a light, open-concept layout. Porcelain tile flooring set on a diagonal flows through the main living areas, while plantation shutters, recessed lighting and ceiling fans add style and comfort. Expansive sliding glass doors anchor the living space, seamlessly blending indoor and outdoor living while framing picturesque views of the beautiful Rookery golf c

Enjoy a rare and optional immediate full golf membership and skip the waitlist at the prestigious Members Club at Marco, offering access to the championship Rookery and Hammock Bay courses, two elegant clubhouses and private beach privileges at JW Marriott, an exceptional opportunity in the award-winning community of Fiddler’s Creek. Better than new, completed in 2020 and offered designer furnished, this exceptional residence in Oyster Harbor captures southeastern exposure and tranquil long lake views while showcasing superior craftsmanship and extensive custom upgrades throughout. Quality built by Gulf Bay, the sought-after Hibiscus floor plan features four bedrooms plus a study and three-and-a-half baths, offering the look and quality of new construction without the wait, delays or added expense. A grand foyer with a coffered shiplap ceiling and designer sconces opens to a light-filled interior defined by volume ceilings, detailed trim work, engineered hardwood flooring and expansive

10,000k price drop. Lowest priced home in antilles! This upgraded residence is exempt from flood insurance! This upgraded residence is exempt from flood insurance! This light and bright second floor classic coach home features 3 bedrooms and 2 bathrooms and was built in 2023. High ceilings residence with partial water view consists of almost 2000 sq ft, this spectacular residence features a one-car garage and a spacious master bedroom, with an elegant ensuite featuring an extended floor to ceiling tile in shower and flooring, dual sinks, and an expansive walk-in closet. Additionally, you'll discover a generously proportioned guest bedroom, a versatile office that can easily be converted into a third bedroom and a well-appointed laundry room furnished with a washer, dryer. The interior is complemented by stainless steel appliances and a beautiful view from lanai. The master bedroom is big, with an amazing walk-in closet and a big bathroom, while the guest bedroom offers a big closet and

One or more photo(s) has been virtually staged, AI generated or rendered. Experience the best of Florida coastal living in this stunning Pinellas Transitional single-story home, ideally located in one of Naples’ premier gated communities. Designed with an open-concept layout and upscale finishes throughout, this residence blends timeless style with everyday comfort. A grand foyer opens to a spacious great room and casual dining area, flowing seamlessly to an expansive covered lanai—perfect for year-round outdoor dining, relaxing, and enjoying the Florida lifestyle. The chef-inspired kitchen features elegant quartz countertops, two-toned cabinetry, stainless steel appliances, a natural gas cooktop, and a large walk-in pantry—ideal for both everyday living and entertaining. The private primary suite offers dual walk-in closets and a spa-like bath with a glass-enclosed shower and dual-sink vanity. Two additional bedrooms share a full bath, while a versatile flex room provides space for a

Experience refined living in the sought-after Mallard’s Landing neighborhood of Fiddler’s Creek in this exquisite three-bedroom, two-bath residence built by Gulf Bay. Featured in Naples Home & Design magazine, this home exemplifies timeless design, elegance and craftsmanship. This Cape Cod-style provides a seamless move-in opportunity and an exceptional blend of comfort and style. Set against a tranquil backdrop of breathtaking lake views, this residence offers outstanding privacy and serenity. From the spacious screened lanai, enjoy unobstructed vistas of the water, vibrant birdlife and glowing sunsets. The thoughtfully designed Bayview split-bedroom floor plan ensures comfort and privacy, while large windows and multiple glass sliders flood the home with natural light and create effortless indoor-outdoor living. The living room opens to the lanai overlooking the heated pool and spa with waterfall feature, surrounded by spacious covered outdoor areas ideal for entertaining or relaxing

Brand new luxury townhome offering deeded single-family ownership — you own the land your townhome sits on — providing the privacy of a home with the convenience of low-maintenance living. CURRENT BUYER INCENTIVE SPECIALS – $20,000 in Designer Upgrades & Up to $10,000 in Lender Incentives when using our preferred lender. New Construction in the Heart of Naples, Available for Fall 2026 Occupancy! One or more photo(s) has been virtually staged or an architectural rendering. The Clubhouse heated pool is under construction, with excavation completed, further enhancing the resort-style lifestyle planned for this community. Elegant New Construction Townhome in Gated Southeast Naples Community Discover contemporary luxury in this beautifully designed new construction townhome, located in a private, gated enclave in sought-after Southeast Naples. The bel air. Model type b. Offering 3 bedrooms + LOFTu002FDEN, 2.5 bathrooms, and a spacious 2-car garage, this residence is perfect for those who de

Brand new luxury townhome offering deeded single-family ownership — not a condominium — providing the privacy of a home with the convenience of low-maintenance living. CURRENT BUYER INCENTIVE SPECIALS – $20,000 in Designer Upgrades & Up to $10,000 in Lender Incentives when using our preferred lender. New Construction in the Heart of Naples, Available for Summer 2026 Occupancy! One or more photo(s) has been virtually staged or an architectural rendering. The Clubhouse heated pool is under construction, with excavation completed, further enhancing the resort-style lifestyle planned for this community. Luxury New Construction Townhome with 1st-Floor Primary BD Suite in Southeast Naples off of Santa Barbara and South of Davis. Experience elevated living in this impeccably crafted new construction townhome, ideally situated in one of Southeast Naples’ most exciting new luxury communities, Santa Barbara Place. THE ASHTON-Model Type A, This thoughtfully designed residence offers 3 bedrooms, a