128 properties for sale in Winding Cypress

Experience the ultimate in luxury living with this bright and spacious second-floor coach home at Legacy in prestigious Lely Resort. This stunning three-bedroom plus den, three-bath residence offers a blend of elegance, comfort and functionality, all set next door to the community clubhouse, pool and spa. Enjoy panoramic eastern lake views from your private lanai, creating a serene and picturesque backdrop for everyday living. The open-concept great room design seamlessly connects the living, dining and gourmet kitchen areas, ideal for entertaining and relaxing. The thoughtful split floor plan allows for privacy and flexibility, featuring a large guest bedroom and a versatile bonus room that can serve as a second owner's suite, home office or media room. This home features numerous enhancements, such as ceramic tile, hardwood and luxury vinyl plank flooring throughout. The owner's suite is fitted with plantation shutters, while the living and guest rooms have custom blinds. Additional

This 3-bed + den, 3-bath home delivers style, space, and an unbeatable view. Enjoy plantation shutters, crown molding, and 5” baseboards for a polished look. The chef’s kitchen features granite counters, tile backsplash, stainless steel appliances (2021), a gas stove, and tons of storage. The primary suite boasts TWO walk-in closets, a walk-in tile shower, a garden tub, and double vanities. Guests will love their private quarters with walk-in shower. Tile floors, recessed lighting, and a freshly painted exterior make this home move-in ready. Relax on your 14x32 screened lanai with views of the golf course and lake. New Au002FC (2023), water heater (2019), and a spacious 2-car garage complete the package

Location, location, location! Expansive golf and water view coach home with sunset western exposure in Cherry Oaks and exceptional privacy. Experience refined living in this spacious second-floor end-unit residence, quality-built by reputable Gulf Bay and offered furnished with recently redecorated interiors and like-new, barely used furniture in the desirable community of Fiddler’s Creek. Offering over 3,000 square feet under air with three spacious bedrooms plus a study, three full baths, and an attached private two-car garage, this tranquil, light-filled home lives like a single-family residence and captures breathtaking Rookery golf course and water views with desired western exposure for spectacular nightly sunsets. Ideal adjacent to the community pool, the home offers the rare convenience of enjoying poolside living just steps away, like having your own pool without the maintenance, while the building’s unique positioning provides added privacy on the lanai with no neighboring la

Located in the popular Deer Crossing village within the award-winning gated community of Fiddler's Creek, this beautifully maintained second-floor end-unit coach home offers an exceptional blend of comfort, privacy, and SW Florida resort-style living, ideal as a full-time residence or seasonal retreat. It features the desirable Ironwood floor plan with three bedrooms, two full baths and a two-car garage. The spacious open-concept layout is thoughtfully designed for both comfortable everyday living and effortless entertaining. Large sliding glass pocket doors open to the screened and tiled lanai, creating a seamless indoor-outdoor connection and inviting in natural light and peaceful surroundings. Interior finishes include diagonal 18-inch porcelain tile flooring throughout the main living areas, wood-look tile flooring on the stairs and in all bedrooms, plantation shutters throughout, fresh decorator paint, a separate dining area, and a charming breakfast nook. The well-appointed kitch

In the private, guard-gated natural gas community of Lakoya at Lely Resort, this upgraded Tivoli III residence combines contemporary comfort with the resort lifestyle that defines Naples living. Built in 2015 and offered turnkey furnished, the home sits on a spacious pie-shaped lot featuring privacy hedges and a long southern lake view, among the most desirable in Lakoya. The three-bedroom plus den, three-bath floor plan is designed for seamless indoor-outdoor living, with large format tile laid on the diagonal, upgraded lighting and ceiling fans, and impact-resistant windows and doors throughout. The gourmet white kitchen features stainless steel GE appliances, quartz countertops and a custom backsplash, while the oversized two-car garage provides ample storage. Ownership includes membership in the Players Club and Spa, offering resort-style pools with waterfalls and a kids' area, a fitness/wellness center, tennis and pickleball facilities, a full-service spa, and multiple dining venu

Best Views. Impeccably Maintained. Barely Lived In. Experience luxury waterfront living in this meticulously maintained 2021 Toll Brothers Serino floor plan, perfectly positioned on the main lake in Azure at Hacienda Lakes. Enjoy breathtaking panoramic water views from the extended covered lanai, one of the community's premier waterfront settings. Tastefully curated furnishings are negotiable, making this move-in-ready home an effortless choice for Southwest Florida living. This elegant residence offers 3 bedrooms, a private officeu002Fden, 2.5 baths, and a 2-car garage. Grand double entry doors open to bright, open-concept living spaces featuring soaring tray ceilings and oversized polished white tile flooring. The gourmet kitchen showcases quartz countertops, white cabinetry, an oversized island, designer lighting, a natural gas cooktop, stainless steel appliances, a spacious pantry, and a brand-new microwave and wall oven. The lakefront primary suite features bay windows, two walk-i

Welcome to 3721 Sapphire Cove Circle, a stunning expression of refined coastal luxury located within the exclusive gated enclave of Sapphire Cove. Spanning over 2,600 square feet, this meticulously designed residence offers 3 bedrooms and 3.5 baths, showcasing a true no-expense-spared approach with high-end finishes and thoughtful upgrades throughout. The heart of the home is a gourmet Wolf and Sub-Zero kitchen featuring custom Omega cabinetry and a striking backlit Cristallo quartzite backsplash, seamlessly flowing into the open living spaces enhanced by a full home entertainment system controlled directly from your mobile device. Designed for both relaxation and entertaining, the outdoor living area is nothing short of spectacular, with an oversized, panoramic screened lanai overlooking serene lake frontage, a custom pool and spa, and a fully equipped outdoor kitchen complete with a Lynx Professional gas grill and underlit Cristallo countertop. Every detail of this home has been care

A rare opportunity to own one of Cascada's coveted private units — this is a must-see you won't want to miss! Welcome to this immaculate and meticulously maintained 3-bedroom + den, 2-bath coach home in the highly sought-after Cascada Village at Fiddler's Creek. Offered turnkey and tucked behind Cascada's own private gate within the exquisite, tropically landscaped community, this residence offers the rare combination of a secure gated setting, zero through-traffic, and total privacy on your own cul-de-sac — all just steps from Fiddler's Creek Club and Spa. The large paver driveway offers plenty of extra parking and makes for the perfect spot to grill out and entertain, while unobstructed garages and a pristine interior round out the home's move-in-ready appeal. Nothing else in Cascada compares to this unit's southern exposure and view. The expansive lanai showcases desirable southwestern exposure, delivering abundant natural light, stunning sunsets, and a front-row seat to the beautif

Brand new roof! Welcome to your slice of Paradise! This is a rare opportunity to own 1.19 acres in the hidden gem of Myrtle Cove Acres, where space, privacy, and flexibility come together with NO HOA and an unbeatable location. This property offers the peaceful feel of country living while keeping you close to everything Naples has to offer. The floor plan has been thoughtfully configured into a spacious 3-bedroom, 2-bath layout by combining two bedrooms into an oversized guest suite. The flexible design is ideal for visiting family and friends, a home office, hobby room, or multigenerational living. At the heart of the home is the open concept kitchen, featuring NEW stainless steel appliances, granite countertops, abundant cabinetry, and a bright, cozy breakfast area. The kitchen flows seamlessly into the main living spaces, making it perfect for both everyday living and entertaining. The interior is filled with natural light thanks to double pane windows and French doors, while large

One or more photo(s) has been virtually staged, AI generated or rendered. Welcome to the Montura—set on a private homesite, this beautifully crafted new construction residence features a southern-exposed backyard with lush landscaping and a spacious covered lanai, creating the perfect setting for relaxing afternoons, entertaining guests, or enjoying the Florida lifestyle in comfort and style. Inside, a thoughtfully designed open layout flows from the foyer into an expansive great room and a gourmet kitchen complete with a large quartz island, premium stainless steel appliances including a gas cooktop, abundant cabinetry, and a walk-in pantry. The primary suite serves as a peaceful retreat with an oversized walk-in closet and a spa-like bath featuring dual vanities and a luxurious walk-in shower. Two additional guest bedrooms provide comfortable accommodations, along with a dedicated office room ideal for working from home or flexible use, while a separate en suite bedroom offers added

This stunning and beautifully furnished residence in the sought-after Marsh Cove enclave of Fiddler’s Creek showcases the Avila II floor plan, designed to maximize lakefront living with private wide water views. Built in 2020, this three-bedroom plus den, three-bath home with a three-car garage blends timeless elegance with modern comfort, offering a light-filled interior and seamless indoor-outdoor living. The exterior boasts a wide brick paver driveway, elegant tile roof, and full storm protection with impact glass and StormSmart electric shutters on the lanai. The expansive outdoor living area is a true retreat, complete with a picture frame screen enclosure, recessed lighting, a ceiling fan, and a summer kitchen featuring granite counters and backsplash, a FireMagic built-in two-burner gas grill, Zephyr stainless steel beverage refrigerator and a sink. The sparkling pool and spa with a sun deck and water feature overlook tranquil lake views, surrounded by a pavered lanai perfect fo

Are you searching for a home with expansive, unobstructed views of the lake and golf course, framed by lush tropical landscaping and designed for elevated coastal living? In the desirable Runaway Bay enclave of Fiddler’s Creek, this rarely available, two-story Lantana floor plan offers a spacious and refined lifestyle with four bedrooms, two dens, a family room, a bonus room that can serve as a fifth bedroom, three full baths and two half baths. This gracious single-family residence includes a side-entry three-car garage with epoxy flooring, a tankless water heater, all impact-resistant doors and windows, and a two-zone HVAC system for optimal comfort. A wide brick-paved driveway leads to a welcoming entrance, where travertine flooring spans the main level and is accented by tray ceilings, crown molding and arched walkways. The gourmet kitchen is a standout, featuring a center island, bar seating, pantry, tile backsplash, recessed lighting and stainless steel appliances, including a na

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. Extensively updated for enhanced comfort, efficiency and peace of mind, the residence features a new roof, new windows, new appliances, new pool equipment, electronic hurricane shutters at front and rear, and numerous additional replacements and upgrades. This Cape Cod-style residence offers a seamless move-in opportunity, combining significant recent improvements with timeless character and craftsmanship. 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 privac

Welcome to 3206 Cotuit Lane in Marsh Cove! Beautifully designed Navarra II model, offering four bedrooms plus a den/office and 4.5 baths, with 2,813 square feet of thoughtfully curated living space. In the award-winning Fiddler's Creek community, this exceptional home showcases Ashton Woods' signature craftsmanship, high standards and inspirational design throughout. Positioned on a hand-selected, manicured lot with southern exposure, the home captures stunning long lake views and offers the rare opportunity to enjoy sunrise and sunset daily. Designed for effortless entertaining and refined everyday living, the open-concept floor plan features a spacious great room filled with natural light and picturesque views through expansive sliding glass doors. The gourmet kitchen is the heart of the home and every chef's dream, featuring a large island with elegant pendant lighting, white 42-inch cabinetry, a tiled backsplash, wall oven, walk-in pantry, ample storage and warm LED under-cabinet l

On a lakefront homesite in the desirable Mallard's Landing neighborhood of Fiddler's Creek, this sought-after Driftwood floor plan offers exceptional privacy, captivating wide lake views, and an inviting blend of comfort and sophistication. A brick-paver driveway leads to this beautifully maintained and spacious three-bedroom, three-full bath residence designed for relaxed living and effortless entertaining. Inside, diagonal tile flooring, volume ceilings, and expansive windows fill the home with natural light and enhance its open, airy feel. The popular layout includes a formal living and dining area, an open great room and a well-appointed kitchen featuring custom Italian cabinetry, granite countertops, GE Profile stainless steel appliances, a new refrigerator with icemaker, natural gas cooking and a pantry. A breakfast area and counter seating provide ideal spaces for casual dining. The owner's suite is a private retreat showcasing tray ceilings, arched windows and French doors open

Welcome to Cranbrook Colony, one of Royal Woods finest condo villages. This two bedroom + den with single-car garage property is perfectly priced, turn-key furnished and ready for you to start living the Florida lifestyle. Upon entering the eat-in kitchen is to the left with a big window offering plenty of sunshine. The common area offers vaulted ceilings with a light airy vibe. This unit has a large walk-in closet in the primary bedroom and a large laundry room with washer, dryer, and plenty of room to store your golf clubs or beach supplies. Additional highlights include electric and roll-down shutters on every single window offering peace of mind. Private screened in lanai is perfect to enjoy your favorite beverage while watching the golfers in the beautiful Florida weather. Meet your new neighbors at the clubhouse with restaurant, community poolu002Fspa, fitness center, yoga studio, tennis courts, library & more. Newer free standing pro shop and 70 new golf carts add to the fun. Go

Welcome home! This is the one you have been waiting for! Gorgeous three bedroom + den, two-bath single. Family pool home with two-car garage boasts gorgeous views of the golf course on the fourth fairway. Enjoy a morning swim in your own private pool with spa or relax with a favorite beverage and enjoy the property's westerly view of Naples spectacular nightly sunsets from the screened-in lanai. One of the last homes built in this community this home boasts soaring ceilings, a living, family and dining room along with a wet bar area and eat-in kitchen. This property has been meticulously maintained and offers plenty of upgrades including a newer tile roof (2018), Au002FC, hot water heater, appliances, washer, dryer, pool equipment, fresh interior paint and more. Additional highlights include a whole house filtration system, security system and hurricane shutters for storm protection. Walk or ride your bike to the clubhouse & enjoy the restaurant, fitness center offering a variety of cl

Welcome to your slice of paradise in Naples! This beautifully maintained 2-bedroom, 2-bathroom first-floor condo offers comfort, style, and convenience in one of Southwest Florida’s most desirable locations. Step inside to find an updated kitchen featuring modern finishes and ample cabinetry, perfect for both everyday living and entertaining. The spacious layout is enhanced by custom closets, providing smart storage solutions throughout. Enjoy relaxing mornings or peaceful evenings on the private papered patio, ideal for soaking in the Florida lifestyle. Designed for peace of mind, the unit is equipped with hurricane-impact windows and doors. As a desirable bottom-floor unit, you’ll appreciate easy access and added convenience. Brand new 2026 HVAC, 2024 water heater, upgraded pavers on lanai and outside grilling pad as well, upgraded tubu002Fshower combo to make this a move in ready condo! Residents enjoy a variety of community amenities, including a sparkling pool, pickleball courts,

Fabulous new price: end unit with golf, lake views & pickleball onsite! This beautifully updated 2BRu002F2BA plus den condo offers a bright and open layout! A closed-in lanai adds another 4 season room and allows for perfect enjoyment with serene mornings and magnificent views! As an end unit, it provides extra windows for natural light and privacy. The spacious master suite features a large bedroom, 2 XLarge closets, and plenty of storage. All interior door hardware has been upgraded. An updated kitchen kitchen sink and eat-in countertop adds convenience, The spectacular views of the golf course and lake create a true Naples lifestyle retreat. Forest Glen is a member-owned, debt-free bundled golf community and home to an award-winning 18-hole championship course designed by Arthur Hills—voted the #1 course in the USA by GolfNow. Com! Amenities include a clubhouse with member pub, poolside bar & grill, a very active tennis program with tennis pro, pickleball, nature trails, 24u002F7 fi

Welcome to 5715 Clarendon Drive, an exceptional furnished lakefront residence with coveted northwest sunset exposure in the Isles of Collier Preserve. Built in 2018 and offering nearly 2,900 square feet, this beautifully maintained home features 3 bedrooms plus a den, 3.5 baths, and a spacious three-car garage. Designed for effortless indoor-outdoor living, the bright open great room showcases expansive windows and sliding glass doors that frame long lake views and stunning evening skies. The main living areas flow seamlessly to the screened lanai, where a resort-style pool and spa, outdoor kitchen, and multiple seating areas create the perfect setting for entertaining or relaxing in privacy. Offered tastefully furnished and move-in ready, this home delivers the ultimate Naples lifestyle from day one

Best deal in the building! Here is a gorgeous residence with a resort style pool view provoking that vacation feeling you are seeking. Professionally decorated and offered fully furnished this is a stand out condo that is ready to move right in and start enjoying the 5 star lifestyle. This has a gourmet kitchen with all the modern features including stainless appliances, granite counters, custom cabinets and kitchen bar. Just off the kitchen is a family room with a big window perfect for entertaining. The living room has a unique and bold curved window wall that is jaw dropping. Enjoy a large lanai with ample space for any outdoor living you have in mind. The living room is stunning with the furniture style and design offering an open concept with the spacious dining room. The luxurious primary suite has lanai access and a view of the hotel style amenities out back. The primary bath has marble flooring a jetted tub, frameless shower door, and posh dual sinks. On the other end of this s

Experience the ease of luxury living in this beautifully furnished first-floor coach home, ideally in the sought-after Rialto enclave of the prestigious, gated Hammock Bay Golf & Country Club. Offering the spacious feel of a single-family residence paired with low-maintenance convenience of condominium living, this thoughtfully designed home features three bedrooms, two baths and a two-car garage, making it equally suited for seasonal enjoyment or year-round living. Southwestern exposure enhances the expansive screened lanai, where peaceful golf course views create a seamless extension of the indoor living space. Inside, abundant natural light highlights tile flooring throughout the main living areas, creating a bright and welcoming atmosphere. The open-concept kitchen is well-appointed with white cabinetry, recessed lighting, a pantry and a full suite of stainless steel appliances, including a new refrigerator and microwave added in 2024, along with a range and dishwasher. The light-f

This luxurious condominium on the 18th floor offers stunning window walls that provide unparalleled views of marco island. Enjoy bright, sunny daytime vistas, and the shimmering night lights of marco island reflecting over the water. Inside, the furnished sky home features a designer kitchen equipped with rich granite countertops and elegant stainless appliances. The beautiful primary suite boasts a marble bath with a soaking tub, marble counters, and a spacious shower, along with direct access to the lanai. The gorgeous screened lanai is poised to sit relax and enjoy the views of sunny marco island. On the opposite end of the condo, you will find two guest bedrooms, each with open lanai access, along with a posh second bedroom. A sleek powder room, conveniently located just off the dining room, is perfect for entertaining guests. The grand salon features a curved window wall that floods the space with natural light and offers ample opportunities to admire the breathtaking views. Lesin

One or more photo(s) has been virtually staged, AI generated or rendered. Significant price reduction! Immediate occupancy available! This charming 2-Bed, 2-Bath Villa in Lakewood is a Hidden Gem! Welcome to your slice of paradise in the sought-after Lakewood community! This GROUND FLOOR villa offers the ultimate in privacy—no neighbors above—and comes with COVERED PARKING and EXTRA STORAGE CLOSET for all your Florida lifestyle essentials. Step inside to discover diagonally laid CERAMIC TILE FLOORS throughout—NO CARPET anywhere! The spacious layout flows seamlessly into an enclosed lanai with IMPACT-RATED sliding doors, leading to an extended patio where you’ll soak in serene lake views and lush tropical landscaping. Enjoy peace of mind with IMPACT WINDOWS and a 2018 ROOF REPLACEMENT, plus a host of recent upgrades: Range, dishwasher & water heater (2019), Microwave (2022), HVAC system (2017), and Brand-new reverse osmosis water system under sink (2025), new plumbing fixtures in guest

Big price improvement! Now welcoming a new owner who appreciates spacious condominium living in a well-maintained, conveniently located Naples community. This 3-bedroom, 2-bath residence offers high ceilings, generous living space, a private screened lanai, and an attached one-car garage. Located just 2.5 miles from Fifth Avenue South, Crown Pointe delivers an ideal blend of convenience and affordability. Enjoy the ease of a swimming pool just outside your lanai, with the community center nearby offering a fitness center, tennis and pickleball courts, a larger resort-style pool, and clubhouse—perfect for both active days and relaxed afternoons in the sun. Community dues cover nearly all expenses, leaving electric as the only monthly utility bill. The home has been well cared for, while still presenting opportunities for cosmetic updates to enhance long-term value. A short-term seasonal rental agreement has been in place the last two years effectively covering annual HOA fees, property