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Winding Cypress, 7057 Live Oak Dr, Naples, Florida 34114, image 1
$679,000 $20K
  • 3 Beds
  • 2 Baths
  • 2,230 SqFt
  • $304/SqFt
House for sale in Winding Cypress
7057 Live Oak Dr, Naples, FL 34114
Winding cypress – price reduced to sell- property sits approximately 2+ feet above fema base flood elevation. Fema loma in process — flood insurance not required by lender. Rare opportunity to purchase in this community at this price point. Lowest priced 4 bedroom home in winding cypress. Welcome to your florida dream home in the sought-after gated community of winding cypress! This immaculate residence built in 2016, offers the perfect blend of modern luxury and relaxed coastal living. Featuring 2, 230’sq under air, 4 bedrooms. Two full baths, and an open-concept floor plan, this home is designed for comfort and entertaining. Step inside to find upgraded tile flooring, beautiful crown molding, a gourmet kitchen with granite countertops, stainless steel appliances, and a large center island ideal for gathering with friends and family. The spacious great room opens through sliding glass doors to a screened lanai, creating seamless indoor-outdoor living. This home also features a "sunroom" addition and an oversized garage. Enjoy peaceful views of the lush landscaping and lake—the perfect backdrop for morning coffee or sunset cocktails. The primary suite offers a spa-like bath with dual sinks, walk-in shower, and large walk-in closet. Additional features include plantation shutters, impact-resistant windows and doors, whole house water purification system, new electric hurricane screens, a "sunroom" addition not included in other floor plans, and an oversized garage and a 2-car extended garage with epoxy flooring. Located within minutes of downtown naples and the gulf beaches, winding cypress offers resort-style amenities including a lagoon-style pool, on-site restaurant, tennis, pickleball, fitness center, dog park, and miles of nature trails. Move-in ready, this is the best priced home of its size in winding cypress — this home combines style, value, and an unbeatable location.
Winding Cypress, 7638 Jacaranda Ln, Naples, Florida 34114, image 1
$509,900 $30K
  • 2 Beds
  • 2 Baths
  • 1,574 SqFt
  • $324/SqFt
Villa for sale in Winding Cypress
7638 Jacaranda Ln, Naples, FL 34114
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.
Winding Cypress, 6825 Greenbriar Ct, Naples, Florida 34114, image 1
$1,050,000 $100K
  • 4 Beds
  • 3 Baths
  • 3,036 SqFt
  • $346/SqFt
House for sale in Winding Cypress
6825 Greenbriar Ct, Naples, FL 34114
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.
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Winding Cypress, 7666 Jacaranda Ln, Naples, Florida 34114, image 1
$575,000
  • 2 Beds
  • 2 Baths
  • 1,574 SqFt
  • $365/SqFt
Villa for sale in Winding Cypress
7666 Jacaranda Ln, Naples, FL 34114
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.
Winding Cypress, 7248 Live Oak Dr, Naples, Florida 34114, image 1
$634,999 $10K
  • 2 Beds
  • 2 Baths
  • 1,685 SqFt
  • $377/SqFt
House for sale in Winding Cypress
7248 Live Oak Dr, Naples, FL 34114
Single family home in winding cypress -ready for the season!! This charming model is the perfect fit featuring an inviting open-floor concept where natural light streams through the windows. The kitchen boasts granite counters, stainless appliances and a center island and extra storage for everyday use and easy entertaining. The pantry closet has plenty of space for all of your staple goods. Tile floors are throughout much of the space. There's a den/flex room with french doors that can be used as an additional bedroom when needed or office, hobby or quiet sitting room. Additional guest bedroom and bathroom with combined tub and shower and granite topped vanity offers privacy for your family and guests. The laundry room features a spacious storage area with shelving for your all your supplies. There are storage racks in the two car garage to house your coolers for the beach. Be sure to take time to relax and enjoy your morning beverage and the beautiful sunsets on the screened lanai that overlooks the oversized lot with mature landscaping complete with an outdoor kitchen with grill, sink, and fridge for your convenience. Winding cypress is a sought after, gated community and is appreciated for its active, social lifestyle and world class amenities. It’s nestled within 800 acres of natural preserve and 80 acres of serene lakes teeming with migratory wildlife. Head over to the clubhouse with state-of-the-art fitness center, locker rooms with showers, movement room for classes, internet café, event room, catering kitchen, resort-style pool with spa and cabanas, restaurant with bar, firepit, pickleball, tennis and bocce courts. Take the pups to play in the dog park. Walk or ride your bike on the many paths including the peaceful preserve boardwalk. If gardening is your passion, there is a community garden to grow your favorite vegetables. Hoa management and friendly staff are onsite to assist and coordinate regular events for all to enjoy. Minutes from beaches, golfing, fishing, boating, shopping, and cultural activities. It's time to enjoy the florida lifestyle!
Winding Cypress, 7255 Live Oak Dr, Naples, Florida 34114, image 1
$639,900 $20K
  • 2 Beds
  • 2 Baths
  • 1,659 SqFt
  • $386/SqFt
House for sale in Winding Cypress
7255 Live Oak Dr, Naples, FL 34114
This home has just been freshly painted inside and out. Professionally painted kitchen and bath cabinets, nice private south west waterview , screened lanai able to enlarge or even add a pool. Previous owner had a great workshop in garage with 8 overhead lights, addition dual media cat5/rg6 charging station for a tesla , framed peg boards for hanging tools , custom storage cabinets and a pull down staircase for added storage. Home features 2 bedrooms 2 baths plus den a whole house generator and attached manual and electric storm shutters. Remaining furniture in home is staying. Live oak is a beautiful mature tree lined street on cul de sac and just a short walk to the amenity center, dog park or community garden this home is ready for immediate occupancy winding cypress amenity center offers so much within its gates, its own shady palm restaurant, resort pool , gym , bocci and pickleball courts, dog park , walking trails and so much more. Winding cypress is a gated community located just mins to 75, downtown and marco island. Photos to be uploaded on 1/24
Winding Cypress, 7733 Jacaranda Ln, Naples, Florida 34114, image 1
$599,999
  • 2 Beds
  • 2 Baths
  • 1,554 SqFt
  • $386/SqFt
Villa for sale in Winding Cypress
7733 Jacaranda Ln, Naples, FL 34114
Discover effortless luxury in this impeccably maintained villa—your private oasis in naples' premier gated community, winding cypress. This inviting 2-bedroom + den, 2-bath home delivers exceptional comfort and versatility. Both bedrooms feature generous walk-in closets. The guest suite offers true privacy with a hallway pocket door that creates a secluded en-suite retreat. Bathrooms showcase floor-to-ceiling porcelain tile, frameless 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. The flexible den, enclosed by beautiful glass panel doors, adapts effortlessly as a home office or third bedroom. Step into the expansive great room with soaring ceilings for an open, airy vibe—perfect for entertaining or unwinding after a day 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 throughout, paired with smooth-finish walls for a clean, modern, low-maintenance aesthetic. Outside, a premium lot provides generous spacing between villas and captivating views over the community's second-largest lake—where the serene water vistas create an unparalleled sense of tranquility and timeless appeal. West-facing orientation captures breathtaking sunsets reflecting off the shimmering waters, while 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.
Winding Cypress, 6770 Pennyroyal Dr, Naples, Florida 34114, image 1
$825,000 $74K
  • 3 Beds
  • 3 Baths
  • 2,128 SqFt
  • $388/SqFt
House for sale in Winding Cypress
6770 Pennyroyal Dr, Naples, FL 34114
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!
Winding Cypress, 7460 Blackberry Dr, Naples, Florida 34114, image 1
$850,000 $49K
  • 3 Beds
  • 2 Baths
  • 2,188 SqFt
  • $388/SqFt
House for sale in Winding Cypress
7460 Blackberry Dr, Naples, FL 34114
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.
Winding Cypress, 6754 Pennyroyal Dr, Naples, Florida 34114, image 1
$845,000 $30K
  • 3 Beds
  • 3 Baths
  • 2,158 SqFt
  • $392/SqFt
House for sale in Winding Cypress
6754 Pennyroyal Dr, Naples, FL 34114
This gorgeous mystique floor plan features 3 bedrooms, a den, a rare 3 full bathrooms, heated pool, and a 2-car garage. Inside the home is loaded with upgrades, impact windows and doors, custom built-in cabinetry in the living & laundry room, crown molding, tray ceilings, recessed lighting, electric blinds, designer hardware and lighting, and abundant storage throughout. Embrace the florida lifestyle with the open-concept zero-corner slider connecting the indoor and outdoor living spaces. The pool deck offers a spacious covered lanai, a modern pool, added privacy, and highly desirable southwest exposure. No detail has been spared in the garage, which features a built-in workbench and storage, an electric screen garage door, epoxy flooring, and plenty of room for bikes and more. 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 two dog parks for your furry friends. This pet-friendly community allows rentals, has low fees, and boasts a prime location—convenient to marco island, 5th avenue, and i-75.
Winding Cypress, 7121 Live Oak Dr, Naples, Florida 34114, image 1
$630,000
  • 2 Beds
  • 2 Baths
  • 1,554 SqFt
  • $405/SqFt
House for sale in Winding Cypress
7121 Live Oak Dr, Naples, FL 34114
Situated within the gated, amenity-rich community of winding cypress, this thoughtfully designed 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 hot tub with ample seating, and picture-frame lanai screens that showcase peaceful preserve surroundings. Additional highlights include a whole-house 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 golf cart is included for effortless access throughout the neighborhood.
Winding Cypress, 7639 Jacaranda Ln, Naples, Florida 34114, image 1
$649,000 $16K
  • 2 Beds
  • 2 Baths
  • 1,554 SqFt
  • $418/SqFt
Villa for sale in Winding Cypress
7639 Jacaranda Ln, Naples, FL 34114
Sunset water views stretch across a sparkling long lake from your private pool and spa, creating a breathtaking backdrop for everyday living and entertaining from the fully equipped natural gas outdoor kitchen. This beautifully maintained home stands out with major recent upgrades including a brand new ac system (2026), new washer and dryer, new hot water heater, and new carpet, offering peace of mind and allowing the home to live comfortably and effortlessly from day one. The open floor plan feels light, bright, and inviting with updated flooring and elegant quartz and granite surfaces throughout. The thoughtfully designed layout offers two spacious bedrooms plus a flexible den with an alcove ideal for adding a closet, making it perfect for guests, a home office, or additional sleeping space. The gourmet kitchen blends style and function with granite countertops, a tasteful tiled backsplash, staggered cabinetry, and bar seating for casual gatherings, while natural gas service and ceiling-mounted garage storage racks add everyday convenience. Gently lived in as a pet-free, smoke-free seasonal residence, the property shows like new. Located in the resort-style community of winding cypress, residents enjoy more than 800 acres of preserved natural landscape and exceptional amenities including a clubhouse with a heated pool, on-site restaurant, fitness center, white sand beach, tennis and pickleball courts, dog park, and scenic nature trails, all with low hoa fees and an ideal location just 25 minutes to fifth avenue south, 20 minutes to marco island, and minutes to major shopping and dining, creating a lifestyle that blends luxury, convenience, and unforgettable views.
Winding Cypress, 6902 Winding Cypress Dr, Naples, Florida 34114, image 1
$875,000 $25K
  • 3 Beds
  • 2 Baths
  • 2,084 SqFt
  • $420/SqFt
House for sale in Winding Cypress
6902 Winding Cypress Dr, Naples, FL 34114
Stunning 3-bedroom + den home in sought-after winding cypress – welcome to your dream home in the prestigious, resort-style community of winding cypress in naples, fl. Built in 2022, this impeccably maintained 3-bedroom + den, 2-bathroom residence blends modern design with everyday comfort. Step inside to find an open-concept floor plan featuring, abundant natural light, and contemporary finishes throughout. The kitchen boasts quartz countertops, stainless steel appliances, a large center island, and a spacious pantry—perfect for entertaining or casual family meals. The flexible den space offers the ideal setup for a home office, media room, or guest overflow. The primary suite is a serene retreat with a large walk-in closet and a spa-like ensuite bathroom featuring dual vanities and a walk-in shower. Recently installed lights on the lanai make the area glow at night. Very private preserve views! Also recently installed are electric retractable hurricane screens for added safety. Enjoy florida living at its best with a screened lanai, ideal for relaxing or dining alfresco, with a large heated pool. The home also includes a 2-car garage, impact windows, and smart home features for added peace of mind. Residents of winding cypress enjoy resort-caliber amenities including a large clubhouse, fitness center, resort pool & spa, on-site restaurant, tennis & pickleball courts, fire pit, dog park, and over 800 acres of preserved natural space with walking/biking trails. Conveniently located just minutes from downtown naples, white sand beaches, shopping, and dining. Don’t miss this rare opportunity to own a move-in ready home in one of naples’ most desirable communities!
Winding Cypress, 6787 Pennyroyal Dr, Naples, Florida 34114, image 1
$919,000 $20K
  • 3 Beds
  • 2 Baths
  • 2,186 SqFt
  • $420/SqFt
House for sale in Winding Cypress
6787 Pennyroyal Dr, Naples, FL 34114
The view !!!!!!!! Built in 2022 move in ready ! Like new contemporary style mystique model 3 bdrm den 2bath in winding cypress. Location location with this breathtaking long lake view , last home on street on long landscaped corner affords plenty of privacy.Some of the upgraded features consist of a widened paved recently sealed driveway comfortably fitting 2 cars side by side, zero clearance corner doors that invites the outside in, plus overhead storage with mini a/c split in garage . Whole house generator, impact windows and doors, outdoor kitchen numerous designer interior upgrades. Tile marble look floors customs walls and designer closet system . Full office set up for those working from home or seller will remove and redo room if requested. Great opportunity to live in winding cypress and all that this community has to offer
Winding Cypress, 7679 Winding Cypress Dr, Naples, Florida 34114, image 1
$949,000
  • 3 Beds
  • 2 Baths
  • 2,186 SqFt
  • $434/SqFt
House for sale in Winding Cypress
7679 Winding Cypress Dr, Naples, FL 34114
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.
Winding Cypress, 7670 Jacaranda Ln, Naples, Florida 34114, image 1
$698,500 $11K
  • 3 Beds
  • 2 Baths
  • 1,594 SqFt
  • $438/SqFt
Villa for sale in Winding Cypress
7670 Jacaranda Ln, Naples, FL 34114
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.
Winding Cypress, 7072 Live Oak Dr, Naples, Florida 34114, image 1
$1,499,900 $100K
  • 4 Beds
  • 4 Baths
  • 3,350 SqFt
  • $448/SqFt
House for sale in Winding Cypress
7072 Live Oak Dr, Naples, FL 34114
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.
Winding Cypress, 7247 Clamshell Ln, Naples, Florida 34114, image 1
$1,645,000
  • 4 Beds
  • 4 Baths
  • 3,656 SqFt
  • $450/SqFt
House for sale in Winding Cypress
7247 Clamshell Ln, Naples, FL 34114
Rarely available, highly sought after 4-bedroom home in prestigious winding cypress, with uninterrupted water and preserve views (no homes) both front and back, heavily upgraded and designed to mirror the model home. Over 3, 600 sq ft of luxurious living in a small enclave, just a couple of minutes’ walk from the amenity center, yet removed from community density — delivering luxury, privacy, nature and location in an exceptional, one of a kind offering. Enjoy sophisticated florida indoor-outdoor living with zero-corner sliding glass doors that open to an expansive oversized lanai with multiple seating areas for entertaining on a large scale; an oversized lap pool with a generous baja shelf for lounging; a panoramic screen showcasing uninterrupted long views of water, preserve and large flocks of birds in winter. Moving over to the front of the home, all rooms face serene preserve views, not other homes. Inside, elegance meets functionality. The expansive open floor plan has a great room with defined living and dining areas that flow seamlessly around a dream kitchen with a 10-foot quartz island, designer lighting, premium soft-close cabinetry, premium appliances, gas cooking, a walk-in pantry and upgraded tile flooring. The main level also includes a primary suite overlooking the pool, two picturesque bedrooms with walk-in closets, and a den/flex room to work or curl up cozily in. Wide crown molding all through, generous wainscoting, ceiling features and light fixtures were designed to replicate the model home. Upstairs, a huge bedroom, full bath, and a huge multi-purpose loft provide exceptional flexibility — perfect for guests, multigenerational living, media lounge, game room, fitness studio, or additional workspace. Multiple upgrades include impact doors and windows for full hurricane protection; smart home wiring; oversized 3 car garage; oversized lanai and pool. This home has an abundance of storage and is a one owner home. Located in sought-after winding cypress, residents pay surprisingly low hoa fees but enjoy a full range of world class amenities including guard-gated security, full landscaping maintenance, tennis, pickleball, bocce, restaurant/bar, 2 dog parks, walking trails and a truly stunning clubhouse with a state of the art fitness center, event space, an amazing resort-style pool and a full calendar of organized activities. Close to beaches, boating, downtown naples, marco island, and just minutes to golf, shopping, dining, and healthcare facilities. This is a rare opportunity!
Winding Cypress, 6844 Winding Cypress Dr, Naples, Florida 34114, image 1
$949,900
  • 3 Beds
  • 2 Baths
  • 2,100 SqFt
  • $452/SqFt
House for sale in Winding Cypress
6844 Winding Cypress Dr, Naples, FL 34114
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 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
Winding Cypress, 7545 Geranium Way, Naples, Florida 34114, image 1
$989,000
  • 2 Beds
  • 2 Baths
  • 2,036 SqFt
  • $486/SqFt
House for sale in Winding Cypress
7545 Geranium Way, Naples, FL 34114
Experience refined naples living in this impeccably maintained, fully furnished residence in the prestigious gated community of winding cypress. Featuring two bedrooms plus a den, two baths, plus an extended additional den leading to the waterfront pool area, and an extended 2-car garage; this home has been thoughtfully designed and is move-in ready - blending comfort, elegance, and effortless luxury. Inside, tiled wood-plank flooring flows seamlessly throughout, complemented by plantation shutters throughout the home that add both timeless elegance and privacy. The beautifully curated furnishings enhance each space, delivering a polished, designer feel from the moment you enter. The gourmet kitchen serves as the heart of the home, featuring a large center island with seating, a pantry closet, gas stove, and abundant cabinetry. Ideal for both everyday living and entertaining, the kitchen opens to the spacious dining and living areas, allowing for easy gatherings and relaxed conversation. The versatile den provides the perfect setting for a private office, media room, or additional guest accommodations. The primary suite is a luxurious retreat, complete with a spa-inspired bath and a recently customized walk-in closet designed for optimal organization and style. The guest bedroom and bath provide comfort and privacy for visitors. Step outside to your private oasis—a covered lanai with comfortable seating that transitions seamlessly to the screened-in pool and spa area. The expansive pavered deck surrounds a sparkling pool and spa accented by a tranquil waterfall feature, all overlooking a peaceful lake view. Storm smart lanai shutters offer added protection and convenience, while upgraded landscaping and lanai lighting create a stunning ambiance day and night. The beautifully landscaped lawn enhances the serene setting, delivering exceptional curb appeal and a tranquil outdoor backdrop. An underground gas generator provides an additional layer of security and peace of mind, ensuring uninterrupted comfort year-round. Winding cypress elevates the lifestyle even further with an impressive array of resort-style amenities. Residents enjoy a stunning clubhouse, state-of-the-art fitness center, resort-style pool and spa, tennis and pickleball courts, bocce, an on-site restaurant, community garden, dog park, and miles of scenic walking and biking trails. A vibrant social calendar and beautifully maintained grounds make every day feel like a private resort experience. Ideally situated just minutes from the world-class dining, upscale shopping, art galleries, and white-sand beaches of downtown naples, this home offers the perfect combination of luxury, location, and lifestyle. An exceptional opportunity to own a furnished, lakefront retreat in one of naples’ most sought-after communities.
Winding Cypress, 7457 Winding Cypress Dr, Naples, Florida 34114, image 1
$1,098,000 $33K
  • 3 Beds
  • 2 Baths
  • 2,166 SqFt
  • $507/SqFt
House for sale in Winding Cypress
7457 Winding Cypress Dr, Naples, FL 34114
Finally, your own private & serene oasis, you’ll never get tired of. This is not your typical rear lanai view, it is an actual expansive preserve view! This exceptional setting provides a rare sense of seclusion and tranquility, creating an authentic florida paradise lifestyle. This is a unique residence in winding cypress. This residence offers unmatched privacy and outdoor living, with exceptional standout features: an expansive screened lanai with custom multi-color accent lighting, saltwater, heated, multi-color lite pool, plus an outdoor dry bar with refrigerator and cabinetry—all designed to create your own private resort overlooking nature. Inside, every detail reflects model-quality craftsmanship and upgrades galore! The home showcases a chef’s kitchen with alexa-linked gas 5 burner stove/oven, upgraded cabinetry with pull-out drawers, upgraded appliances. A butler’s wine bar with under cabinet lighting cabinetry throughout, upgraded wine dual temp refrigerator, pantry shelving, all add elegance and convenience. Additional upgrades include custom wall features, garage hallway bench with storage unit, and abundant built-in closet storage. The primary suite is highlighted by a custom walk-in closet with cabinetry, blending function and style. Custom front and lanai accent lighting enhance both curb appeal and evening ambiance. Prewired for vitex audio video home automation. Winding cypress is one of naples’ premier resort-style communities, surrounded by 800 acres of preserve and 80 acres of lakes. Residents enjoy a zero-entry resort pool and spa, the shady palm café with full-service bar and grill, a state-of-the-art fitness center, pickleball and tennis courts, dog park, community garden, walking/biking trails, and a full social calendar curated by the on-site activities’ director. All of this is just minutes from downtown naples, marco island, beaches, world-class golf, shopping, and dining—yet with the peace and seclusion of a preserve setting. This is more than a home; it is a rare lifestyle opportunity combining privacy, luxury, and nature in perfect harmony.
Similar Communities & Listings
Results 3 of 38
Esplanade At Hacienda Lakes, 8209 W Lucello Ter, Naples, Florida 34114, image 1
$650,000
  • 2 Beds
  • 2 Baths
  • 1,558 SqFt
  • $417/SqFt
House for sale in Esplanade At Hacienda Lakes
8209 W Lucello Ter, Naples, FL 34114
Private, peaceful setting at the end of cul-de sac sits this brand new furnished villa with screened-in lania over looking the preserve. One story living, hassle free lifestyle, with 2 bedrooms, den/office, 2 baths, and 2- car garage. The decor is sleek with tones of grey and white contemporary lighting and fixtures gives a high energy “vibe”. Enjoy the resort lifestyle here at esplanade of hacienda lakes which includes 6, 500 sq. Ft. Club house, 24/7 fitness gym, circular resistance pool and spectacular lap pool, hot tub, fire-pit , umbrellas by the pool, and music, pickleball, tennis, bocce courts , playground dog park. Fun social events social & card room plus billiards. Everyone is raving about the amazing “over the top events “ the club put on.
Marbella Isles, 13419 Silktail Dr, Naples, Florida 34109, image 1
$625,000 $49K
  • 2 Beds
  • 2 Baths
  • 1,858 SqFt
  • $336/SqFt
Villa for sale in Marbella Isles
13419 Silktail Dr, Naples, FL 34109
Beautifully appointed attached villa featuring 2 bedrooms plus a den and 2 bathrooms, thoughtfully designed with an open and inviting layout. The home showcases custom wood flooring, brand-new carpet in the bedrooms, crown molding throughout, and elegant wainscoting in the dining room, creating a refined yet comfortable living space. A glass front door welcomes in natural light, while the impact-rated sliding glass door opens to a private screened-in lanai, perfect for relaxing or entertaining. Recent upgrades include a brand-new a/c system with a 10-year transferable warranty and uv light, offering peace of mind and energy efficiency. Located in the heart of naples within marbella isles, an active, resort-style community that delivers the ultimate luxury lifestyle. Residents enjoy an expansive clubhouse with a resort-style pool, private cabanas, kids’ splash park, and playground. Stay active with a state-of-the-art fitness center, game room, indoor basketball court, three tennis courts, four pickleball courts, and bocce courts, all fostering a vibrant and social atmosphere. Ideally situated with two convenient entrances, marbella isles is just 10 minutes from naples’ pristine beaches, mercato, and waterside shops, 15 minutes to downtown naples, and 25 minutes to the airport—offering the perfect blend of comfort, convenience, and coastal living.
Esplanade At Hacienda Lakes, 8111 Calle Canovas St, Naples, Florida 34114, image 1
$539,900 $20K
  • 2 Beds
  • 2 Baths
  • 1,552 SqFt
  • $348/SqFt
Villa for sale in Esplanade At Hacienda Lakes
8111 Calle Canovas St, Naples, FL 34114
Living in paradise made easy...Move-in ready! Step into effortless elegance and coastal comfort. Nestled in the popular esplanade of hacienda lakes, this charming villa is being offered "turnkey" and features 2 bedrooms and a versatile den, perfect for an additional guest room or office space. The extended screened in lanai backs to a tranquil preserve featuring a private garden area as an ideal space for pets or your own enjoyment. Enjoy cooking at home in this chef's delight gas cooking kitchen. Expansive countertops and a breakfast bar are ideal for entertaining in this large open concept living area with formal dining space. Laundry is made easy with new touch control lg washer & dryer in the large laundry rm w/ set tub. The attached 2 car garage offers plenty of storage and a convenient quick entry. The esplanade is a natural gas community~ you will truly enjoy this amazing location and being at the crossroads of marco island and naples beaches and iconic 5th ave. Residents enjoy access to the 6, 500 sq ft clubhouse with full time lifestyle director, 24/7 fitness center, resistance pool, lap pool, hot tub, yoga studio, pickleball, har-tru tennis courts, bocce, playground and dog parks. Very low hoa fees~ only $390 per month! Located on the hospital grid..No flood required. Come be my neighbor and enjoy this really fun community with amazing social events!
1 - 3 of 38 Results
Subdivision Amenities
Bike And Jog Path
Bocce Court
Business Center
Cabana
Clubhouse
Community Room
Dog Park
Fitness Center
Hobby Room
Internet Access
Library
Park
Pickleball
Play Area
Pool
Private Membership
Restaurant
Shuffleboard Court
Sidewalk
Spa/Hot Tub
Streetlight
Tennis Court(s)
Underground Utility
Barbecue
Bike And Jog Path
Bocce Court
Clubhouse
Frequently Asked Questions

The current monthly maintenance fee at Winding Cypress is ~0.23 per unit SqFt.

The single_family_home dues at Winding Cypress cover: Insurance, Irrigation Water, Lawn/Land Maintenance, Legal/Accounting, Manager, Master Assn. Fee Included, Pest Control Exterior, Rec Facilities, Repairs, Reserve, Street Lights, Street Maintenance, Irrigation Water, Cable, Internet/Wi Fi Access, Security, Trash Removal, Lawn/Land Maintenance, Sewer, .

Winding Cypress Interior features include: French Doors, Pantry, Smoke Detectors, Tray Ceiling(s), Laundry Tub, Window Coverings, Laundry Tub, Volume Ceiling, Built-In Cabinets, French Doors, Walk-In Closet(s), Foyer, Pantry, Wired for Sound, Vaulted Ceiling(s), Bar, Coffered Ceiling(s), Pull Down Stairs, Zero/Corner Door Sliders, Foyer, Closet Cabinets, Closet Cabinets, Built-In Cabinets

Winding Cypress unit views: Landscaped Area, Preserve, Trees/Woods, Lake, Preserve, Landscaped Area, Water, Privacy Wall

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Scores
Walk Score®
Car-Dependent. Almost all errands require a car.
0

100
Transit Score®
Minimal Transit. It is possible to get on a bus.
0

100
Bike Score®
Somewhat Bikeable. Minimal bike infrastructure.
29

100
Sound Score®
Very loud.
0

100
Naples
Mid-Tier Homes & Condos
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