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Winding Cypress Naples Florida Homes for Sale

Naples Florida Real Estate

Winding Cypress Naples Real Estate

Homes For Sale29$549K - $1.8M
Sold30$529K - $1.9M
Last updated at 5:45am 05/23/2024

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$1,775,000
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$75K
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Winding Cypress

6932 Cocoplum St, Naples, FL 34114

Homes - 2,515 ft² / 3,400 ft² - 3 Car Garage

3+Den / 3 Baths / Pool / Spa

Built 2019
Winding Cypress Naples Homes for Sale: A staggering mix of natural beauty and fabulous Naples living. This jewel box home is situated on one of the most desirable lots in Winding Cypress. Look at the aerial view, simply breathtaking. Lot location had a $125,000 premium.Coveted Southern exposure Peaceful and full of nature. Well-designed, expansive floor plan offering generous size rooms, an outstanding white kitchen that is perfect for the serious cook or entertaining. You will love the large island, wine cooler, massive pantry, and natural gas. Split living area with unique closets and storage everywhere. Soaring ceilings. The west wing encompasses an impressive size Owner suite complete with massive walk-in closet. More than 2 cars? No worries, there is garage parking for 3. For the enjoyment of nature spend time in your southern exposure, spacious salt water pool/spa or patio with outdoor kitchen or relax on your lounger in the pool. A patio you can use year round unlike west facing patios that are so hot . Additional peace of mind is offered with impact windows and a generator. Please note this is not the base Pinnacle floor plan, this is top of the line and highly upgraded. Located off the main road on a cul de sac street. You must see this home. Winding Cypress is a wonderful community. Amenity rich with a low HOA. Amenity rich with low HOA Look what the community offers: Neighborhood Features Natural Gas Community ,800+ Acres of Natural Preserves, Heated Resort-Style Pool & Spa Poolside. sugar-sand beach and cabanas ,17,500 sq. ft. Clubhouse with Activity Room, Catering Kitchen & Library, State of the Art Fitness Center & Movement Studio. Outdoor Barefoot Bar and Grill, Natural Gas Fire Pit , Activity Director, 4 Bocce Ball Courts ,Tennis Courts, 4 Pickleball Courts, Dog Park, Community Garden, Boardwalk with Pavilion and Bird Wading. Overlook 80 Acres of Lakes.Home Lawn Maintenance included. Entry Gate with Guard House. Less than 3 miles from US-41 ,10 Minutes to I-75 ,15 Minutes to Fifth Avenue and Third Street Shopping & Dining, 20 Minutes to Naples Pier and magnificent area beaches. 20 Minutes to Marco Island prepared with care but subject to errors and ommissions Buyer to verify everything to their satisfaction



$1,600,000
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Winding Cypress

6909 Winding Cypress Dr, Naples, FL 34114

Homes - 2,522 ft² / 3,501 ft² - 3 Car Garage

3+Den / 3 Baths / Pool / Spa

Built 2019
Winding Cypress Naples Homes for Sale: Welcome to your dream home in the coveted natural gas community of Winding Cypress. This stunning residence epitomizes luxury living in paradise. Prepare to be captivated as you step through the leaded glass door into a haven of elegance and comfort. This meticulously crafted Pinnacle Model features an array of upgrades, ensuring a lifestyle of sophistication, convenience and peace of mind. You're secure with the hurricane impact windows, zero corner slider, and whole house generator. From the moment you enter, the attention to detail is evident with the expansive 11-foot ceilings adorned with coffered trays, crown molding, LED lighting and wood flooring throughout. The open-concept layout seamlessly blends indoor and outdoor living, creating a space perfect for both relaxation and entertaining. The chef's kitchen, where culinary delights await include Quartz countertops, 42-inch luxury cabinets with soft closures and pull-out drawers, under-cabinet lighting, top-of-the-line appliances ,a natural gas cooktop and separate wall oven. A built in entertainment area with wine or beverage cooler adds a touch of glamour, perfect for hosting gatherings with friends and family. Retreat to the spacious owner's suite, with custom California Closets and luxurious ensuite bathroom with enlarged shower, upgraded fixtures and faucets. Two additional large bedrooms with custom closets systems, including a second ensuite, offer ample space for guests or family members. The additional den or study provides the ideal setting for productivity and creativity. Step outside to your own private oasis, where breathtaking long lake sunset views are unobstructed through the panoramic screen. The outdoor living area is a true sanctuary, featuring a custom heated saltwater pool with additional water features, a custom gas summer kitchen, and expansive dining and sitting areas. Electric Storm Smart Kevlar Screens provide added comfort and protection, allowing you to fully enjoy the Florida lifestyle year-round. Beyond the luxurious amenities of the home, Winding Cypress offers a wealth of community features, including a residents-only restaurant, resort-style pool with spa and cabanas, pickleball, tennis, and bocce courts. The expansive community center boasts an event room with catering kitchen, library, internet cafe, awesome fitness center, and lounge areas with gas fireplaces. Nature enthusiasts will appreciate the boardwalk nature trail, providing a serene escape into the preserve. Conveniently located just minutes from the pristine beaches of Marco Island and the vibrant dining, shopping, and entertainment of downtown Olde Naples it's the perfect blend of tranquility and convenience. Enjoy plenty of golf options just around the corner. Don't miss this opportunity to make this exquisite home your own. With all the features and upgrades already in place and no wait to move in, this property represents an exceptional value compared to new construction.



$1,599,900
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Winding Cypress

6962 Winding Cypress Dr, Naples, FL 34114

Homes - 2,952 ft² / 4,247 ft² - 3 Car Garage

3+Den / 3 Baths / 1 Half / Pool

Built 2020
Winding Cypress Naples Homes for Sale: This home is truly a showstopper , priced below market value and offering a "wow" factor that is hard to beat. The Stonewater model is the largest home built in Winding Cypress built in 2020 and still looks and feels like brand new. With approx.3000 sq. ft. of grand open space you'll be captivated from the moment you walk through the double front doors into the gracious foyer. The home features 13ft. coffered ceiling in the great room , formal dining area or custom for your use, office with glass French doors , 3 bdrms , 3 baths three car garage The lanai boasts a sought-after pool with pool bath ,a relaxing backdrop of the lake and peaceful preserve complete with an outdoor kitchen and hurricane shutter. Lanai furniture included in sale. This light and bright home is impeccable maintained and truly in like new condition. Added bonus a whole house generator adding peace of mind. Winding Cypress offers a wealth of amenities including a beautiful resort pool and restaurant. Don't miss the opportunity to see and appreciate the beauty of this exceptional home. Winding Cypress is conveniently located just 15 min to Marco Island , 75 and Downtown Naples



$1,575,000
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Winding Cypress

7478 Winding Cypress Dr, Naples, FL 34114

Homes - 2,619 ft² / 3,097 ft² - 3 Car Garage

3+Den / 3 Baths

Built 2016
Winding Cypress Naples Homes for Sale: Introducing a stunning home for sale in the prestigious Winding Cypress community of Naples, Florida, crafted by the renowned DiVosta Builders. This exquisite property presents the highly sought-after Infinity Model, an exceptional residence celebrated for its expansive open floor plan and unparalleled luxury features. Nestled within the coveted Winding Cypress community, this home stands out as one of only three Infinity Models among over 750 homes, making it a rare gem in an already exclusive neighborhood. Boasting meticulous attention to detail and an array of upgrades, this residence offers a lifestyle of opulence and sophistication. Step inside to discover an inviting ambiance accentuated by soaring 11-foot plus tray ceilings adorned with elegant crown molding. The vast living space encompasses a generously proportioned great room, a gourmet kitchen, separate dining and eat-in areas, as well as a casual and inviting conversation space, perfect for hosting guests or simply relaxing in style. The chef-inspired kitchen is a culinary masterpiece, featuring top-of-the-line Thermador gas cooktop and range, a luxurious Liebherr refrigerator encased in custom built-in cabinets, quartz-leather finish countertops, and a spacious center island with a breakfast bar, ideal for entertaining with flair. Designed for luxury, convenience, and peace of mind, this home boasts an array of upgrades, including hurricane impact windows and doors, a zero-corner slider, custom closets and shelving, a built-in outdoor kitchen, whole house generator, tankless water heater, extended 3-car garage with epoxy floor and additional cabinets, insulated door, and mini-split air conditioner. Further enhancing the living experience are the whole house water filtration system, central vacuum, solid 8-foot doors, custom floor tiles, home security system, extended lanai, laundry tub, plus a utility tub in the garage, custom faucets and fixtures, designer window treatments and shades, and upgraded attic insulation throughout. Winding Cypress offers an unparalleled lifestyle with its wealth of amenities and prime location. Just 10 minutes from the pristine beaches of Marco Island and 15 minutes to the vibrant downtown area of Olde Naples, residents enjoy easy access to fine dining, boutiques, and entertainment options. Within the gated confines of Winding Cypress, residents are treated to resort-style amenities, including a spectacular pool and spa, residents-only restaurant, state-of-the-art fitness center, pickleball, tennis, and bocce courts, as well as a community center with conference rooms, library, internet cafe, gas fireplaces, and a picturesque boardwalk along a nature trail. Spanning over 1200 acres, with 800 acres dedicated to green space, Winding Cypress offers a serene and private setting, ensuring residents will enjoy the ultimate Florida lifestyle surrounded by natural beauty and luxury amenities.



$1,499,900
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Winding Cypress

7039 Winding Cypress Dr, Naples, FL 34114

Homes - 2,496 ft² / 3,600 ft² - 3 Car Garage

3+Den / 3 Baths / Pool

Built 2016
Winding Cypress Naples Homes for Sale: This exquisite Pinnacle-Style estate home is located in the highly sought community of Winding Cypress and is just a short walk to all of the community amenities. As you step inside you'll be impressed by the meticulous attention to detail throughout the home. Beautiful balance of rich dark woods balanced with white cabinets , zero corner clearance door for that wow effect allowing the outside in, to the custom California Closets , motorized shades in primary bedroom and dining room, no detail has been overlooked. The home also features impact-resistance windows , hurricane screens on lanai and front entry , a whole house generator.and an added bonus a mini split A/C in garage to keep your cars and storage cool . Enjoy your outdoor lanai with heated pool and out- door kitchen overlooking the lake .This home is a must see Winding Cypress is just 15 mins to Marco Island , 15 min to 75 and 15 mins to downtown the perfect location



$1,375,000
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Winding Cypress

7415 Chenille Ct, Naples, FL 34114

Homes - 2,532 ft² / 3,518 ft² - 3 Car Garage

3+Den / 3 Baths

Built 2016
Winding Cypress Naples Homes for Sale: Welcome to your dream home in the heart of Naples, Florida's coveted Winding Cypress community, where luxury living meets natural splendor. Nestled on a spacious estate lot along a tranquil cul-de-sac, this stunning residence is your choice for Florida living. Step into the highly desired Pinnacle model, crafted by the esteemed builders DiVosta and prepare to be enchanted by its elegant design and thoughtful upgrades. Boasting 3 bedrooms plus den/office and 3 full bathrooms, including an expansive owner's suite with a custom built-in closet system along with additional built in vanity area, this home offers both comfort and style at every turn. As you explore, you'll discover a chef's kitchen that will delight culinary enthusiasts, complete with dovetail and soft closure cabinets, a separate bar/ wine cooler, quartz countertops, and under-cabinet lighting. The attention to detail is evident throughout, from the 11 ft coffered-tray ceilings to the custom Granite Wall, double crown moldings. Plantation shutters, 8-foot doors, custom draperies and designer light fixtures throughout. No luxury has been spared in this residence, with custom tile adorning every room, hurricane impact windows and a whole house generator ensuring peace of mind during storm season. Enjoy the convenience of a tankless hot water heater, reverse osmosis water purifier, whole house surge protector, security system and built in overhead surround sound system making everyday living effortless and efficient. Entertain guests in style with a zero-corner slider seamlessly connecting the indoor and outdoor living spaces and complete outdoor kitchen for an alfresco dining option. Private rear area offers you plenty of space to design your own custom pool or extended outdoor living area of your choice. Beyond the confines of this exceptional home lies the vibrant community of Winding Cypress, where residents enjoy an unparalleled array of amenities. Dive into relaxation at the resort-style pool and spa, savor delicious meals at the residents-only restaurant, or host gatherings in the expansive community center with event room, library and outdoor fireplace. Stay active and connected with state-of-the-art fitness facilities and a boardwalk nature trail within the 800 acres of preserved green space. With its prime location just 15 minutes from iconic downtown Olde Naples and 10 minutes from the pristine shores of Marco Island, Winding Cypress offers the perfect blend of luxury, convenience, and natural beauty. Don't miss your chance to call this exquisite property home and experience the best that Naples has to offer. Start living the Florida lifestyle of your dreams.



$1,300,000
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$50K
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Winding Cypress

6906 Winding Cypress Dr, Naples, FL 34114

Homes - 2,124 ft² / 2,961 ft² - 2 Car Garage

3+Den / 3 Baths / Pool

Built 2022
Winding Cypress Naples Homes for Sale: This gorgeous Mystique pool home is being offered turnkey furnished and was inspired by the model home. It features 3 bedrooms, plus a den, 3 full bathrooms, and a 2 car extended garage. The endless upgrades feature zero corner sliders, tile throughout, Hunter Douglas electric blinds, exterior cameras, two toned cabinets, upgraded and built in appliances, whole home water filtration system, cabinets in the laundry room, extended garage, extra long driveway, and so much more! The outdoor oasis features a saltwater pool with an upgraded Pentair MT400 rodent proof heater, gorgeous lanai and landscape (front and backyard) lighting, preserve view, and additional landscaping to ensure privacy. Winding Cypress has amenities galore! Enjoy dining at Shady Palm, the onsite restaurant, play pickleball, bocce, tennis, workout in the state of the art fitness center or lounge by the resort style pool, garden at the community garden, or take fido to the dog park! Winding Cypress is pet friendly, allows rentals, has low fees and is centrally located between Marco Island, 5th Ave, & I75 making it an ideal location!



$1,300,000
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Winding Cypress

7493 Winding Cypress Dr, Naples, FL 34114

Homes - 2,914 ft² / 3,892 ft² - 2 Car Garage

4+Den / 3 Baths / Pool / Spa

Built 2020
Winding Cypress Naples Homes for Sale: Gorgeously appointed turnkey furnished 2 story Summerwood for sale featuring 4 bedrooms, 3 bathrooms, den, loft, extended 2 car garage, pool & spa! This home has it all when it comes to upgrades, from the zero corner sliders, built in appliances, plantation shutters, in ceiling Sonos speakers, crown molding, storm smart shutters all around, 2 separate living rooms with the loft and so much more. The outdoor oasis features an extended covered lanai, outdoor kitchen, mounted tv, pool and spa overlooking a gorgeous preserve for the utmost privacy! Winding Cypress has amenities galore...Enjoy dining at Shady Palm, the onsite restaurant, play pickleball, bocce, tennis, workout in the state of the art fitness center or lounge by the resort style pool, garden at the community garden, or take fido to the dog park! Winding Cypress is pet friendly, allows rentals, has low fees and is centrally located between Marco Island, 5th Ave, & I75 making it an ideal location!



$1,150,000
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$125K
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Winding Cypress

7063 Winding Cypress Dr, Naples, FL 34114

Homes - 2,496 ft² / 3,656 ft² - 3 Car Garage

3+Den / 3 Baths

Built 2016
Winding Cypress Naples Homes for Sale: Wow Wow Wow a Pinnacle model at Winding Cypress offered at 1,150,000 !!!!!!! This spacious home offers nearly 2500 sq/ft of living space with an extended lanai, perfect for adding your own custom pool not a stock builders pool. to enjoy the lake views. With 3 bedrooms three full baths office/den and a three-car garage. The expensive items such as hurricane impact windows whole House generator, and storm screens on the lanai have been done for peace of mind. This home is ready for your personal touches to design for your needs . This home is located within walking distance to club house dog park, community gardens resort pool, pool side restaurant and all the amenities Winding Cypress offers sure to keep you entertained all year long. Priced for immediate sale , a must-see for those who can envision the value and potential equity with adding their own custom touches.



$1,100,000
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Winding Cypress

7554 Blackberry Dr, Naples, FL 34114

Homes - 2,867 ft² / 3,648 ft² - 2 Car Garage

3+Den / 3 Baths / Pool

Built 2017
Winding Cypress Naples Homes for Sale: Welcome to the award-winning Martin Ray home in the prestigious and central Winding Cypress resort community in Naples. This exceptional home boasts a stunning custom pool and lanai, complete with an in-water sundeck, ideal for soaking the Florida sunshine. Relax and unwind as you enjoy the picturesque views of the private waterfront. Inside, you'll find a bright and airy ambiance, highlighted by top-of-the-line quartz finishes and gourmet appliances powered by natural gas. Whether you're hosting a lavish gathering or enjoying a quiet evening in, this home offers the ideal blend of elegance and comfort. A bonus loft offers a cool option for guests or in-home entertainment with plenty of room for a pool table or even a home theater! Residents will enjoy the luxurious Winding Cypress clubhouse, offering a state-of-the-art fitness center, catering kitchen, community room and activity room. Outdoor amenities abound, from pickleball, resort-style and lap pools to a spa, outdoor movement studio, barefoot bar, bocce ball courts, five Har-Tru tennis courts, fire pit, bird-watching overlook and a nature boardwalk with a picnic pavilion. In ideal proximity to the pristine shores of Marco Island and vibrant downtown Naples, this amazing resort location provides the ideal backdrop for an unparalleled lifestyle.



$1,048,000
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Winding CypressNEW

6801 Greenbriar Ct, Naples, FL 34114

Homes - 2,152 ft² / 2,582 ft² - 2 Car Garage

4 Bed / 3 Baths / Pool

Built 2022
Winding Cypress Naples Homes for Sale: Like new, two years old four bedroom, three-bathroom residence in Winding Cypress. House has been totally custom remodeled. This furnished home showcases new furniture and TVs, finished with 9’ ceilings, 8’ doors, pristine tile floors. The gourmet kitchen features high end appliances with gas cooking, pullout drawer cabinets, designer backsplash, pantry, and a large center island. Each bedroom has an in-suite bathroom. Outside, you’ll find a WiFi-controlled heated pool and screened lanai with build- in barbeque grill. Extended driveway, two-car garage , epoxy floor, and overhead storage. Winding Cypress residents have access to a clubhouse with a social room, library, fitness center, resort-style pool and spa, outdoor bar and grill, tennis, pickleball, bocce, dog park, and a full social calendar. Just 15 minutes to downtown Naples and Marco Island. CDD paid in full.



$995,000
Decrease*
$155K
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Winding Cypress

7592 Winding Cypress Dr, Naples, FL 34114

Homes - 2,159 ft² / 2,550 ft² - 2 Car Garage

4 Bed / 2 Baths / Pool

Built 2021
Winding Cypress Naples Homes for Sale: Welcome to your FULLY FURNISHED TURNKEY dream home nestled in the amenity rich community of Winding Cypress, where luxury living meets serene surroundings in beautiful Naples. This meticulously maintained residence presents a rare opportunity to indulge in modern elegance and comfort. Upon entering through the leaded glass front door, you're greeted by an inviting atmosphere accentuated by the spectacular open floor plan living. The seamless integration of space creates an airy ambiance, perfect for both relaxation and entertainment. The unique custom detailed millwork interior adds a touch of sophistication, elevating the home's aesthetic appeal. The heart of the home lies in its chef-inspired kitchen, you will be delighted with abundant storage, granite counters, gas cooking, while a breakfast bar offers a casual dining option. Whether preparing a gourmet meal or enjoying a quick snack, this kitchen is sure to inspire culinary creativity. This residence offers plenty of space for family and guests alike. The master retreat is a sanctuary of comfort, featuring a spacious layout, walk-in closets, and a spa-like ensuite bath, providing the perfect retreat after a day of coastal adventures. Step outside to discover where relaxation and recreation blend seamlessly. A pristine heated saltwater pool offers a refreshing swim from the sun-drenched afternoons. Host gatherings with ease in the full outdoor kitchen, complete with a grill, and ample seating space. Covered sitting areas provide shade and tranquility, ideal for unwinding with a good book or enjoying alfresco dining under the stars. You will enjoy the ease of accordion hurricane shutters along with electric Kevlar Storm Smart screens that provide added safety and peace of mind. Winding Cypress offers an array of resort-style amenities for residents to enjoy. From scenic walking trails, a resident's only restaurant, pickleball and tennis courts, to a state-of-the-art fitness center and clubhouse, there's something for everyone to indulge in. Located just 10 minutes from the pristine beaches of Marco Island and a short drive from the vibrant boutiques, restaurants, and shops of iconic 5th Avenue in Olde Naples, this home offers the perfect blend of tranquility and convenience. Don't miss your chance to own a piece of paradise in Winding Cypress.



$925,000
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Winding Cypress

7420 Winding Cypress Dr, Naples, FL 34114

Homes - 2,198 ft² / 2,626 ft² - 2 Car Garage

4 Bed / 2 Baths / Pool / Spa

Built 2017
Winding Cypress Naples Homes for Sale: Winding Cypress is the ultimate Naples resort community, and this home serves as the ultimate poolside retreat. The long southwest water views seamlessly blend waterfront serenity, preserved nature, and privacy. Adorning the oversized covered lanai is a deluxe outdoor kitchen complete with every conceivable feature and top-grade finishes. This award-winning Summerwood floor plan boasts every builder upgrade, including a double oven gourmet kitchen, top-of-the-line cabinets, crown molding, tray ceilings, easy-glide retractable storm shutters, and more. The open concept layout is enhanced with strategically placed windows, optimizing natural light and facilitating flexible furniture arrangement, making this home an ideal canvas for any decor. Residents can indulge in the luxurious Winding Cypress clubhouse, featuring a state-of-the-art fitness center, catering kitchen, community room, and activity room. Outdoor amenities abound, encompassing pickleball courts, resort-style and lap pools, a spa, an outdoor movement studio, a barefoot bar, bocce ball courts, five Har-Tru tennis courts, a fire pit, bird-watching overlook, and a nature boardwalk with a picnic pavilion. Ideally situated near the pristine shores of Marco Island and the vibrant downtown Naples, this resort community offers an unparalleled lifestyle.



$899,999
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$98K
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Winding Cypress

7454 Winding Cypress Dr, Naples, FL 34114

Homes - 2,673 ft² / 3,682 ft² - 3 Car Garage

3+Den / 3 Baths

Built 2016
Winding Cypress Naples Homes for Sale: As you enter this 2 Story Martin Ray model located in beautiful Winding Cypress, the long water view is breathtaking not to mention the peaceful sunset views from the SSW exposure. This home has many Upgrades and Storage Galore!! Hurricane Impact Windows throughout the house, Master Bedroom on First Floor, Foam insulation upstairs, 4 Extra feet of length in the Tandem Garage allow for Plenty of space for a Golf cart or your Boat. Porcelain tile throughout the downstairs and Wood Floors upstairs. Crown molding, Built-in Kitchen appliances, 8ft door downstairs. Oversized Lot with 67' frontage makes it easy to add a Pool. Extended Paver Lanai, Paver walkway on the side of the home, Full house Generator, Split Unit A/C in the Garage, Additional insulation over the garage, Pull down stairs to attic, Widened Driveway, Ballistic Nylon Hurricane Shutters for the covered part of the Lanai, Plus additional Shade Flower Trees Planted. All this and more make this home Your piece of Paradise! Seller is a Florida licensed Real Estate Broker.



$899,900
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$50K
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Winding Cypress

7467 Blackberry Dr, Naples, FL 34114

Homes - 2,198 ft² / 2,663 ft² - 2 Car Garage

3 Bed / 2 Baths

Built 2017
Winding Cypress Naples Homes for Sale: Welcome home to the popular Winding Cypress gated community! Spectacular private water and nature preserve views from your own premium lot’s lanai and backyard. This fresh and pristine home will exceed your expectations. An impressive custom door welcomes you inside to an open great room with elevated, coffered ceilings & high end finishes throughout. Great flow and spaciousness, expanding through the sunroom. The kitchen showcases a huge island, SS appliances, premium cabinetry, marble backsplash, quartz countertops, & pantry. The dining area has an elegant crystal chandelier. The primary suite features a tray ceiling, crystal chandeliers, and European wide plank wood flooring. (This flooring is in all bedrooms). The luxury bath is complete with double sinks, frameless shower, linen closet, and special Ballard Design fitted closet. The Study/den has French doors & wood floors. Large tile set on the diagonal complete the upgraded flooring (no carpet). Plantation shutters in all 3 bedrooms and study. Upgraded laundry room. Motorized weather protection panels installed (lanai & sunroom). This community consists of 1100 acres, 800 acres of which are preserved and natural. Resort Amenities. Landscape maintenance included. Close to hospitals, restaurants, shopping, beaches and the posh downtown area. Come See!



$799,900
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$50K
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Winding Cypress

7670 Jacaranda Ln, Naples, FL 34114

Homes - 1,594 ft² / 1,964 ft² - 2 Car Garage

3 Bed / 2 Baths / Pool

Built 2018
Winding Cypress Naples Homes for Sale: Step into the lap of luxury with this stunning villa in Winding Cypress. This exquisite property is not just a home; it's an embodiment of sophistication and comfort, offering a lifestyle that is truly unparalleled. The villa is being offered fully furnished, ensuring that every inch of this residence reflects a tasteful and cohesive design. As you enter, you'll be captivated by the elegance that defines every detail. The gas-heated pool beckons, inviting you to relax and unwind in your private oasis. The outdoor kitchen adds a touch of opulence, making it an ideal space for entertaining guests or enjoying alfresco dining under the clear Florida skies. The chef's dream kitchen is a masterpiece in itself, featuring top-of-the-line Samsung appliances and stunning quartz countertops. The list of updates is extensive, a testament to the commitment to maintaining this villa in peak condition. While it's impossible to detail every enhancement, rest assured that no expense has been spared in ensuring that this property remains at the pinnacle of luxury living.



$789,000
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Winding CypressNEW

7247 Live Oak Dr, Naples, FL 34114

Homes - 1,910 ft² / 2,435 ft² - 2 Car Garage

2+Den / 2 Baths

Built 2015
Winding Cypress Naples Homes for Sale: Welcome to one of the most desirable neighborhoods in Naples. Winding Cypress boasts resort style living with pickleball, tennis, bocci, large gym, movement room, library, internet cafe, banquet room with kitchen, restaurant, and resort style pool with waterfall and lap lane. Currently the only Summerwood model for sale with peaceful panoramic water and preserve views. This impeccably kept, two bedrooms with a den that could easily be a third bedroom, 2 bath home with large laundry room with tons of custom cabinetry. An oversized garage with golf cart area and four foot extension, custom storage gives you plenty of room for all your toys.



$769,000
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Winding Cypress

7793 Jacaranda Ln, Naples, FL 34114

Homes - 1,554 ft² / 1,898 ft² - 2 Car Garage

2+Den / 2 Baths / Pool

Built 2019
Winding Cypress Naples Homes for Sale: Rare opportunity to own the crème de la crème villa in Winding Cypress. This pool home features 2 bedrooms, plus den, 2 bathrooms and a 2 car garage and is being offered turnkey furnished! The property boasts exceptional upgrades, including impact windows, a whole-house generator, crown molding, tile throughout, electric hurricane screens, upgraded appliances, closet systems throughout and so much more. The outdoor oasis features a gorgeous outdoor kitchen, remote control awning for additional shade, and arguably one of the best lake views in all of Winding Cypress! Winding Cypress has amenities galore! Enjoy dining at Shady Palm, the onsite restaurant, play pickleball, bocce, tennis, workout in the state of the art fitness center or lounge by the resort style pool, garden at the community garden, or take fido to the dog park! Winding Cypress is pet friendly, allows rentals, has low fees and is centrally located between Marco Island, 5th Ave, & I75 making it an ideal location!



$745,900
Decrease*
$23.1K
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Winding Cypress

7248 Live Oak Dr, Naples, FL 34114

Homes - 1,685 ft² / 2,300 ft² - 2 Car Garage

2+Den / 2 Baths

Built 2016
Winding Cypress Naples Homes for Sale: Live the good life. Time to enjoy life. So well cared for. 2+Den but den could have a closet making it a 3/2. Enjoy the private park like back yard. Extended screened patio with outdoor kitchen perfect for dining al fresco. Light bright home with all the goodies. Community even has a dog park for Fido. Amenity rich community with low HOA Look what the community offers Neighborhood Features Natural Gas Community 800+ Acres of Natural Preserves Heated Resort-Style Pool & Spa Poolside sugar-sand beach and cabanas 17,500 sq. ft. Clubhouse with Activity Room, Catering Kitchen & Library State of the Art Fitness Center & Movement Studio Outdoor Barefoot Bar and Grill Natural Gas Fire Pit Activity Director 4 Bocce Ball Courts Tennis Courts 4 Pickleball Courts Dog Park Community Garden Boardwalk with Pavilion and Bird Wading Overlook 80 Acres of Lakes Home Lawn Maintenance included Entry Gate with Guard House Less than 3 miles from US-41 10 Minutes to I-75 15 Minutes to Fifth Avenue and Third Street Shopping & Dining 20 Minutes to Naples Pier and magnificent area beaches 20 Minutes to Marco Island prepared with care but subject to errors and ommissions Buyer to verify everything to thier satisfaction



$725,000
Decrease*
$174K
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Winding Cypress

7267 Live Oak Dr, Naples, FL 34114

Homes - 2,230 ft² / 2,634 ft² - 2 Car Garage

3+Den / 2 Baths

Built 2015
Winding Cypress Naples Homes for Sale: Just reduced $64K! Looking for the best valued single family home in Naples? As the lowest price home (without a pool) in the Winding Cypress community, you will enjoy the quiet, intimate, and naturally beautiful environment with lovely amenities and low HOA fees. With state-of-the art design, this home enjoys both privacy and a lush botanical view, with its glorious gardens and plantings. The gourmet kitchen boasts walnut cabinets, high-end granite countertops, a large center island with breakfast bar and stainless-steel appliances including natural gas cooking. You will find ample room to entertain your family and guests with three bedrooms; the Owners Suite is generously sized with double vanity sinks and large shower. Finishes include plantation shutters, wainscoting, crown moldings and tile floors everywhere. Dine at the breakfast bar and also separate dining area. French Doors lead to a private office/den. Relax or entertain in the bright and spacious gathering room with an added sunroom that walks out to a screened lanai. Step outdoors and savor a sanctuary of comfort and tranquility from another paver-lined outdoor patio where you can enjoy a raised herb garden and colorful flowering trees of many varieties while you sip your morning coffee or afternoon tea. And not to worry…there is hurricane protection on the windows including Storm Smart hurricane screens on the lanai. Winding Cypress residents have access to a clubhouse with a social room, library, fitness center, resort-style pool and spa, outdoor bar and grill, tennis, pickleball, bocce, dog park, and a full social calendar. It is a pet friendly neighborhood with two off-leash gated dog runs. This home is conveniently located between Marco Island and downtown Naples and is in the perfect location to enjoy all that Southwest Florida has to offer.



$700,000
Decrease*
$20K
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Winding Cypress

7781 Jacaranda Ln, Naples, FL 34114

Homes - 1,554 ft² / 1,898 ft² - 2 Car Garage

2+Den / 2 Baths / Pool

Built 2018
Winding Cypress Naples Homes for Sale: Arguably one of the best views in Winding Cypress! Don't miss your chance to snag this 2 bedroom plus den, 2 bath, 2 car garage Serenity villa with a heated saltwater pool! This home features a view that can't be beat, a huge pie shaped lot offering extensive privacy, a pool water feature, granite countertops, trey ceilings, tile on the diagonal, glass French doors to the den, and so much more. This home has never had pets and has hardly been lived in! Winding Cypress has amenities galore! Enjoy dining at Shady Palm, the onsite restaurant, play pickleball, bocce, tennis, workout in the state of the art fitness center or lounge by the resort style pool, garden at the community garden, or take fido to the dog park! Winding Cypress is pet friendly, allows rentals, has low fees and is centrally located between Marco Island, 5th Ave, & I75 making it an ideal location!



$687,000
Decrease*
$32K
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Winding Cypress

7113 Live Oak Dr, Naples, FL 34114

Homes - 1,554 ft² / 2,748 ft² - 2 Car Garage

3 Bed / 2 Baths / Pool

Built 2016
Winding Cypress Naples Homes for Sale: Discover this stunning 3-bedroom, 2-bathroom villa with a 2-car garage and a luxurious gas heated pool that is ideally situated on a premium pie-shaped lot adjacent to nature preserve and near to the vibrant Winding Cypress Amenity Center is the perfect place to make your own paradise. The flex room offers endless possibilities as a third bedroom or as a home office/den. The Serenity Model offers the perfect blend of charm and sophistication, whether you seek a year-round haven or a seasonal escape to enjoy Florida's renowned lifestyle. Indulge in effortless entertaining as the seamless open floor plan leads you to a covered lanai and expansive brick paver pool deck that gazes out onto a serene nature preserve. Witness breathtaking sunsets that paint the sky in hues of warmth while serenaded by the harmonious symphony of nature within your private screened enclosure in the prestigious Winding Cypress community. This home has features including stainless-steel appliances, elegant granite countertops, a beautifully tiled backsplash in the kitchen, and 20" ceramic tile flooring throughout the main living spaces. Noteworthy accents such as plantation shutters, rich wood flooring in the den, accordion hurricane shutters, an electric rolldown hurricane shutter at the lanai, and a host of other upscale finishes. Nestled within a secure, amenity-rich enclave, residents enjoy access to a lavish Community Center, overseen by a full-time activities’ director, offering an array of recreational facilities from card/game rooms and a library to a poolside bar and restaurant. Stay active with a state-of-the-art gym, outdoor Yoga and movement studios, group exercise classes, a resort-style pool with a dedicated lap lane, inviting fire pits, dog parks for both large and small dogs, illuminated tennis courts, pickleball and bocce courts, and sprawling lakes and nature preserves spanning nearly 800 acres, providing boundless walking and riding trails for outdoor enthusiasts. Perfectly positioned in proximity to upscale shopping, dining venues, the sandy beaches of Naples and nearby Marco Island, the ambiance of downtown Naples along 5th Avenue & 3rd Street, as well as convenient access to medical facilities, educational institutions, places of worship, I-75, RSW International Airport, and the breathtaking wonders of the Florida Everglades.



$665,000
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Winding Cypress

7663 Jacaranda Ln, Naples, FL 34114

Homes - 1,554 ft² / 1,898 ft² - 2 Car Garage

3 Bed / 2 Baths

Built 2017
Winding Cypress Naples Homes for Sale: Welcome to the ultimate villa in Winding Cypress. This is the rare opportunity to own the unique and wildly popular Serenity model with the fully expanded lanai screened and paver play deck with the bonus third bedroom den option and newly added whole-home generator powered by direct natural gas. Enjoy outstanding privacy and ample space inside and out, with a fully landscaped private lanai featuring a large roof covered seating and entertaining area. The layout inside includes an extremely spacious owner's suite, along with a modern, open natural gas cook's kitchen and convenient breakfast bar setup. Guests’ privacy is ensured with a split floor plan en-suite bed and bath. This nearly new home boasts builder-installed upgrades, including quartz finishes throughout, high-end porcelain floors, a glass-tiled backsplash, hurricane Kevlar sliders and motorized retractable lanai storm shutter doors. The Club at Winding Cypress is a must-see, offering a massive resort pool, sunset sand cabanas, bocce ball, eight pickleball courts, clay tennis courts, a yoga deck, a massive gym facility, fire pits, a boardwalk nature trail, locker rooms, a full-time activities director, a sand bar pool side restaurant and more. Winding Cypress stands out as one of Naples' most unique, resort-style, non-golf communities, encompassing over 800 acres of pristine preserve, ensuring an ideal location. Perfectly in the center point between Marco Island and 5th Avenue in downtown Naples, this community offers a lifestyle of unparalleled luxury and convenience.



$625,000
Decrease*
$100K
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Winding Cypress

7574 Jacaranda Ln, Naples, FL 34114

Homes - 1,554 ft² / 1,898 ft² - 2 Car Garage

2+Den / 2 Baths / Pool

Built 2016
Winding Cypress Naples Homes for Sale: Villa w/ PEACEFUL view! Attached villa Serenity floor plan that lives like a single family home w/ luxury features throughout- tray ceilings, 18" tile flooring, quartz countertops, custom tile backsplash in kitchen, convection double oven, designer light fixtures, high-end cabinetry, crown molding, French door entry to den, frameless glass enclosure in master shower, custom built heated pool, & a built-in Generac generator system & transferrable home warranty. The outdoor living space is the GEM of the home- massive pool deck, solar & gas heated pool, large covered area w/ enough room for dining set & lounging area, & having a serene lake view. Meticulously maintained & updated w/ new accordion hurricane shutters, whole home water filtration system for optimum water quality, & freshly painted exterior. The roof was just power washed this past summer. This natural gas community has over 800 acres of lakes & preserve, resort- style pool, fire pit, community rm, restaurant, tennis, bocce ball, pickleball, cabanas, yoga deck, fitness facility, locker rooms, full time activities director, catering room, catering kitchen, activity room, nature board walk, garden, small & large dog parks.



$615,000
Decrease*
$65K
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Winding Cypress

7579 Jacaranda Ln, Naples, FL 34114

Homes - 1,554 ft² / 1,934 ft² - 2 Car Garage

2+Den / 2 Baths

Built 2016
Winding Cypress Naples Homes for Sale: Beautiful, well-kept, light-and-bright villa with a long lake view to the Southwest to catch the all-day sun. Tile floors throughout for comfort and cleanliness. Lanai has no-see-um netting for year-round use. Bright kitchen with desirable gas cooktop. Split bedroom floor plan for guest privacy. Den and office with glass doors. Superb seasonal home or full-time Florida living. The clubhouse has a large pool, exercise facility, tennis and pickleball courts, and bar and restaurant for convenient stay-in community living. Short drive to Marco Island beaches or downtown Naples and beaches. Make the Florida lifestyle yours in this gorgeous villa.



$614,500
Decrease*
$20K
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Winding Cypress

7658 Jacaranda Ln, Naples, FL 34114

Homes - 1,554 ft² / 1,914 ft² - 2 Car Garage

2+Den / 2 Baths

Built 2018
Winding Cypress Naples Homes for Sale: 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 kitchen and bathrooms, den with French doors, and much more. The full list of upgrades is in supplements. Located near downtown Naples and Marco Island, the community features a clubhouse with a resort style pool, spa, state of the art fitness room, restaurant, tennis, bocce and pickleball. Shopping and restaurants are nearby. The 800+ acre preserve with a boardwalk adds to the outdoor appeal. Ideal for those seeking a stylish home in a prime location.



$609,900
Decrease*
$15K
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Winding Cypress

7602 Jacaranda Ln, Naples, FL 34114

Homes - 1,554 ft² / 2,142 ft² - 2 Car Garage

2+Den / 2 Baths

Built 2017
Winding Cypress Naples Homes for Sale: NEW IMPROVED PRICE...WHAT A DEAL! Discover EXCEPTIONAL VALUE in this captivating attached villa nestled in the HIGHLY SOUGHT-AFTER Naples locale within the vibrant community of Winding Cypress. Boasting 2 bedrooms, 2 full bathrooms, a den, and a two-car garage, this residence is meticulously designed for comfort and style. The bright and white kitchen, adorned with popular finishes, complements the seamless tile flooring in main areas and plush carpeting in bedrooms. An ideal home or vacation retreat, the property enjoys proximity to 5th Avenue, Marco Island, I-75, shopping, dining, beaches, and entertainment. Immerse yourself in the dream-like lifestyle provided by Winding Cypress' resort amenity campus, featuring a resort-style pool and spa, a pool side restaurant, yoga lawn, outdoor fireplace, tennis and pickleball courts, a state-of-the-art fitness center, and more. Furniture is negotiable. Seize the opportunity to relish the quintessential Florida lifestyle in this splendid Naples home.



$609,900
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Winding Cypress

7561 Jacaranda Ln, Naples, FL 34114

Homes - 1,554 ft² / 1,962 ft² - 2 Car Garage

2+Den / 2 Baths

Built 2016
Winding Cypress Naples Homes for Sale: Welcome to your serene and private retreat in Naples! This charming lake view and corner villa is nestled within a gated community, offering both privacy and security and lots of natural light. Inside, you'll find sophisticated touches such as an upgraded kitchen with Stainless Steel appliances, 9" x 40" wood plank style porcelain tiles throughout the entire home in a neutral tone, modern plantation shutters, and crown moulding throughout the home. The entire villa has been freshly painted, both inside and out and fresh, new landscaping has been installed. There is plenty of storage available with custom closet organization in the master bedroom, second bedroom and the garage with heavy duty shelving. Enjoy purified drinking water from a Reverse Osmosis System from Kinetico. The paved and screened lanai was extended and has been pre-plumbed for your future outdoor kitchen and ready for your outdoor TV. The Winding Cypress community offers a range of amenities to enrich your lifestyle. Stay active with access to a fitness center, tennis courts, and pickleball courts. There is a beautiful resort style pool, hot tub, and the Shady Palm Cafe serving delicious food and refreshing drinks. The Clubhouse has a wonderful library and can be rented out for events with a full kitchen. There is dog park and community garden that all residents can enjoy. Winding Cypress is centrally located near Marco Island, Downtown Naples, I-75, and plenty of shopping options.



$549,000
Decrease*
$10K
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Winding Cypress

7202 Live Oak Dr, Naples, FL 34114

Homes - 1,554 ft² / 1,914 ft² - 2 Car Garage

3 Bed / 2 Baths

Built 2015
Winding Cypress Naples Homes for Sale: This Villa is a true masterpiece of design and comfort. Enjoy your new Naples lifestyle, total relaxation and resort living or use it as a rental income property investment. A gorgeous unit featuring a tasteful interior that's highlighted with palm trees, tropical flowers & foliage to view from a private lanai with room to add a pool. This highly desirable unit has a weather protected screened lanai with automated blinds for privacy! The remote control in the dish on the coffee table with an up and down arrow, controls the installed, automated privacy shades that go all the way down to the ground, for privacy. Step further inside this home, feel the open layout & be impressed. The open concept design encompasses a gourmet kitchen, adorned with granite countertops & island that looks out onto the living room & dining room for entertaining friends and family. This Villa Retreat is a compliment of tasteful interior & tranquility. Updates throughout include tray ceiling in primary, crown molding, plantation shutters, quartz countertops. New Home Generator 2023. Fabulous amenities include the Clubhouse, Restaurant, Community Pool, Dog Park, Community Room, Exercise Room, Streetlights, Tennis Courts, and Library. This Community is centrally located just North of Marco & East of downtown 5th Avenue Naples & Beaches! Enjoy your new Naples lifestyle, total relaxation and resort living.



$529,000
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Winding Cypress

7191 Live Oak Dr, Naples, FL 34114

Homes - 1,554 ft² / 1,898 ft² - 2 Car Garage

2+Den / 2 Baths

Built 2015
Winding Cypress Naples Homes Under Contract: Incredible opportunity to own an attached villa in amenity rich Winding Cypress in spectacular Naples Florida. This home features 2 split bedrooms, each with walk in closets, plus a den with French doors. Granite countertops in both bathrooms, Plantation Shutters, tile flooring throughout and designer light fixtures. Kitchen has upgraded 42” cabinets, granite countertops and stainless steel appliances. The laundry room has overhead cabinets and utility sink. The attached 2 car garage includes built in cabinets and shelving. Enjoy the extended lanai with private preserve views. There is a natural gas full house generator and accordion storm shutters on all windows and electric storm screen on the lanai. Indulge in the amazing amenities Winding Cypress has to offer. It includes 800 acres of preserve and is centrally located between the beaches of Marco Island and the beaches of gorgeous downtown Naples. It includes a dog park and community vegetable garden. The Club at Winding Cypress boasts a resort-style pool, sunset sand cabanas, bocce ball, pickleball, clay tennis courts, yoga deck, exercise facility, fire pits, restaurant, and nature boardwalk. Resort living at its finest!



$1,600,000
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Winding Cypress

6880 Cocoplum St, Naples, FL 34114

Homes - 2,515 ft² / 3,077 ft² - 3 Car Garage

3+Den / 3 Baths / Pool / Spa

Built 2020
Winding Cypress Naples Homes Under Contract: An amazing opportunity to purchase a Pinnacle estate home in Winding Cypress! This home features 3 bedrooms, den, 3 bathrooms, pool & spa with a 3 car garage! No expense has been spared in this meticulously maintained home with tons of upgrades including built in appliances, hard flooring throughout, zero corner slider, crown molding, trey ceilings, electric hurricane shutters on lanai, natural gas, and so much more! The outdoor oasis features a large pool and spa with water features, huge backyard, built-in outdoor kitchen and a gorgeous lake view. Winding Cypress has amenities galore! Enjoy dining at Shady Palm, the onsite restaurant, play pickleball, bocce, tennis, workout in the state of the art fitness center or lounge by the resort style pool, garden at the community garden, or take fido to the dog park! Winding Cypress is pet friendly, allows rentals, has low fees and is centrally located between Marco Island, 5th Ave, & I75 making it an ideal location!



$1,150,000
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Winding Cypress

7615 Winding Cypress Dr, Naples, FL 34114

Homes - 2,018 ft² / 2,502 ft² - 2 Car Garage

3+Den / 2 Baths / Pool / Spa

Built 2019
Winding Cypress Naples Homes Under Contract: Ideally located equidistant between Downtown Naples and Marco Island, Winding Cypress coexists with the natural flora and fauna of Southwest Florida. Enjoy bird songs along with deer and wild turkey sightings while walking or biking through the community. Get to know your neighbors while basking in the sun at the resort style community pool complete with gorgeous waterfall and cabana beach area or grabbing a bite to eat at the Shady Palm Cafe. There's never a dull moment with non-stop neighborhood activities and groups. And if tennis, pickleball, or bocce ball are your sport, we have you covered. Call this 3 bedroom plus a den, 2 bath, 2 car garage Summerwood model residence your home and you can enjoy all Winding Cypress has to offer. On quiet days relax on the ample lakefront lanai and swim or soak in the gas heated pool and spa. Delight in trying out new recipes in the well appointed kitchen with granite countertops, stainless steel appliances, and gas stove. With the ADT home security system and impact glass doors and windows this house will be your sanctuary.



$895,000
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Winding Cypress

7673 Jacaranda Ln, Naples, FL 34114

Homes - 2,063 ft² / 2,539 ft² - 2 Car Garage

3+Den / 3 Baths / Pool

Built 2019
Winding Cypress Naples Homes Under Contract: Furnished, 1-1/2 story, 2019 pool home at Winding Cypress blends luxurious amenities with top-tier safety features. Nestled on a preserve and corner lot, it offers extra privacy at the pool and a serene environment. The main floor presents a versatile layout with (1) the primary suite with a lavish bath and large walk-in closet, (2) a second bedroom and full guest bath, and (3) a den with double doors, which may be converted to a guest room. The bright, modern kitchen seamlessly connects to the dining and living areas, perfect for entertaining. Upstairs, a spacious loft, 3rd bedroom and additional full bath ensure ample living space. Modern conveniences like central vac, plantation shutters and keyless entry enhance comfort and security. Outside, the 1,000+ square foot lanai, heated pool and outdoor kitchen (with natural gas grill) allow for year-round enjoyment. With a whole home generator & impact windows/sliders, it guarantees peace of mind. Set in a popular and active resort-style community, residents gain access to various amenities such as a resort-style pool, poolside restaurant, fitness center, bocce, tennis & pickleball courts.



$679,000
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Winding Cypress

7627 Jacaranda Ln, Naples, FL 34114

Homes - 1,554 ft² / 1,898 ft² - 2 Car Garage

2+Den / 2 Baths / Pool

Built 2017
Winding Cypress Naples Homes Under Contract: This stunning lake view villa pool home with 2 car garage in the low fee community of Winding Cypress offers a luxurious lifestyle with its serene lake views and exceptional amenities. Home features include: Premium Wide Lake View: Step out onto your patio and soak in the breathtaking vistas of the tranquil lake. Whether it’s morning coffee or evening sunsets, this view will captivate you. Tile on the Diagonal: The elegant diagonal tile flooring flows seamlessly throughout the home, adding a touch of sophistication. Recessed and Cabinet Lighting: Illuminate your living spaces with style. Whether you’re hosting a dinner party or enjoying a quiet evening, the lighting sets the mood just right. Heated Pool: Take a refreshing dip in the heated pool year-round. Imagine relaxing by the water, surrounded by lush greenery and the soothing sounds of nature. Trey Ceiling: The main living area features a trey ceiling, adding architectural interest and a sense of spaciousness. White Cabinetry Throughout: The timeless white cabinetry complements any decor and keeps the home bright and airy. Gorgeous Sunsets: As the day winds down, enjoy spectacular sunsets from your own backyard oasis. New Quartz Countertops: The kitchen, master bath, and guest bath have been upgraded with beautiful quartz countertops. The sinks and faucets are also new. New Tile Plank: The master bedroom, master bath, and guest bedroom now feature stylish tile plank flooring. LED Lanai Lights: Illuminate your pool area for evening gatherings and relaxation. Custom Garage Shelving: Organize your garage space efficiently. New Dishwasher and Clothes Washer: Modern appliances for your convenience. New Pool Cage Screens: Fresh screens enhance the pool area. Motorized Sunscreen for Lanai: Control sunlight and create a comfortable outdoor space. Whole House Water Filter System: Enjoy pure filtered throughout your home. Winding cypress features include: Shady Palm Restaurant: Onsite dining for residents. Treat yourself to delicious meals without leaving the community. Pickleball, Bocce, Tennis: Stay active and social. Engage in friendly matches with neighbors and friends. State-of-the-Art Fitness Center: Achieve your fitness goals. Whether it’s cardio, strength training, or yoga, the fitness center has you covered. Resort-Style Pool: Lounge by the pool, soak up the sun, and enjoy the Florida weather. Community Garden: Green thumbs welcome! If you love gardening, this is the place to nurture your plants. Dog Park: Fido-approved fun! Let your furry friend run and play in the designated dog park. Location: Centrally situated between Marco Island, 5th Ave, and I75, this home offers convenience and easy access to all that Naples, Florida, has to offer. Don’t miss out on this exceptional opportunity! Contact your agent today to schedule a viewing.



$619,000
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Winding Cypress

7790 Jacaranda Ln, Naples, FL 34114

Homes - 1,554 ft² / 1,962 ft² - 2 Car Garage

2+Den / 2 Baths

Built 2019
Winding Cypress Naples Homes Under Contract: Beautiful, like-new furnished single family attached villa with long lake view. Built in 2019, this move-in ready Serenity floor plan includes two bedrooms plus den, two bathrooms, upgraded tile floors, extended lanai with Storm Smart hurricane screens, hurricane impact windows/doors throughout. Southern exposure. Natural gas community. Quartz countertops, stainless appliances, plantation shutters. A highly sought after community, Winding Cypress has over 800 acres of lakes and preserves, resort-style pool and spa, restaurant, tennis, bocce & pickleball, fire pit, state-of-the-art fitness center, nature boardwalk, small & large dog parks. Restaurants and shopping nearby. Enjoy resort-style living at its best in this lovely home.



$1,895,000
Sold Price:
$1,895,000
Sold Date:
01/04/2024
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Winding Cypress

7513 Winding Cypress Dr, Naples, FL 34114

Homes - 2,900 ft² / 9,148 ft² - 3 Car Garage

3+Den / 3 Baths / 1 Half / Pool / Spa

Built 2018
Winding Cypress Naples Homes: A world of sophistication & style awaits in this Winding Cypress masterpiece w/lake views. As you navigate the open-concept home, the marriage of textures, materials & high-end furnishings creates a sensory experience, where each turn reveals a new awe-inspiring surprise. Stunning coffered ceilings w/tongue & groove designs & shiplap accent walls grace the living spaces, while designer lighting fixtures serve as works of art, casting a warm & inviting glow throughout. For the culinary enthusiast, a natural gas kitchen awaits. The expansive lanai is a destination in itself, where luxury & nature seamlessly converge w/a saltwater pool/spa, outdoor kitchen w/built-in gas grill & al fresco dining. Whether it's a quiet dinner under the stars or a lively celebration w/friends & family, the peaceful outdoor ambiance enhances every moment. The master suite is a testament to the designer's vision, with a blend of textures & colors that create a harmonious retreat. The master bath, w/its gorgeous tile work, becomes a spa-like sanctuary, inviting relaxation & indulgence. Discover the epitome of high-end living in this one of a kind home in the amenity-rich community of Winding Cypress.



$1,649,000
Sold Price:
$1,550,000
Sold Date:
03/25/2024
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Winding Cypress

6920 Cocoplum St, Naples, FL 34114

Homes - 2,952 ft² / 3,513 ft² - 3 Car Garage

3+Den / 3 Baths / 1 Half

Built 2019
Winding Cypress Naples Homes: Discover luxury living in this exquisite Stonewater resort home in one of the most outstanding communities in South Naples on one of the best lakefront land sites imaginable. Boasting nearly 3,000 square feet of living space, this residence offers a spacious and open floor plan with high tray ceilings, architecturally stunning alcoves and arches, and top-level finishes throughout adorned in high-end, custom-designed light fixtures. Enjoy the tranquility of southern exposure and breathtaking lake views from the oversized covered lanai. The interior features a designer kitchen with soft-close cabinets, quartz countertops and natural gas cooking. Residents enjoy exclusive access to the Winding Cypress Club, complete with restaurant and bar, full-time activity director, a state-of-the-art fitness center, resort-style pool, lap pool, spa, outdoor movement studio, bocce ball courts, pickleball and tennis courts, fire pit, bird-watching overlook and nature boardwalk with a picnic pavilion. This home showcases the best in Florida living and is conveniently located at an ideal counterpoint between downtown Naples and Marco Island.



$1,250,000
Sold Price:
$1,200,000
Sold Date:
04/11/2024
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Winding Cypress

7565 Blackberry Dr, Naples, FL 34114

Homes - 2,948 ft² / 3,239 ft² - 2 Car Garage

3+Den / 3 Baths / Pool / Spa

Built 2017
Winding Cypress Naples Homes: Located in the highly sought after and amenity rich community of Winding Cypress, this 3 Bedroom + Den, 3 Bath Summerwood boasts a hard to find spacious loft that adds an additional 900+ sq ft of living area. The meticulously maintained home has numerous upgrades that include an extended finished garage with utility sink and space for a golf cart, upgraded flooring, cabinetry, countertops and appliances, extended kitchen island, crown molding, built in speaker system, outdoor kitchen and much, much more. The beautifully appointed lanai is a haven with a covered living area next to the heated pool and spa with gorgeous views of the preserve. Residents enjoy access to an exceptional Amenity Center complete with a state-of-the-art fitness center, resort style pool and spa, restaurant, bocce ball, tennis and pickleball courts, and full time activity director. It is a pet friendly neighborhood with 2 off-leash dog runs. This home is conveniently located between Marco Island and downtown Naples and is in the perfect location to enjoy all that Southwest Florida has to offer. Why wait for a new home when you can make this yours now!



$1,150,000
Sold Price:
$1,145,000
Sold Date:
02/06/2024
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Winding Cypress

6818 Greenbriar Ct, Naples, FL 34114

Homes - 2,152 ft² / 2,582 ft² - 2 Car Garage

3+Den / 3 Baths / Pool / Spa

Built 2021
Winding Cypress Naples Homes: Meticulously maintained three-bedroom plus den, three-bathroom residence in Winding Cypress with breathtaking lake views. You’ll be greeted by an open layout bathed in natural light from a corner pocketing impact glass slider. This furnished home showcases new furniture and TVs, finished with 9’ ceilings, 8’ doors, pristine tile floors, closet built-ins, and plantation shutters throughout. The gourmet kitchen features KitchenAid appliances with gas cooking, pullout drawer cabinets, designer backsplash, pantry, and a large center island. Each bedroom boasts an en-suite bathroom. Outside, you’ll find a WiFi-controlled heated pool and spa under a screened lanai with a stunning backdrop of the lake. Additional features include Vitex smart home, StormSmart electric shutters, 22kW whole home generator, water filtration system, extended driveway, and a two-car garage with AC, epoxy floor, and overhead storage. Winding Cypress residents have access to a clubhouse with a social room, library, fitness center, resort-style pool and spa, outdoor bar and grill, tennis, pickleball, bocce, dog park, and a full social calendar. Just 15 minutes to downtown Naples and Marco Island. CDD paid in full.



$1,150,000
Sold Price:
$1,200,000
Sold Date:
04/05/2024
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Winding Cypress

6695 Pennyroyal Dr, Naples, FL 34114

Homes - 2,148 ft² / 3,200 ft² - 2 Car Garage

3+Den / 3 Baths / Pool / Spa

Built 2022
Winding Cypress Naples Homes: Beautifully appointed TURNKEY FURNISHED 3 bedroom plus den, 3 full bath, single family pool home in sought after Winding Cypress. The home is finished with meticulously crafted upgrades including luxury designer furnishings and fixtures throughout. Chef's kitchen features quartz counters, Kitchen Aid SS appliance package, natural gas, large island & breakfast room. The extended gathering room leads to the covered lanai with summer kitchen, bar and pool/spa with water features. Zero corner sliding glass doors seamlessly integrate the living areas, creating an inviting atmosphere for relaxation & entertainment. Amenity rich Winding Cypress features a resort style pool, restaurant/bar, fire pit, fitness center, out door yoga deck, pickle-ball, tennis, bocce ball, community garden, dog park, and a nature trail boardwalk.



$1,100,000
Sold Price:
$1,043,000
Sold Date:
02/21/2024
View Details

Winding Cypress

6846 Greenbriar Ct, Naples, FL 34114

Homes - 2,107 ft² / 2,525 ft² - 2 Car Garage

3+Den / 2 Baths / Pool / Spa

Built 2020
Winding Cypress Naples Homes: This excessively upgraded Martin Ray floorplan features 3 bedrooms, den, 2 baths, extended 2 car garage, pool, spa, lake view and more! Inside this home you will find endless luxury from built in appliances, impact windows & doors, custom closets in master & laundry room, tile floor throughout, built in bar, crown molding, trey ceiling, surround sound, Murphy bed, screened front door, A/C garage and insulated garage door. The outdoor oasis has a picture window screen to appreciate the gorgeous lake view, built in outdoor kitchen with extra large hood, salt water pool and spa with autofill, hurricane screens for double protection, extended pavers between house and pool, landscape and lanai cage lighting, rock speakers, irrigation to potted plants on deck and so much more. Winding Cypress has amenities galore! Enjoy dining at Shady Palm, the onsite restaurant, play pickleball, bocce, tennis, workout in the state of the art fitness center or lounge by the resort style pool, garden at the community garden, or take fido to the dog park! Winding Cypress is pet friendly, allows rentals, has low fees and is centrally located between Marco Island, 5th Ave, & I75 making it an ideal location!



$1,090,000
Sold Price:
$1,050,000
Sold Date:
04/19/2024
View Details

Winding Cypress

6830 Greenbriar Ct, Naples, FL 34114

Homes - 2,105 ft² / 2,528 ft² - 2 Car Garage

2+Den / 2 Baths / 1 Half / Pool

Built 2021
Winding Cypress Naples Homes: LIKE NO OTHER FOR SALE IN WINDING CYPRESS! This "PRESTIGE MODEL" POOL home must be seen to be appreciated for all that it has to offer! BEING SOLD TURNKEY WITH ALL DESIGNER DECOR ALL YOU NEED TO DO IS BRING YOUR TOOTHBRUSH AND CLOTHES! GORGEOUS LAKE VIEWS THROUGH THE PICTURE WINDOW SCREEN! This home has over 2,100 square feet of living space with 2 Bedrooms Plus Den (Den is a 3rd Bedroom option) and 2.5 baths complete this space. Lots of upgrades that will give you no reason to do anything but move in and enjoy all the work that was put into this home. The Gourmet Kitchen creates the perfect gathering area and expands into the Living and Dining Area providing tons of room for entertaining. It offers wood cabinets with soft close doors, crown molding on the cabinets, tile backsplash, upgraded Quartz counters, pantry, and stainless steel appliances. Oversized tile on a diagonal throughout the entire home! Plantation Shutters, Crown Molding, IMPACT WINDOWS & DOORS, and a Roll Down Hurricane screen across the back. HOME IS PRE-PLUMBED FOR OUTDOOR KITCHEN! The gorgeous lake views beyond the large heated pool will help you relax the day away creating your own tropical oasis.



$1,075,000
Sold Price:
$1,000,000
Sold Date:
04/30/2024
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Winding Cypress

7634 Arrowhead Way, Naples, FL 34114

Homes - 2,230 ft² / 2,940 ft² - 2 Car Garage

3+Den / 2 Baths / Pool

Built 2019
Winding Cypress Naples Homes: Discover Your Dream Home Nestled W/in The Prestigious Community Of Winding Cypress. This Exquisite Residence Epitomizes Luxury Living W/ Its Open-Concept Design Seamlessly Integrating The Spacious Living Areas, Creating An Inviting Atmosphere For Both Relaxation & Entertainment. As You Step Inside, You'll Be Greeted By A Breathtaking Long Lake View That Sets The Stage For Tranquil Living. You'll Enjoy Peace Of Mind & Security During Stormy Seasons With Hurricane Impact Windows & Doors Throughout. The Home Is Adorned W/ Meticulously Crafted Upgrades Throughout. From The Gourmet Kitchen Featuring Stainless Steel Appliances, Quartz Countertops & White Shaker Cabinets, To The Master Suite That Is A Sanctuary Of Comfort, Offering Tranquility & Style, This Home Is A Testament To Luxury. Step Outside To Your Private Oasis, Where A Sparkling Pool Awaits, Inviting You To Take A Refreshing Dip Or Soak Up The FL Sun On The Large Screened Lanai. This Naples Gem Is Not Just A Home; It's A Lifestyle. Winding Cypress Offers A Wealth Of Amenities, Including A Clubhouse, Fitness Center, Tennis & Pickleball Courts, Restaurant, & Much More, Ensuring That Every Day Is Filled W/ Leisure & Recreation.



$1,025,000
Sold Price:
$1,015,000
Sold Date:
12/12/2023
View Details

Winding Cypress

6723 Pennyroyal Dr, Naples, FL 34114

Homes - 2,094 ft² / 3,129 ft² - 2 Car Garage

3 Bed / 2 Baths / Pool / Spa

Built 2021
Winding Cypress Naples Homes: Welcome to this single-family home, a mere 2 years old, offering a slice of paradise. The popular Mystique floor plan boasts almost 2,100 sq ft of indoor living space, with 3 bedrooms, a den, and two bathrooms. Additionally, you'll find a sprawling spectacular outdoor living area, featuring a Saltwater custom pool and spa, complete with a sun shelf and water feature, and a picturesque water view from the screened-in extended lanai and patio. The zero corner sliding doors seamlessly blend the indoor and outdoor living spaces. This home is loaded with upgrades, including tile and carpet flooring, an extended and epoxied garage, overhead lighting & ceiling fans throughout, custom blinds, upgraded appliances, and a Kinetico water filtration system. Perfectly situated in the VERY DESIRABLE COMMUNITY of WINDING CYPRESS, you'll be conveniently close to 5th Avenue, Marco Island, I-75, shopping, dining, beaches, and entertainment. However, there's little reason to venture far, as Winding Cypress offers a dream-like lifestyle with its resort amenity campus. You can revel in the delights of a resort-style pool and spa, restaurant, yoga lawn, outdoor fireplace, tennis or pickleball, state-of-the-art fitness center and exercise studios, and more. This property is offered turnkey furnished, waiting for your personal touches to make it your own. Simply pack your bags and move in to start living the Florida dream.



$998,500
Sold Price:
$1,000,000
Sold Date:
05/10/2024
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Winding Cypress

7123 Lily Way, Naples, FL 34114

Homes - 2,998 ft² / 3,860 ft² - 2 Car Garage

3+Den / 3 Baths / Pool

Built 2015
Winding Cypress Naples Homes: Welcome to the ultimate Naples resort community of Winding Cypress. Presenting this lakeview Summerwood home, set on an exceptionally private homesite with a beautiful, long lake view. Features include every builder option and upgrade, plus a very cool upstairs bonus loft bedroom and living room, perfect for guests or as a homeowner's retreat. This home includes top-level finishes throughout along with easy glide window shutters from top to bottom, motorized lanai storm shutters, an oversized covered lanai, a two-car tandem storage garage, a whole house generator, and a beautiful lakefront pool. Residents can indulge in the luxurious Winding Cypress clubhouse, offering a state-of-the-art fitness center, catering kitchen, community room, and activity room. Outdoor amenities abound, offering pickleball, resort-style and lap pools, a spa, an outdoor movement studio, a barefoot bar, bocce ball courts, five Har-Tru tennis courts, a fire pit, a bird-watching overlook, and a nature boardwalk with a picnic pavilion. In ideal proximity to the pristine shores of Marco Island and the vibrant downtown Naples, this amazing resort location provides the ideal backdrop for an unparalleled lifestyle.



$895,000
Sold Price:
$875,000
Sold Date:
04/05/2024
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Winding Cypress

7491 Blackberry Dr, Naples, FL 34114

Homes - 2,282 ft² / 3,586 ft² - 2 Car Garage

3+Den / 3 Baths / Pool / Spa

Built 2017
Winding Cypress Naples Homes: This rarely available two-story “Abbeyville” model with a Premium Waterfront Location has a preferred Southern Exposure and has been meticulously maintained. Located in the highly sought-after, gated, amenity rich community of Winding Cypress. There is a ground floor Primary Suite with spacious walk-in closet, a guest bedroom and bath, and a den/office. Plus, the home also boasts a hard-to-find large loft area with a third bedroom and full bath upstairs. This home features a heated saltwater pool and spa, (New heater and filter 2023) stainless steel appliances, gas range and tankless water heater (added 2021). Recent improvements include new washer dryer 2022, and all new smoke and carbon monoxide detectors. Residents enjoy access to an exceptional Amenity Center complete with a state-of-the-art fitness center, resort pool and spa, restaurant, bocce ball, tennis and pickleball courts, and a full-time activity director. This home is conveniently located at an ideal counterpoint between the beautiful Gulf beaches and fine dining options of both Naples and Marco Island.



$865,000
Sold Price:
$845,000
Sold Date:
04/19/2024
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Winding Cypress

7346 Mockingbird Ct, Naples, FL 34114

Homes - 2,230 ft² / 2,667 ft² - 2 Car Garage

4 Bed / 2 Baths

Built 2016
Winding Cypress Naples Homes: In the ultimate Naples resort community, this exceptional property in Winding Cypress stands out for its distinctive features, offering an ideal blend of waterfront tranquility, preserved nature and the allure of privacy. This award-winning Summerwood floor plan boasts every builder option and upgrade, on a completely private corner lot on a tranquil cul-de-sac. Highlights include top-level finishes, impact windows throughout, and a perfectly designed open great room concept with strategically placed windows for optimal natural light and furniture layout. Residents can indulge in the luxurious Winding Cypress clubhouse, offering a state-of-the-art fitness center, catering kitchen, community room and activity room. Outdoor amenities abound, from pickleball, resort-style and lap pools to a spa, outdoor movement studio, barefoot bar, bocce ball courts, five Har-Tru tennis courts, fire pit, bird-watching overlook and a nature boardwalk with a picnic pavilion. In ideal proximity to the pristine shores of Marco Island, and the vibrant downtown Naples, this amazing resort location provides the ideal backdrop for an unparalleled lifestyle.



$845,000
Sold Price:
$840,000
Sold Date:
04/30/2024
View Details

Winding Cypress

6828 Winding Cypress Dr, Naples, FL 34114

Homes - 2,089 ft² / 2,536 ft² - 2 Car Garage

3 Bed / 2 Baths

Built 2021
Winding Cypress Naples Homes: The luxury, nature and privacy is waiting for you on our Paradise Coast! Every upgrade has been selected for this immaculate home. To start, it has an upgraded lot, 8ft doors, crown molding, 6" base boards, trey ceiling in family room, upgraded waterproof laminate flooring in main living area, 22×22 porcelain tile in bathrooms and laundry room, 42" upper shaker soft closing cabinets, Kitchen Aid appliances, marble splash-back, owned solar electric system, 50 Amp plug in garage for electric vehicle charger, extended patio with forest view. Hurricane impact windows and sliders extended driveway capable of parking four cars, modern light fixtures and ceiling fans, tankless water heater, and the list goes on. Winding Cypress is a community like no other. You have seen the rest, now come see the best.




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