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Winding Cypress Naples Florida Homes for Sale

Naples Florida Real Estate

Winding Cypress Naples Real Estate

Homes For Sale26$549K - $1.8M
Sold33$529K - $1.9M
Last updated at 8:30am 05/06/2024

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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. 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. 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. 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



$1,699,500
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$196K
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Winding Cypress

6903 Cocoplum St, Naples, FL 34114

Homes - 3,656 ft² / 5,000 ft² - 3 Car Garage

4+Den / 4 Baths / Pool / Spa

Built 2021
Winding Cypress Naples Homes for Sale: Motivated Seller !! An exquisite Furnished residence offering a blend of timeless elegance & resort-style living that sets it apart in a class of its own in Winding Cypress. The open floor plan harmoniously integrates the kitchen, dining area & great room, creating a central hub where daily life unfolds w/effortles s elegance. The gourmet kitchen is a chef's dream, complete w/a natural gas cooktop, wall oven & large island w/extra storage for your cookware. The magic unfolds as you open the pocket sliders, dissolving the boundaries between the interior & enchanting outdoor lanai. Enjoy 5-star resort amenities right at home, from the azure pool waters & sun shelf, rejuvenating spa & cascading waterfall features. while an outdoor kitchen beckons culinary enthusiasts. Discover a sprawling game room & media room upstairs, transforming your home into a haven for recreation & relaxation. The 2nd floor offers a bed & bath, making it suitable for family & guests alike. A whole home generator is included, an extended 3 car garage with epoxy flooring, an oversized private lot and a Natural Gas Community. See Upgrade list attached. Winding Cypress has country club like amenities with a private restaurant with a resort pool, fitness center and so much more !



$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 CypressNEW

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, built-in Sonos surround sound package, 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 and 3 full bathrooms, including an expansive owner's suite with a custom built-in closet system along with additional 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 coffered-tray ceilings to the custom Granite Wall, double crown moldings. Plantation shutters, 8-foot doors with volume 11 ft ceilings, custom draperies and designer light fixtures flow 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 a private alfresco dining option. 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.



$1,350,000
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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 CypressNEW

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 centrally located Winding Cypress resort community in Naples. This exceptional home boasts a stunning custom pool and lanai, complete with an in-water sundeck, perfect for soaking up 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 perfect blend of elegance and comfort. A bonus loft offers a very 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 the vibrant downtown Naples, this amazing resort location provides the ideal backdrop for an unparalleled lifestyle.



$1,099,000
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Winding Cypress

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 three-bedroom plus den, 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.



$1,050,000
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$100K
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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.



$924,900
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$73.1K
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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.



$725,000
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$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
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$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.



$635,000
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$90K
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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
View Details

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
View Details

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
View Details

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.




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*Just Listed: new properties that came on the market within the last 30 days.
*Decrease/Increase: listing values that are being recorded within the last 30 days.
*Foreclosures/Short Sale: Please note, all properties are subject to bank approval. Buyers must be pre-approved or show proof of funds before submitting an offer.

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