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Winding Cypress Naples Florida Homes for Sale

Naples Florida Real Estate

Winding Cypress Naples Real Estate

Homes For Sale9$599K - $1.8M
Sold19$549K - $1.9M
Last updated at 11:35am 12/08/2023

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$1,765,000
Decrease*
$100K
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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: Presenting the exclusive Stonewater model in Winding Cypress. This impeccably maintained home is nearly new, offering three bedrooms, a versatile den and three baths, plus a pool bath. Step onto the expansive panoramic screened lanai, featuring a custom pool, built-in outdoor kitchen, and be captivated by the serene lake and tree-lined backdrop for privacy. The gourmet kitchen seamlessly connects to the inviting gathering room and dining area, with sliders that open to the covered lanai, creating an ambiance of pure Naples luxury. The primary bedroom is a sanctuary, featuring a full en-suite bath and a generously sized walk-in closet. The main guest en suite offers a charming bay window design, perfect for visitors. Motorized storm shutters and a whole-house generator are just a few of the many bonuses of this incredible estate home. The luxurious Winding Cypress clubhouse amenities include full-time activity director, a cutting-edge fitness center, access to a resort-style pool, lap pool, spa, outdoor movement studio, outdoor barefoot bar, bocce ball courts, pickleball and tennis courts, fire pit and even a bird-watching overlook and nature boardwalk with a picnic pavilion.



$1,699,000
Decrease*
$66K
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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 for Sale: 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.



$1,095,000
Decrease*
$105K
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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 for Sale: 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.



$949,900
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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: Exquisite Summerwood floor plan featuring a Prime lot Location with Views of the Pond and Preserve. A Beautiful and Peaceful respite that can be enjoyed from the panoramic screened Lanai. The entire home comes with Upgraded Flooring, no carpet. 3 Bedrooms, with Wide Oak, blonde Plank Wood, the Den offers Hand Scraped Wood Flooring with French Doors. Living areas feature Large Tile set on the Diagonal. The Great Room features Elevated Coffered Ceilings and Merges perfectly with the Large Gourmet Kitchen (Gas Cooking) and Dining Space, Sun Room. Quartz Counter Tops, a Marble Backsplash and a Huge Island that easily seats 5. Light colored Cabinets supply Ample Storage. Additional living spaces, (see photos) one for Formal Dining, and a beautiful Sun room leading one to the Lanai. The Owner's Suite also Features Elevated Tray Ceilings adding Volume to the room, the bath comes with Dual Sinks, Quartz counter tops, Walk-in-Shower, Ballard designed Closet, and make-up area. Plantation Shutters in 3 Bedrooms and Den, Upgraded Fixtures and Fans all in a Well Kept home. Winding Cypress is situated on 1100 acres, 800 are Natural Preserve. Luxury Clubhouse, Pool, Restaurant, Fitness Center.



$765,000
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Winding Cypress

7108 Lily Way, Naples, FL 34114

Homes - 1,685 ft² / 2,034 ft² - 2 Car Garage

2+Den / 2 Baths / Pool

Built 2015
Winding Cypress Naples Homes for Sale: Located within the amenity-rich Winding Cypress community, this 2-bedroom plus den, 2-bathroom Abbeyville has been meticulously maintained. Builder upgrades include additional drawers added in primary bathroom dual sink vanity, outdoor kitchen plumbed for water along with gas line, floor tile set on diagonal, Whirlpool stainless appliances, granite, garage utility sink, upgraded lighting package in garage with GFCIs on dedicated circuit. Free-form pool with plenty of screened lanai space, view of landscaped area and pond. A perfect spot to watch beautiful FL sunsets. Solar pool heater added in 2020. Gas pool heater hook-up also available. Accordion hurricane shutters on all windows; electric hurricane shutters on lanai controlled by interior switch. Custom queen-size Murphy bi-fold bookcase bed with tilting headboard and bed lights installed in Flex/Den. Privacy doors added to ensure your guests total privacy. All interior recessed lighting and pendants recently updated to LED fixtures. Custom drop zone bench seat with drawers, coat hooks, storage cabinets offer convenience and additional storage. Board and batten wall details added in foyer. Scenic Winding Cypress is a gated natural gas community, with full-time activities director, offering resort-style pool, tennis, pickleball, bocce ball, a pool-side restaurant, fitness center, dog park, walking/biking trails and more.



$680,000
Decrease*
$19K
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Winding Cypress

7175 Live Oak Dr, Naples, FL 34114

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

3 Bed / 2 Baths / Pool / Spa

Built 2016
Winding Cypress Naples Homes for Sale: V11010 Beautifully updated 3 bedroom in Winding Cypress. This Serenity floorplan features granite kitchen with under cabinet lighting, pantry plus a hands-free faucet. Open living/dining area with tile, plantation shutters and large slider overlooking heated salt water pool. Private preserve views, ample closets plus a 2-car garage with AC and built-in storage. Impact glass throughout plus the lanai has both no-see-um screens and Storm Smart shutters. Winding Cypress offers fabulous amenities including a resort-style pool with poolside restaurant, spa and fitness center. Enjoy the fire pit, bocce ball, pickleball & tennis, outdoor yoga deck plus movement studio, dog park and community garden. Convenient to Naples dining, shopping and watersports. Offered turnkey furnished.



$667,000
Decrease*
$13K
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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.



$659,900
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Winding Cypress

7630 Jacaranda Ln, Naples, FL 34114

Homes - 1,542 ft² / 1,914 ft² - 2 Car Garage

2+Den / 2 Baths

Built 2017
Winding Cypress Naples Homes for Sale: PRISTINE LIKE NEW CONDITION! This two bedroom, two bath plus den and two car garage attached villa home built in 2017 is offered FULLY FURNISHED and features a roomy 1,542 air conditioned living space, kitchen with quartz counter tops, tile back-splash, breakfast bar, stainless steel appliances, 42" upper cabinets, natural gas range, plantation shutters, large block tile in the main living areas and baths, plush carpeted bedrooms, recessed lighting, modern ceiling fans and light fixtures, tray ceiling in the primary bedroom with frameless shower door and double sink vanity in it's en suite bath, laundry room with wash basin, impact windows and manual shutters, a private screened lanai and brick paver driveway. Awesome casual living at Winding Cypress offers an impressive clubhouse, resort-style pool, spa, fitness center, tennis, pickleball, bocce and pool-side full service restaurant. The community is comprised of 1,100 acres with 800 acres of preserve and lakes. Residents enjoy an untouched natural setting, from the boardwalk, pavilion and bird wading overlook, to the linear park and community garden. Just minutes to Naples and Marco Island beaches, 5th Ave and RSW Airport!



$599,000
Decrease*
$20K
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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 for Sale: 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!



$1,150,000
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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 Under Contract: 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.



$749,900
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Winding Cypress

7370 Mockingbird Ct, Naples, FL 34114

Homes - 1,805 ft² / 2,222 ft² - 2 Car Garage

2+Den / 2 Baths

Built 2016
Winding Cypress Naples Homes Under Contract: PRICED TO SELL!!! This beautiful home in highly desirable neighborhood of Winding Cypress boasts beautiful lake and preserve views and located on a quiet cul-de-sac. Sit on your lanai and enjoy watching all the wildlife. Amenities galore with large community pool, hot tub, restaurant, large gym, separate work out room, wireless internet café, library, tennis, bocce, and pickleball. Very active community with full time activity director. Ten minutes to Marco Island and 20 minutes to 5th Ave makes this home close to everything that makes Naples living unique. Winding Cypress has over 800 acres of preserve that gives this home tons of privacy. A must see.



$729,000
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Winding Cypress

7244 Live Oak Dr, Naples, FL 34114

Homes - 1,878 ft² / 3,427 ft² - 2 Car Garage

2+Den / 2 Baths / Pool

Built 2016
Winding Cypress Naples Homes Under Contract: Nestled within Naples' scenic Winding Cypress community, this 2-bedroom plus den, 2-bathroom home, built in 2016, embodies the quintessential Florida lifestyle. The interior boasts coffered ceilings, impact-resistant windows and doors, and an extended kitchen island - a chef's dream! Natural gas availability enhances cooking and heating efficiency, while the primary bedroom features a charming beadboard accent wall. Crown molding adds an elegant finish throughout, and the master bath boasts double sinks for added luxury. Tile floors! Practical features include a golf cart parking area in the garage and a 13KW Generac generator, ensuring uninterrupted comfort during power outages. Step into the backyard oasis, where a heated pool beckons beneath a vast screen enclosure, ideal for year-round enjoyment. Winding Cypress offers an array of amenities, including a community restaurant, pool, scenic walking trails, pickleball and tennis courts, all enhancing your quality of life. It is time to enjoy all that SWFL has to offer!



$549,095
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Winding Cypress

7097 Live Oak Dr, Naples, FL 34114

Homes - 1,542 ft² / 2,091 ft² - 2 Car Garage

2+Den / 2 Baths

Built 2015
Winding Cypress Naples Homes Under Contract: Special Financing available.  Contact a Sales Consultant for more information. Your final opportunity to own a new home at Winding Cypress is here! This serenity villa home features 2 bedrooms, 2 baths, a den, and a covered lanai on a preserve view just a short distance away from the incredible amenity center. Inside the home you will find granite countertops throughout, stainless steel gas appliances, tile flooring throughout, exterior door to an extended covered lanai from owner's suite, impact glass windows, and a private nature view. From the moment you arrive at the stunning entry, Winding Cypress invites you in. This natural gas, resort-style community, remaining almost 2/3 preserve, welcomes you with a streetscape of superb views and new homes designed for the way you live. This premier Naples location offers highly attractive fees for the variety of world-class amenities right in your own backyard, including a grand clubhouse, resort pool, sports courts, dog park, community garden, and more. Photos are for illustration purposes only, options may vary.



$1,895,000
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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 Under Contract: 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.



$1,100,000
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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 Under Contract: 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!



$1,025,000
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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 Under Contract: 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.



$1,725,000
Sold Price:
$1,690,000
Sold Date:
08/24/2023
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Winding Cypress

6919 Cocoplum St, Naples, FL 34114

Homes - 2,923 ft² / 5,898 ft² - 3 Car Garage

3 Bed / 3 Baths / 1 Half / Pool / Spa

Built 2020
Winding Cypress Naples Homes: Spectacular Stonewater Well Appointed Home. Located in Winding Cypress a Premier Community with 800 Acres of Natural Preserves. Coffered Volume Ceilings. Gourmet Kitchen with Wolf Steam Oven + Additional Full Oven & Warming Drawer. Luxurious Primary Suite. Guest Bedrooms with Ensuite's. Outdoor Living at it's Best. Panoramic Sunsets over a Tropical Lake & Preserve View from Your Lanai. Large Heated Pool with Swim Platform, Spa & Fountain. Impact Windows & Doors. Tankless Gas Water Heater & Generac Natural Gas Whole House Generator. And More...Amenities Include Community Center, Shady Palm Bar & Grille, Fitness Center, Heated Pool & Spa. Pickle Ball, Tennis, Bocce Ball, Nature Trail & Bird Sanctuary. Dog Park. Short Distance from Marco Island & Naples Beaches & Restaurants. MUST SEE!!!



$1,599,000
Sold Price:
$1,550,000
Sold Date:
10/18/2023
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Winding Cypress

6907 Cocoplum St, Naples, FL 34114

Homes - 2,515 ft² / 3,818 ft² - 3 Car Garage

3+Den / 3 Baths / Pool / Spa

Built 2020
Winding Cypress Naples Homes: Welcome to your DREAM HOME in the prestigious and highly sought after Naples lifestyle community of WINDING CYPRESS. Located on an oversized preserve lot with a pond view, this stunning  ''Pinnacle floor plan'' boasts over 2,500 sq feet under air with 3 large bedrooms 3 bathrooms plus a spacious den. This beautiful and well cared for home was built in 2020 and has everything already anyone could possibly want including a large ''picture window'' screened in gas heated saltwater pool and spa, custom outdoor kitchen, brick paver large lanai with a perfect covered area for entertaining. Hurricane shutters on the entire home for protection and newly installed electric hurricane screen for the covered lanai. Park all of your vehicles in the oversized and epoxy 3 car garage with hurricane rated/insulated garage doors with additional insulation in the attic to accommodate the separate garage A/C for optional cooling.  Brand new whole house generator that was recently installed which also accommodates additional power for the pool and spa. Plenty of space in your custom designed closet in the master bedroom and pantry done by one of the finest in the industry, California Closets. Stunning white quartz countertop kitchen with high end stainless steel KitchenAid appliances including an additional beverage refrigerator and gas cooktop. Located in an X flood zone with no flood insurance required.



$1,500,000
Sold Price:
$1,500,000
Sold Date:
11/08/2023
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Winding Cypress

7383 Mockingbird Ct, Naples, FL 34114

Homes - 3,696 ft² / 3,914 ft² - 3 Car Garage

4+Den / 4 Baths / Pool / Spa

Built 2016
Winding Cypress Naples Homes: Impressive 4bed/4 bath Home in the highly sought after community of Winding Cypress! Pinnacle, two-story model w/ many upgrades. End lot provides great privacy. Outdoor living space offers extended lanai area, outdoor gas kitchen, beautiful pool/spa & premium LONG lake views. Storm Smart electric lanai screens, wood-like tile flooring throughout & expanded kitchen island with bar seating for 5 or more. Kitchen includes: wine fridge and custom cabinetry w/ soft-close, & stainless steel appliance package. Sizable Master Suite with walk-in closet and large Master bathroom. Upstairs loft has a massive living area featuring a sitting area, bathroom, and separate bedroom. Big garage where you can park three cars. Winding Cypress features: An AMAZING active lifestyle community with something for everyone. Beach entry pool, waterfalls, poolside bar and grill, state-of-the-art fitness center, tennis, bocce, pickleball, social activities (off-site events, clubs, groups, classes) & miles of walking paths and boardwalks. Act fast this property is sure not to last!



$965,000
Sold Price:
$965,000
Sold Date:
10/02/2023
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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: H10980 Enter the brick paved driveway to this gorgeous three bedroom three bath plus den home in the prestigious community of Winding Cypress. This lake view home offers a large living area with Plantation shutters throughout, 90 degree corner sliders to bring the outside in, whole house water filtration and impact windows and sliders, open kitchen with island, stainless Kitchenaide appliances, include a gas stove and plentiful cabinetry with adjacent dining area. The bedrooms are spacious each with their own bath and a large den with built in Murphy bed. The master en-suite offers a large walk in shower and his and her sinks with an expansive walk in closet. Expansive lanai, also with brick pavers and under cover area for dining and lots of sunning spots around the pool and spa with beautiful waterfall feature. Oversized garage. Winding Cypress is conveniently located in South Naples, just a 15 minute ride to Marco Island or 5th Ave and the beaches. Offering a very active lifestyle with miles of walking paths, boardwalk, beautiful clubhouse with fitness, resort style pool, pickleball, tennis and plenty of social gatherings.



$950,000
Sold Price:
$925,000
Sold Date:
07/27/2023
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Winding Cypress

6898 Winding Cypress Dr, Naples, FL 34114

Homes - 2,117 ft² / 2,590 ft² - 2 Car Garage

2+Den / 2 Baths / 1 Half / Pool / Spa

Built 2021
Winding Cypress Naples Homes: Rare Prestige model for sale with every imaginable upgrade! This home features 2 bedrooms (second bedroom has convenience of an ensuite bath) a den, 2.5 bath, pool and spa. The upgrades are endless including soaring ceilings, a whole house generator, impact windows and doors, electric hurricane screens, outdoor kitchen, picture window lanai screen, trey ceilings, built in appliances, air conditioned and insulated garage, wider driveway with a paved walkway to pool area and 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!



$949,000
Sold Price:
$900,000
Sold Date:
11/17/2023
View Details

Winding Cypress

7408 Winding Cypress Dr, Naples, FL 34114

Homes - 2,198 ft² / 2,584 ft² - 2 Car Garage

4 Bed / 2 Baths / Pool / Spa

Built 2016
Winding Cypress Naples Homes: This coveted SW exposure pool home with has a beautiful long lake view! This Summerwood floorplan features 4BR/2BA and a 2 car garage. Impressive upgrades including electric storm smart hurricane screens, built in summer kitchen, expanded driveway, trey ceiling, crown molding, security system, cameras, finished laundry room and more! Winding Cypress has amazing amenities; onsite restaurant, pickle ball, bocce, tennis, state of the art fitness center and a resort style pool! Winding Cypress has no condos and is low density and is centrally located with easy access to Marco Island, 5th Ave, & I75 making it an ideal location! Homes is sold furnished – turnkey!



$900,000
Sold Price:
$900,000
Sold Date:
07/14/2023
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Winding Cypress

6762 Pennyroyal Dr, Naples, FL 34114

Homes - 2,884 ft² / 3,113 ft² - 2 Car Garage

3+Den / 3 Baths / Pool

Built 2021
Winding Cypress Naples Homes: LOWEST PRICE PER SQUARE FOOT IN WINDING CYPRESS. 2884 square feet under air. Stunning Summerwood POOL home with EXPANSIVE LOFT (1000 sqft) in Winding Cypress, a premier Naples Location. Better than new, barely lived in 3 BEDROOM plus DEN, 3 FULL BATH home. Live Naples at its best. This is the perfect SECOND home, with lots of room for guests, or a PRIMARY Home with all the comfort you need. This home offers a HEATED SALT WATER pool, EXTENDED COVERED LANAI, EXTENDED Epoxy GARAGE with enough room to park 3 cars, Extra refrigerator, 2 A/C units (Loft and Downstairs), Wireless Access Points (Loft and Lanai), Keyless Entry Front Door, HIGH IMPACT Windows and Sliders, and more. Winding Cypress is a beautiful natural gas, fiber network, resort-style community with world-class amenities which include a restaurant, pickelball, tennis, bocce, gorgeous community pool with Fire Pits, Dog Park, and more. All of this a short drive from Naples amazing shopping and dining and Marco Island beautiful sandy beaches.



$819,000
Sold Price:
$793,000
Sold Date:
08/22/2023
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Winding Cypress

7768 Winding Cypress Dr, Naples, FL 34114

Homes - 1,893 ft² / 3,253 ft² - 2 Car Garage

2+Den / 2 Baths / Pool

Built 2021
Winding Cypress Naples Homes: H8344. Desirable 2021 built Summerwood within the gated natural gas community of Winding Cypress. Wood plank laminate floor throughout common living spaces and den. Brown/grey shaker cabinets and white quartz countertops in kitchen and bathrooms. Luxurious carpet in bedrooms, extra storage space in garage, upgraded higher ceiling with coffered design in the living area. Enjoy the pool with custom water feature while admiring the private water and preserve view. Must see to appreciate. Take advantage of everything Winding Cypress has to offer: resort-style pool, tennis, pickleball, dining venue, fitness center, dog park, trails and more.



$759,900
Sold Price:
$745,000
Sold Date:
11/16/2023
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Winding Cypress

7441 Winding Cypress Dr, Naples, FL 34114

Homes - 1,685 ft² / 2,189 ft² - 2 Car Garage

2+Den / 2 Baths

Built 2017
Winding Cypress Naples Homes: This rarely available Abbeyville with a Premium Waterfront location has been meticulously maintained. The open concept will astound while walking into the light kitchen featuring Quartz counters, sleek stainless-steel appliances and large center island perfect for entertainment. Custom detailed shiplap wall in the dining area sets this apart. Spacious primary suite complete with a walk-in closet, double vanity, walk in shower and separate water closet. Your ensuite guest bedroom offers an adjoining full bath for guests' privacy. The den could easily be a 3rd bedroom. Upgrades include screen enclosed foyer, leaded glass front door, elegant tray ceilings, crown molding, Energy Saving Quiet DC fans, Full House Surge protection along with a NEW 22KW GENERATOR (with warranty) oversized to accommodate everything here plus more. With the best private waterfront and preserve views you have the option to plan your own custom pool with plenty of space. Extended driveway flows into the garage with newly installed Epoxy flooring and plenty of storage. Amenity rich community offering full time activities will keep you entertained and living the Florida lifestyle right in your own neighborhood.



$729,900
Sold Price:
$710,000
Sold Date:
09/05/2023
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Winding Cypress

7714 Jacaranda Ln, Naples, FL 34114

Homes - 1,554 ft² / 1,848 ft² - 2 Car Garage

2+Den / 2 Baths / Pool

Built 2019
Winding Cypress Naples Homes: Welcome to your new home in paradise. This MUST SEE Serenity villa is a 2 bedroom & den/bedroom with French doors, 2 bath, has a 2 car garage, with a heated saltwater pool and extended covered lanai. Gas cooking for all you chefs. Lots of upgrades including, 20" tile on the diagonal, outdoor kitchen, whole house gas generator, crown molding, quartz counters with white cabinets, 5 upgraded fans, designer light fixtures and pendants, water filtration system, Ring doorbell, 2 Nest cameras front and back of home, window coverings, and updated closets, Garage is insulated and has an A/C unit, workbench, storage lockers, slat walls, and an epoxy floor. Winding Cypress is a fabulous active lifestyle community with something for all, a poolside bar and grill, beach entry pool, hot tub, waterfalls, state-of-the-art fitness center, tennis, bocce, pickleball, lots of activities with social director, miles of walking paths, boardwalks, and is a short drive to Marco Island and downtown Naples.



$629,000
Sold Price:
$605,000
Sold Date:
08/21/2023
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Winding Cypress

7646 Jacaranda Ln, Naples, FL 34114

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

2+Den / 2 Baths

Built 2017
Winding Cypress Naples Homes: Stunning Serenity villa in Winding Cypress for sale! This home features 2 bedrooms plus a den, 2 bathrooms, with a 2 car garage - and some of the furniture is negotiable. This light an airy villa features tile floor throughout, recessed lighting, upgraded cabinets and counters in all areas, 8 foot doors, gorgeous landscaping, room for a pool 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!



$609,000
Sold Price:
$590,000
Sold Date:
08/29/2023
View Details

Winding Cypress

7594 Jacaranda Ln, Naples, FL 34114

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

2+Den / 2 Baths

Built 2017
Winding Cypress Naples Homes: Presenting resort living at its best with the extremely popular DiVosta Serenity model in Winding Cypress of Naples. This home is set on a tremendous private, pie-shaped lot with a large, covered lanai. The extra space surrounding the home makes it unique to the neighborhood. The home includes a modern, fully upgraded kitchen and breakfast bar setup alongside an open dining area. This nearly new home includes an immense amount of builder-installed upgrades as well. The split layout inside allows guests privacy and features a large owners' suite, guest bedroom suite and two full baths. The Club at Winding Cypress is a must-see and boasts a massive resort pool, sunset sand cabanas, bocce ball, pickleball, clay tennis courts, yoga deck, large gym workout facility, fire pits, nature trail, locker rooms, a full-time activities director, sandbar restaurant and much more. Winding Cypress is one of Naples most unique resort-style, non-golf communities ever built. It includes over 800 acres of pristine preserve, insulating the ideal location. It is perfectly situated in the heart of Marco Island and close to 5th Avenue in downtown Naples.




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