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Winding Cypress Naples Florida Homes for Sale

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Winding Cypress Naples Real Estate

Last updated at 8:35am 01/28/2023

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$1,595,000
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Winding CypressNEW

7483 Blackberry Dr, Naples, FL 34114

Homes - 2,911 ft² / 3,969 ft²

3+Den / 3 Baths / 1 Half

Build 2018
Winding Cypress Homes: Wow! This beautifully designed and meticulously maintained home is spectacular. Featuring the highly desirable and rarely available Stonewater floor plan, you are welcomed through a double-door entryway and onto a Great Room like few others. At approx. 37' X 22', with ceiling heights of approx. 13', it is perfect for entertaining or simply relaxing at home after a nice day out. The kitchen features upgraded appliances, quartz countertops, an oversized island and walk-in pantry. The two guest bedrooms feature en suite bathrooms and there is a dedicated pool bathroom on the lanai. Other features include tile throughout all common areas, a large laundry/utility room with plenty of cabinets, natural gas and a 3-car garage. The rear, picturesque lake and preserve land view is wonderful and provides privacy. To top it all off, this magnificent home resides in the highly prized community of Winding Cypress. An onsite restaurant, modern fitness center, community pool and a full calendar of social gatherings are a nice walk, bike or golf cart ride away. Great home. Great community. Great location. This property checks all the right boxes for the time of your life in beautiful Naples, FL.



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$1,500,000
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Winding Cypress

7383 Mockingbird Ct, Naples, FL 34114

Homes - 3,696 ft² / 3,914 ft²

4+Den / 4 Baths

Build 2016
Winding Cypress Homes: This is your Next Home 4bed/4 bath + den. Gorgeous Pulte/DeVosta expanded, Pinnacle, two-story model with many upgrades. This is the largest home on the street built w/ a lot upgrades, no neighbors on the left of the home, extended lanai area, outdoor gas kitchen, beautiful pool/spa & premium LONG lake views. Peace of mind with Storm Smart electric lanai screens, solid surface flooring throughout & an expanded kitchen island with bar seating for 5 or more. The kitchen includes: wine fridge and custom cabinetry with soft-close, & stainless steel appliance package. Crown molding throughout. 2 Ground floor suites for entertaining your guests, main suite features an extended, tiled walk-in shower and an enormous closet. The upstairs loft is a massive living area featuring a sitting area, bathroom, and separate bedroom. The garage has a 4' garage extension, 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.



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$1,400,000
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$275K
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Winding Cypress

7068 Live Oak Dr, Naples, FL 34114

Homes - 3,656 ft² / 4,467 ft²

4+Den / 4 Baths

Build 2015
Winding Cypress Homes: Expanded Pinnacle model with nearly every builder's upgrade possible. The home includes zero-corner sliding glass doors with a beautiful pool, spa and lake views. All impact windows and a whole-house generator give the owner of this home maximum security and comfort! There's tile throughout the first floor and the expanded kitchen island with 5+ bar seats. The kitchen's entertainment option includes bar, wine cooler and custom cabinetry. Appliances are upgraded Whirlpool stainless with a natural gas cooktop and Bosch dishwasher. Crown molding in great room. Downstairs bedrooms have walk-in closets. Master suite has huge walk-in shower and sprawling closet. Upstairs loft is a massive flex room and had a fourth bedroom and bath. LED lighting throughout. Tankless gas water heater. The garage has the 4' garage extension, epoxy floor and extra attic storage. Turnkey-furnished with quality furnishings. The clubhouse is elegant with a beach entry pool, waterfalls and poolside bar and grill. Enjoy a state-of-the-art fitness center, tennis, bocce, pickleball, social activities and miles of walking paths and boardwalks through the preserve.



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$1,250,000
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$75K
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Winding Cypress

7453 Winding Cypress Dr, Naples, FL 34114

Homes - 2,496 ft² / 2,982 ft²

3+Den / 3 Baths

Build 2016
Winding Cypress Homes: Combining the unique privacy of a long lake view with the unparalleled value offered in Winding Cypress, this Pinnacle model is everything you are seeking in your new Naples home! Enjoy relaxing or entertaining on your spacious lanai with (gas) outdoor kitchen and saltwater pool and spa with a less than year-old heater. Or, take advantage of the gourmet kitchen and wine bar with family and friends as you flow into the open and inviting great room while enjoying the whole-home Vitex sound system. Whether for family or overnight guests, you will appreciate the separation in the 3 bedrooms (+den) as well as the convenience of 3 full baths. Speaking of baths, the main bedroom provides the luxury of an extended shower design as well as a spacious walk-in closet. When you venture out of your home, the luxurious clubhouse amenities covered by your very affordable HOA dues include a grand fitness center, meeting/activity rooms, catering kitchen, library, and more. Just outside the clubhouse doors you will find a resort pool, lap pool, spa, bocce, tennis, pickleball, etc. Designed to mesh with nature, Winding Cypress also offers a dog park, community garden, nature paths, and more.



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$1,125,000
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$25K
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Winding Cypress

7235 Live Oak Dr, Naples, FL 34114

Homes - 2,668 ft² / 5,100 ft²

3+Den / 3 Baths

Build 2015
Winding Cypress Homes: Pristine 3+den pool home with lake views in highly sought-after Winding Cypress. They spared no expense with upgrades everywhere to include custom saltwater pool, walk-in pantry, oversized two car garage, and spacious walk in closets. All appliances are up to date with two new ACs, new gas pool heater, new refrigerator, new flooring, spacious family room on the second floor, washer and dryer included. Winding Cypress features world class amenities to include a state of the art fitness center, luxury clubhouse, resort style pool with poolside dining, dog park, bocce, pickle-ball, tennis courts and much more!



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$998,900
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Winding CypressNEW

6754 Pennyroyal Dr, Naples, FL 34114

Homes - 2,158 ft² / 3,256 ft²

3+Den / 3 Baths

Build 2020
Winding Cypress Homes: NICER THAN A MODEL HOME!!! Spacious 3 bedroom + den, 3 FULL bathroom house with FULL impact glass doors and windows. $138,000 in builder upgrades PLUS over $110,000 in CUSTOM upgrades that were done after closing. Built in 2020, the home has luxurious features you would find in a MODEL home such as: luxury vinyl and carpet flooring, crown molding, interior re-painted, outdoor landscaping lighting, a designer front door, garage door screen, custom hardware throughout, home alarm system, custom cabinets in the living and laundry rooms, custom lighting, and more. Winding Cypress has TONS of activities is a natural GAS community and offers RESORT STYLE amenities such as: a resort style pool, food and drinks at the outdoor Barefoot Bar, a state of the art fitness center, a movement studio, multiple dog parks, tennis, bocce, pickle ball, a nature walk trail, a bird watching overlook and more. Winding Cypress has TWO entrances/exits so within minutes you can you can on Marco Island or at the FAMOUS shopping and dining on 5th Avenue South. This home “may” be the best value in Winding Cypress and possibly anywhere in Naples. VIRTUAL TOUR LINK AVAILABLE TO CLICK ON THAT INCLUDES A VIDEO



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$995,000
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Winding CypressNEW

7211 Live Oak Dr, Naples, FL 34114

Homes - 2,230 ft² / 2,667 ft²

3+Den / 2 Baths

Build 2015
Winding Cypress Homes: The ultimate waterfront home site in the resort community of Winding Cypress in Naples. This Summerwood model has every option and add-on imaginable. From impact windows to a whole-house generator system. The fully extended covered lanai and pavered pool deck extend over a curved pie-lot water view. The home includes three bedrooms, a den, two baths, a gourmet kitchen opening to the gathering room, dining area and the sunroom for the perfect poolside living nook for TV or reading. The lanai features wide-open spaces for sun loungers and 2nd largest structured covered lanai of any model in Winding Cypress. The master bedroom is a full en suite and includes a large custom walk-in closet. The luxurious Winding Cypress clubhouse amenities include a state-of-the-art fitness center, catering kitchen, community room and activity room. Residents have access to a resort-style pool, lap pool, spa, outdoor movement studio, outdoor barefoot bar, full bocce and pickleball courts, tennis courts, a fire pit and even a birdwatching overlook and nature boardwalk with a picnic pavilion.



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$989,000
Decrease*
$110K
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Winding Cypress

7546 Blackberry Dr, Naples, FL 34114

Homes - 2,188 ft² / 4,611 ft²

3+Den / 2 Baths

Build 2018
Winding Cypress Homes: Beautifully appointed Summerwood floorplan, with over $150,000.00 in builder design option upgrades, heated pool and spa, raised ceilings, and more. The owners have added over $45,000.00 in additional improvements including a whole house Generator, hurricane shutters, hurricane glass front windows and entry door, landscaping and lighting, window treatments, garage overhead storage, and more. Home is being sold partially furnished. This great lakefront home offers, 3 bedrooms, 2 bathrooms, den, full kitchen with quartz countertops and central island. Winding Cypress offers natural gas. Enjoy the great amenities at Winding Cypress including a full resort clubhouse with restaurant and bar, heated pool, tennis, pickleball, and even a community garden with fresh veggies and herbs. Winding Cypress is centrally located a short drive south to the white sand beaches of Marco Island and west to all the activities of downtown Naples. The community is located near shopping, restaurants, grocery stores, and medical facilities. Welcome to Winding Cypress, your Piece of Paradise.



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$985,000
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Winding Cypress

7464 Blackberry Dr, Naples, FL 34114

Homes - 2,107 ft² / 2,469 ft²

3+Den / 2 Baths

Build 2017
Winding Cypress Homes: Presenting the rarely offered Martin Ray model with upgraded tray-raised ceilings in Winding Cypress. This best-selling Divosta home plan features three bedrooms, a den, two baths, and pool with spa overlooking expansive long lake views. The natural gas gourmet kitchen and gathering island open to a well-defined, yet open dining area and spacious living and entertaining areas. The lanai features a beautiful wide-open and spaces great sun lounging areas to look over the lake. The entire home features top luxury upgrades including quartz, high-end porcelain tile and a motorized hurricane shutter. The luxurious Winding Cypress clubhouse amenities include a state-of-the-art fitness center, catering kitchen, community room and activity room. Residents have access to a resort-style pool, lap pool, spa, outdoor movement studio, outdoor barefoot bar, bocce ball courts, tennis courts, a fire pit and even a bird-watching overlook and nature boardwalk with a picnic pavilion.



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$979,000
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Winding CypressNEW

6762 Pennyroyal Dr, Naples, FL 34114

Homes - 2,577 ft² / 3,113 ft²

3+Den / 3 Baths

Build 2021
Winding Cypress Homes: Stunning Summerwood POOL home with expansive LOFT 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 for a PRIMARY Home with all the comfort you need. This home offers a heated SALTED pool, EXTENDED covered LANAI, EXTENDED Epoxy GARAGE with Extra refrigerator, 2 A/C units (Loft and Downstairs), Wireless Access Points (Loft and Lanai), Keyless Entry Front Door, High Impact Windoews 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.



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$975,000
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Winding CypressNEW

7021 Live Oak Dr, Naples, FL 34114

Homes - 2,078 ft² / 2,474 ft²

4 Bed / 3 Baths

Build 2015
Winding Cypress Homes: Just water and trees. This ultra-premium home and lot has waterfront, preserve, and sunset western views set in the ultimate Naples resort community of Winding Cypress. This Abbeyville home features every builder option and upgrade, plus a very cool bonus upstairs loft bedroom and living room for a sweet retreat. The home includes top-level finishes along with impact windows from top to bottom, Swat outdoor bug system, central vacuum, fully remote automated SunPro awning system with night lights on the lanai, and many more. The luxurious Winding Cypress clubhouse amenities include a state-of-the-art fitness center, catering kitchen, community room and activity room. Residents have access to a resort-style pool, lap pool, spa, outdoor movement studio, outdoor barefoot bar, bocce ball courts, tennis courts, a fire pit and even a bird-watching overlook and nature boardwalk with a picnic pavilion.



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$950,000
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Winding Cypress

7760 Winding Cypress Dr, Naples, FL 34114

Homes - 2,047 ft² / 2,704 ft²

3+Den / 2 Baths

Build 2020
Winding Cypress Homes: Immaculate pool home with breathtaking sunsets! Featuring over 150k in builder upgrades, including zero corner sliding glass doors, pool fountain, extended lanai, upgraded appliances. Owner added improvements (over 40k) include pool heater, outdoor kitchen, storm protection screens on lanai, plantation shutters, and custom closet. Winding Cypress is a resort style community located near all that Naples has to offer and is only a short drive to Marco Island. Enjoy relaxing at the resort style pool, have dinner at the restaurant, or play a game of tennis or pickleball. Enjoy walking on the trails all of the surrounding beauty in Winding Cypress. Schedule your showing today!



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$879,000
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Winding CypressNEW

7768 Winding Cypress Dr, Naples, FL 34114

Homes - 1,893 ft² / 3,253 ft²

2+Den / 2 Baths

Build 2021
Winding Cypress 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.



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$869,000
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$30K
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Winding Cypress

7673 Jacaranda Ln, Naples, FL 34114

Homes - 2,063 ft² / 2,539 ft²

3+Den / 3 Baths

Build 2019
Winding Cypress Homes: Immaculate Move-In-Ready 2019 Pool Home, Preserve & Corner Lot. An absolute safe haven with Generac Whole Home Generator & all hurricane impact windows & sliders. During Hurricane Ian: full electricity, water, satellite TV, & zero damage. Main floor with spare bedroom, full bath, & den with double doors. Happy & bright kitchen with pantry & open concept to dining & living areas. Laundry room with storage is adjacent to master suite with oversized walk-in closet in master bath. Spacious loft upstairs with 3rd bedroom, full bath, & walk-in closets. Central Vac System, plantation shutters, recessed lighting, & brand new ceiling fans throughout & smart wired with keyless entry. Pool with safety fence panels & upgraded with new high efficiency pool heater. Extended length garage, perfect for storing small boat or golf cart. Resort-style pool with poolside restaurant, bar, and sandy beach cabanas as well as community nature boardwalk, garden, birdwatch pavilion, and dog park. Clubhouse includes fitness center, pickle ball, tennis, bocce, & a variety of events. This is a true complete home set in a lush, nature-rich community.



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$739,990
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$10K
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Winding Cypress

7811 Jacaranda Ln, Naples, FL 34114

Homes - 1,574 ft² / 1,964 ft²

2+Den / 2 Baths

Build 2019
Winding Cypress Homes: The rarely available Winding Cypress villa floor plan features a dedicated private front entrance and foyer. The long water view from the pool deck is a must-see. The open layout home includes an endless amount of builder-installed upgrades including all quartz finishes, high-end porcelain floors and much more. The natural gas-powered whole-house generator and electronic hurricane shutters make for tremendous add-ons. Winding Cypress is one of Naples' most unique resort communities ever built. It includes over 800 acres of pristine preserve insulating the ideal location. Perfectly situated in the center point of Marco Island, 5th Avenue and downtown Naples. It includes a dog park and a community vegetable garden. The Club at Winding Cypress is a must-see, boasting a massive resort-style pool, sunset sand cabanas, bocce ball, pickleball, clay tennis courts, yoga deck, large gym facility, fire pits, nature trail, locker rooms, full-time activities director, sand bar, and restaurant. These homes all feature a Naples rarity, natural gas.



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$650,000
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$25K
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Winding Cypress

7770 Jacaranda Ln, Naples, FL 34114

Homes - 1,574 ft² / 1,960 ft²

2+Den / 2 Baths

Build 2018
Winding Cypress Homes: Rare opportunity to purchase a meticulously maintained and upgraded Cressida villa in Winding Cypress. This home features 2 bedrooms+den, 2 bathrooms, 2 car garage, and an extended lanai to appreciate the gorgeous lake view and massive side yard! The extensive upgrades include, hurricane screens throughout, whole house natural gas generator, upgraded appliance package, trey ceilings, plantation shutters, quartz counters with white cabinets throughout, custom pantry system, master closet system, front screen door for airflow, floored attic for storage, and so much more. In the outdoor oasis there is an extended lanai with an outdoor kitchen, a built in natural gas fire pit (no need to exchange tanks!), and privacy for miles with the large yard and no homes across the lake. Winding Cypress has amenities galore and is a natural gas community! Dine at Shady Palm, the onsite restaurant, play pickleball, bocce, tennis, workout in the state of the art gym or lounge by the resort 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 central to Marco Island, 5th Ave, & I75 making it an ideal location!




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