Winding Cypress Real Estate

Recently Sold Listings in Winding Cypress, Naples, FL

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All Sold in Winding Cypress, Naples, FL

$1,050,000
2 Beds ⋅ 2.5 Baths ⋅ 224009153 MLS
LIKE NO OTHER FOR SALE IN WINDING CYPRESS! This "PRESTIGE MODEL" POOL home must be seen to be appreciated for all that it has to offer! BEING SOLD TURNKEY WITH ALL DESIGNER DECOR ALL YOU NEED TO DO IS BRING YOUR TOOTHBRUSH AND CLOTHES! GORGEOUS LAKE VIEWS THROUGH THE PICTURE WINDOW SCREEN! This home has over 2,100 square feet of living space with 2 Bedrooms Plus Den (Den is a 3rd Bedroom option) and 2.5 baths complete this space. Lots of upgrades that will give you no reason to do anything but move in and enjoy all the work that was put into this home. The Gourmet Kitchen creates the perfect gathering area and expands into the Living and Dining Area providing tons of room for entertaining. It offers wood cabinets with soft close doors, crown molding on the cabinets, tile backsplash, upgraded Quartz counters, pantry, and stainless steel appliances. Oversized tile on a diagonal throughout the entire home! Plantation Shutters, Crown Molding, IMPACT WINDOWS & DOORS, and a Roll Down Hurricane screen across the back. HOME IS PRE-PLUMBED FOR OUTDOOR KITCHEN! The gorgeous lake views beyond the large heated pool will help you relax the day away creating your own tropical oasis.

6830 Greenbriar CT, Naples
$1,043,000
3 Beds ⋅ 2 Baths ⋅ 223086995 MLS
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!

6846 Greenbriar CT, Naples
$1,025,000
4 Beds ⋅ 2 Baths ⋅ 226013964 MLS
This beautifully designed and impeccably maintained home offers the perfect blend of elegance and comfortable Naples living. Featuring the highly sought-after Summerwood floor plan with a spacious Great Room extension, the open layout creates an impressive, light-filled space perfect for entertaining guests or relaxing with family after a day exploring beautiful Naples, FL. The gourmet kitchen shines with upgraded stainless appliances, elegant quartz countertops, an oversized island perfect for casual dining and hosting, and a generous walk-in pantry. This home features a generous primary Master bedroom plus three versatile guest bedrooms. Any of the three guest bedrooms can easily function as a bedroom, home office, den, or media room to suit your lifestyle. The fourth bedroom is a major advantage for leasing the home, providing extra flexibility that can help attract tenants, support higher rental rates, and appeal to a wider range of renters who need extra space for guests, etc. It also functions well as internal storage space or could be used to expand the Master closet. Interior finishes include high-grade porcelain tile flooring throughout, a practical laundry/utility room with storage and sink. And natural gas service is used for cooking, water heating, and efficient clothes drying. Step outside to your private resort-style lanai. This expansive space features custom pavers, a built-in outdoor kitchen, and plenty of room for outdoor gatherings or quiet relaxation. Enjoy a swim in the heated pool and spa, soak up the southern Florida sunshine, or simply take in the spectacular eastern water views framed by a large portrait “no-see” lanai screen. These serene vistas consistently draw “wows” from everyone who visits. For added peace of mind and year-round comfort, the home includes impact-resistant hurricane doors and windows throughout. These premium features provide excellent storm protection, improve energy efficiency, and help reduce insurance premiums while eliminating the hassle of traditional shutters. Elegant Bahama shutters offer additional beauty and protection. The elevated lot is also not in a mandatory flood insurance zone, adding to the worry-free lifestyle. Nestled in the prestigious gated community of Winding Cypress, residents enjoy an onsite restaurant, modern fitness center, community pool, tennis courts, pickleball courts, and a full calendar of social events—all just a walk, bike, or golf cart ride away. Conveniently located between downtown Naples and Marco Island, you’re minutes from pristine beaches, upscale shopping, and fine dining. Offered fully furnished and move-in ready, this exceptional home truly checks every box: Impressive Great Room. (Check.) Gourmet kitchen & flexible living spaces. (Check.) Resort-style outdoor living with water views. (Check.) Outstanding community & prime location. (Check.) Ready for the Naples lifestyle you’ve dreamed of? This beautiful home delivers it all.

7631 Winding Cypress DR, Naples
$1,015,000
3 Beds ⋅ 2 Baths ⋅ 223080921 MLS
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.

6723 Pennyroyal DR, Naples
$1,000,000
3 Beds ⋅ 3 Baths ⋅ 225067249 MLS
Location, location! This meticulously maintained and decorated Pinnacle model located on a corner lot with privacy on both sides including a lake and wooded area view is unique! Conveniently located within walking distance to clubhouse! The home features 3 bedrooms plus a den, 3 full baths and 3 car garage in this highly sought after natural gas community of Winding Cypress! This large lanai features a custom gas outdoor kitchen and a beautiful custom pool and spa! A must see to be appreciated! Home protection includes impact windows, sliders and electric shutters Winding Cypress offers a beautiful clubhouse, resort style pool and spa and waterfall feature! In addition to pickleball, tennis, bocce, state of the art fitness center and on-site director for classes! A dog park, community garden and plenty of biking and walking trails to enjoy!

7235 Clamshell LN W, Naples
$1,000,000
3 Beds ⋅ 3 Baths ⋅ 224039468 MLS
Welcome to the award-winning Martin Ray home in the prestigious and central Winding Cypress resort community in Naples. This exceptional home boasts a stunning custom pool and lanai, complete with an in-water sundeck, ideal for soaking the Florida sunshine. Relax and unwind as you enjoy the picturesque views of the private waterfront. Inside, you'll find a bright and airy ambiance, highlighted by top-of-the-line quartz finishes and gourmet appliances powered by natural gas. Whether you're hosting a lavish gathering or enjoying a quiet evening in, this home offers the ideal blend of elegance and comfort. A bonus loft offers a cool option for guests or in-home entertainment with plenty of room for a pool table or even a home theater! Residents will enjoy the luxurious Winding Cypress clubhouse, offering a state-of-the-art fitness center, catering kitchen, community room and activity room. Outdoor amenities abound, from pickleball, resort-style and lap pools to a spa, outdoor movement studio, barefoot bar, bocce ball courts, five Har-Tru tennis courts, fire pit, bird-watching overlook and a nature boardwalk with a picnic pavilion. In ideal proximity to the pristine shores of Marco Island and vibrant downtown Naples, this amazing resort location provides the ideal backdrop for an unparalleled lifestyle.

7554 Blackberry DR, Naples
$1,000,000
3 Beds ⋅ 3 Baths ⋅ 224023526 MLS
Welcome to the ultimate Naples resort community of Winding Cypress. Presenting this lakeview Summerwood home, set on an exceptionally private homesite with a beautiful, long lake view. Features include every builder option and upgrade, plus a very cool upstairs bonus loft bedroom and living room, perfect for guests or as a homeowner's retreat. This home includes top-level finishes throughout along with easy glide window shutters from top to bottom, motorized lanai storm shutters, an oversized covered lanai, a two-car tandem storage garage, a whole house generator, and a beautiful lakefront pool. Residents can indulge in the luxurious Winding Cypress clubhouse, offering a state-of-the-art fitness center, catering kitchen, community room, and activity room. Outdoor amenities abound, offering pickleball, resort-style and lap pools, a spa, an outdoor movement studio, a barefoot bar, bocce ball courts, five Har-Tru tennis courts, a fire pit, a bird-watching overlook, and a nature boardwalk with a picnic pavilion. In ideal proximity to the pristine shores of Marco Island and the vibrant downtown Naples, this amazing resort location provides the ideal backdrop for an unparalleled lifestyle.

7123 Lily WAY, Naples
$1,000,000
3 Beds ⋅ 2 Baths ⋅ 223065392 MLS
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.

7634 Arrowhead WAY, Naples
$995,000
3 Beds ⋅ 3 Baths ⋅ 224055933 MLS
Ready for immediate occupancy! home is now vacant and has a nice clean open slate to custom this home to your liking .Take a look at this Pinnacle style home located in the sought after community of Winding Cypress features 3 bdrms 3 baths, office and 3 car garage , hurricane protection measures include whole house generator , impact doors and windows and hurricane storm screen on lanai. Extended oversized Lanai facing the lake has plenty of room for entertaining , practice your putting , or custom a new pool or spa. come and take a look at this Pinnacle style home in Winding Cypress, use your vision to custom this home to your own personal taste, You can't beat the floor plan with almost 2500 soft of living space and is a great value compared to other Pinnacle models sold here in Winding Cypress. Home is located within walking distance to all the amenities Winding Cypress has to offer,, beautiful resort pool , pool side resturant and bar, gym, sports courts and more . Walk to to the dog park and community garden. P

7063 Winding Cypress DR, Naples
$992,500
2 Beds ⋅ 2 Baths ⋅ 224090027 MLS
The most private homesite in Winding Cypress Resort community, this exceptional home offers views abundant with trees and lake, bordered by a lush preserve and expansive buffer zones. Breathtaking southwestern water views provide the ideal backdrop, rivaling the most stunning beach sunsets. Step outside to the largest covered lanai in the community, complete with a sparkling pool and spa, creating an idyllic space for relaxation and entertaining. Step inside to discover a home that has been expanded and meticulously designed, with raised ceilings and professionally finished interiors that exude sophistication. This home is equipped with premium features, including whole house generator, reverse osmosis water system, impact-resistant glass, natural gas and top-tier finishes throughout. The expansive layout offers views from every angle, ensuring that every room feels connected to the beautiful outdoor surroundings. Residents can indulge in the luxurious Winding Cypress Club, which features a state-of-the-art fitness center, catering kitchen, community room and activity room. Outdoor amenities abound, including pickleball, a resort-style pool with a lap section, spa, outdoor movement studio, barefoot bar, bocce ball courts, five Har-Tru tennis courts, a fire pit, a bird-watching overlook and a nature boardwalk with a picnic pavilion. At the center point between the pristine shores of Marco Island and the vibrant downtown Naples, this incredible resort location provides the ideal backdrop for an unparalleled lifestyle.

7404 Winding Cypress DR, Naples
$990,000
3 Beds ⋅ 2 Baths ⋅ 225048066 MLS
Wow! This beautifully designed and meticulously maintained home checks all the right boxes. Featuring the highly desirable Summerwood floor plan with Great Room extension, it is perfect for entertaining or simply relaxing at home after a nice day out in beautiful Naples, FL. The kitchen features upgraded appliances, quartz countertops, an oversized island and walk-in pantry. The two guest bedrooms provide enough room for guests. The office/den can easily serve as a 4th bedroom if desired. Other interior features include high-grade porcelain tile throughout, a laundry/utility room with plenty of storage and natural gas for cooking, heated water and clothes drying. Exterior upgrades abound with a one-of-a-kind extended lanai with custom pavers and a built-in outdoor kitchen. There is plenty of space for outdoor gatherings, cookouts, an afternoon nap, a dip in the pool or just taking in some Florida sunshine. Looking through the huge portrait "no-see" lanai screen is one of the very best long water views in the entire community. The view is simply gorgeous, inspiring "wows" from all. The driveway and side walkway are extended. There is over $100k in upgrades to this magnificent home. Just pack your bags and head on down to enjoy our very special slice of tropical paradise. Worried about maintenance and insurance costs, and/or storms? Newer construction (2021) negates a large future roof replacement cost for some time. And a newer A/C system should provide many more years of solid service. Hurricane impact doors and windows are throughout providing for great energy efficiency and home protection. Also, the lot of this property is elevated. It is not in a mandatory flood insurance zone. And there is a whole home gas generator too should the need ever arise. All aforementioned should assist in obtaining lower insurance premiums and keep maintenance costs down. This home offers easy peasy and worry-free living by any measure. To top it all off, this sensational 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 with some of the best Naples residents around are a nice walk, bike or golf cart ride away. Also, located conveniently between downtown Naples and Marco Island, opportunities to visit some of our finest beaches, shopping and dining locations are just minutes away. Great home. (Check.) Great view. (Check.) Great community. (Check.) Great location. (Check.) This property checks all the right boxes for the time of your life in beautiful Naples, FL.

6767 Pennyroyal DR, Naples
$975,000
3 Beds ⋅ 3 Baths ⋅ 226014585 MLS
This 2 Story Mystique Model, located in the desireable community of Winding Cypress, absolutely has to be seen to appreciate all that it offers. Instead of using AI to draft a lofty, fluffy, low information description of this home, we are just going to just list a few of the features and upgrades of this 3-year-new beauty! WHOLE HOUSE GENERATOR, HEATED SALTWATER POOL W/SPA & WATER FEATURE, HURRICANE IMPACT WINDOWS & DOORS, ELECTRIC LANAI SUNSHADES, EXTENDED 3 CAR GARAGE W/MINI SPLIT AC, INSULATED OVERHEAD DOOR, EPOXY FLOORS & ADDITIONAL BUILT-IN/UNDER STAIRS CUBBY STORAGE, UPGRADED 2-TONE KITCHEN CABINETS W/UNDER CABINET LIGHTING, QUARTZ COUNTERS, BLACK STAINLESS APPLIANCE PACKAGE, OUTDOOR SUMMER KITCHEN WITH GRANITE/LEATHER TOP COUNTER, 2 HVAC UNITS W/DOWNSTAIRS & UPSTAIRS ZONES, AMAZING GLASS WALL ENCLOSED FLEX ROOM, UPGRADED LAUNDRY CENTER W/BUILT-IN CABINETS/COUNTERS & 2ND REFRIGERATOR, HUGE 2ND FLOOR AREA W/LARGE BEDROOM & FULL BATH, MURPHY BED, 2ND FLOOR FLEX SPACE FOR THEATER/MEDIA ROOM & ADDITIONAL DEN/OFFICE, PLANK TILE FLOOR THROUGHOUT DOWNSTAIRS, ALL UPGRADED FAUCETS/FIXTURES/LIGHTING/HARDWARE, IN-FLOOR OUTLETS, TRAY CEILING, SMART HOME CAT-6 WIRED W/MONITORED ALARM SYSTEM, & ALL THIS ON A DEAD END CUL-DE-SAC. Winding Cypress is noted for it's incredible high value amenities that include a private, resident's only, full-service restaurant and bar, Las Vegas styled resort pool & spa, pickelball, tennis & bocce courts, an amazing fitness center, nature trail/boardwalk, community garden, a dog park, all surrounded by 1250 total community acres that includes 800+ acres of preserve, green space & lakes. You are just 15 minutes to downtown Olde Naples & 10 minutes to Marco Island & I75. This home, and the Winding Cypress Community are very special!

6678 Pennyroyal DR, Naples
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