Sold in Winding Cypress, Naples, FL

Nestled within the gated, amenity-rich community of Winding Cypress, this thoughtfully designed turnkey furnished two-bedroom plus den, two-bath residence offers an exceptional blend of comfort, quality, and relaxed Florida living. The open floor plan is enhanced by wood flooring throughout the main living areas, along with crown molding, and a distinctive coffered ceiling in the living and dining area, creating a refined yet inviting atmosphere. The kitchen is both elegant and functional, featuring 42" white cabinetry, granite countertops, tile backsplash, undercabinet lighting, and stainless-steel appliances—ideal for everyday living and entertaining alike. A flexible den with French doors provides the option for a private home office, media room, or additional guest space. Seamless indoor-outdoor living is achieved through the expansive custom lanai, designed for entertaining with an outdoor kitchen complete with gas grill, refrigerator, and sink, an above-ground HotSprings hot tub with beautiful outdoor furnishings including a dining table for six, over-sized parasol umbrellas that provide shade, and picture-frame lanai screens that showcase peaceful preserve surroundings. Additional highlights include a whole-house gas generator, two-car garage, and plantation shutters. Winding Cypress is a natural gas community thoughtfully designed around preserved natural beauty and an active, social lifestyle. At its heart is an impressive clubhouse with a heated resort-style pool and spa, poolside dining at The Shady Palm, state-of-the-art fitness center, library, and community gathering rooms. Other amenities include pickleball and tennis courts, bocce courts, dog parks, a community garden, and scenic walking and nature trails. Known for its welcoming atmosphere and beautifully maintained grounds, Winding Cypress offers a true sense of community while remaining conveniently close to everything Naples has to offer. A six-passenger well-maintained golf cart is included for effortless access throughout the neighborhood.

7121 Live Oak 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

$615,000

2 Beds ⋅ 2 Baths ⋅ 226005934 MLS

Sunset water views stretch across a sparkling long lake from your private pool and spa, creating a breathtaking backdrop for everyday living and entertaining from the fully equipped natural gas outdoor kitchen. This beautifully maintained home stands out with major recent upgrades including a brand new AC system (2026), new washer and dryer, new hot water heater, and new carpet, offering peace of mind and allowing the home to live comfortably and effortlessly from day one. The open floor plan feels light, bright, and inviting with updated flooring and elegant quartz and granite surfaces throughout. The thoughtfully designed layout offers two spacious bedrooms plus a flexible den with an alcove ideal for adding a closet, making it perfect for guests, a home office, or additional sleeping space. The gourmet kitchen blends style and function with granite countertops, a tasteful tiled backsplash, staggered cabinetry, and bar seating for casual gatherings, while natural gas service and ceiling-mounted garage storage racks add everyday convenience. Gently lived in as a pet-free, smoke-free seasonal residence, the property shows like new. Located in the resort-style community of Winding Cypress, residents enjoy more than 800 acres of preserved natural landscape and exceptional amenities including a clubhouse with a heated pool, on-site restaurant, fitness center, white sand beach, tennis and pickleball courts, dog park, and scenic nature trails, all with low HOA fees and an ideal location just 25 minutes to Fifth Avenue South, 20 minutes to Marco Island, and minutes to major shopping and dining, creating a lifestyle that blends luxury, convenience, and unforgettable views.

7639 Jacaranda LN, Naples

$905,000

2 Beds ⋅ 2 Baths ⋅ 226009304 MLS

Experience refined Naples living in this impeccably maintained, fully furnished residence in the prestigious gated community of Winding Cypress. Featuring two bedrooms plus a den, two baths, plus an extended additional den leading to the waterfront pool area, and an extended 2-car garage; this home has been thoughtfully designed and is move-in ready - blending comfort, elegance, and effortless luxury. Inside, tiled wood-plank flooring flows seamlessly throughout, complemented by plantation shutters throughout the home that add both timeless elegance and privacy. The beautifully curated furnishings enhance each space, delivering a polished, designer feel from the moment you enter. The gourmet kitchen serves as the heart of the home, featuring a large center island with seating, a pantry closet, gas stove, and abundant cabinetry. Ideal for both everyday living and entertaining, the kitchen opens to the spacious dining and living areas, allowing for easy gatherings and relaxed conversation. The versatile den provides the perfect setting for a private office, media room, or additional guest accommodations. The primary suite is a luxurious retreat, complete with a spa-inspired bath and a recently customized walk-in closet designed for optimal organization and style. The guest bedroom and bath provide comfort and privacy for visitors. Step outside to your private oasis—a covered lanai with comfortable seating that transitions seamlessly to the screened-in pool and spa area. The expansive pavered deck surrounds a sparkling pool and spa accented by a tranquil waterfall feature, all overlooking a peaceful lake view. Storm Smart lanai shutters offer added protection and convenience, while upgraded landscaping and lanai lighting create a stunning ambiance day and night. The beautifully landscaped lawn enhances the serene setting, delivering exceptional curb appeal and a tranquil outdoor backdrop. An underground gas generator provides an additional layer of security and peace of mind, ensuring uninterrupted comfort year-round. Winding Cypress elevates the lifestyle even further with an impressive array of resort-style amenities. Residents enjoy a stunning clubhouse, state-of-the-art fitness center, resort-style pool and spa, tennis and pickleball courts, bocce, an on-site restaurant, community garden, dog park, and miles of scenic walking and biking trails. A vibrant social calendar and beautifully maintained grounds make every day feel like a private resort experience. Ideally situated just minutes from the world-class dining, upscale shopping, art galleries, and white-sand beaches of downtown Naples, this home offers the perfect combination of luxury, location, and lifestyle. An exceptional opportunity to own a furnished, lakefront retreat in one of Naples’ most sought-after communities.

7545 Geranium WAY, Naples

$595,000

2 Beds ⋅ 2 Baths ⋅ 225072028 MLS

This charming model is the perfect fit featuring an inviting open-floor concept where natural light streams through the windows. The kitchen boasts granite counters, stainless appliances and a center island and extra storage for everyday use and easy entertaining. The pantry closet has plenty of space for all of your staple goods. Tile floors are throughout much of the space. There's a den/flex room with french doors that can be used as an additional bedroom when needed or office, hobby or quiet sitting room. Additional guest bedroom and bathroom with combined tub and shower and granite topped vanity offers privacy for your family and guests. The laundry room features a spacious storage area with shelving for your all your supplies. There are storage racks in the two car garage to house your coolers for the beach. Be sure to take time to relax and enjoy your morning beverage and the beautiful sunsets on the screened lanai that overlooks the OVERSIZED lot with mature landscaping complete with an outdoor kitchen with grill, sink, and fridge for your convenience. Winding Cypress is a sought after, gated community and is appreciated for its active, social lifestyle and world class amenities. It’s nestled within 800 acres of natural preserve and 80 acres of serene lakes teeming with migratory wildlife. Head over to the clubhouse with state-of-the-art fitness center, locker rooms with showers, movement room for classes, internet café, event room, catering kitchen, resort-style pool with spa and cabanas, restaurant with bar, firepit, pickleball, tennis and bocce courts. Take the pups to play in the dog park. Walk or ride your bike on the many paths including the peaceful preserve boardwalk. If gardening is your passion, there is a community garden to grow your favorite vegetables. HOA management and friendly staff are onsite to assist and coordinate regular events for all to enjoy. Minutes from beaches, golfing, fishing, boating, shopping, and cultural activities. It's time to enjoy the Florida lifestyle!

7248 Live Oak DR, Naples

$1,475,000

3 Beds ⋅ 3.5 Baths ⋅ 225016804 MLS

3 bedroom and 3 bath Stonewater Model home in Winding Cypress

6912 Cocoplum ST, Naples

$800,000

3 Beds ⋅ 3 Baths ⋅ 226004334 MLS

This gorgeous Mystique floor plan features 3 bedrooms, a den, a rare 3 full bathrooms, heated pool, and a 2-car garage. Inside the home is loaded with upgrades, impact windows and doors, custom built-in cabinetry in the living & laundry room, crown molding, tray ceilings, recessed lighting, electric blinds, designer hardware and lighting, and abundant storage throughout. Embrace the Florida lifestyle with the open-concept zero-corner slider connecting the indoor and outdoor living spaces. The pool deck offers a spacious covered lanai, a modern pool, added privacy, and highly desirable southwest exposure. No detail has been spared in the garage, which features a built-in workbench and storage, an electric screen garage door, epoxy flooring, and plenty of room for bikes and more. Winding Cypress is a natural gas community with resort-style amenities. Dine at Shady Palm, the onsite restaurant, or enjoy pickleball, bocce, tennis, a state-of-the-art fitness center, a resort-style pool, a community garden, and even two dog parks for your furry friends. This pet-friendly community allows rentals, has low fees, and boasts a prime location—convenient to Marco Island, 5th Avenue, and I-75.

6754 Pennyroyal DR, Naples

$835,000

3 Beds ⋅ 2 Baths ⋅ 225065830 MLS

Stunning 3-Bedroom + Den Home in Sought-After Winding Cypress – Welcome to your dream home in the prestigious, resort-style community of Winding Cypress in Naples, FL. Built in 2022, this impeccably maintained 3-bedroom + den, 2-bathroom residence blends modern design with everyday comfort. Step inside to find an open-concept floor plan featuring, abundant natural light, and contemporary finishes throughout. The kitchen boasts quartz countertops, stainless steel appliances, a large center island, and a spacious pantry—perfect for entertaining or casual family meals. The flexible den space offers the ideal setup for a home office, media room, or guest overflow. The primary suite is a serene retreat with a large walk-in closet and a spa-like ensuite bathroom featuring dual vanities and a walk-in shower. Recently installed lights on the lanai make the area glow at night. Very private preserve views! Also recently installed are electric retractable hurricane screens for added safety. Enjoy Florida living at its best with a screened lanai, ideal for relaxing or dining alfresco, with a large heated pool. The home also includes a 2-car garage, impact windows, and smart home features for added peace of mind. Residents of Winding Cypress enjoy resort-caliber amenities including a large clubhouse, fitness center, resort pool & spa, on-site restaurant, tennis & pickleball courts, fire pit, dog park, and over 800 acres of preserved natural space with walking/biking trails. Conveniently located just minutes from downtown Naples, white sand beaches, shopping, and dining. Don’t miss this rare opportunity to own a move-in ready home in one of Naples’ most desirable communities!

6902 Winding Cypress DR, Naples

$599,900

2 Beds ⋅ 2 Baths ⋅ 226002887 MLS

This home has just been freshly painted inside and out. professionally painted kitchen and bath cabinets, nice private south waterview , screened lanai able to enlarge or expand with a pool. Previous owner had a great workshop in garage with 8 overhead lights, addition dual media cat5/rg6 charging station for a Tesla , framed peg boards for hanging tools , custom storage cabinets and a pull down staircase for added storage. Home features 2 bedrooms 2 baths plus den a whole house generator and attached manual and electric storm shutters. Remaining furniture in home is staying. Live Oak is a beautiful mature tree lined street on cul de sac and just a short walk to the amenity center, dog park or community garden .Rarely will you find a single family home at this price in Winding Cypress . Great Value ! Winding Cypress amenity center offers so much within its gates, its own Shady Palm restaurant, resort pool , gym , bocci and pickleball courts, dog park , walking trails and so much more. Winding Cypress is a gated community located just mins to 75, downtown and Marco Island. Photos to be uploaded on 1/24

7255 Live Oak DR, Naples

$890,000

3 Beds ⋅ 3 Baths ⋅ 225082316 MLS

Discover resort-style living in this rare three-bedroom plus den, three-bath natural gas home in the highly sought-after community of Winding Cypress. Designed for privacy and effortless indoor–outdoor living, it features an oversized fully custom pool with integrated seamless spa and a panoramic barless screen lanai, integrated home theater sound, all overlooking lush, tranquil landscaping. The great room opens with a dramatic zero-corner disappearing slider, and the home is nearly brand new with 2022 construction still under the renowned DiVosta builder warranty. Located on a private cul-de-sac, this home offers peaceful living while keeping you close to world-class amenities. Winding Cypress boasts private nature trails, community gardens, and an impressive 18,000-square-foot resort clubhouse with a poolside restaurant, full-time activities director, lap lanes, zero-edge resort pool with waterfall, fire pit, pickleball, tennis, and more. The community now features two grand entrances/exits on both Tamiami Trail (U.S. 41) and Collier Boulevard (951), offering exceptional convenience.

6698 Pennyroyal DR, Naples

$625,000

3 Beds ⋅ 2 Baths ⋅ 225074768 MLS

Winding Cypress – PRICE REDUCED TO SELL- Property sits approximately 2+ feet above FEMA base flood elevation. FEMA LOMA in process — flood insurance not required by lender. Rare opportunity to purchase in this community at this price point. Lowest priced 4 bedroom home in Winding Cypress. Welcome to your Florida dream home in the sought-after gated community of Winding Cypress! This immaculate residence built in 2016, offers the perfect blend of modern luxury and relaxed coastal living. Featuring 2,230’sq under air, 4 bedrooms. Two full baths, and an open-concept floor plan, this home is designed for comfort and entertaining. Step inside to find upgraded tile flooring, beautiful crown molding, a gourmet kitchen with granite countertops, stainless steel appliances, and a large center island ideal for gathering with friends and family. The spacious great room opens through sliding glass doors to a screened lanai, creating seamless indoor-outdoor living. This home also features a "sunroom" addition and an oversized garage. Enjoy peaceful views of the lush landscaping and lake—the perfect backdrop for morning coffee or sunset cocktails. The primary suite offers a spa-like bath with dual sinks, walk-in shower, and large walk-in closet. Additional features include plantation shutters, impact-resistant windows and doors, whole house water purification system, new electric hurricane screens, a "sunroom" addition not included in other floor plans, and an oversized garage and a 2-car extended garage with epoxy flooring. Located within minutes of downtown Naples and the Gulf beaches, Winding Cypress offers resort-style amenities including a lagoon-style pool, on-site restaurant, tennis, pickleball, fitness center, dog park, and miles of nature trails. Move-in ready, this is the best priced home of its size in Winding Cypress — this home combines style, value, and an unbeatable location.

7057 Live Oak DR, Naples

$635,000

2 Beds ⋅ 2 Baths ⋅ 226009024 MLS

This gorgeous Serenity villa features 2 bedrooms, a den, a pool, and a 2-car garage, and is being offered turnkey furnished. The pool deck showcases one of the best lake views in the community, complete with spectacular sunsets, a picture-window screen, a spacious covered lanai, and a pool heated by both electric and solar—helping keep energy costs down. Enjoy peace of mind with impact windows and doors throughout, a whole-home generator, and a hurricane screen for added lanai protection. Inside, the home is loaded with upgrades, including plantation shutters, under-cabinet lighting, a tray ceiling, custom shelving in the living room and den, and more. Winding Cypress is a natural gas community with resort-style amenities. Dine at Shady Palm, the onsite restaurant, or enjoy pickleball, bocce, tennis, a state-of-the-art fitness center, a resort-style pool, a community garden, and even two dog parks for your furry friends. This pet-friendly community allows rentals, has low fees, and boasts a prime location—convenient to Marco Island, 5th Avenue, and I-75.

7717 Jacaranda LN, Naples

Recently Sold Listings in Winding Cypress, Naples, FL

Be the First to Know About New Winding Cypress Homes

Winding Cypress Real Estate Map Search

All Sold in Winding Cypress, Naples, FL

How much is your home worth?

How much is your home worth?

Fahey Team

Search

Resources

About