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$1,475,000
3 Beds ⋅ 4 Baths ⋅ Winding Cypress SubDv.
3 bedroom and 3 bath Stonewater Model home in Winding Cypress

6912 Cocoplum Street, Naples
$1,025,000
4 Beds ⋅ 2 Baths ⋅ Winding Cypress SubDv.
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 Drive, Naples
$975,000
3 Beds ⋅ 3 Baths ⋅ Winding Cypress SubDv.
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 Drive, Naples
$963,000
3 Beds ⋅ 2 Baths ⋅ Winding Cypress SubDv.
Rare opportunity in Winding Cypress this Marten Ray Floor Plan sits on a premium lot with unobstructed lake and protected preserve views. Experience, complete privacy and a resort-style outdoor setting in one of Naples’ most desirable communities. Experience one of the most desirable homes in Winding Cypress, offering a rare combination of premium lot, complete upgrades, and true move-in ready convenience. Perfectly situated on what is believed to be one of the only homes in the community with a full, unobstructed rear exposure, this property showcases sweeping views of a permanent lake and protected state/federal preserve, delivering exceptional privacy with no future development behind you. Designed for effortless Florida living, the home features a resort-style outdoor setting with a heated-saltwater pool, multi-color lighting, in pool and lanai, expansive lanai, dry bar with cabinetry & refrigerator, outdoor TV and audio—ideal for entertaining or relaxing in a private natural setting. Inside, the residence has been extensively upgraded beyond builder-grade, to deliver a “better than new” experience, with no projects or additional investment required. The designer kitchen includes gas cooking, enhanced cabinetry, under-cabinet lighting, and a built-in wine bar with dual-zone cooler. Additional highlights include tile flooring throughout, upgraded lighting, a high-efficiency air conditioning system, custom pantry and primary closet cabinetry, and a fully optimized garage with added storage and functionality. The flexible floor plan offers 2 additional bedrooms for versatile guest accommodations and workspace options, including a dedicated office and an additional guest space, ideal for visiting family, remote work, or multi-purpose use. This home is well suited for buyers seeking quality, privacy, and ease of ownership in one of Naples’ most sought-after communities.

7457 Winding Cypress Drive, Naples
$962,500
3 Beds ⋅ 2 Baths ⋅ Winding Cypress SubDv.
This impeccable Martin Ray truly has it all. The home features 3 bedrooms + den, 2 bathrooms, a 2-car garage with a 4-foot extension, and a custom pool perfectly positioned on a premier lot surrounded by lake views. Structurally designed for both style and peace of mind, the home offers soaring 11+ foot ceilings, impact windows and doors throughout, a whole-house generator that powers the pool as well, and hurricane screens for added protection. Inside, the upgrades are endless, including crown molding, tray ceilings, under-cabinet lighting, handmade Forge lighting fixtures, custom drop-zone cabinetry, plantation shutters, a California Closet mini bar, and so much more. The outdoor living space is a true showstopper, offering privacy, water views while overlooking the preserve. Added in 2022, the 34-foot custom pool features a flush spa, salt system, auto fill, 4 waterfalls, 2 whisper-quiet high-end pumps, gorgeous wet-edge pebble finish with glass accents, and imported Turkish non-slip marble pool decking. Even the pool cage was thoughtfully upgraded, with vertical support beams filled with concrete for enhanced stability. The garage is equally impressive with epoxy flooring, electric vehicle charging, double whole-house surge protection, and keyless entry. Outside, the home continues to impress with a rare custom 5-car paver driveway, updated timed lighting, extensive landscaping, a paver walkway, and a screened front entry. 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 2 dog parks for your furry friend. This pet-friendly community allows rentals, has low fees, and boasts a prime location—convenient to Marco Island, 5th Avenue, and I-75.

7343 Mockingbird Court, Naples
$905,000
2 Beds ⋅ 2 Baths ⋅ Winding Cypress SubDv.
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
$900,000
4 Beds ⋅ 2 Baths ⋅ Winding Cypress SubDv.
This Summerwood floorplan is being offered turnkey furnished and features 4 bedrooms, 2 bathrooms, a gas heated pool, and an extended 2-car garage. The home includes valuable storm-ready features such as a whole-home generator and electric hurricane screens on the lanai. Inside, the home is loaded with upgrades such as a crown molding, plantation shutters, California Closets cabinetry in the laundry room, pantry and primary closet. Embrace the Florida lifestyle with the open-concept layout seamlessly connecting indoor and outdoor living spaces. The pool deck features a spacious covered lanai and an expansive outdoor kitchen. No detail has been spared in the garage as well, it features a mini split, cabinets, and an extra 4 feet of length, allowing room for tools, 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 2 dog parks for your furry friend. This pet-friendly community allows rentals, has low fees, and boasts a prime location—convenient to Marco Island, 5th Avenue, and I-75.

7473 Winding Cypress Drive, Naples
$900,000
3 Beds ⋅ 2 Baths ⋅ Winding Cypress SubDv.
On a private corner homesite with breathtaking long lake views, this like-new contemporary residence built in 2022 offers an exceptional blend of style, comfort and modern functionality within the sought-after community of Winding Cypress. Designed with a great room and split-bedroom floor plan, this three-bedroom plus den, two-bath home with a two-car garage showcases light-filled interiors, neutral paint tones, recessed lighting, crown molding and elegant marble-look tile flooring throughout the main living areas. Move-in ready and thoughtfully upgraded, the home captures the essence of effortless Florida living with a refined, modern aesthetic. Crown molding, expansive lake views and zero-corner sliding glass doors enhance the open and airy living room, seamlessly inviting the outdoors in to create an indoor-outdoor experience. Just beyond, the spacious screened lanai offers multiple seating areas, a ceiling fan and a full outdoor kitchen, all overlooking a large heated pool, ideal for entertaining or relaxing in complete privacy. The adjacent dining area features marble tile flooring, crown molding, an updated hanging light fixture and tranquil water views, ideally positioned off the kitchen for everyday living and hosting. The well-appointed kitchen is a standout, featuring white cabinetry, a tile backsplash, a large island with pendant lighting and a three-seater bar. Premium KitchenAid stainless steel appliances include a gas cooktop with a hood, a wall oven, a microwave, a dishwasher and a French door refrigerator, complemented by upgraded cabinetry and finishes. The den offers a functional workspace with recessed lighting and French double doors, ideal for working from home. The primary suite is a serene retreat with a tray ceiling, recessed lighting, a designer accent wall and a spacious walk-in closet with custom built-ins. The en-suite bath is thoughtfully designed with a double vanity, an expanded walk-in shower with additional sprayer, linen closet and private water closet. Guest bedrooms are equally inviting, each filled with natural light, including one with plantation shutters and custom moldings. Additional highlights include a widened and recently sealed driveway, impact windows and doors, a whole-house generator, custom wood backing for mounted televisions, upgraded molding throughout, and a garage with overhead storage and a mini-split air conditioning system. The laundry room is equipped with a Whirlpool front-load washer and dryer, utility sink and overhead cabinetry. Offering privacy as the last home on the street and showcasing extensive designer upgrades throughout, this residence presents a rare opportunity to enjoy luxurious lakefront living in one of Naples desirable communities. Resort-style perks include the on-site Shady Palm Café for casual dining and drinks, a state-of-the-art fitness center, a resort pool and spa, tennis, pickleball and bocce courts.

6787 Pennyroyal Drive, Naples
$890,000
3 Beds ⋅ 3 Baths ⋅ Winding Cypress SubDv.
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 Drive, Naples
$835,000
3 Beds ⋅ 2 Baths ⋅ Winding Cypress SubDv.
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 Drive, Naples
$815,000
3 Beds ⋅ 2 Baths ⋅ Winding Cypress SubDv.
Paradise at your fingertips. This modern three-bedroom plus den residence in the prestigious resort style living gated community of Winding Cypress, offers a bright, expansive open floor plan, breathtaking lake views, ceramic tile throughout and a gorgeous and functional updated kitchen featuring solid maple shaker cabinetry, premium hardware, and spacious pantry. This residence is also equipped with gas stove, brand new LG Studio refrigerator and stove to enjoy a fabulous culinary experience. The magnificent quartz island, ideal to entertain and savor your favor meals is illuminated by one of a kind showstopper custom abalone shell chandelier which mirrors the one in the dining room creating a one of kind ambiance. The large family room flows harmoniously to an inviting bar area to taste your favorite drink. The Master bedroom provides high ceilings, custom made cabinetry and serene lake views. Both bathrooms feature Aquadome LED fog-free mirrored medicine cabinets adding a touch of functionality and elegance. Life al fresco is enjoyed to the fullest in the spectacular extended back patio, with outdoor kitchen and several sitting areas. This enclosed lanai with panoramic premium screens allows for breathtaking unobstructed water and sky views. Also available is an initial electrical connection to install a jacuzzi if desired. Ample storage and full hurricane protection plus generator to provide extra peace of mind. Additional traits are the Wakaflex installed on all vents, openings and roof crown for maximum weather protection, the Eufy home security system, recently painted inside and out, Maytag Washer and Dryer, Culligan reverse osmosis water filter, front entry screened enclosure and driveway expanded to accommodate 3 vehicles. The 2-car garage comes with overhead storage. Winding Cypress offers world-class amenities, including a clubhouse, on-site restaurant, fitness center, resort pool, and tennis/pickleball courts. Positioned between the sun-drenched beaches of Marco Island and upscale dining, shops and galleries of downtown Naples, this home offers the ultimate setting for relaxation, comfortable living and sophisticated entertaining.

7460 Blackberry Drive, Naples
$800,000
3 Beds ⋅ 3 Baths ⋅ Winding Cypress SubDv.
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 Drive, Naples
$700,000
3 Beds ⋅ 2 Baths ⋅ Winding Cypress SubDv.
Welcome to your beautiful Summerwood floor plan home ... Enjoy Florida living in this IMPECCABLY maintained STUNNING home featuring 3 bedrooms, den/sitting room, 2 full bathrooms. Enjoy a spacious living room which is open to the gourmet kitchen featuring a NATURAL GAS range, a large pantry and an island, with ample prep space, for gathering with friends and family. There is tile flooring throughout! Step outside to the a very sought after outdoor living life with the EXTENDED LANAI!! On the Lanai is a built in kitchen for all of your entertaining needs! The home has a FULL HOUSE GENERATOR & IMPACT RESISTENCE WINDOWS. The window and sliding door to the Lanai are storm protected with a STORM SMART SCREEN!! The primary suite is a private retreat with a walk-in closet, dual-sink vanity, and a large step in with glass shower. The dining room offers tranquil views of the expansive lanai. A 2 car garage has a huge extra space for storage. The brick-paver driveway provides ample parking. Set on a beautiful homesite, this residence blends privacy with proximity to the best of South Naples. The subdivision hosts an amazing club, with all residents enjoying access to the community’s restaurant, resort style pool, exercise room/gym, tennis, bocce, and pickleball courts. Experience unparalleled luxury, comfort, and location here, an absolute must-see!

7022 Live Oak Drive, Naples
$635,000
2 Beds ⋅ 2 Baths ⋅ Winding Cypress SubDv.
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 Lane, Naples
$625,000
3 Beds ⋅ 2 Baths ⋅ Winding Cypress SubDv.
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 Drive, Naples
$615,000
2 Beds ⋅ 2 Baths ⋅ Winding Cypress SubDv.
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 Lane, Naples
$599,900
2 Beds ⋅ 2 Baths ⋅ Winding Cypress SubDv.
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 Drive, Naples
$595,000
2 Beds ⋅ 2 Baths ⋅ Winding Cypress SubDv.
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 Drive, Naples
$580,000
2 Beds ⋅ 2 Baths ⋅ Winding Cypress SubDv.
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 Drive, Naples
$575,000
3 Beds ⋅ 2 Baths ⋅ Winding Cypress SubDv.
Rare villa opportunity in Winding Cypress! This turnkey, fully furnished villa sits on an extra-large, ultra-private lot with exceptional spacing between neighbors, creating a peaceful and open feel that is hard to find. The backyard is a retreat, featuring a saltwater private pool framed by mature cypress trees, colorful landscaping and wide natural preserve views. Inside, the home offers thoughtful upgrades including 8-foot interior doors, new bedroom flooring, refreshed landscaping and built-in garage storage that helps keep everything organized. As a natural gas home, it features gas cooking and provides flexibility for future enhancements, offering efficiency and convenience. Living in Winding Cypress means enjoying resort-style amenities without the high fees. Residents have access to an expansive resort pool with beach entry, a full-service restaurant and bar, a state-of-the-art fitness center, pickleball, tennis and bocce courts, a dog park, and miles of scenic walking and biking trails. The beautifully designed clubhouse includes a social hall, gathering spaces and a library, creating opportunities to connect and engage with neighbors. This home blends nature, privacy, comfort and community into one exceptional offering.

7167 Live Oak Drive, Naples
$565,000
2 Beds ⋅ 2 Baths ⋅ Winding Cypress SubDv.
Discover effortless luxury in this lovely villa—your private oasis in a premier gated Naples community, Winding Cypress. This inviting 2-bedroom + den, 2-bath home delivers exceptional comfort and versatility with a bright, open layout designed for effortless living and entertaining. Step into the expansive Great Room with high ceilings, creating an open, airy vibe—perfect for gathering with friends or unwinding after a day out in Naples. The chef's kitchen impresses with premium quartz countertops, solid wood soft-close cabinets, and natural gas cooking. High-traffic porcelain tile flooring flows seamlessly throughout the entire villa, paired with smooth-finish walls for a clean, modern, low-maintenance aesthetic. The flexible den, enclosed by beautiful glass panel doors, adapts effortlessly as a home office or third bedroom. Both bedrooms feature generous walk-in closets, and the bathrooms showcase floor-to-ceiling porcelain tile, glass showers, and spa-like sophistication. The master bath elevates your routine with a dramatic full-wall custom mirror and elegant drop-down designer lighting. Outside, this premium lot offers generous spacing between villas and captivating views over the community's second-largest lake—where serene water vistas create an unparalleled sense of tranquility and timeless appeal. The west-facing orientation captures breathtaking sunsets reflecting off the shimmering waters, while the south-facing exposure floods the interior with natural light. Plenty of space awaits an extended lanai or private pool, all enhanced by the soothing backdrop of the lake. Built for peace of mind: impact windows and doors boost energy efficiency, reduce noise, and lower insurance premiums—no flood insurance required in FEMA Zone X. Appliances, A/C, and water heater have performed flawlessly since new. Fiber optic connectivity ensures ultra-fast internet and seamless 4K streaming. Natural gas powers cooking, drying, hot water, and preps for a whole-home generator. Nestled in gated Winding Cypress—praised as Naples' best lifestyle value with remarkably low HOA fees that cover comprehensive maintenance (lawn care, irrigation, community upkeep) plus full access to extensive high-end amenities—you'll embrace the pet-friendly lifestyle with two dedicated dog parks, miles of scenic walking/biking trails across 800+ acres of preserved natural land, and a vibrant social calendar with events curated by the on-site activities director. Resort-style perks include the on-site Shady Palm Café for casual dining and drinks, state-of-the-art fitness center with movement/yoga room, sparkling resort pool and spa, lighted tennis and pickleball courts, bocce courts, community garden, fire pit, and more—all accessible by foot, bike, or golf cart. Conveniently located between downtown Naples and Marco Island, you're minutes from pristine beaches, upscale shopping, and fine dining. Paradise is calling.

7733 Jacaranda Lane, Naples
$550,000
2 Beds ⋅ 2 Baths ⋅ Winding Cypress SubDv.
The one and only Cressida Villa plan with the unique front entrance and foyer layout in Winding Cypress with an expanded lanai and a sweeping, wide-water views that feels endless. This light-filled, impeccably maintained residence showcases all quartz countertops, premium cabinetry, porcelain tile, natural gas, and seamless indoor-outdoor living designed for entertaining or quiet sunset evenings. The oversized lanai captures panoramic water views, creating a private, tranquil backdrop rarely available. Move-in ready and in amazing condition, this home stands out for its scale, upgrades and setting. In the resort community of Winding Cypress, a low-fee, resort-style guard-gated community with 800 acres of preserve, full-time activities director, resort and lap pool, on-site restaurant, fitness center, pickleball and tennis courts, and miles of recreational, biking and nature trails.

7785 Jacaranda Lane, Naples
$470,000
2 Beds ⋅ 2 Baths ⋅ Winding Cypress SubDv.
OPPORTUNITY AWAITS – LOWEST PRICE AVAILABLE! Welcome to the largest villa model in Winding Cypress, featuring a rare private front entrance and expanded foyer that sets the tone for this thoughtfully designed home. This spacious 2-bedrooms and massive den offers an open yet defined living concept with abundant natural light and seamless indoor-outdoor flow. Enjoy a long list of builder upgrades including granite countertops, high-end porcelain tile flooring, a glass-tiled backsplash, premium cabinetry and crown molding throughout. Step outside to your expansive private yard and lanai offering plenty of space to add a pool or design your dream sundeck. Winding Cypress is one of Naples’ most sought-after resort-style communities spanning over 800 acres of pristine preserve and ideally located between Marco Island and downtown Naples’ 5th Avenue. Residents enjoy exceptional amenities including a dog park, community garden and the stunning 18,000 square foot clubhouse featuring a resort-style pool with sand cabanas, on-site restaurant and bar, pickleball, bocce and clay tennis courts, yoga deck, nature trails, state-of-the-art fitness center, fire pits, social lounges and a full-time professional activities director creating a vibrant lifestyle where every day feels like a vacation.

7638 Jacaranda Lane, Naples