Winding Cypress - Naples, FL Homes for Sale - Search All Homes & Real Estate for Sale in Winding Cypress Naples, Florida

3 Beds ⋅ 2 Baths ⋅ 226017662 MLS

$935,000

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

Courtesy of Premier Sotheby's Int'l Realty

$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 Drive, Naples

Courtesy of William Raveis Real Estate

3 Beds ⋅ 2 Baths ⋅ 2026015957 MLS

$725,000

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

Courtesy of John R. Wood Properties

$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 Drive, Naples

Courtesy of Premiere Plus Realty Company

3 Beds ⋅ 4 Baths ⋅ 225016804 MLS

$1,475,000

3 bedroom and 3 bath Stonewater Model home in Winding Cypress

6912 Cocoplum Street, Naples

Courtesy of William Raveis Real Estate

2 Beds ⋅ 2 Baths ⋅ 226008984 MLS

$550,000

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

Courtesy of Premier Sotheby's Int'l Realty

2 Beds ⋅ 2 Baths ⋅ 226009304 MLS

$905,000

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

Courtesy of Coldwell Banker Realty

2 Beds ⋅ 2 Baths ⋅ 226009024 MLS

$635,000

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

Courtesy of Realty One Group MVP

2 Beds ⋅ 2 Baths ⋅ 226008768 MLS

Experience elevated resort-style living in the highly desirable community of Winding Cypress. This impeccably maintained and tastefully updated 2-bedroom plus den, 2-bath villa offers soaring 9’4” ceilings and an attached two-car garage, delivering both comfort and functionality in a truly move-in-ready residence. Thoughtful upgrades include a newer refrigerator and hot water heater, upgraded pavers, plantation shutters, and additional enhancements that add both style and peace of mind. The flexible den provides the perfect space for a home office, guest retreat, or additional lounge area. Winding Cypress is designed for those who value lifestyle. Nearly two-thirds of the community is preserved as tranquil natural landscape and wooded conservation, creating a serene, private atmosphere rarely found this close to everything. Ideally located just 8 miles from Downtown Naples and 9 miles from Marco Island, you are moments from world-class dining, shopping, and Gulf beaches. Residents enjoy an impressive amenity package featuring pickleball, bocce, clubhouse, resort-style pool and spa, community park, social rooms, and more. Opportunities like this are rare. Schedule your private showing today.

7666 Jacaranda Lane, Naples

Courtesy of EXP Realty LLC

$834,999

3 Beds ⋅ 2 Baths ⋅ 226007913 MLS

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

Courtesy of Premier Sotheby's Int'l Realty

$565,000

2 Beds ⋅ 2 Baths ⋅ 226006913 MLS

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

Courtesy of Premiere Plus Realty Company

2 Beds ⋅ 2 Baths ⋅ 226006762 MLS

$580,000

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

Courtesy of John R Wood Properties

3 Beds ⋅ 2 Baths ⋅ 226005365 MLS

$949,900

Welcome to newest and last phase of homes built in 2020 in the vibrant well maintained community of Winding Cypress. Located just off Collier and 41 and minutes to 75 , Marco Island and downtown Naples This summer wood model is sure to please with 3 bdrms den and 2 baths with full showers , primary bath with custom mirrors. custom closet , plantation shutters mini a/c in garage, whole house water purifier, generator, storm screens on lanai ,outdoor kitchen , pool and spa. with private views to the preserve ,vaulted ceilings, ceiling fans in every room , and oversized neutral tile through out placed on the diagonal . some furniture can remain with the house . exlcuded dining light fixture

6844 Winding Cypress Drive, Naples

Courtesy of Royal Shell Real Estate, Inc.

$460,000

2 Beds ⋅ 2 Baths ⋅ 226005810 MLS

This property is nestled in one of Naples’ most desirable communities. This home features two spacious bedrooms, two elegant baths, and a flexible den—perfect for a home office, hobby room or additional guest area. The upgraded kitchen is equipped with stainless steel appliances, quartz counter tops in kitchen and both bathrooms, and bright 42” cabinetry with under lighting, creating an inviting space for entertaining. Enjoy the open-concept living and dining area with stylish tile flooring on the diagonal throughout, plantation shutters on all windows, and 2 interior pocket doors that provide privacy to the owners and guest suite areas. The sliding doors lead to a private covered screened lanai ideal for relaxing or dining outdoors. A large rear lot where you can design your own pool area if so desired. This property provides ample space for both relaxation and functionality as a vacation home or easy full-time Florida living.

7658 Jacaranda Lane, Naples

Courtesy of William Raveis Real Estate

2 Beds ⋅ 2 Baths ⋅ 226005934 MLS

$615,000

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

Courtesy of Premier Sotheby's Int'l Realty

3 Beds ⋅ 3 Baths ⋅ 226004334 MLS

$800,000

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

Courtesy of Realty One Group MVP

2 Beds ⋅ 2 Baths ⋅ 226002887 MLS

$599,900

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

Courtesy of Royal Shell Real Estate, Inc.

3 Beds ⋅ 2 Baths ⋅ 226000537 MLS

$520,000

Welcome to effortless, refined living in the highly desirable Winding Cypress community. Set on the largest homesite in the neighborhood, this impeccably upgraded 3-bedroom, 2-bath villa offers exceptional privacy, expansive outdoor space, and a true lock-and-leave lifestyle. Furnishings are negotiable, making this a flexible opportunity for both full-time and seasonal residents. Designed for relaxed everyday living and easy entertaining, the open floor plan feels light, inviting, and polished without being formal. Thoughtful designer touches throughout create a warm, comfortable atmosphere that flows naturally from indoors to outdoors. The extended screened lanai becomes an everyday retreat, ideal for morning coffee, sunset unwinding, or hosting friends, while the outdoor summer kitchen makes casual gatherings effortless. Peace of mind is a defining feature of this home, with over $100,000 in safety and security upgrades already in place. A whole-house backup generator, advanced security system, hurricane protection, and smart access features allow you to travel or entertain with confidence, knowing everything is covered. Living in Winding Cypress means enjoying a resort-style lifestyle every day. Residents have access to a beautifully appointed clubhouse with on-site dining, resort and lap pools, a jacuzzi, fitness center, tennis, pickleball, bocce courts, and a dog park. The community is surrounded by natural preserves and lakes, creating a serene setting while remaining minutes from shopping, dining, and daily conveniences. This is a rare opportunity to own a premier villa in one of Southeast Naples’ most sought-after gated communities. Priced competitively and offering flexibility on furnishings, this home delivers comfort, security, and lifestyle in one exceptional package.

7176 Live Oak Drive, Naples

Courtesy of John R Wood Properties

3 Beds ⋅ 2 Baths ⋅ 226000187 MLS

$910,000

This Summerwood floorplan is situated on a gorgeous lake and features 3 bedrooms, a den, 2 bathrooms, a gas heated pool and spa, and an extended 2-car garage. The home includes valuable storm-ready features such as a whole-home generator, impact-resistant windows and doors, and electric hurricane screens for added protection. Inside, the home is loaded with upgrades such as a custom built-in bar, TV stand and vanity, custom cabinetry in the primary closet, pantry, and laundry room, crown molding, tray ceiling, and a modern curated accent wall. Upgraded kitchen appliances and abundant storage complete the space. Embrace the Florida lifestyle with the open-concept layout seamlessly connecting indoor and outdoor living spaces. The pool deck features a spacious covered lanai overlooking the lake with a highly desirable southwest exposure, along with an outdoor kitchen and a custom saltwater pool and spa complete with a sun ledge. No detail has been spared in the garage as well, it features a mini split, insulated door, 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.

6779 Winding Cypress Drive, Naples

Courtesy of Realty One Group MVP

3 Beds ⋅ 4 Baths ⋅ 225083620 MLS

$1,150,000

This home is an amazing value for Winding Cypress!! Once you compare, you'll agree. The Stonewater model is the largest one floor living within The Community. The sought after "open area concept" footprint boasts 3 expansive bedrooms including a most impressive owner's suite, 3 full baths PLUS and additional POOL BATH , a large den-flex room with glass French doors, desirable 3 car garage with additional storage racks overhead. Upgrades include an executive waterfront and private preserve view lot, pool with integral spa.

7716 Winding Cypress Drive, Naples

Courtesy of William Raveis Real Estate

3 Beds ⋅ 2 Baths ⋅ 225083676 MLS

$835,000

Check out this impeccably maintained residence offers an exceptional living experience. The open floor plan features THREE spacious bedrooms, a versatile den or flex room, and two full bathroom. Elegant details include crown molding, tray ceilings, plantation shutters, Hunter Douglas blinds, and updated flooring provides a tranquil space for relaxation or entertaining. The custom gourmet kitchen equipped with under-cabinet lighting, granite countertops, a wall oven with microwave, gas cooktop, matching range hood, soft-close drawers with pull outs, and a walk-in pantry for more than ample storge. This property sits on an OVERSIZED PRIVATE lot with tropical landscaping, a newly screened lanai, and a large pool.

7211 Live Oak Drive, Naples

Courtesy of William Raveis Real Estate

3 Beds ⋅ 3 Baths ⋅ 225082316 MLS

$890,000

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

Courtesy of Premier Sotheby's Int'l Realty

4 Beds ⋅ 3 Baths ⋅ 225081501 MLS

$940,000

Spacious & Immaculate accurately describe this outstanding retreat in the sought-after community of Winding Cypress. This rare, two-story Mystique footprint boasts 4 bedrooms, 3 full baths, a large den/office, and over 3160 square feet of adjusted living space, 3036 square feet under air. This residence was one of the last built in the community, 3 years new, and shows like a model home. Located on a very private lot on a cul-de-sac, this salt water pool home with private spa is meticulously one-owner maintained, beautifully decorated, and loaded with builder upgrades. For peace of mind, the owners added a whole house generator as well. The expansive, upstairs addition includes a huge private bedroom, a full bathroom, and an incredible flex area that can accommodate a 5th bedroom, cinema room, office, or however this extra space can benefit your living wants and needs. Winding Cypress is an amenity rich and active community with on-site management and a full-time Activities Director. It's perfectly situated just 15 minutes away from the restaurants, shoppes, and beaches of downtown Olde Naples, and only 10 minutes to all the entertainment of Marco Island.

6825 Greenbriar Court, Naples

Courtesy of William Raveis Real Estate

3 Beds ⋅ 2 Baths ⋅ 225079293 MLS

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

Courtesy of Premier Sotheby's Int'l Realty

3 Beds ⋅ 2 Baths ⋅ 225078259 MLS

$875,000

This extended Summerwood floorplan is situated on a private street and features 3 bedrooms, a den, 2 bathrooms, a gas heated pool and spa, and an extended 2-car garage. The home includes valuable storm-ready features such as a whole-home generator, impact-resistant windows and doors, and electric hurricane screens for added protection. The open-concept layout seamlessly connects indoor and outdoor living spaces. The pool deck features a large covered lanai ideal for enjoying sunset views over the lake and preplumb of electric, gas, and water providing the option to add a built-in outdoor kitchen. Additional upgrades include tile flooring throughout, plantation shutters, trey ceiling, custom screened entryway, widened walkway & driveway and generous storage space. Turnkey furnishings are available with the sale, some exclusions. 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.

7355 Mockingbird Court, Naples

Courtesy of Realty One Group MVP

3 Beds ⋅ 2 Baths ⋅ 225074768 MLS

$625,000

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

Courtesy of Premiere Plus Realty Company

3 Beds ⋅ 2 Baths ⋅ 225075399 MLS

Perfection is the only way to describe this home! It shows like a model as it has been rarely lived in since built barely three years ago. Welcome to the desirable Pulte/DiVosta Mystique Model located in the popular amenity rich community of Winding Cypress. This waterfront property sits on a dead-end cul-de-sac and is loaded with owner and builder upgrades. It's impeccably decorated and furnished and could come turnkey providing the new owner with everything you'll ever need to begin living in paradise! The Mystique’s footprint, a 3 bed, 2 bath plus optional den offers the sought after open kitchen, great room, and dining area concept with split bedrooms to ensure comfort and privacy. All the bedrooms are large with the primary suite being expansive. This home's upgrades include a whole-house generator, a hurricane impact zero-corner sliding glass door that provides a spectacular indoor/outdoor living area combining an expansive great room to the under roof lanai dining and and separate sitting section. That's just part of the lighted lanai. There's an extended paver area for you to soak in the sun while you admire the custom pool with a soothing water feature. Looking out over the beautiful lake is made easy with the option "picture window" lanai screen. Electric StormSmart metal shutters enclose the lanai providing additional peace of mind, safety and security. Additional enhancements include a chef's kitchen layout with quartz counters, a natural gas cooktop and range, upgraded cabinets with above and under lighting, expansive island with an overhang to sit three, an upgraded backsplash and a large walk-in pantry. This home also boasts upgraded tile plank flooring, custom 8' doors throughout, high-end interior plantation shutters on all windows, an expanded laundry area with cabinets, counters, a utility sink, and extra storage. The 2 car garage has an insulated overhead door. Winding Cypress is optimally located just 15 minutes to Olde Naples, 10 minutes to both Marco Island and I75, and 30 minutes to RSW Airport. For this price point, the amenities at Winding Cypress are second to none. A resident's only full service restaurant, resort pool with spa that rivals a Las Vegas hotel, pickleball, tennis, and bocce courts, the best fitness center around, an vibrant community center with onsite management and Activities Director, a dog park, community garden, and a boardwalk nature trail are just a few of the things that make Winding Cypress so special. With only 766 single-family homes spread out over 1250 total acres that includes 850+ acres of spectacular preserve and lakes, enjoy the peace, serenity and beautiful wildlife that few communities are able to offer.

6699 Pennyroyal Drive, Naples

Courtesy of William Raveis Real Estate

3 Beds ⋅ 2 Baths ⋅ 225067825 MLS

$963,000

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

Courtesy of Gulf Coast International Prop

2 Beds ⋅ 2 Baths ⋅ 225072028 MLS

$595,000

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

Courtesy of William Raveis Real Estate

3 Beds ⋅ 2 Baths ⋅ 225071664 MLS

$858,500

Sense the comfort and beauty of this magnificent home the minute you enter the foyer and see the view out to the inviting pool and spa. This 3 bedroom, plus separate den, great room floor-plan is perfect for entertaining or just a lovely place to call home. These original owners have impeccably maintained the home making it feel brand new. Built in 2021 it boasts a chef's delight kitchen with stainless steel appliances, center island and breakfast bar, natural gas cooktop/range, pull-out drawers, quartz counter-tops, recessed and pendant lighting, and more! The cook of the house will love it! The great room and dining area are adjacent to the kitchen. An extra plus is the den with double raised paneled doors and a window for natural light. The main bedroom is approx 14' x 16' and sits on its own separate wing from the other bedrooms. You will love the main bathroom with its 9' x 3'3" tiled shower with multiple shower heads, dual sinks, quartz counter-tops, walk-in closet and separate toilet closet. It is very spacious! Another plus to this home is the zero corner doors off the great room extending your great room out to your covered lanai. The extended lanai is all plumbed for the outdoor kitchen of your liking. Enjoy the Florida sunshine in your pool and spa in the privacy of your own backyard which backs up to a preserve. Some of the other features of this lovely home are a 9' x 7' laundry room with cabinets, folding counters, sink, and storage closet, 2 car garage with a 4 foot extension and epoxy flooring, and impact resistant windows and sliders. The home boasts beautiful tile and light colors throughout. The white plantation shutters in many of the rooms add to the character of the home. Winding Cypress is a newer, well maintained community offering an abundance of amenities. You will find a resort-style pool and separate spa, cabanas, Shady Palm Cafe, pickleball, bocce, tennis, state-of-the-art fitness center, community garden and a dog park for your fur babies. Winding Cypress sits in a great location in Collier County, less than 30 minutes from beautiful 5th Avenue in Naples, and the white sand beaches of Marco Island. This home is a must see!

6856 Winding Cypress Drive, Naples

Courtesy of Berkshire Hathaway FL Realty

4 Beds ⋅ 4 Baths ⋅ 225067265 MLS

$1,495,000

Motivated Seller! Luxurious Lakeside Living in Winding Cypress – Rare One Owner Pinnacle Model! Welcome to this stunning lake view home offering 3,656 sq. ft. of modern elegance in the prestigious, amenity-rich community of Winding Cypress. With 4 bedrooms, 4 bathrooms, a den, bonus room, and 2,5-car garage, this home is thoughtfully designed for both everyday living and entertaining on a grand scale. Step inside to discover a light-filled open floor plan accented with tile flooring in the main living areas, brand-new luxury vinyl plank flooring in all three downstairs bedrooms, and crown molding throughout the first floor. The chef’s kitchen is a showstopper, boasting quartz countertops, premium KitchenAid stainless steel appliances, a new natural gas cooktop, soft-close cabinetry, walk-in pantry, new dishwasher, and upgraded sink—all designed for style and function. Enjoy seamless indoor-outdoor living with zero-corner sliding doors that open to an expansive lanai featuring a picture screen enclosure, heated pool and spa, and a custom outdoor kitchen with built-in hub. With southwestern exposure overlooking the long lake and preserve, sunsets here are simply unforgettable. Retreat to the primary suite with a spa-like bathroom and custom walk-in closets, while guests enjoy privacy with an en suite bedroom on the main level. Upstairs, the bonus room offers endless flexibility for a game room, theater, or additional living space. This home is equipped with hurricane-impact windows, built-in Sonos surround sound system, smart home features, and abundant storage—ensuring comfort, safety, and convenience. As a resident of Winding Cypress, you’ll enjoy world-class amenities, including:Heated resort-style & lap pools, hot tub, and gas fire pit, covered outdoor restaurant bar & grill, expansive clubhouse with fitness center, library, and event space, pickle ball, bocce, and tennis courts, miles of scenic sidewalks & boardwalk trails, two dog parks for furry family members. Perfectly positioned on a premium lot, close to the community center and surrounded by excellent local infrastructure, this home is one of the rarely available larger homes in Winding Cypress—ideal for hosting family and friends in comfort and style. Experience the best of modern Naples living in this extraordinary home.

7412 Winding Cypress Drive, Naples

Courtesy of Manuela Realty

2 Beds ⋅ 2 Baths ⋅ 225069223 MLS

Welcome to this charming 2-bedroom plus den, 2-bath beautiful villa in the highly desirable community of Winding Cypress. Built in 2017, this residence offers 1,544 square feet of thoughtfully designed living space. The interior is light and bright, featuring easy-care tile floors in the main living areas, a breakfast bar for casual dining, and carpet in the bedrooms for added comfort. The den with French doors provides the perfect space for a home office or flex room, while the primary suite offers a private retreat with dual sinks and a walk-in shower. For added peace of mind, the home is equipped with a built-in Taexx pest control system. Step outside to your private backyard oasis, complete with a sparkling inground pool — NEW Pentair 1.5 HP SuperFlo Variable Speed pool pump installed September 2025 — perfect for relaxing or entertaining guests year-round. Winding Cypress is known for its resort-style amenities, including a large clubhouse, community pool with cabanas, fitness center, tennis, pickleball, and bocce courts, plus walking and biking trails surrounded by natural preserves. Ideally located in East Naples, you’re just a short drive from Marco Island, Downtown Naples, shopping, dining, and world-famous Gulf beaches. This home is the perfect combination of comfort, convenience, and community living.

7659 Jacaranda Lane, Naples

Courtesy of Premiere Plus Realty Company

3 Beds ⋅ 3 Baths ⋅ 225067249 MLS

$1,000,000

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 Lane W, Naples

Courtesy of Downing Frye Realty Inc.

3 Beds ⋅ 2 Baths ⋅ 225068633 MLS

$800,000

Enjoy resort-style living in this Winding Cypress community near 5th Avenue and Marco Island. This home features a private pool, sunroom and the community’s largest covered lanai. Designed for year-round comfort, it offers a new air-conditioning system with additional cooling in the primary suite, impact glass throughout, and natural gas for efficiency and gourmet cooking. Inside, the oversized primary shower, upgraded tile and premium counters elevate everyday living. Set on a quiet street just a short distance to the Club at Winding Cypress, you’ll have dining, pickleball, tennis, bocce and a resort pool at your fingertips. Mature landscaping and preserve views ensure privacy while the open layout makes entertaining effortless. With nearly 2,300 square feet of living space, this residence blends comfort, convenience and the best of the Florida lifestyle with resort living just around the corner.

7049 Live Oak Drive, Naples

Courtesy of Premier Sotheby's Int'l Realty

3 Beds ⋅ 2 Baths ⋅ 225065830 MLS

$835,000

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

Courtesy of Waterfront Realty Group Inc

3 Beds ⋅ 2 Baths ⋅ 225064762 MLS

$860,000

This turnkey furnished Mystique home feels like a model — impeccably maintained, thoughtfully laid out, and filled with cozy, stylish touches throughout! The floorplan features 3 bedrooms + den, 2 baths, pool and spa, and an oversized car garage. The open-concept layout features a dramatic zero-corner slider, seamlessly connecting indoor and outdoor spaces, while the whole home generator, exterior cameras, and impact windows and doors provide peace of mind. Inside, extensive upgrades are everywhere. The kitchen boasts a spacious island with upgraded appliances, perfect for entertaining. Additional highlights include tray ceilings, crown molding, tile flooring throughout, upgraded showers in both bathrooms, and an upgraded washer and dryer. You will have tons of storage space in the air conditioned and insulated garage with an extra 4 feet of space. Outside, the pool and spa is heated by gas and hurricane screens add a second layer of protection. There are plenty of seating areas, and a picture window lanai screen to enhance the quiet, private preserve view. 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 a dog park for your furry friend. This pet-friendly community allows rentals, has low fees, and boasts a prime location, central to Marco Island, 5th Avenue, and I- 75.

6870 Winding Cypress Drive, Naples

Courtesy of Realty One Group MVP

3 Beds ⋅ 3 Baths ⋅ 225034039 MLS

$975,000

This home is an amazing value for Winding Cypress!! Once you compare, you'll agree. The Pinnacle model is clearly the most popular floorplan in The Community. The sought after "open area concept" footprint boasts 3 expansive bedrooms including a most impressive owner's suite, 3 full baths, a large den, desirable 3 car garage, and 2496 square feet of indoor living space under air. Builder and owner upgrades include an executive waterfront premium lot, kitchen appliance package, pool with new heater integral spa, quartz counters, upgraded cabinet package, den/office, zero corner sliding glass doors, plank tile flooring, plumbed for a summer kitchen, inviting lead glass front entry door.

7530 Geranium Way, Naples

Courtesy of William Raveis Real Estate

2 Beds ⋅ 2 Baths ⋅ 224076682 MLS

$530,000

Absolutely the best deal on a 2 bedroom plus den with French doors, 2 baths, 2 car garage attached villa with your own POOL in Winding Cypress. You better Hurry. Furniture negotiable too, move right in for season, nicely furnished. What's Special: *Open floor plan *Epoxy garage floor *Granite countertops *3 ft. bathroom countertops *Remote controlled garage screen *Remote controlled hurricane shutters on the lanai *California Closets in all bedrooms *Pool. Den can be converted to a 3rd bedroom too. Come see this beautifully designed pool home boasting of an inviting open floor plan, perfect for entertaining and family living. The kitchen highlights its elegant backsplash and granite countertops that provide both beauty and durability. Each bathroom has been designed with 3 ft. of countertops for added space and comfort. California Closet's custom-design can be found in each closet to maximize storage and organization throughout. The home has also been designed with 8' doors, adding to the modern, airy feel. The garage is finished with epoxy flooring and comes with remote controlled garage screen for added ventilation and convenience. Step out to the back lanai where you will find remote controlled weather/hurricane shutters for those rainy afternoons or storm seasons, giving you peace of mind. Enjoy the private pool. perfect for relaxation and entertainment. The home has been smoke-free and pet-free, ensuring a clean, fresh environment for the next owners. With thoughtful upgrades and premium features, this home is ready to welcome you. Winding Cypress includes: *Over 800 acres *Natural preserve *Nature trails *Dog park, *Low HOA *Clubhouse activity room *Fitness center *Heated resort-style pool *White sandy lounge area *Bar and grill *Library *Catering kitchen *Tennis and pickleball courts *Natural gas *15 minutes from 5th Ave. *20 minutes from Marco Island *Major shopping brands 5 minutes away.

7702 Jacaranda Lane, Naples

Courtesy of Berkshire Hathaway FL Realty

2 Beds ⋅ 2 Baths ⋅ 225011172 MLS

$453,000

Don’t miss this exceptional opportunity to own an upgraded Cressida villa in the sought-after community of Winding Cypress! This front-entry home lives like a single-family residence, offering 2 bedrooms + den, 2 bathrooms, a 2-car garage, and a stunning expanded patio with extra covered space—more than most villas. Inside, enjoy luxury upgrades including white cabinetry, quartz countertops, crown molding, and more. The outdoor space is equally impressive, featuring a built-in hood for effortless grilling and gorgeous mature landscaping. 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 a dog park for your furry friend. This pet-friendly community allows rentals, has low fees, and boasts a prime location—central to Marco Island, 5th Avenue, and I-75.

7686 Jacaranda Lane, Naples

Courtesy of Realty One Group MVP

3 Beds ⋅ 3 Baths ⋅ 225022390 MLS

$855,000

Built in 2022, this 2,124-square-foot Mystique model by DiVosta offers a rare turnkey opportunity, fully furnished with over $100,000 in luxury personal property, including indoor and outdoor furniture, artwork, decor, cookware, bedding, and more. Virtually everything photographed is included, ensuring effortless move-in-ready elegance. The residence blends sophisticated design with functionality, featuring porcelain tile flooring, premium finishes, and custom furnishings throughout. The chef’s kitchen, a centerpiece, showcases two-tone cabinetry, a quartz island, and stainless-steel appliances, ideal for culinary enthusiasts. The open-concept living area flows to a screened lanai, where a heated saltwater pool and paver deck are framed by serene wilderness preserve views, perfect for relaxation or entertaining. The primary suite offers a spa-inspired bathroom with dual vanities and an expansive walk-in closet. Practical features include hurricane storm protection, a spacious laundry room with built-in storage, and a two-car garage. Dramatic landscape lighting adds vibrant depth to the exterior, enhancing curb appeal and creating a refined nighttime ambiance. This meticulously crafted home elevates modern luxury with timeless comfort. This 3-bedroom, 3-bathroom residence, complete with a den, balances elegance and practicality. The two guest bedrooms, each with full bathroom access, ensure privacy and comfort. The den, ideal as a home office, features built-in shelving and natural light. The great room, with 10-foot ceilings and large windows, frames tranquil preserve views. Smart-home technology, including automated lighting and climate control, enhances efficiency. The heated saltwater pool, with a sun shelf and lighting, and the paver deck with manicured landscaping, create a refined outdoor retreat. Upgraded fixtures, such as rainfall showerheads in the primary bathroom and recessed lighting throughout, elevate the home’s sophisticated aesthetic. The exterior features low-maintenance tropical landscaping, complementing the preserve backdrop. Nestled in the gated Winding Cypress community in Southeast Naples, this home is part of a prestigious enclave of 766 residences. Spanning 800 acres of preserves and 80 acres of lakes, Winding Cypress blends natural beauty with luxury. Residents enjoy low HOA fees and amenities, including a resort-style pool with cabanas, a fitness center with modern equipment, and courts for pickleball, bocce, and tennis. The clubhouse, a social hub, offers an internet café, event spaces, and a catering kitchen. A dog park, community garden, and trails through lush preserves cater to diverse lifestyles. Located minutes from Marco Island’s beaches, Naples’ vibrant 5th Avenue, and I-75, this home ensures access to fine dining, shopping, and cultural attractions. Winding Cypress offers a close-knit community, making this turnkey home a standout in Naples luxury living.

6906 Winding Cypress Drive, Naples

Courtesy of Berkshire Hathaway FL Realty

2 Beds ⋅ 2 Baths ⋅ 225033541 MLS

$510,000

Welcome to your dream home in the heart of one of Naples' most sought-after communities! This stunning FRONT entrance Cressida villa offers the perfect blend of comfort, style, and convenience. Featuring two spacious bedrooms, two full baths, and a versatile den/flex room that can be used as an in-home office or guest area. The open concept living/dining space includes a custom-built dry bar/coffee station, light tile flooring, and sliders that open to a private screened lanai. The covered lanai area is plumbed for an outdoor kitchen, allowing you to create the perfect space for entertaining. Winding Cypress offers a plethora of activities to enjoy the Florida lifestyle.

7650 Jacaranda Lane, Naples

Courtesy of William Raveis Real Estate

3 Beds ⋅ 2 Baths ⋅ 224091808 MLS

$880,000

This exquisite 2021 residence showcases the meticulous care of its single owner and boasts numerous upgrades throughout. It features a HEATED POOL, THREE BEDROOMS, TWO BATHROOMS, and a DEN, providing ample space for living and entertaining. Situated on a picturesque lake in the serene WINDING CYPRESS Community. The heart of the home is a spacious, light-filled living area and a large kitchen with a generous island for seating. Culinary enthusiasts will appreciate the FIVE-BURNER GAS STOVE and the convenience of a BUTLER'S PANTRY. The exquisite QUARTZ COUTERTOPS complete the perfect setting for entertaining and everyday living. The home is adorned with IMPACT WINDOW AND SLIDERS, allowing natural light to flood in, and is accented with 8-foot doors and CUSTOM CROWN MOLDING in the primary bedroom. The large primary bathroom features a WALK-IN SHOWER, dual sinks, a dedicated toilet room, and access to the large walk-in closet with built in shelves, and enough room for a small crafts station. Additional highlights include two spacious guest bedrooms, elegant TILE FLOORING throughout, and a two-car garage with a durable EPOXY FINISH. Relax in your well-placed den with views of the natural preserve across the street or convert the space into a spacious home office. Outdoors, you can unwind in your PRIVATE POOL and enjoy the exquisite under-truss patio area. The ELECTRIC ROLL-DOWN SCREENS and remote-controlled awning provide a perfect spot to relax poolside, savor the shade, and take in the tranquil lake views. The PAVER DRIVEWAY has been widened and extended, while the pool deck pavers have recently been power washed and sealed for added appeal. The pie shaped lot is an added bonus giving you a large front yard and plenty of room between you and your neighbors. The conveniently situated lot location is not far from the resident's entrance, providing easy access in and out of the community. Winding Cypress is conveniently located near shopping and dining options and is enveloped by 800 acres of natural preserve and 80 acres of stunning lakes. Winding Cypress enhances the community experience with a wonderful dog park making it an ideal place for pet lovers This dedicated space allows residents and their furry friends to enjoy the outdoors socialize and stay active. Residents can avail themselves of various amenities, including the Shady Palm Café, a resort-style pool and spa, a fitness center, social programs, and sports facilities such as pickleball, tennis courts, and bocce ball. There is also a walking trail for those who love to explore nature. This home exemplifies the essence of Southwest Florida living at its finest. Schedule a showing today. BE SURE TO CLICK THE FULL VIRTUAL TOUR LINKS FOR DETAILS!

6763 Winding Cypress Drive, Naples

Courtesy of Coldwell Banker Sunstar Realty

2 Beds ⋅ 2 Baths ⋅ 225057502 MLS

$710,000

Step inside through a welcoming entryway and discover an open-concept floor plan. The heart of the home is the great room with tray ceiling and crown moldings, the modern kitchen, beautifully appointed with granite countertops, sleek stainless-steel appliances, and a generous center island suited for both everyday living and effortless entertaining. The primary suite offers a peaceful retreat with a walk-in closet, double vanity, walk-in shower. This beautifully cared-for home offers a rare opportunity to enjoy an elevated lifestyle in a sought-after Winding Cypress Community—

6787 Winding Cypress Drive, Naples

Courtesy of William Raveis Real Estate

3 Beds ⋅ 2 Baths ⋅ 225034820 MLS

$885,000

Located in the highly sought-after community of Winding Cypress, this beautifully updated 3-bedroom, 2-bath home offers a perfect blend of luxury, comfort, and breathtaking lake views. Surrounded by 800 acres of natural preserve and 80 acres of serene lakes, this home provides a tranquil lifestyle immersed in nature, with access to all the incredible amenities this community has to offer. Inside, the open-concept layout features coffered ceilings in the living room, adding architectural elegance and a sense of spaciousness. Plantation shutters throughout enhance the light-filled spaces, creating an inviting and sophisticated atmosphere. The chef-inspired kitchen is equipped with a large walk-in pantry, perfect for all your storage needs, and flows seamlessly into the extended great room—ideal for both casual living and entertaining. The home also boasts a den with elegant French doors, providing a private and versatile space for an office, study, or cozy retreat. The large laundry room adds practicality and convenience, while the epoxy floor in the garage combines style and durability, creating a clean and functional space. Step outside to your own private oasis with an outdoor kitchen perfect for grilling and entertaining. The sparkling pool and hot tub, surrounded by a "no-see-um" screened enclosure, offer the perfect retreat with panoramic lake views. The lanai is equipped with hurricane storm screens for added peace of mind, and a whole-house generator ensures you’ll never be without power, even during the most unpredictable weather. Winding Cypress is more than just a neighborhood; it’s a lifestyle. Residents enjoy access to the Shady Palm Café, a spacious clubhouse, and luxurious resort-style amenities such as a pool and spa, fitness center, social programs, pickleball, tennis courts, bocce, and a scenic boardwalk walking trail. Surrounded by top-tier restaurants and grocery stores, and just a short drive to Downtown Naples, this community offers everything you need for both relaxation and convenience. Don’t miss your chance to own this exceptional home in one of the most desirable communities in the area.

7451 Blackberry Drive, Naples

Courtesy of Downing Frye Realty Inc.

2 Beds ⋅ 2 Baths ⋅ 224079403 MLS

$470,000

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

Courtesy of Premier Sotheby's Int'l Realty

3 Beds ⋅ 3 Baths ⋅ 225038123 MLS

$1,100,000

Introducing a luxury estate with landscaped privacy corner lot home in Winding Cypress with pool and spa. Step into elegance with this stunning Pinnacle model estate home, set in the prestigious, gated community of Winding Cypress. This home stands out with its soaring raised tray ceilings, rare privacy and spacious yard, impact glass for peace of mind, and an expansive open layout filled with natural light and outstanding upgrades. Designed for those who love to entertain, the chef-inspired gourmet kitchen features top-tier finishes, premium appliances, and a spacious expanded island, the ideal gathering space for family and friends. With three bedrooms, three baths, a versatile den and an upgraded oversized three-car garage, this home offers flexibility and space to suit your lifestyle. Outside, a private backyard oasis awaits, complete with lush landscaping, a serene water view and a sprawling grassy yard, a rare find in this community. Take a refreshing dip in your sparkling pool and spa, designed for ultimate relaxation in a peaceful setting. Beyond your doorstep, Winding Cypress offers resort-style living like no other. The nearly 18,000-square-foot clubhouse boasts a zero-entry infinity pool with a lap section, a poolside restaurant, beach cabanas and even a sandy beach. Stay active with numerous pickleball courts, clay tennis courts, bocce, an outdoor yoga movement studio, and a vibrant community hall managed by a full-time activity director. Winding Cypress is a resort gated community at the midpoint between Marco Island and downtown Naples, and this home delivers the ultimate combination of luxury, convenience and an unmatched lifestyle. Don’t miss your chance to own one of the desirable and private estate homes in Winding Cypress of Naples.

7520 Blackberry Drive, Naples

Courtesy of Premier Sotheby's Int'l Realty

2 Beds ⋅ 2 Baths ⋅ 225031142 MLS

$750,000

Thoughtful price improvements, upgraded finishes throughout, an expanded kitchen island & a rare 4-foot extension in the garage sets this home apart - topped off by a stunning private pool overlooking the lake. This property offers exceptional appeal. This is a stunning Abbeyville home in Winding Cypress, a move-in ready! This immaculate residence is a must-see, featuring a fresh neutral palette, offering a spacious open split-bedroom floor plan with 2 bedrooms, a flex/den & 2 full bathrooms. Entertainment is elevated with flat-screen TVs mounted in both bedrooms & living area. Soaring ceilings enhanced by elegant molding, tray & coffered details, along with extra recessed lighting. Plantation shutters in the front bedroom, flex/den & over the kitchen sink add both privacy & style. Enjoy matching tile flooring throughout the main areas, with warm wooden plank flooring accentuating the flex/den room. A new HVAC unit, installed in December 2021 & serviced bi-annually ensures year-round comfort. The gourmet kitchen is a chef’s delight with upgraded white shaker cabinets, quartz countertops, a stylish subway tile backsplash & stainless steel appliances including a gas range & hood, dishwasher, built-in microwave, & a stainless steel sink with in-sink disposal. Exquisite cabinet lighting brightens the space, while a large extended kitchen island with additional cabinets provides ample storage. The primary suite features a luxurious walk-in shower with a glass enclosure, dual vanities with a quartz countertop, leading onto a fabulous walk-in closet with built-in organizers. The guest bathroom similarly boasts upgraded features with a tub & shower/glass enclosure, quartz countertop & spacious linen closet. The convenient laundry room is outfitted with upgraded front-load washer & dryer along with built-in cabinets & organizers. Outside, the stunning outdoor oasis beckons with a crystal-clear kidney-shaped pool offering serene lake views. Privacy hedges frame the pool cage, which features both covered & uncovered lanai areas - the perfect balance for year-round enjoyment. Upgrades include new pool cage screens & a pool heater (December 2022). Additional features include built-in easy-to-slide high-end accordion hurricane shutters & an extended 2-car garage with epoxy flooring. Located in the premier Winding Cypress community - A highly sought-after natural gas community set among 800 acres of natural preserves & 80 acres of lakes - this home offers resort-style amenities including a lap pool with spa, screened-in outdoor bar & grill (The Shady Palm), fire pits, fireplace, two dog parks, a community garden, tennis, bocce & pickleball courts, a state-of-the-art clubhouse with a fitness center plus event rooms. Ideally situated just minutes from Downtown Naples, several beaches, Marco Island & US-41/I-75, this property blends luxury & convenience effortlessly. Don’t miss out on this incredible opportunity!

7128 Lily Way, Naples

Courtesy of Premiere Plus Realty Company

2 Beds ⋅ 2 Baths ⋅ 225053774 MLS

$900,000

The perfect move in ready home for sale! This Summerwood floorplan features 2 bedrooms, 2 baths+den, saltwater pool and spa, and a 2+car garage offering a blend of style, comfort, and functionality. The open-concept layout features a dramatic zero-corner slider, seamlessly connecting indoor and outdoor spaces, while the whole home generator, exterior cameras, and impact windows and doors provide peace of mind. Inside, extensive upgrades are everywhere. The kitchen boasts built-in appliances and a spacious island, perfect for entertaining. Additional highlights include built-in Sonos speakers, crown molding, hard flooring throughout, custom primary closet, and a Murphy bed in the den—ideal for guests or a home office. The thoughtful laundry room has an upgraded washer and dryer and custom cabinets with a dedicated spot for charging your vacuum. You will have tons of storage space in the air conditioned tandem garage which can accommodate up to three cars. Outside, the saltwater pool and spa are heated by both gas and solar (a smart money-saving combo), expansive outdoor kitchen, hurricane screens for a second layer of protection, privacy lanai screening, plenty of seating areas, gorgeous lush landscaping, and areas for storage. This home has been meticulously maintained, most recently the duct work was cleaned and pavers sealed. 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 a dog park for your furry friend. This pet-friendly community allows rentals, has low fees, and boasts a prime location—central to Marco Island, 5th Avenue, and I- 75.

6848 Winding Cypress Drive, Naples

Courtesy of Realty One Group MVP

3 Beds ⋅ 2 Baths ⋅ 225048066 MLS

$990,000

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 Drive, Naples

Courtesy of Premiere Plus Realty Company

2 Beds ⋅ 2 Baths ⋅ 225021309 MLS

$620,000

PRICED TO SELL!! This beautiful Cressida model villa in highly sought-after Winding Cypress is move-in-ready. Freshly painted inside and out. Roof and all pavers have been power washed and sealed This beautiful villa offers two bedrooms, two baths plus a den along with a two-car air-conditioned garage. The den can be easily converted into a third bedroom. Step onto your lanai with the largest pool and hot tub available in a villa. Couple that with a spectacular long lake view and you truly have a one-of-a-kind home. Winding Cypress offers resort-style living with a large amenity center, gym, exercise room, library, internet cafe, event room and restaurant. The resort-style pool has a lap lane and waterfall. Other amenities include pickleball, tennis, bocce, community garden and dog park. The community boardwalk allows you to walk deep into the preserve. Winding Cypress boasts 800 acres of untouched preserve surrounding our one-of-a-kind community.

7815 Jacaranda Lane, Naples

Courtesy of Coldwell Banker Realty

3 Beds ⋅ 2 Baths ⋅ 225050266 MLS

$674,000

Welcome to this beautifully appointed 3-bedroom, 2-bathroom + den home in the vibrant and sought-after community of Winding Cypress in Naples. Perfectly positioned on a prime lakefront lot, this residence offers serene, long water views that extend to the untouched beauty of the preserve beyond. Thoughtfully designed for both comfort and style, this home features tall interior doorways, an extended screened-in lanai, a fully equipped outdoor kitchen—ideal for entertaining or enjoying peaceful evenings overlooking the lake, and Enjoy the convenience of an extended garage — perfect for extra storage, a workshop space, or oversized vehicles.. Storm shutters provide added security and peace of mind, while the open and versatile layout includes a den perfect for a home office or flex space. The well-appointed kitchen boasts a gas range, catering to culinary enthusiasts, and a natural gas whole-home generator ensures uninterrupted comfort during any weather event. Additional conveniences include an HOA that covers landscaping and irrigation water, allowing for low-maintenance living. Winding Cypress is a gated, resort-style community offering an exceptional array of amenities. Residents enjoy a luxurious clubhouse, a tropical pool with waterfall features, a soothing spa, and a state-of-the-art fitness center. Recreational and social opportunities abound with pickleball, tennis, bocce, and a full calendar of community events. The Shady Palm Café serves delicious food and drinks poolside, while a scenic boardwalk winds through the community’s pristine natural surroundings. A spacious, secure dog park makes this neighborhood perfect for pet lovers as well. Conveniently located just off US-41, Winding Cypress offers easy access to world-class dining, shopping, entertainment, and the white-sand beaches that define Naples living. Experience the perfect blend of privacy, luxury, and vibrant community life in this exceptional home.

7445 Winding Cypress Drive, Naples

Courtesy of KW Elevate Luxury

3 Beds ⋅ 3 Baths ⋅ 225046502 MLS

$1,175,000

EXCEPIONAL in design and setting, this Pinnacle model commands southwest-facing LAKE AND PRESERVE VIEWS from one of the most private parcels within Winding Cypress. The residence is enhanced by an extended, Climate-Controlled 3 CAR GARAGE with a high-performance Polymer finish—offering utility and Esthetic. Interior features include 12’ ceilings, Tray Ceilings, tile flooring throughout, Plantation Shutters, and custom millwork. The open-concept floor plan includes a great room with Electric Sliding Doors leading to the lanai. The kitchen is equipped with Quartz countertops, a large island with built-in wine cooler, KitchenAid and Whirlpool appliances, and a natural gas cooktop. The primary suite includes custom closets and an en-suite bath. The home is equipped with a whole-house Generac Generator, whole-house Water Purification with Reverse Osmosis, and a Built-in Surround sound system in the great room, primary bedroom, and lanai. A full home security system is also installed. Outdoor living space features an extended lanai with a custom Aragon Pool and Spa and an Upgraded Outdoor Kitchen great for Entertaining... Winding Cypress amenities include a clubhouse, fitness center, resort-style pool, tennis courts, pickleball, bocce, dog park, and nature trails.

7597 BLACKBERRY Drive, Naples

Courtesy of Coldwell Banker Realty

2 Beds ⋅ 2 Baths ⋅ 225035628 MLS

$455,000

Tucked Away Treasure in Winding Cypress- Step into a slice of serenity with this charming attached villa, nestled in one of the most peaceful corners of Naples. Unlike the typical coastal designs so common in the area, this home offers a more rustic warmth—perfect for those who appreciate natural textures, cozy finishes, and a relaxed, grounded lifestyle. With 2 bedrooms, a versatile den, 2 full bathrooms, and a 2-car garage, this villa checks all the boxes for comfort and functionality. The open layout is inviting yet intimate, ideal for both quiet evenings and casual entertaining. The kitchen is equipped with natural gas—a rare find that’s perfect for those who love to cook and value energy efficiency. Step outside to the screened-in lanai where mornings are best spent with coffee in hand, surrounded by the sounds of nature and a view of your private backyard oasis. An extended outdoor patio provides the perfect space to unwind under the stars. Located within the gated, master-planned community of Winding Cypress, this home offers so much more than just a beautiful space—it’s part of a vibrant lifestyle. Developed by Divosta Homes and surrounded by over 800 acres of natural preserves and 80 acres of lakes, Winding Cypress is a nature lover’s dream, tucked beside the Picayune Strand Forest. Residents enjoy top-tier amenities including the Shady Palm Café, a stunning resort-style waterfall pool, clubhouse, fitness center, tennis, bocce, and pickleball courts, and scenic walking trails. Plus, you’re just minutes from shopping and dining at Tamiami Crossing and Freedom Square. If you’ve been waiting for a home that feels like a true escape—but still close to it all—7642 Jacaranda Ln is calling.

7642 Jacaranda Lane, Naples

Courtesy of Downing Frye Realty Inc.

3 Beds ⋅ 3 Baths ⋅ 225060759 MLS

$1,260,000

This Pinnacle floorplan is situated on the largest lake in the neighborhood and features 3 bedrooms, a den, 3 bathrooms, a pool and spa, and a 3-car garage. The open-concept layout includes a dramatic zero-corner slider that seamlessly connects indoor and outdoor living spaces. Peace of mind comes with a whole-home generator and impact-resistant windows and doors. Inside, you'll find extensive upgrades throughout. The kitchen boasts built-in appliances and a spacious island—perfect for entertaining. Additional highlights include soaring tray ceilings, crown molding in the den and entry, and tile flooring throughout. The air-conditioned 3-car (extended by 4 ft) garage offers ample storage with custom shelving and a built-in workbench. Outdoors, the heated pool and spa are powered by both gas and solar, a smart, energy-efficient combination. The expansive outdoor kitchen, hurricane screens for added protection, and generous deck space create an ideal setting for sunset views. Other exterior features include lush landscaping with low-voltage lighting, an extra-wide driveway (recently sealed), a custom designed screened-in entryway, and panoramic wide lake views. 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.

6839 Winding Cypress Drive, Naples

Courtesy of Realty One Group MVP

2 Beds ⋅ 2 Baths ⋅ 224103914 MLS

$645,000

Welcome to your dream home at 7370 Mockingbird Court in beautiful Naples, FL! This charming 2-bedroom, 2-bathroom residence, with a versatile den that can easily be converted into a third bedroom, offers a spacious 1,805 square feet of living space, perfectly nestled on an 8,276 square foot lot. Step inside to discover a welcoming interior featuring both carpet and tile floors, ideal for comfort and style. The open living area is enhanced by new ceiling fans and pendant lighting, creating a bright and airy atmosphere. The kitchen is a chef's delight with brand new quartz countertops, a new sink and faucet, and a suite of new appliances including a dishwasher, refrigerator, and garbage disposal. The master suite offers a serene retreat with a new toilet in the master bath, ensuring modern convenience. Enjoy the luxury of central AC and gas heat throughout the home. The attached garage, equipped with a new garage door opener, provides ample space for parking and storage. Outdoor enthusiasts will appreciate the common outdoor space, private outdoor areas, and stunning lakefront views. The community amenities are second to none, featuring a pool, hot tub, gym, tennis court, and pickleball facilities. For those who love the water, the property is waterfront with lake views, perfect for tranquil evenings. Plus, there is room to add a pool, allowing you to customize your outdoor oasis. Additional features include a new gas hot water heater, added landscape lights, and a recently cleaned roof. Plus, enjoy the convenience of laundry in the building and a washer/dryer in the unit. Conveniently situated just minutes from shopping, dining, and all the attractions Naples has to offer, this home combines tranquility with exceptional lifestyle opportunities. This home is a true gem, offering a blend of comfort, style, and community amenities that make it a perfect place to call home. Don't miss the opportunity to make it yours!

7370 Mockingbird Court, Naples

Courtesy of Compass Florida LLC

3 Beds ⋅ 3 Baths ⋅ 225001834 MLS

$1,255,000

Discover luxury living in this breathtaking Pinnacle estate home, situated on one of the most coveted lakefront sites in the south Naples resort community of Winding Cypress. Step inside to an open and spacious floor plan, enhanced by soaring tray ceilings, architecturally stunning alcoves and graceful arches. The home’s designer kitchen serves as the centerpiece, featuring every upgrade possible — soft-close cabinetry, quartz countertops, a fully vented natural gas range and hood and an all-premium KitchenAid appliance package with pull-outs in all lower cabinets. Adjacent is a large pantry complete with a water filter system for added convenience. The primary suite is a private oasis with towering ceilings and full walk-in shower and massive walk-in closet, while guest quarters include an expansive bay window en suite, ensuring comfort and privacy for family and friends. Additional living spaces include a versatile den or hobby room with upgraded French glass doors and foyer layout. Outdoor living is equally impressive. Relax by the saltwater pool and spa while enjoying serene wide-open lake views. Host gatherings with ease, thanks to a fully equipped outdoor kitchen featuring an integrated hood, all set within an expansive lanai with an upgraded oversized pocket slider door. The screened front porch, extended paver paths and custom landscaping further enhance the home’s curb appeal. Practical features include a 4-foot garage extension with custom flooring for three cars, all-impact glass windows, Storm Smart Kevlar shutters and energy-efficient LED lighting throughout. Additional upgrades include raised tray with crown-trimmed ceilings, a heated fireplace with customizable colors and custom state-of-the-art lighting systems that add a touch of sophistication to every room. Located in the resort-style community of Winding Cypress, residents enjoy exclusive access to a wealth of amenities, including a restaurant and bar, state-of-the-art fitness center, resort-style and lap pools, a spa and sports facilities for bocce, pickleball and tennis. The community also boasts a fire pit, bird-watching overlooks, a nature boardwalk and a picnic pavilion. Perfectly positioned between downtown Naples and Marco Island, this home offers the ultimate in luxurious Florida living. From its high-end finishes to its extraordinary location, it’s a property that truly has it all.

7675 Winding Cypress Drive, Naples

Courtesy of Premier Sotheby's Int'l Realty

3 Beds ⋅ 3 Baths ⋅ 224088928 MLS

$975,000

Nestled within an exclusive gated community and surrounded by a serene nature preserve, this elegant 3-bedroom, 3-bathroom home with a spacious den/office is the epitome of refined Florida living. The open, airy floor plan flows seamlessly, with high ceilings and large windows that capture abundant natural light and offer unobstructed views of the lush preserve behind the home. This home has natural gas, generator, upgraded oversized garage, Sentricon system, central vac system, and many more upgrades. Step into the gourmet kitchen, complete with premium appliances, custom cabinetry, and an expansive island that's perfect for entertaining or family gatherings. Each bedroom is generously sized, featuring high-end finishes and ample storage, while the den/office provides an ideal, private space for working from home or additional relaxation. The master suite is a tranquil retreat with a luxurious en-suite bathroom featuring dual vanities, and a walk-in shower. Outdoors, your private paradise awaits, with a sparkling gas heated salt water pool and spa surrounded by a spacious patio, perfect for sunbathing, al fresco dining, or evening cocktails under the stars. The 3-car garage offers plenty of room for vehicles, storage, and hobbies. Living in this community comes with exceptional amenities that rival a luxury resort. Enjoy an on-site restaurant, a spectacular resort-style pool, tennis courts, pickleball, bocce, and a dog park, all thoughtfully designed to elevate your lifestyle. The well-appointed fitness center, internet café, and an engaging calendar of year-round social events ensure that there's always something to do. Centrally located between the pristine beaches of Marco Island and Naples, this home places you just moments away from world-class shopping, dining, and entertainment, yet offers a peaceful, nature-filled escape in your own backyard. Don't miss the opportunity to make this luxurious haven yours!

7788 Winding Cypress Drive, Naples

Courtesy of Royal Shell Real Estate, Inc.

2 Beds ⋅ 2 Baths ⋅ 225056443 MLS

Set against private garden views with tranquil eastern exposure, this beautifully appointed villa in Winding Cypress offers a peaceful retreat and effortless indoor-outdoor living. Featuring two bedrooms plus a den, two baths, and a two-car garage, this thoughtfully designed residence combines quiet luxury with meticulous updates in one of Naples’ most dynamic lifestyle communities. The screened lanai is ideal for entertaining or unwinding, complete with brick paver flooring, a saltwater pool with waterfall feature, pool heater, and recent upgrades including a new salt generator and pool pump. A custom outdoor kitchen with a stainless steel gas grill with matching hood and sink further enhances the outdoor living experience. Electric hurricane shutters protect the lanai, while manual shutters cover the remainder of the home. Inside, tile flooring extends throughout, accented by crown molding, recessed lighting, and white plantation shutters. The living room opens to the lanai through expansive glass sliders, anchored by a modern ceiling fan. The kitchen features white Shaker-style cabinetry, quartz countertops, a tile backsplash, pantry, and stainless steel appliances including a gas range, refrigerator with icemaker, microwave, and dishwasher. A modern chandelier defines the dining area, which flows easily into the main living space. The primary suite is a private haven with a tray ceiling, garden views, custom closet, and a spa-inspired bath featuring dual quartz vanities, full-width mirrors, and a frameless glass walk-in shower. The second bedroom includes a walk-in closet and an adjacent bath with a shower-tub combination. A den with French doors offers flexible space for a home office or reading room. Additional highlights include a mini-split air conditioning system in the garage, a brand-new water heater, and recent property updates including a full exterior repaint (approximately two years ago) and interior paint touch-ups. Residents of Winding Cypress enjoy access to resort-style amenities including a pool, an attended fitness center, an on-site restaurant, five tennis courts, four bocce ball courts, four pickleball courts, a community garden, and a dog park. With a vibrant social calendar, low HOA fees, rental-friendly policies, and a prime location near Marco Island, downtown Naples, 5th Avenue, and I-75, this villa offers elevated living in a premier Naples community.

7690 Jacaranda Lane, Naples

Courtesy of Premier Sotheby's Int'l Realty

2 Beds ⋅ 2 Baths ⋅ 225059100 MLS

$635,000

On a premium oversized lot, this beautifully upgraded villa offers one of the most stunning sunset water views in all of Winding Cypress. The extended screened lanai features a panoramic no-see-um screen, heated saltwater pool, and a fully equipped outdoor kitchen with a five-burner Bull Grill, stainless steel sink, premium refrigerator, and a 42-inch lighted vent hood, an entertainer’s dream and the ultimate space to relax and take in the view. Hurricane-impact windows and doors throughout the home provide peace of mind, while a stylish glass entry door, two ceiling-mounted garage storage racks, and attic access in the garage and primary closet add smart functionality. Inside, the open floor plan is elegant and inviting with diagonal tile flooring, plantation shutters and upgraded LED recessed lighting. The home includes two furnished bedrooms plus a flexible den with 8-foot French doors and a new Murphy bed, ideal for guests or a home office. The gourmet kitchen features granite countertops, a tasteful tiled backsplash, staggered cabinetry with under- and over-cabinet lighting, and bar seating. California Closets have been added to the primary suite and kitchen pantry for optimal organization. This smart home includes a Nest thermostat, video doorbell, cameras at garage and lanai, Nest Protect smoke and CO2 detectors and Leviton Wi-Fi lighting switches. Gently lived in as a pet-free, smoke-free seasonal home, it shows like new. Winding Cypress offers over 800 acres of natural preserves, a resort-style clubhouse with a heated pool, restaurant, fitness center, white sand beach, tennis and pickleball courts, dog park and scenic nature trails. With low HOA fees and a natural gas community, all just 25 minutes to 5th Avenue, 20 minutes to Marco Island and five minutes to major shopping, this home blends luxury, peace of mind and lifestyle in one incredible package.

7773 Jacaranda Lane, Naples

Courtesy of Premier Sotheby's Int'l Realty

3 Beds ⋅ 3 Baths ⋅ 224083667 MLS

$830,000

Welcome to a beautiful Pinnacle Model in the desirable, amenity rich community of Winding Cypress. This waterfront home. Original owner care is apparent throughout. Builder and owner upgrades include; chef's kitchen with upgraded appliances, sink & faucet, soft close pull out cabinets including under-side lighting, custom quartz countertops, custom plank tile flooring, hurricane impact windows, slider, and entry door, upgraded & expansive lanai outdoor living area with Storm Smart Kevlar screen enclosure & ready for you to design your own outdoor kitchen.

7544 Winding Cypress Drive, Naples

Courtesy of William Raveis Real Estate

2 Beds ⋅ 2 Baths ⋅ 225025806 MLS

$675,000

This move in ready furnished Winding Cypress Serenity 2 bedroom plus den Attached Villa with POOL & SPA is a unique quality find. This Serenity floor plan with the kitchen conveniently tucked away behind peninsula island allows for optimal entertaining space. Kitchen features Quartz countertops, natural gas range & SS appliances. Other high quality highlights include, plantation shutters, crown molding, Lutron shades at slider, recessed & under cabinet lighting, upgraded lighted mirrors in both baths, laundry room cabinets & sink, privacy door for guest suite, pull down attic stairs in garage, wide, driveway, pest control piping in the walls, Storm Smart electric hurricane shades on lanai and landscaped lighting around lanai. Slight pie shape lot and lush landscaping offers extra privacy for lanai and pool area. Located in sought after Winding Cypress Community with it's rich amenities including a resort style pool, restaurant/bar, fire pit, fitness center, outdoor yoga deck, pickle-ball, tennis, bocce ball, community garden, dog park, and a nature trail boardwalk that wanders through protected natural preserves. Centrally located between Marco Island and 5th Ave allows easy access to the surrounding areas beautiful beaches, restaurants and entertainment.

7742 Jacaranda Lane, Naples

Courtesy of R L Bailey Realty Inc.

3 Beds ⋅ 2 Baths ⋅ 225023660 MLS

$925,000

A MOST INCREDIBLE OFFERING MARTIN RAY. THIS HOME HAS IT ALL. HURRICANE IMPACT WINDOWS & SLIDING GLASS DOOR, HURRICANE IMPACT MAIN ENTRANCE DOOR WITH LEADED GLASS, CEILINGS WITH TRAYS, COFFERS, & WIDE MOLDINGS, EXTERIOR LIGHTING PACKAGE, KITCHEN CABINET PACKAGE INCLUDING SOFT CLOSE DOORS, QUARTZ COUNTERTOPS,2 CAR GARAGE WITH UTILITY SINK, EXTENDED DRIVEWAY & MAIN ENTRANCE PAVERS, PAVER SIDEWALKS ON BOTH SIDES TO LANAI, PROFESSIONALLY LANDSCAPED AROUND ENTIRE RESIDENCE, HOME HAS BEEN PROFESSIONALLY DESIGNED & DECORATED.

6854 Greenbriar Court, Naples

Courtesy of William Raveis Real Estate

2 Beds ⋅ 2 Baths ⋅ 223047593 MLS

$710,000

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

7714 Jacaranda Lane, Naples

Courtesy of Downing Frye Realty Inc.

2 Beds ⋅ 2 Baths ⋅ 225023743 MLS

$760,000

This beautifully upgraded 2-bedroom plus den, 2-bath Mystique floorplan home in Winding Cypress offers the perfect blend of style, comfort, and functionality. The open-concept design features a zero-corner slider, seamlessly connecting indoor and outdoor spaces, while impact windows and doors provide security and energy efficiency. A whole-home generator ensures uninterrupted comfort and peace of mind. Inside, thoughtful upgrades enhance every space. The gourmet kitchen boasts built-in appliances and a spacious island, perfect for entertaining. Additional highlights include crown molding, built-in speakers, a custom living room accent wall, and built-in drop zone cabinetry for added style and organization. The den features a Murphy bed, making it a flexible space for a home office or extra bedroom. The laundry room is equipped with built-in cabinets, offering ample storage. Outside, the private backyard is a true retreat, featuring a pool and spa for ultimate relaxation. The outdoor kitchen is perfect for entertaining, while lush landscaping enhances the home’s peaceful ambiance. A tandem garage has the ability to accommodate up to three cars, providing plenty of parking and storage. 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 a dog park for your furry friend. This pet-friendly community allows rentals, has low fees, and boasts a prime location—central to Marco Island, 5th Avenue, and I- 75.

6758 Pennyroyal Drive, Naples

Courtesy of Realty One Group MVP

2 Beds ⋅ 2 Baths ⋅ 225021743 MLS

$537,000

Price Negotiable! Seller is highly motivated!! Discover your slice of paradise in this stunning 2-bedroom plus den villa, located in the resort-style community of Winding Cypress. With exquisite builder-installed upgrades, this home features a sleek open floor plan, granite countertops, and elegant porcelain tile throughout. The kitchen is outfitted with stainless appliances and gas stove complemented by a stylish backsplash. The spacious den, equipped with French doors, can easily transform into a third bedroom, while California Closets in every room provide exceptional storage and organization and Plantation Shutters. Your attached 2-car garage is enhanced with Monkey Bar storage for maximum efficiency! Step outside to enjoy a wealth of amenities, including a restaurant and bar, a state-of-the-art fitness center, resort-style pools, and vibrant sports facilities for bocce, pickleball, and tennis. Unwind by the fire pit or explore the nature boardwalk and bird-watching overlooks. Perfectly situated between downtown Naples and Marco Island, this beautifully upgraded home offers the ultimate Florida lifestyle. Don’t miss out on this incredible opportunity

7591 Jacaranda Lane, Naples

Courtesy of Keller Williams Marco Realty

3 Beds ⋅ 2 Baths ⋅ 225018609 MLS

$890,000

Discover luxury living in this modern and bright single-family Martin Ray home, located in the resort-style community of Winding Cypress. With 2,107 square feet of living space, this open concept 3-bedroom plus den, 2-bathroom home offers a harmonious blend of elegance and functionality. Natural light and coffered ceiling details create a bright and airy atmosphere while modern design and neutral colors provide a sense of elegance and refinement. The kitchen showcases stainless steel appliances, gorgeous quartz countertops, white cabinetry, 42” upper cabinets, a walk-in pantry, under cabinet lighting, tile backsplash, ample storage space, and a large center island which blends seamlessly into the family and dining room creating the highly sought after open concept, perfect for families and entertaining. The master suite, located in the back of the home, provides a serene retreat with a spacious bedroom, tray ceiling, walk-in closet and a well-appointed en-suite bathroom featuring dual sinks, separate water closet, modern tile, and a walk-in shower. Two additional bedrooms and an adjacent bathroom, offer ample space and privacy for the entire family. Beautiful impact, tuck away sliding glass doors lead to an expansive lanai complete with picture window screens, serene NW lake views, and a heated saltwater pool with sun shelf and spa, providing a seamless transition between indoor and outdoor living. Other enhancement that set this home apart from the rest include impact windows and doors, coffered ceiling in the living room, crown molding, 6-inch baseboards, 8-foot doors, screened in front entry, separate laundry room with a sink and cabinetry, window blinds/curtain panels, glass doors on the den, upgraded landscaping, outdoor kitchen, auto pool filler, decorative Bahama shutters, Sentinel Storm Shades on the back lanai, and an extended 2-car garage with utility sink and epoxy flooring. Winding Cypress is a gated, resort-style community featuring 766 homes located in Naples, FL. Nestled within over 1,100 acres of natural preserves and 80 acres of serene lakes, this community offers residents a laid-back lifestyle surrounded by nature. Residents enjoy a wide array of amenities, including the Shady Palm pool side café, a spacious Clubhouse, resort-style pool/spa, lap pool, pickleball, tennis, bocce, fitness center, movement room, nature boardwalk, and dog park. Centrally located near shopping, restaurants, and the pristine beaches of Naples and Marco Island, Winding Cypress seamlessly merges the elegance of modern living and the serene beauty of its natural surroundings.

7556 Winding Cypress Drive, Naples

Courtesy of Orchid Realty International

3 Beds ⋅ 2 Baths ⋅ 225008365 MLS

$860,000

Don't miss out on this stunning impeccably maintained Summerwood model in the highly coveted Winding Cypress community. This beautifully designed home offers 3 bedrooms, plus a dedicated home office, perfect for today’s lifestyle. The charming front porch, an inviting space to unwind with your morning coffee, and be greeted by a designer glass entry door. Inside, you’ll find a bright and open layout enhanced by crown moldings, luxury tile flooring, and classic plantation shutters, creating an atmosphere of elegance throughout. Take full advantage of the abundant space and natural light pouring in through the sunroom. The extended 2-car garage is more than just a place to park—it includes a mini-split A/C system and epoxy flooring, offering extra room for storage.

6763 Pennyroyal Drive, Naples

Courtesy of William Raveis Real Estate

2 Beds ⋅ 2 Baths ⋅ 225001830 MLS

$635,000

Rare villa opportunity in Winding Cypress! For the first time in over a year, a villa with a private pool and spa on an extra-large lot is available. Enjoy unmatched privacy with huge space between neighbors and serene ultra-private preserve views. This turnkey, fully furnished home features impact windows, 8-foot doors, new bedroom flooring, fresh landscaping and more. This natural gas community offers all hookups for an outdoor kitchen on your lanai, with gas, water and drain ready. Plus, extra garage storage is built in, making organization a breeze. Step into your own backyard oasis with a heated pool and spa, ideal for relaxing or entertaining in the Florida sunshine. Whether hosting guests or unwinding solo, this home offers the ideal blend of comfort and luxury. In the sought-after Winding Cypress community, residents enjoy resort-style amenities without the high fees. Dive into the expansive resort pool, stay active in the state-of-the-art fitness center, or explore miles of scenic nature with recreational and biking trails. The full-service restaurant and bar provide a social hub, while the tennis and bocce courts, garden and pickleball courts offer endless recreation options. The clubhouse also features a stunning social hall, library, and event spaces to connect with neighbors and friends or hold special celebrations.

7199 Live Oak Drive, Naples

Courtesy of Premier Sotheby's Int'l Realty

3 Beds ⋅ 3 Baths ⋅ 225001831 MLS

Welcome to the award-winning Martin Ray home in the prestigious and centrally located Winding Cypress resort community in Naples. This exceptional home features an expansive lanai set on a protected and private preserve, with room for a pool, providing the perfect space to enjoy the serene Florida sunshine. Inside, the bright and airy ambiance is enhanced by a newly enlarged center island with top-of-the-line quartz finishes throughout the kitchen, gourmet natural gas appliances, reverse osmosis water system, high-quality wood grain ceramic tile flooring and impact-resistant glass. Elegant design upgrades also include custom dining area millwork, crown molding, new lighting, plantation shutters, custom drapes and a professionally built closet system in the primary bedroom. Whether you’re hosting a lavish gathering or enjoying a quiet evening at home, this residence seamlessly blends elegance and comfort. A bonus loft offers a versatile space for guests or in-home entertainment, with ample room for a pool table or home theater. Residents of Winding Cypress enjoy an array of luxurious amenities, including a clubhouse with a state-of-the-art fitness center, catering kitchen, community room and activity space. Outdoor amenities abound, featuring pickleball courts, a lap pool, spa, outdoor movement studio, The Shady Palm Café poolside restaurant, bocce ball courts, five Har-Tru tennis courts, a fire pit, bird-watching overlook and a nature boardwalk with a picnic pavilion. Ideally located near the pristine shores of Marco Island and vibrant downtown Naples, this resort-style community provides the perfect backdrop for an unparalleled lifestyle.

7073 Live Oak Drive, Naples

Courtesy of Premier Sotheby's Int'l Realty

2 Beds ⋅ 2 Baths ⋅ 224101522 MLS

$710,000

WOW! HERE IS A GORGEOUS RESIDENCE THAT WAS PROFESSIONALLY DECORATED AND IS IN PRISTINE CONDITION. THE HOME HAS A RESORT STYLE LARGE PAVER DECK SALT WATER POOL WITH A PICTURE FRAME SCREENED LANAI. ENJOY AN EXPANSIVE DECK AREA TO RELAX, SOAK UP THE SUN, OR JUST TAKE IN THE STUNNING LAKE VIEW. THE GOURMET KITCHEN HAS STATE OF THE ART APPLIANCES, QUARTZ COUNTERS, TILE BACK SPLASH WITH HAND CRAFTED WOOD CABINETRY. THE LUXURIOUS PRIMARY SUITE HAS A VIEW OF THE POOL AND LAKE WITH CUSTOM WOOD FLOORING AND A HUGE WALK IN CLOSET. THE HOTEL INSPIRED OWNERS BATH IS SURE TO IMPRESS. ON THE FRONT END OF THE HOME IS A GUEST BEDROOM WITH LOTS OF NATURAL LIGHT, AND A IMPRESSIVE GUEST BATH. ADDITIONALLY THE RESIDENCE HAS A NICE SIZED DEN, OR POSSIBLE THIRD BEDROOM. ADDITIONAL UPGRADES INCLUDE, WHOLE HOUSE GENERATOR, ACCORDION SHUTTERS, EXTENDED GARAGE, HARD WOOD AND TILE FLOORS THROUGHOUT, DESIGNER FIXTURES AND MORE. WINDING CYPRESS IS A GATED COMMUNITY RICH IN AMENITIES, WITH A RESTAURANT AND POOL BAR RIGHT ON SITE.

7263 Live Oak Drive, Naples

Courtesy of Island Realty Marco

2 Beds ⋅ 2 Baths ⋅ 224089763 MLS

$775,000

This pristine Abbeyville home in Winding Cypress has it all and is not to be missed! Built in 2021, this property has a fresh neutral palate and features a spacious open split bedroom floor plan with 2 bedrooms + den + sunroom and 2 full bathrooms. The 2-car garage has upgraded features including AC, an insulated garage door, a 4' extension, and extra lighting. 10' ceilings add to the spaciousness of this home! Wood look plank tile flooring throughout, crown molding, tray & coffered ceilings, extra canned lighting throughout, and plantation shutters in the front bedrooms, den, and over the kitchen sink elevate this home. The contemporary kitchen offers white shaker cabinets, quartz countertops, subway tile backsplash, stainless steel appliances including a gas range & hood, dishwasher, built-in microwave, stainless steel sink, undercabinet lighting, and a large extended kitchen island with additional cabinets on one side. The primary bath features a walk-in shower, granite countertop with dual vanities & drawers, comfort height toilet, and a large walk in closet with a built-in organizer. The guest bath includes granite countertop, a comfort height toilet and an upgraded walk-in shower with glass enclosure. The spacious laundry room has plenty of storage with built-in cabinets and organizers. Relax and enjoy your own heated pool with its lovely serene preserve view. Extra clusia hedges on both sides of the pool cage provide ultimate privacy. Move in ready, the sellers have thought of it all including added features such as a widened driveway, a paved walkway from the driveway to the lanai, lush landscaping with solar outdoor lighting, whole house gutters, Ring doorbell, and even a Generac 18KW whole home generator with a warranty! Winding Cypress is a highly sought after natural gas community containing 800 acres of natural preserves and 80 acres of lakes. Top notch amenities include a resort style pool with lap lanes & spa, a screened in outdoor bar and grill The Shady Palm, fire pits & fireplace, 2 dog parks, community garden, tennis, bocce, pickleball courts, in addition to a beautiful clubhouse featuring a fitness center and community & event rooms. Conveniently located within close proximity to downtown Naples, several beaches, Marco Island, & US-41.

6852 Winding Cypress Drive, Naples

Courtesy of DomainRealty.com LLC

2 Beds ⋅ 2 Baths ⋅ 224090027 MLS

$992,500

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 Drive, Naples

Courtesy of Premier Sotheby's Int'l Realty

3 Beds ⋅ 3 Baths ⋅ 224083615 MLS

$1,495,000

6883 Cocoplum Street, Naples

Courtesy of William Raveis Real Estate

3 Beds ⋅ 2 Baths ⋅ 224082513 MLS

$935,000

Live the Vacation Lifestyle Every Day in Winding Cypress Welcome to a home that feels like a never-ending vacation. This stunning Summerwood residence, nestled in the resort-style community of Winding Cypress, is more than a home—it’s a lifestyle. From the moment you step through the dramatic entry hall, you’re greeted by breathtaking lake views that set the tone for tranquility and relaxation. The zero-clearance sliding glass doors seamlessly blend indoor elegance with outdoor splendor, leading to an expansive lanai designed for ultimate leisure and entertainment. Imagine starting your mornings with serene sunrises over the lake, enjoying your coffee on the lanai surrounded by picturesque scenery. The fully equipped bar—complete with a KitchenAid grill, refrigerator, freezer, and ample seating for seven—makes hosting sunset cocktail parties a breeze. Whether you prefer lounging in the shaded comfort or basking in the sun, this home caters to your every mood. Winding Cypress offers an unparalleled array of resort-style amenities: • A tropical pool oasis with cascading waterfalls, a hot tub, and a poolside bar serving refreshing drinks and delicious meals. • Social activities for every interest, from pickleball, tennis, and bocce to art clubs, gardening, and game nights. • Themed parties, live music, and dancing that make every evening unforgettable. When you’re ready to explore beyond the gates, you’re just nine miles from Marco Island’s pristine beaches and downtown Naples’ vibrant dining, shopping, and cultural scenes. From galleries to holiday snowfall in December, there’s always something to enjoy. This home is move-in ready, fully furnished down to the dishes. All that’s left is for you to pack your suitcase and embrace the dream vacation lifestyle—every single day.

7683 Winding Cypress Drive, Naples

Courtesy of John R Wood Properties

2 Beds ⋅ 2 Baths ⋅ 224074690 MLS

$785,000

Welcome to Winding Cypress, where modern elegance meets comfort in this stunning Abbeyville model, Pulte home built in 2021. A beautiful lake view frames the backyard of this meticulously maintained, well designed residence featuring two spacious bedrooms plus a versatile den, perfect for a home office or additional guest space. Step inside to discover a thoughtfully laid out floor plan, highlighting an abundance of natural light, neutral colors, tile flooring and high-end finishes throughout. The heart of the home is the open-concept living area, seamlessly connecting the kitchen, dining, and 2 living spaces—ideal for entertaining family and friends. Enjoy the luxury of your gas heated salt water pool, perfect for soaking up the sun or hosting summer gatherings. The home is equipped with natural gas, ensuring efficient cooking and heating, while hurricane windows and doors provide peace of mind during storm season. The garage boasts abundant storage options and an epoxy floor, adding both durability and style, and there are countless upgrades including a widened driveway to accommodate 3 across parking, a screened entry, custom closet organizer system in main bedroom and chrome pullout shelving in all kitchen and bathroom cabinets that elevate its charm and functionality. In addition, Winding Cypress is a Luxury Community offering Resort style amenities such as a heated pool with zero entry and lap lanes, restaurant, tennis, pickleball, clubhouse, fitness center and so much more. Perfectly located only 8 miles to downtown Naples attractions and beaches and also convenient to shopping, dining and Marco Island. Don't miss the opportunity to make this exquisite property your own, where every detail has been carefully curated for a sophisticated lifestyle in a serene community. Note: This home is a great opportunity with $25,000 in upgrades and listed below appraised value! *Appraisal report available upon request

6792 Bromeliad Drive, Naples

Courtesy of John R Wood Properties

3 Beds ⋅ 2 Baths ⋅ 224074239 MLS

$690,000

Welcome to this stunning 3-bedroom, 2-bathroom oasis, perfectly designed for both relaxation and entertaining. Step inside to find a beautifully appointed open floor plan featuring elegant crown molding, recessed lighting, and gleaming tile laid on the diagonal, creating a seamless flow throughout the home. The heart of the house is the gourmet kitchen, where you'll be inspired to cook and gather. It boasts sleek granite countertops, a stylish tile backsplash, stainless steel appliances, and a spacious island with extra storage and a convenient breakfast bar. Retreat to your private backyard paradise with a sparkling screened-in heated salt-water pool and spa, perfect for year-round enjoyment. The large laundry room was completely built out with cabinets and utility sink. Located in the beautiful gated community of Winding Cypress with world-class amenities. Featuring an on-site restaurant, the Shady Palm, a resort-style pool, tennis, pickleball & bocce courts, outdoor yoga deck, a dog park, fitness center, community garden and nature trails, internet café and an array of social events. Centrally located and just a short drive to Naples pristine beaches, shops and dining.

7256 Live Oak Drive, Naples

Courtesy of John R Wood Properties

3 Beds ⋅ 3 Baths ⋅ 224055933 MLS

$995,000

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 Drive, Naples

Courtesy of Royal Shell Real Estate, Inc.

2 Beds ⋅ 2 Baths ⋅ 224051672 MLS

$775,000

In the prestigious Naples community of Winding Cypress, this exceptional property stands out for its distinctive features, seamlessly blending nature and luxury with a resort lifestyle. Complemented by the rare convenience of direct natural gas, the award-winning Abbeyville floor plan boasts multiple builder upgrades. The unique custom pool and spa integration with bench seating offers a relaxing respite at the end of the day. Enjoy meticulous landscaping through your “picture window” lanai screen, effortlessly merging indoor and outdoor living spaces. A thoughtfully designed open concept optimizes natural light through an abundance of windows. Additional amenities include laundry area with utility sink, walk-in closet and cabinets. Built-in custom closets are throughout, including cabinetry and Murphy bed in your bonus flex room. Other amenities include diagonal tile flooring, crown molding and primary tray ceiling, wainscoting in the sunroom and a Lennox Fresh-Aire UV purifier. The epoxy-finished garage offers plenty of storage. For peace of mind, a natural gas-powered whole-house Generac generator ensures reliable power on demand. You’ll enjoy Winding Cypress’s luxurious amenity center, featuring a state-of-the-art fitness center, catering kitchen, community great room and activity room. Outdoor enthusiasts can take advantage of pickleball, tennis, bocce, resort-style waterfall pool, spa/cabana area, outdoor café with classically trained executive chef, fire pit and fireplace areas, dog park and nature boardwalk with picnic pavilion. Ideally just 20 minutes from the pristine shores of Marco Island and vibrant downtown Naples, this sought-after resort community offers an unparalleled lifestyle against a backdrop of natural beauty.

7507 Blackberry Drive, Naples

Courtesy of Premier Sotheby's Int'l Realty

4 Beds ⋅ 3 Baths ⋅ 224052264 MLS

$945,000

Like new, two years old four bedroom, three-bathroom residence in Winding Cypress. House has been totally custom remodeled. This furnished home showcases new furniture and TVs, finished with 9’ ceilings, 8’ doors, pristine tile floors. The gourmet kitchen features high end appliances with gas cooking, pullout drawer cabinets, designer backsplash, pantry, and a large center island. Each bedroom has an in-suite bathroom. Outside, you’ll find a WiFi-controlled heated pool and screened lanai with build- in barbeque grill. Extended driveway, two-car garage , epoxy floor, and overhead storage. Winding Cypress residents have access to a clubhouse with a social room, library, fitness center, resort-style pool and spa, outdoor bar and grill, tennis, pickleball, bocce, dog park, and a full social calendar. Just 15 minutes to downtown Naples and Marco Island. CDD paid in full.

6801 Greenbriar Court, Naples

Courtesy of Realty One Group MVP

4 Beds ⋅ 4 Baths ⋅ 224050943 MLS

$1,450,000

Welcome to an unparalleled blend of luxury and comfort in the prestigious Winding Cypress community. This exquisite 2-story furnished Pinnacle model home, boasting over 3,600 square feet of meticulously designed living space, offers an extraordinary lifestyle experience. As you enter this breathtaking residence, you'll be captivated by the open floor plan that seamlessly connects the living room and kitchen, perfect for both everyday living and entertaining. The kitchen is a chef’s dream, featuring a premium gas cooktop, quartz countertops, soft-close cabinets, and a generous island that serves as a focal point for gatherings. The zero corner impact glass sliders create the perfect Florida indoor/outdoor lifestyle by extending the living space into the private outdoor oasis. Here, you’ll find an incredible pool with a raised spa featuring an infinity edge, a sun shelf, and fountains. The premier outdoor kitchen makes alfresco dining a pleasure, set against the backdrop of a panoramic screen that offers unobstructed views of the serene estuary. Retreat to the opulent owner's suite, where luxury meets tranquility. The spa-like ensuite bathroom is designed to pamper, with dual vanities, a spacious shower, and a walk-in custom closet that provides ample storage. Two additional well-appointed bedrooms on the first floor offer comfort and privacy; one with its own en-suite bath, and the other with a bathroom conveniently located just outside the door. The second floor adds an impressive 1,168 square feet of living space, featuring an additional bedroom and full bathroom. This area is an entertainer’s dream, offering a flexible space that can be tailored to your specific needs—be it a guest suite, home office, or media room. Practicality is not forgotten in this luxurious setting. A whole-house on-demand natural gas generator ensures you’re never without power, adding peace of mind to the comfort and elegance of your home. The extended 3-car garage with epoxy floor has Wi-fi enabled garage door openers, a large utility sink, and plywood decking in the attic for extra storage. Winding Cypress is more than just a neighborhood; it’s a community designed to enhance your lifestyle. Enjoy the resort-style clubhouse with its expansive swimming pool, state-of-the-art fitness center, community garden, boardwalk trail, and poolside restaurant and bar. Relax by the fire pits or take advantage of the various recreational facilities. Pet owners will be delighted with the special park dedicated to dogs, ensuring every member of the family feels at home. Discover the epitome of modern living in this resort-style, amenity-rich community. Embrace a lifestyle of luxury and leisure in your new home at Winding Cypress, where every detail is designed with your utmost comfort and enjoyment in mind. Welcome home.

6903 Cocoplum Street, Naples

Courtesy of Realty One Group MVP

3 Beds ⋅ 3 Baths ⋅ 224048727 MLS

$1,175,000

Enjoy stunning peaceful views of the long lake and natural preserve from your spacious screened-in lanai with private pool and spa. This beautiful Pinnacle model home offers 3 bedrooms plus den/office, 3 full bathrooms and 3-car garage. Freshly painted inside and out and featuring luxury upgrades throughout, including Zero Corner sliders to lanai, wood-look tile in living areas and plush carpet in the bedrooms, plantation shutters, custom light fixtures, impact resistant windows & doors, natural gas (cooktop, pool, spa, water heater, full house generator) and more! The stunning chef’s kitchen includes upgraded stainless-steel appliances, center island with extra cabinet space, tile backsplash and crisp white cabinets. Enjoy your private backyard with brick pool deck, a large sitting area that has been pre plumbed for outdoor kitchen, heated pool and spa, and tranquil views. The large laundry room was completely built out with cabinets and utility sink. Located in the beautiful gated community of Winding Cypress with world-class amenities. Featuring an on-site restaurant, the Shady Palm, a resort-style pool, tennis, pickleball & bocce courts, a dog park, well-appointed fitness center, internet café and an array of social events. Centrally located and just a short drive to Naples pristine beaches, shops and dining.

7628 Winding Cypress Drive, Naples

Courtesy of John R Wood Properties

2 Beds ⋅ 2 Baths ⋅ 224041079 MLS

$720,000

JUST REDUCED AND PRICED TO SELL! Welcome to one of the most desirable neighborhoods in Naples. Winding Cypress boasts resort style living with pickleball, tennis, bocci, large gym, movement room, library, internet cafe, banquet room with kitchen, restaurant, and resort style pool with waterfall and lap lane. Currently the only Summerwood model for sale with peaceful panoramic water and preserve views. This impeccably kept two bedrooms with a den that could easily be a third bedroom, 2 bath home with large laundry room with tons of custom cabinetry. The oversized garage with four-foot extension makes one side of the garage 37' which can accommodate a 21' boat and trailer or third car, custom storage gives you plenty of room for all your toys. A real must-see home!

7247 Live Oak Drive, Naples

Courtesy of Coldwell Banker Realty

2 Beds ⋅ 2 Baths ⋅ 224041080 MLS

$690,000

Rare opportunity to own the crème de la crème villa in Winding Cypress. This pool home features 2 bedrooms, plus den, 2 bathrooms and a 2 car garage and is being offered turnkey furnished! The property boasts exceptional upgrades, including impact windows, a whole-house generator, crown molding, tile throughout, electric hurricane screens, upgraded appliances, closet systems throughout and so much more. The outdoor oasis features a gorgeous outdoor kitchen, remote control awning for additional shade, and arguably one of the best lake views in all of Winding Cypress! 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!

7793 Jacaranda Lane, Naples

Courtesy of MVP Realty Associates LLC

3 Beds ⋅ 3 Baths ⋅ 224039811 MLS

$1,400,000

Welcome to your dream home in Winding Cypress. This stunning residence epitomizes luxury living in paradise. As you step through the door into a haven of elegance and comfort. This meticulously crafted residence features an array of upgrades.

6909 Winding Cypress Drive, Naples

Courtesy of William Raveis Real Estate

3 Beds ⋅ 3 Baths ⋅ 224039468 MLS

$1,000,000

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 Drive, Naples

Courtesy of Premier Sotheby's Int'l Realty

4 Beds ⋅ 3 Baths ⋅ 224036182 MLS

$1,120,000

Gorgeously appointed turnkey furnished 2 story Summerwood for sale featuring 4 bedrooms, 3 bathrooms, den, loft, extended 2 car garage, pool & spa! This home has it all when it comes to upgrades, from the zero corner sliders, built in appliances, plantation shutters, in ceiling Sonos speakers, crown molding, storm smart shutters all around, 2 separate living rooms with the loft and so much more. The outdoor oasis features an extended covered lanai, outdoor kitchen, mounted tv, pool and spa overlooking a gorgeous preserve for the utmost privacy! 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!

7493 Winding Cypress Drive, Naples

Courtesy of MVP Realty Associates LLC

3 Beds ⋅ 3 Baths ⋅ 224032357 MLS

As you enter this 2 Story Martin Ray model located in beautiful Winding Cypress, the long water view is breathtaking not to mention the peaceful sunset views from the SSW exposure. This home has many Upgrades and Storage Galore!! Hurricane Impact Windows throughout the house, Master Bedroom on First Floor, Foam insulation upstairs, 4 Extra feet of length in the Tandem Garage allow for Plenty of space for a Golf cart or your Boat. Porcelain tile throughout the downstairs and Wood Floors upstairs. Crown molding, Built-in Kitchen appliances, 8ft door downstairs. Oversized Lot with 67' frontage makes it easy to add a Pool. Extended Paver Lanai, Paver walkway on the side of the home, Full house Generator, Split Unit A/C in the Garage, Additional insulation over the garage, Pull down stairs to attic, Widened Driveway, Ballistic Nylon Hurricane Shutters for the covered part of the Lanai, Plus additional Shade Flower Trees Planted. All this and more make this home Your piece of Paradise! Seller is a Florida licensed Real Estate Broker.

7454 Winding Cypress Drive, Naples

Courtesy of Schulz Realty LLC

3 Beds ⋅ 4 Baths ⋅ 224034128 MLS

$1,495,000

HURRICANCE READY!!!! NEW PRICE Improvement.This home is truly a showstopper , priced below market value and offering a "wow" factor that is hard to beat. The Stonewater model is the largest home built in Winding Cypress built in 2020 and still looks and feels like brand new. With approx.3000 sq. ft. of grand open space you'll be captivated from the moment you walk through the double front doors into the gracious foyer. The home features 13ft. coffered ceiling in the great room , formal dining area or custom for your use, office with glass French doors , 3 bdrms , 3 baths three car garage The lanai boasts POOL BATH WITH STORAGE ,a relaxing backdrop of the lake and peaceful preserve complete with an outdoor kitchen and hurricane shutter. Lanai furniture included in sale. A FEELING OF LIGHT AND SPACIOUSNESS IS WHAT YOU FEEL WHEN YOU WALK IN THE FRONT DOOR WITH ITS SOARING 13FT CEILING IN FOYER AND AND GREATROOM. This home is impeccable maintained and in like new condition. HURRICANE READY WITH ITS BRAND NEW whole house generator for peace of mind. Winding Cypress offers a wealth of amenities including a beautiful resort pool and restaurant. Don't miss the opportunity to see and appreciate the beauty of this exceptional home. Winding Cypress is conveniently located just 15 min to Marco Island , 75 and Downtown Naples

6962 Winding Cypress Drive, Naples

Courtesy of Royal Shell Real Estate, Inc.

4 Beds ⋅ 2 Baths ⋅ 224031113 MLS

$950,000

This meticulously maintained residence presents a rare opportunity to indulge in modern elegance and comfort. Upon entering through the leaded glass front door, you're greeted by an inviting atmosphere accentuated by the spectacular open floor plan living. The heart of the home lies in its chef-inspired kitchen, you will be delighted with abundant storage, granite counters, gas cooking, while a breakfast bar offers a casual dining option. Whether preparing a gourmet meal or enjoying a quick snack, this kitchen is sure to inspire culinary creativity. A pristine heated saltwater pool offers a refreshing swim from the sun-drenched afternoons. Host gatherings with ease in the full outdoor kitchen, complete with a grill, and ample seating space. Covered sitting areas provide shade and tranquility, ideal for unwinding with a good book or enjoying alfresco dining under the stars.

7592 Winding Cypress Drive, Naples

Courtesy of William Raveis Real Estate

3 Beds ⋅ 3 Baths ⋅ 224028845 MLS

$1,525,000

A staggering mix of natural beauty and fabulous Naples living. This jewel box home is situated on one of the most desirable lots in Winding Cypress. Look at the aerial view, simply breathtaking. Lot location had a $125,000 premium.Coveted Southern exposure Peaceful and full of nature. Well-designed, expansive floor plan offering generous size rooms, an outstanding white kitchen that is perfect for the serious cook or entertaining. You will love the large island, wine cooler, massive pantry, and natural gas. Split living area with unique closets and storage everywhere. Soaring ceilings. The west wing encompasses an impressive size Owner suite complete with massive walk-in closet. More than 2 cars? No worries, there is garage parking for 3. For the enjoyment of nature spend time in your southern exposure, spacious salt water pool/spa or patio with outdoor kitchen or relax on your lounger in the pool. A patio you can use year round unlike west facing patios that are so hot . Additional peace of mind is offered with impact windows and a generator. Please note this is not the base Pinnacle floor plan, this is top of the line and highly upgraded. Located off the main road on a cul de sac street. You must see this home. Winding Cypress is a wonderful community. Amenity rich with a low HOA. Amenity rich with low HOA Look what the community offers: Neighborhood Features Natural Gas Community ,800+ Acres of Natural Preserves, Heated Resort-Style Pool & Spa Poolside. sugar-sand beach and cabanas ,17,500 sq. ft. Clubhouse with Activity Room, Catering Kitchen & Library, State of the Art Fitness Center & Movement Studio. Outdoor Barefoot Bar and Grill, Natural Gas Fire Pit , Activity Director, 4 Bocce Ball Courts ,Tennis Courts, 4 Pickleball Courts, Dog Park, Community Garden, Boardwalk with Pavilion and Bird Wading. Overlook 80 Acres of Lakes.Home Lawn Maintenance included. Entry Gate with Guard House. Less than 3 miles from US-41 ,10 Minutes to I-75 ,15 Minutes to Fifth Avenue and Third Street Shopping & Dining, 20 Minutes to Naples Pier and magnificent area beaches. 20 Minutes to Marco Island prepared with care but subject to errors and ommissions Buyer to verify everything to their satisfaction

6932 Cocoplum Street, Naples

Courtesy of Real Estate of South Florida

4 Beds ⋅ 2 Baths ⋅ 224023546 MLS

$860,000

Winding Cypress is the ultimate Naples resort community, and this home serves as the ultimate poolside retreat. The long southwest water views seamlessly blend waterfront serenity, preserved nature, and privacy. Adorning the oversized covered lanai is a deluxe outdoor kitchen complete with every conceivable feature and top-grade finishes. This award-winning Summerwood floor plan boasts every builder upgrade, including a double oven gourmet kitchen, top-of-the-line cabinets, crown molding, tray ceilings, easy-glide retractable storm shutters, and more. The open concept layout is enhanced with strategically placed windows, optimizing natural light and facilitating flexible furniture arrangement, making this home an ideal canvas for any decor. Residents can indulge in the luxurious Winding Cypress clubhouse, featuring a state-of-the-art fitness center, catering kitchen, community room, and activity room. Outdoor amenities abound, encompassing pickleball courts, 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, bird-watching overlook, and a nature boardwalk with a picnic pavilion. Ideally situated near the pristine shores of Marco Island and the vibrant downtown Naples, this resort community offers an unparalleled lifestyle.

7420 Winding Cypress Drive, Naples

Courtesy of Premier Sotheby's Int'l Realty

2 Beds ⋅ 2 Baths ⋅ 224027020 MLS

$775,000

Beautiful selected finishes and colors. A peaceful beach sand pallet will take away the stress and bring you to your happy place. Casual comfort. 3 bedrooms presently featuring one designed as a den open to living area. Custom upgraded Kitchen cabinets. Stainless appliance with a GAS range. Nice size pantry. Generous laundry room. The Living dining great room is perfect for entertaining and overlook your own private backyard, Outdoor Kitchen on generous screen patio. Oversized garage allows for 3 vehicles. This home is located on one of the nicest streets in the community. Lovely preserve location allows for ultimate privacy. The community center rivals a 5-star resort. Pickle ball, tennis, state of the art fitness, banquet room/kitchen. Pool with cabanas and restaurant. Dog play area. Garden area. Nature trail. 24 hours gated. Look at the low fees. This is a wonderful opportunity. prepared with care but subject to errors and ommissions Buyer to verify everything to thier satisfaction

7465 Winding Cypress Drive, Naples

Courtesy of Real Estate of South Florida

3 Beds ⋅ 2 Baths ⋅ 224024540 MLS

$840,000

The luxury, nature and privacy is waiting for you on our Paradise Coast! Every upgrade has been selected for this immaculate home. To start, it has an upgraded lot, 8ft doors, crown molding, 6" base boards, trey ceiling in family room, upgraded waterproof laminate flooring in main living area, 22×22 porcelain tile in bathrooms and laundry room, 42" upper shaker soft closing cabinets, Kitchen Aid appliances, marble splash-back, owned solar electric system, 50 Amp plug in garage for electric vehicle charger, extended patio with forest view. Hurricane impact windows and sliders extended driveway capable of parking four cars, modern light fixtures and ceiling fans, tankless water heater, and the list goes on. Winding Cypress is a community like no other. You have seen the rest, now come see the best.

6828 Winding Cypress Drive, Naples

Courtesy of John R Wood Properties

3 Beds ⋅ 2 Baths ⋅ 224023172 MLS

$640,000

This beautiful Winding Cypress Villa home offers 1,554 sq. ft. of comfort has 3 bedrooms, 2 full bathrooms, Screened in lanai, salt water pool and spa and a 2-car garage also has lots of upgrades. The list is attached in the Supplements section. Located just minutes to Marco Island and downtown Naples, the community features a clubhouse with a resort style pool, spa, state of the art fitness center, very nice restaurant, tennis, bocce and Pickle Ball of course. Shopping and restaurants are nearby. The 800+ acre preserve with a boardwalk adds to the outdoor appeal. Ideal for those seeking a stylish home in a prime location. Upgrades include: Hurricane windows and doors through out including Lanai sliders, automated Hurricane shutter's on lanai,A.C Unit in garage, Framed mirror's in bathrooms,new pool heater in 2/24, plantation shutter's thru out,full storm door with screen on front door,keyless entry on front door,UV lights in HVAC.

7175 Live Oak Drive, Naples

Courtesy of RealtyQuest, Inc

2 Beds ⋅ 2 Baths ⋅ 224025546 MLS

$615,000

BIG PRICE REDUCTION! THIS IS ONE OF THE LOWEST PRICED VILLA POOL HOME! Discover this stunning 3-bedroom, 2-bathroom villa with a 2-car garage and a luxurious gas heated pool that is ideally situated on a premium pie-shaped lot adjacent to nature preserve and near to the vibrant Winding Cypress Amenity Center is the perfect place to make your own paradise. The flex room offers endless possibilities as a third bedroom or as a home office/den. The Serenity Model offers the perfect blend of charm and sophistication, whether you seek a year-round haven or a seasonal escape to enjoy Florida's renowned lifestyle. Indulge in effortless entertaining as the seamless open floor plan leads you to a covered lanai and expansive brick paver pool deck that gazes out onto a serene nature preserve. Witness breathtaking sunsets that paint the sky in hues of warmth while serenaded by the harmonious symphony of nature within your private screened enclosure in the prestigious Winding Cypress community. This home has features including stainless-steel appliances, elegant granite countertops, a beautifully tiled backsplash in the kitchen, and 20" ceramic tile flooring throughout the main living spaces. Noteworthy accents such as plantation shutters, rich wood flooring in the den, accordion hurricane shutters, an electric rolldown hurricane shutter at the lanai, and a host of other upscale finishes. Nestled within a secure, amenity-rich enclave, residents enjoy access to a lavish Community Center, overseen by a full-time activities’ director, offering an array of recreational facilities from card/game rooms and a library to a poolside bar and restaurant. Stay active with a state-of-the-art gym, outdoor Yoga and movement studios, group exercise classes, a resort-style pool with a dedicated lap lane, inviting fire pits, dog parks for both large and small dogs, illuminated tennis courts, pickleball and bocce courts, and sprawling lakes and nature preserves spanning nearly 800 acres, providing boundless walking and riding trails for outdoor enthusiasts. Perfectly positioned in proximity to upscale shopping, dining venues, the sandy beaches of Naples and nearby Marco Island, the ambiance of downtown Naples along 5th Avenue & 3rd Street, as well as convenient access to medical facilities, educational institutions, places of worship, I-75, RSW International Airport, and the breathtaking wonders of the Florida Everglades.

7113 Live Oak Drive, Naples

Courtesy of Realty One Group MVP

3 Beds ⋅ 3 Baths ⋅ 224025231 MLS

$1,565,000

An amazing opportunity to purchase a Pinnacle estate home in Winding Cypress! This home features 3 bedrooms, den, 3 bathrooms, pool & spa with a 3 car garage! No expense has been spared in this meticulously maintained home with tons of upgrades including built in appliances, hard flooring throughout, zero corner slider, crown molding, trey ceilings, electric hurricane shutters on lanai, natural gas, and so much more! The outdoor oasis features a large pool and spa with water features, huge backyard, built-in outdoor kitchen and a gorgeous lake view. 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!

6880 Cocoplum Street, Naples

Courtesy of MVP Realty Associates LLC

3 Beds ⋅ 3 Baths ⋅ 224023526 MLS

$1,000,000

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

Courtesy of Premier Sotheby's Int'l Realty

3 Beds ⋅ 3 Baths ⋅ 224017405 MLS

Furnished, 1-1/2 story, 2019 pool home at Winding Cypress blends luxurious amenities with top-tier safety features. Nestled on a preserve and corner lot, it offers extra privacy at the pool and a serene environment. The main floor presents a versatile layout with (1) the primary suite with a lavish bath and large walk-in closet, (2) a second bedroom and full guest bath, and (3) a den with double doors, which may be converted to a guest room. The bright, modern kitchen seamlessly connects to the dining and living areas, perfect for entertaining. Upstairs, a spacious loft, 3rd bedroom and additional full bath ensure ample living space. Modern conveniences like central vac, plantation shutters and keyless entry enhance comfort and security. Outside, the 1,000+ square foot lanai, heated pool and outdoor kitchen (with natural gas grill) allow for year-round enjoyment. With a whole home generator & impact windows/sliders, it guarantees peace of mind. Set in a popular and active resort-style community, residents gain access to various amenities such as a resort-style pool, poolside restaurant, fitness center, bocce, tennis & pickleball courts.

7673 Jacaranda Lane, Naples

Courtesy of Keller Williams Marco Realty

2 Beds ⋅ 2 Baths ⋅ 224016819 MLS

$675,000

This stunning lake view villa pool home with 2 car garage in the low fee community of Winding Cypress offers a luxurious lifestyle with its serene lake views and exceptional amenities. Home features include: Premium Wide Lake View: Step out onto your patio and soak in the breathtaking vistas of the tranquil lake. Whether it’s morning coffee or evening sunsets, this view will captivate you. Tile on the Diagonal: The elegant diagonal tile flooring flows seamlessly throughout the home, adding a touch of sophistication. Recessed and Cabinet Lighting: Illuminate your living spaces with style. Whether you’re hosting a dinner party or enjoying a quiet evening, the lighting sets the mood just right. Heated Pool: Take a refreshing dip in the heated pool year-round. Imagine relaxing by the water, surrounded by lush greenery and the soothing sounds of nature. Trey Ceiling: The main living area features a trey ceiling, adding architectural interest and a sense of spaciousness. White Cabinetry Throughout: The timeless white cabinetry complements any decor and keeps the home bright and airy. Gorgeous Sunsets: As the day winds down, enjoy spectacular sunsets from your own backyard oasis. New Quartz Countertops: The kitchen, master bath, and guest bath have been upgraded with beautiful quartz countertops. The sinks and faucets are also new. New Tile Plank: The master bedroom, master bath, and guest bedroom now feature stylish tile plank flooring. LED Lanai Lights: Illuminate your pool area for evening gatherings and relaxation. Custom Garage Shelving: Organize your garage space efficiently. New Dishwasher and Clothes Washer: Modern appliances for your convenience. New Pool Cage Screens: Fresh screens enhance the pool area. Motorized Sunscreen for Lanai: Control sunlight and create a comfortable outdoor space. Whole House Water Filter System: Enjoy pure filtered throughout your home. Winding cypress features include: Shady Palm Restaurant: Onsite dining for residents. Treat yourself to delicious meals without leaving the community. Pickleball, Bocce, Tennis: Stay active and social. Engage in friendly matches with neighbors and friends. State-of-the-Art Fitness Center: Achieve your fitness goals. Whether it’s cardio, strength training, or yoga, the fitness center has you covered. Resort-Style Pool: Lounge by the pool, soak up the sun, and enjoy the Florida weather. Community Garden: Green thumbs welcome! If you love gardening, this is the place to nurture your plants. Dog Park: Fido-approved fun! Let your furry friend run and play in the designated dog park. Location: Centrally situated between Marco Island, 5th Ave, and I75, this home offers convenience and easy access to all that Naples, Florida, has to offer. Don’t miss out on this exceptional opportunity! Contact your agent today to schedule a viewing.

7627 Jacaranda Lane, Naples

Courtesy of Premiere Plus Realty Company

2 Beds ⋅ 2 Baths ⋅ 224015477 MLS

$605,000

Beautiful, like-new furnished single family attached villa with long lake view. Built in 2019, this move-in ready Serenity floor plan includes two bedrooms plus den, two bathrooms, upgraded tile floors, extended lanai with Storm Smart hurricane screens, hurricane impact windows/doors throughout. Southern exposure. Natural gas community. Quartz countertops, stainless appliances, plantation shutters. A highly sought after community, Winding Cypress has over 800 acres of lakes and preserves, resort-style pool and spa, restaurant, tennis, bocce & pickleball, fire pit, state-of-the-art fitness center, nature boardwalk, small & large dog parks. Restaurants and shopping nearby. Enjoy resort-style living at its best in this lovely home.

7790 Jacaranda Lane, Naples

Courtesy of John R Wood Properties

3 Beds ⋅ 2 Baths ⋅ 224015195 MLS

$485,000

Nestled End Unit, Next to The Preserve! This Villa is a true masterpiece of design and comfort. Enjoy your new Naples lifestyle, total relaxation and resort living or use it as a rental income property investment. A gorgeous end unit featuring a tasteful interior that's highlighted with palm trees, tropical flowers & foliage to view from a private lanai with room to add a pool! This highly desirable unit has a weather protected automated screened lanai with automated blinds for privacy! Amazing open concept living, granite counter tops, Gas Stove for cooks, crown molding throughout. Located close to the Amenity Center complete with Pickle Ball, Bocce Ball, Resort Style Pool, Bar & Restaurant. Order drinks at the pool! New Home Generator December 2023. Fabulous amenities include the Clubhouse, Restaurant, Community Pool, Close to 2 Dog Parks, Complete Gym!

7202 Live Oak Drive, Naples

Courtesy of John R Wood Properties

2 Beds ⋅ 3 Baths ⋅ 224009153 MLS

$1,050,000

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 Court, Naples

Courtesy of BHHS Florida Realty

3 Beds ⋅ 2 Baths ⋅ 224008485 MLS

$1,150,000

Ideally located equidistant between Downtown Naples and Marco Island, Winding Cypress coexists with the natural flora and fauna of Southwest Florida. Enjoy bird songs along with deer and wild turkey sightings while walking or biking through the community. Get to know your neighbors while basking in the sun at the resort style community pool complete with gorgeous waterfall and cabana beach area or grabbing a bite to eat at the Shady Palm Cafe. There's never a dull moment with non-stop neighborhood activities and groups. And if tennis, pickleball, or bocce ball are your sport, we have you covered. Call this 3 bedroom plus a den, 2 bath, 2 car garage Summerwood model residence your home and you can enjoy all Winding Cypress has to offer. On quiet days relax on the ample lakefront lanai and swim or soak in the gas heated pool and spa. Delight in trying out new recipes in the well appointed kitchen with granite countertops, stainless steel appliances, and gas stove. With the ADT home security system and impact glass doors and windows this house will be your sanctuary.

7615 Winding Cypress Drive, Naples

Courtesy of Coldwell Banker Realty

2 Beds ⋅ 2 Baths ⋅ 224008394 MLS

$600,000

Villa w/ PEACEFUL view! Attached villa Serenity floor plan that lives like a single family home w/ luxury features throughout- tray ceilings, 18" tile flooring, quartz countertops, custom tile backsplash in kitchen, convection double oven, designer light fixtures, high-end cabinetry, crown molding, French door entry to den, frameless glass enclosure in master shower, custom built heated pool, & a built-in Generac generator system & transferrable home warranty. The outdoor living space is the GEM of the home- massive pool deck, solar & gas heated pool, large covered area w/ enough room for dining set & lounging area, & having a serene lake view. Meticulously maintained & updated w/ new accordion hurricane shutters, whole home water filtration system for optimum water quality, & freshly painted exterior. The roof was just power washed this past summer. This natural gas community has over 800 acres of lakes & preserve, resort- style pool, fire pit, community rm, restaurant, tennis, bocce ball, pickleball, cabanas, yoga deck, fitness facility, locker rooms, full time activities director, catering room, catering kitchen, activity room, nature board walk, garden, small & large dog parks.

7574 Jacaranda Lane, Naples

Courtesy of Keller Williams Realty Naples

2 Beds ⋅ 2 Baths ⋅ 224001602 MLS

$610,000

Fully furnished and ready to move in. Built in 2019, this light, bright, fresh villa is ideal for seasonal or permanent Florida living. Upgraded cabinets, countertops and flooring. Bright, light cabinets, paint and flooring for more contemporary design. Lush, tropical landscaping with a private and peaceful backyard just off the screened lanai. Split bedroom plan for privacy when you have family visiting. Large walk-in shower in primary bath. Great clubhouse with restaurant and community pool for gracious in-community living. Close to Marco Island and a short drive to Naples beaches provides the best of all worlds, private, quiet living and quick access to all the fun, sun and amenities Southwest Florida is known for.

7694 Jacaranda Lane, Naples

Courtesy of Premier Sotheby's Int'l Realty

3 Beds ⋅ 2 Baths ⋅ 224004192 MLS

$650,000

Best-Valued Single-Family Home with Quality Finishes and Resort-Style Amenities in Winding Cypress! This beautifully crafted 3-bedroom, 2-bathroom home, complete with a private office, is the best-valued single-family residence in the desirable Winding Cypress community. Thoughtfully designed with quality finishes, this home features tile flooring throughout, plantation shutters, crown molding, high-end granite countertops and stainless-steel appliances with huge island/breakfast bar in a gourmet kitchen, equipped with natural gas cooking. The separate dining area offers an inviting space for meals and entertaining. Outside, enjoy the private, screened-in lanai surrounded by lush tropical gardens and a raised herb garden. This home is equipped with full hurricane protection on all windows and doors, including Storm Smart hurricane screens on the lanai, ensuring peace of mind in stormy weather. The Sellers have shared that their home has never incurred damage from any of the recent storms. Pre-inspected and move-in ready, with low HOA fees, this home is a true value. Winding Cypress is an amenity-rich, pet-friendly community, featuring a resort-style pool and spa, outdoor bar and grill, tennis, pickleball, bocce courts, and two gated, off-leash dog parks. With a vibrant social calendar, there are endless ways to connect and enjoy the neighborhood. Conveniently located near downtown Naples, with its beautiful beaches, dining, and entertainment, as well as the scenic Marco Island coastline, this home blends luxury, security, and community lifestyle. Don’t miss your chance to make this tropical retreat your own!

7267 Live Oak Drive, Naples

Courtesy of John R Wood Properties

2 Beds ⋅ 2 Baths ⋅ 224002265 MLS

$730,000

Enjoy the relaxing and private views of the lake and preserve with no houses across from you. Some of the many upgrades in this lightly used, two-bedroom plus den, two-bath home are tile throughout, a sunroom addition, all California Closets, volume ceilings, huge walk-in shower, upgraded cabinets and an extended garage. The club at Winding Cypress is a must-see and offers a full-time social activity director, a beautiful resort-style pool, sunset sand cabanas, outdoor bar and grill, pickleball, bocce, clay tennis courts, state-of-the-art gym, fire pit, dog parks, community garden and nature trails set among an 800-acre natural preserve.

7601 Blackberry Drive, Naples

Courtesy of Premier Sotheby's Int'l Realty

4 Beds ⋅ 2 Baths ⋅ 223092117 MLS

$845,000

In the ultimate Naples resort community, this exceptional property in Winding Cypress stands out for its distinctive features, offering an ideal blend of waterfront tranquility, preserved nature and the allure of privacy. This award-winning Summerwood floor plan boasts every builder option and upgrade, on a completely private corner lot on a tranquil cul-de-sac. Highlights include top-level finishes, impact windows throughout, and a perfectly designed open great room concept with strategically placed windows for optimal natural light and furniture layout. 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, 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 the vibrant downtown Naples, this amazing resort location provides the ideal backdrop for an unparalleled lifestyle.

7346 Mockingbird Court, Naples

Courtesy of Premier Sotheby's Int'l Realty

3 Beds ⋅ 3 Baths ⋅ 224000268 MLS

$1,145,000

Meticulously maintained three-bedroom plus den, three-bathroom residence in Winding Cypress with breathtaking lake views. You’ll be greeted by an open layout bathed in natural light from a corner pocketing impact glass slider. This furnished home showcases new furniture and TVs, finished with 9’ ceilings, 8’ doors, pristine tile floors, closet built-ins, and plantation shutters throughout. The gourmet kitchen features KitchenAid appliances with gas cooking, pullout drawer cabinets, designer backsplash, pantry, and a large center island. Each bedroom boasts an en-suite bathroom. Outside, you’ll find a WiFi-controlled heated pool and spa under a screened lanai with a stunning backdrop of the lake. Additional features include Vitex smart home, StormSmart electric shutters, 22kW whole home generator, water filtration system, extended driveway, and a two-car garage with AC, epoxy floor, and overhead storage. Winding Cypress residents have access to a clubhouse with a social room, library, fitness center, resort-style pool and spa, outdoor bar and grill, tennis, pickleball, bocce, dog park, and a full social calendar. Just 15 minutes to downtown Naples and Marco Island. CDD paid in full.

6818 Greenbriar Court, Naples

Courtesy of Premier Sotheby's Int'l Realty

3 Beds ⋅ 3 Baths ⋅ 224000329 MLS

$875,000

This rarely available two-story “Abbeyville” model with a Premium Waterfront Location has a preferred Southern Exposure and has been meticulously maintained. Located in the highly sought-after, gated, amenity rich community of Winding Cypress. There is a ground floor Primary Suite with spacious walk-in closet, a guest bedroom and bath, and a den/office. Plus, the home also boasts a hard-to-find large loft area with a third bedroom and full bath upstairs. This home features a heated saltwater pool and spa, (New heater and filter 2023) stainless steel appliances, gas range and tankless water heater (added 2021). Recent improvements include new washer dryer 2022, and all new smoke and carbon monoxide detectors. Residents enjoy access to an exceptional Amenity Center complete with a state-of-the-art fitness center, resort pool and spa, restaurant, bocce ball, tennis and pickleball courts, and a full-time activity director. This home is conveniently located at an ideal counterpoint between the beautiful Gulf beaches and fine dining options of both Naples and Marco Island.

7491 Blackberry Drive, Naples

Courtesy of Alfred Robbins Realty Group

3 Beds ⋅ 3 Baths ⋅ 223094938 MLS

$1,200,000

Located in the highly sought after and amenity rich community of Winding Cypress, this 3 Bedroom + Den, 3 Bath Summerwood boasts a hard to find spacious loft that adds an additional 900+ sq ft of living area. The meticulously maintained home has numerous upgrades that include an extended finished garage with utility sink and space for a golf cart, upgraded flooring, cabinetry, countertops and appliances, extended kitchen island, crown molding, built in speaker system, outdoor kitchen and much, much more. The beautifully appointed lanai is a haven with a covered living area next to the heated pool and spa with gorgeous views of the preserve. Residents enjoy access to an exceptional Amenity Center complete with a state-of-the-art fitness center, resort style pool and spa, restaurant, bocce ball, tennis and pickleball courts, and full time activity director. It is a pet friendly neighborhood with 2 off-leash dog runs. This home is conveniently located between Marco Island and downtown Naples and is in the perfect location to enjoy all that Southwest Florida has to offer. Why wait for a new home when you can make this yours now!

7565 Blackberry Drive, Naples

Courtesy of Re/Max Affinity Plus

2 Beds ⋅ 2 Baths ⋅ 223094200 MLS

$749,900

Opulence is the word for this villa nestled in the prestigious Winding Cypress community. The modern foyer sets a sophisticated tone for the elegance that permeates the 1,574 sq ft floor plan. French Doors gracefully welcome you to the den, a refined workspace unfold with a quartz countertop desk. The chef's kitchen is a masterpiece boasting marble countertops, upgraded white cabinets that flows with the center island. Step into your private oasis, the gas heated pool & spa beckon with a tranquil waterfall & the outdoor kitchen, adorned with a gas grill, sink, refrigerator & stacked stone accents. Culinary heaven.Revel in long views of your lake. The master bath offers dual vanities, glass shower & voluminous closet. Plantation shutters ensure both privacy & sophistication. With hurricane windows, crown molding, & upgraded 8' doors throughout, this home epitomizes refined living in a community that boasts a gated enclave, the Shady Palm Cafe, two community pools, a spa & beach area with private day beds. A gym, activities center, library, are all yours to enjoy. Take advantage of bocce ball, pickleball, tennis courts, scenic walking trails, dog park, & a private community garden.

7807 Jacaranda Lane, Naples

Courtesy of Gramercy Vale Real Estate

2 Beds ⋅ 2 Baths ⋅ 223089295 MLS

$740,000

Must See this Beautiful two bedrooms, two bathroom, plus den Cresida Model. Features include pro series cabinets in the 2 car garage, french doors, kitchen with quartz counter tops, breakfast island, large pantry, stainless steel appliances, tile back splash , accent wall with built in bar and wine cooler , tile throughout, led lights, built in outdoor kitchen for enteraining, full ensuite with dual sinks, walk -in shower, custom walk- in closet. Winding Cypress is a natural gas community with over 800 acres of lakes and preserve. Perfect location between Marco Island and Downtown Naples, close to RSW. ammenities include resort- syle pool, fire pit, community room, restaurant, tennis, bocce ball, pickleball,cabanas,yoga deck, fitness facility, locker rooms, full time activiities director, catering room, catering kitchen, activity room. There is also a nature board walk, small and large dog parks, and a community garden.

7682 Jacaranda Lane, Naples

Courtesy of Schulz Realty LLC