The community of Winding Cypress is situated in Naples. Superbly situated for access to all of the Naples area amenities and comforts has to offer.

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Active
226014585
  • 3Bedrooms
  • 3196Sq Ft
  • 2022Year Built
$1,050,000

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…

Active
2026015957
  • 3Bedrooms
  • 2078Sq Ft
  • 2016Year Built
$799,900

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…

Active
226013964
  • 3Bedrooms
  • 2186Sq Ft
  • 2018Year Built
$1,099,000

This beautifully designed and impeccably maintained home offers the perfect blend of elegance and comfortable Florida living in Naples. 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. The gourmet…

Pending
225016804
  • 3Bedrooms
  • 2923Sq Ft
  • 2019Year Built
$0

3 bedroom and 3 bath home in Winding Cypress

Active
226012362
  • 4Bedrooms
  • 3965Sq Ft
  • 2023Year Built
$1,750,000

Rare to find, this light-filled 2-story Stonewater model offering 4 bedrooms, den and 4.5 baths on a pie shaped waterfront lot in the highly desirable gated community of Winding Cypress in Naples. This home has been upgraded to include all available options totaling over $650,000 including 2nd floor loft, hurricane windows and doors, upgraded finishes…

Closed
226005810
  • 2Bedrooms
  • 1554Sq Ft
  • 2018Year Built
$0

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…

Closed
225083676
  • 3Bedrooms
  • 2230Sq Ft
  • 2015Year Built
$0

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 …

Active
226008865
  • 4Bedrooms
  • 3656Sq Ft
  • 2016Year Built
$1,645,000

A must-see opportunity—spacious, stunning views, showpiece home and resort style Florida living. A rare opportunity to own a 4 bedroom estate home with breathtaking views in the sought-after community of Winding Cypress, offering top-tier amenities at surprisingly low HOA fees. This award-winning Pinnacle model boasts numerous upgrades and interiors like the builder’s model home and…

Active
225068781
  • 3Bedrooms
  • 1594Sq Ft
  • 2018Year Built
$698,500

Discover refined living with this beautifully appointed villa in Winding Cypress, where luxury and comfort meet in perfect balance. Designed for those who appreciate both elegance and ease, this home offers an unparalleled lifestyle inside and out. Arriving fully furnished and enhanced by the sellers’ two-seater Club Car golf cart, this property delivers a true move-in…

Closed
225038123
  • 3Bedrooms
  • 2496Sq Ft
  • 2017Year Built
$0

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…

Pending
226009304
  • 2Bedrooms
  • 2036Sq Ft
  • 2018Year Built
$0

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…

Closed
226000187
  • 3Bedrooms
  • 2003Sq Ft
  • 2021Year Built
$0

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…

Pending
225065830
  • 3Bedrooms
  • 2084Sq Ft
  • 2022Year Built
$0

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,…

Active
226008768
  • 2Bedrooms
  • 1574Sq Ft
  • 2018Year Built
$575,000

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,…

Active
226007913
  • 3Bedrooms
  • 2188Sq Ft
  • 2016Year Built
$850,000

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,…

Active
226006913
  • 2Bedrooms
  • 1554Sq Ft
  • 2018Year Built
$585,000

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…

Active
226006762
  • 2Bedrooms
  • 1554Sq Ft
  • 2016Year Built
$599,000

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…

Closed
225075399
  • 3Bedrooms
  • 2094Sq Ft
  • 2022Year Built
$0

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…

Pending
225072028
  • 2Bedrooms
  • 1685Sq Ft
  • 2016Year Built
$0

PRICE IMPROVEMENT - 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…

Active
225065477
  • 3Bedrooms
  • 2128Sq Ft
  • 2023Year Built
$825,000

Discover your dream home in the prestigious Winding Cypress community! This newly constructed, pet-friendly residence boasts 3 spacious bedrooms plus a versatile den, perfect for guests or a home office. Designed for seamless entertaining, the open-concept floor plan flows effortlessly, with zero-corner sliders merging the indoor living area with a stylish outdoor kitchen and bar—ideal…

Active
226005365
  • 3Bedrooms
  • 2100Sq Ft
  • 2021Year Built
$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 2 baths with full showers ,…

Closed
225083620
  • 3Bedrooms
  • 2923Sq Ft
  • 2018Year Built
$0

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…

Closed
225021309
  • 2Bedrooms
  • 1574Sq Ft
  • 2019Year Built
$0

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…

Closed
225069223
  • 2Bedrooms
  • 1544Sq Ft
  • 2017Year Built
$0

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…

Pending
226004334
  • 3Bedrooms
  • 2158Sq Ft
  • 2021Year Built
$0

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…

Pending
226002887
  • 2Bedrooms
  • 1659Sq Ft
  • 2015Year Built
$0

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…

Active
224079403
  • 2Bedrooms
  • 1574Sq Ft
  • 2017Year Built
$499,900

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…

Closed
225071664
  • 3Bedrooms
  • 2084Sq Ft
  • 2021Year Built
$0

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…

Active
226000491
  • 3Bedrooms
  • 2186Sq Ft
  • 2019Year Built
$900,000

Welcome to this beautifully designed residence located within one of Naples’ most desirable gated communities. The open-concept floor plan is enhanced by volume and tray ceilings, crown molding, plantation shutters throughout, and an extended driveway, adding both elegance and curb appeal. The spacious kitchen features granite countertops, a gas cooktop, wall oven, and ample cabinetry—making…

Active
225084091
  • 4Bedrooms
  • 3350Sq Ft
  • 2015Year Built
$1,499,900

Welcome to this stunning Tangerly Oak model home, thoughtfully designed with space, style, and Florida living in mind. This expansive 4-bedroom residence with a generous loft offers a flexible floor plan ideal for both everyday living and hosting guests, all enhanced by beautiful designer upgrades throughout. Step outside to an exceptional outdoor living space featuring a…

Active
225067825
  • 3Bedrooms
  • 2166Sq Ft
  • 2017Year Built
$1,098,000

Rare opportunity in Winding Cypress—fully upgraded, move-in ready home 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…

Closed
225078259
  • 3Bedrooms
  • 2198Sq Ft
  • 2016Year Built
$0

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…

Closed
224103914
  • 2Bedrooms
  • 1805Sq Ft
  • 2016Year Built
$0

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…

Active
225081501
  • 4Bedrooms
  • 3036Sq Ft
  • 2022Year Built
$1,050,000

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…

Closed
225060759
  • 3Bedrooms
  • 2515Sq Ft
  • 2021Year Built
$0

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…

Closed
225035628
  • 2Bedrooms
  • 1554Sq Ft
  • 2017Year Built
$0

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…

Closed
225068633
  • 3Bedrooms
  • 2230Sq Ft
  • 2015Year Built
$0

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.…

Closed
225057502
  • 2Bedrooms
  • 1654Sq Ft
  • 2021Year Built
$0

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…

Closed
225067249
  • 3Bedrooms
  • 2512Sq Ft
  • 2015Year Built
$0

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…

Closed
225064762
  • 3Bedrooms
  • 2084Sq Ft
  • 2021Year Built
$0

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…

Closed
225046502
  • 3Bedrooms
  • 2496Sq Ft
  • 2017Year Built
$0

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…

Closed
225059100
  • 2Bedrooms
  • 1554Sq Ft
  • 2018Year Built
$0

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…

Closed
225031142
  • 2Bedrooms
  • 1685Sq Ft
  • 2015Year Built
$0

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…

Closed
224088928
  • 3Bedrooms
  • 2496Sq Ft
  • 2019Year Built
$0

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…

Closed
225050266
  • 3Bedrooms
  • 2198Sq Ft
  • 2016Year Built
$0

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…

Closed
224091808
  • 3Bedrooms
  • 2107Sq Ft
  • 2021Year Built
$0

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,…

Closed
225034820
  • 3Bedrooms
  • 2188Sq Ft
  • 2017Year Built
$0

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…

Closed
224083667
  • 3Bedrooms
  • 2532Sq Ft
  • 2018Year Built
$0

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,…

Closed
225053774
  • 2Bedrooms
  • 1901Sq Ft
  • 2021Year Built
$0

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…

Closed
225001834
  • 3Bedrooms
  • 2496Sq Ft
  • 2020Year Built
$0

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,…

Closed
225033541
  • 2Bedrooms
  • 1579Sq Ft
  • 2018Year Built
$0

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…

Closed
225022390
  • 3Bedrooms
  • 2124Sq Ft
  • 2022Year Built
$0

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…

Closed
225034039
  • 3Bedrooms
  • 2496Sq Ft
  • 2018Year Built
$0

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…

Closed
225011172
  • 2Bedrooms
  • 1574Sq Ft
  • 2018Year Built
$0

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…

Closed
224076682
  • 2Bedrooms
  • 1554Sq Ft
  • 2019Year Built
$0

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…

Closed
225025806
  • 2Bedrooms
  • 1554Sq Ft
  • 2019Year Built
$0

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…

Closed
225023660
  • 3Bedrooms
  • 2118Sq Ft
  • 2020Year Built
$0

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…

Closed
225023743
  • 2Bedrooms
  • 1921Sq Ft
  • 2021Year Built
$0

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,…

Closed
225021743
  • 2Bedrooms
  • 1554Sq Ft
  • 2016Year Built
$0

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…

Closed
225008365
  • 3Bedrooms
  • 2208Sq Ft
  • 2020Year Built
$0

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.…

Closed
224090027
  • 2Bedrooms
  • 2062Sq Ft
  • 2016Year Built
$0

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…

Closed
225001830
  • 2Bedrooms
  • 1554Sq Ft
  • 2015Year Built
$0

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…

Closed
224082513
  • 3Bedrooms
  • 2018Sq Ft
  • 2018Year Built
$0

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…

Closed
225018609
  • 3Bedrooms
  • 2107Sq Ft
  • 2018Year Built
$0

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…

Closed
224025546
  • 2Bedrooms
  • 1554Sq Ft
  • 2016Year Built
$0

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…

Closed
224089763
  • 2Bedrooms
  • 1804Sq Ft
  • 2021Year Built
$0

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…

Closed
224004192
  • 3Bedrooms
  • 2230Sq Ft
  • 2015Year Built
$0

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…

Closed
225001831
  • 3Bedrooms
  • 2867Sq Ft
  • 2016Year Built
$0

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…

Closed
224041079
  • 2Bedrooms
  • 1910Sq Ft
  • 2015Year Built
$0

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…

Closed
224083615
  • 3Bedrooms
  • 2519Sq Ft
  • 2021Year Built
$0

This popular DiVosta Pinnacle Model is situated in the amenity rich community of Winding Cypress. It is possible to purchase this beauty furnished or turnkey furnished as negotiated and agreed upon. This property is a one owner home that's loaded with builder and owner upgrades to include: custom tile plank flooring throughout, 12'+ coffered/tray ceilings…

Closed
224101522
  • 2Bedrooms
  • 1685Sq Ft
  • 2017Year Built
$0

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.…

Closed
224074690
  • 2Bedrooms
  • 1774Sq Ft
  • 2021Year Built
$0

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…

Closed
224055933
  • 3Bedrooms
  • 2496Sq Ft
  • 2016Year Built
$0

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…

Closed
224074239
  • 3Bedrooms
  • 1685Sq Ft
  • 2015Year Built
$0

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…

Closed
224023546
  • 4Bedrooms
  • 2198Sq Ft
  • 2017Year Built
$0

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…

Closed
224051672
  • 2Bedrooms
  • 1805Sq Ft
  • 2017Year Built
$0

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…

Closed
224034128
  • 3Bedrooms
  • 2952Sq Ft
  • 2020Year Built
$0

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…

Closed
224041080
  • 2Bedrooms
  • 1554Sq Ft
  • 2019Year Built
$0

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…

Closed
224052264
  • 4Bedrooms
  • 2152Sq Ft
  • 2022Year Built
$0

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…

Closed
224008394
  • 2Bedrooms
  • 1554Sq Ft
  • 2016Year Built
$0

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…

Closed
224050943
  • 4Bedrooms
  • 3656Sq Ft
  • 2021Year Built
$0

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…

Closed
224028845
  • 3Bedrooms
  • 2515Sq Ft
  • 2019Year Built
$0

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,…

Closed
224039811
  • 3Bedrooms
  • 2522Sq Ft
  • 2019Year Built
$0

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.

Closed
224015195
  • 3Bedrooms
  • 1554Sq Ft
  • 2015Year Built
$0

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 &…

Closed
224039468
  • 3Bedrooms
  • 2867Sq Ft
  • 2017Year Built
$0

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…

Closed
224048727
  • 3Bedrooms
  • 2496Sq Ft
  • 2018Year Built
$0

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…

Closed
224031113
  • 4Bedrooms
  • 2159Sq Ft
  • 2021Year Built
$0

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…

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