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Situated on a private .29 acre, end lot in the highly sought-after gated community of Winding Cypress, this home offers 3,696 square feet of refined Naples living space. Built in 2016, this two-story Pinnacle floor plan features 4 bedrooms, 4 full bathrooms, a versatile den and a spacious 3 car garage. The extended lanai with a premium long lake water view features a custom-built saltwater pool and spa combo plus a fully equipped built-in outdoor gas kitchen, a wonderful place to entertain family and friends. Step inside to discover wood-look tile flooring leading to a gourmet chef’s kitchen, stainless-steel appliances, natural gas cook top, a walk-in pantry and an expansive center island with seating for five or more. The main floor hosts a sizable primary suite with a generous custom walk-in closet and a luxurious primary bath. Upstairs, a massive loft area offers an expansive living and sitting area space accompanied by a private guest bedroom and a full bath, ensuring ideal privacy for visitors or multi-generational living. Winding Cypress residents enjoy an active social calendar and lifestyle including a resort -style pool, a poolside bar and grill, state-of-the-art fitness center, tennis, pickleball, bocce ball and miles of boardwalk trails traversing acres of natural preserves. Winding Cypress is located just minutes from downtown Naples restaurants, pristine beaches and world class golf.

4 Beds ⋅ 4 Baths ⋅ 226038449 MLS

Situated on a private .29 acre, end lot in the highly sought-after gated community of Winding Cypress, this home offers 3,696 square feet of refined Naples living space. Built in 2016, this two-story Pinnacle floor plan features 4 bedrooms, 4 full bathrooms, a versatile den and a spacious 3 car garage. The extended lanai with a premium long lake water view features a custom-built saltwater pool and spa combo plus a fully equipped built-in outdoor gas kitchen, a wonderful place to entertain family and friends. Step inside to discover wood-look tile flooring leading to a gourmet chef’s kitchen, stainless-steel appliances, natural gas cook top, a walk-in pantry and an expansive center island with seating for five or more. The main floor hosts a sizable primary suite with a generous custom walk-in closet and a luxurious primary bath. Upstairs, a massive loft area offers an expansive living and sitting area space accompanied by a private guest bedroom and a full bath, ensuring ideal privacy for visitors or multi-generational living. Winding Cypress residents enjoy an active social calendar and lifestyle including a resort -style pool, a poolside bar and grill, state-of-the-art fitness center, tennis, pickleball, bocce ball and miles of boardwalk trails traversing acres of natural preserves. Winding Cypress is located just minutes from downtown Naples restaurants, pristine beaches and world class golf.

7383 Mockingbird Court, Naples

$1,575,000

Exceptional southern exposure, breathtaking preserve and water views, and one of the most desirable homesites in Winding Cypress set the stage for this highly upgraded Pinnacle residence. Originally selected with a $125,000 lot premium, this exceptional property is tucked away on a quiet cul-de-sac street and offers a rare combination of privacy, natural beauty, and refined Naples living. Far beyond the standard Pinnacle floor plan, the home features soaring ceilings, expansive living spaces, abundant storage, and a sophisticated kitchen designed for entertaining with an oversized island, wine cooler, natural gas cooking, and impressive walk-in pantry. The private owner’s wing offers a spacious retreat with an oversized walk-in closet. A three-car, fully air-conditioned garage provides exceptional versatility, whether used for vehicles, additional storage, a workshop, or climate-controlled space for prized possessions. The outdoor living experience is equally impressive. Coveted southern exposure fills the lanai with beautiful natural light while providing comfortable year-round enjoyment. Relax in the saltwater pool and spa with sun shelf, entertain from the outdoor kitchen, or simply take in the peaceful preserve and water views. Impact-resistant windows and doors and a whole-home generator provide additional peace of mind. Winding Cypress offers more than 800 acres of natural preserves and an outstanding collection of resort-style amenities, including a 17,500-square-foot clubhouse, resort pool and spa, fitness center, Barefoot Bar & Grill, tennis, pickleball, bocce, dog park, community garden, boardwalk and more, all with lawn maintenance included and a staffed gated entrance. Ideally located near US-41 and I-75 with convenient access to Fifth Avenue South, Third Street South, Naples beaches, and Marco Island. This is elevated Winding Cypress living in a truly exceptional setting.

3 Beds ⋅ 3 Baths ⋅ 226033394 MLS

Exceptional southern exposure, breathtaking preserve and water views, and one of the most desirable homesites in Winding Cypress set the stage for this highly upgraded Pinnacle residence. Originally selected with a $125,000 lot premium, this exceptional property is tucked away on a quiet cul-de-sac street and offers a rare combination of privacy, natural beauty, and refined Naples living. Far beyond the standard Pinnacle floor plan, the home features soaring ceilings, expansive living spaces, abundant storage, and a sophisticated kitchen designed for entertaining with an oversized island, wine cooler, natural gas cooking, and impressive walk-in pantry. The private owner’s wing offers a spacious retreat with an oversized walk-in closet. A three-car, fully air-conditioned garage provides exceptional versatility, whether used for vehicles, additional storage, a workshop, or climate-controlled space for prized possessions. The outdoor living experience is equally impressive. Coveted southern exposure fills the lanai with beautiful natural light while providing comfortable year-round enjoyment. Relax in the saltwater pool and spa with sun shelf, entertain from the outdoor kitchen, or simply take in the peaceful preserve and water views. Impact-resistant windows and doors and a whole-home generator provide additional peace of mind. Winding Cypress offers more than 800 acres of natural preserves and an outstanding collection of resort-style amenities, including a 17,500-square-foot clubhouse, resort pool and spa, fitness center, Barefoot Bar & Grill, tennis, pickleball, bocce, dog park, community garden, boardwalk and more, all with lawn maintenance included and a staffed gated entrance. Ideally located near US-41 and I-75 with convenient access to Fifth Avenue South, Third Street South, Naples beaches, and Marco Island. This is elevated Winding Cypress living in a truly exceptional setting.

6932 Cocoplum Street, Naples

$945,000

Preserve views on a quiet cul-de-sac street define this two-story Mystique residence in Winding Cypress, where a saltwater pool with spillover spa, expansive outdoor living and flexible interior spaces create a home designed for relaxation and entertaining. With four bedrooms, a den, an upstairs flex room, three baths and a two-car garage, the floor plan offers exceptional versatility while maintaining an open, connected feel throughout the main living areas. A whole-house generator is on-site, providing added peace of mind during storm-related power outages. A brick paver driveway, tile roof and professional landscaping establish a polished arrival. Inside, wood-look tile flooring, recessed lighting and white plantation shutters carry a clean, cohesive aesthetic throughout the home. The living room is filled with natural light from five windows and anchored by a modern ceiling fan, while the adjacent dining area draws additional light through its windows and sliding glass door, creating an easy transition between indoor and outdoor spaces. Open to the living and dining areas, the kitchen serves as the center of the main level with white shaker-style cabinetry, quartz countertops and a designer marble tile backsplash. A three-seat island provides a natural gathering place, complemented by stainless steel gas cooking appliances and a pantry. Positioned just off the kitchen, the primary suite offers a private retreat with a tray ceiling, walk-in closet and well-appointed en-suite bath. A dual-sink white vanity provides generous preparation space, while the floor-to-ceiling tiled walk-in shower features a built-in bench. A dedicated linen closet adds further storage. Additional guest bedrooms and baths provide comfortable accommodations, while a downstairs den with French doors creates a quiet setting for work or study. Upstairs, the carpeted flex room expands the home’s versatility and can readily serve as a media room, fitness space, office, playroom or secondary lounge. The upstairs bedroom and full bath create a private retreat that is especially well suited for extended family or out-of-town guests, offering added separation and privacy from the main living areas. Outdoors, a covered living area with paver flooring overlooks the screened saltwater pool and spillover spa, both framed by brick pavers. Beyond the pool enclosure, the home backs to a preserve and small creek, providing a natural backdrop and an added sense of privacy. Residents of Winding Cypress enjoy access to a private clubhouse with year-round gatherings, live music, holiday events and community activities. Ideally between downtown Naples and beaches of Marco Island, this residence combines preserve-side privacy, substantial indoor-outdoor living, flexible accommodations and the added security of a whole-house generator in one of Southwest Florida’s well-established communities.

4 Beds ⋅ 3 Baths ⋅ 226034030 MLS

Preserve views on a quiet cul-de-sac street define this two-story Mystique residence in Winding Cypress, where a saltwater pool with spillover spa, expansive outdoor living and flexible interior spaces create a home designed for relaxation and entertaining. With four bedrooms, a den, an upstairs flex room, three baths and a two-car garage, the floor plan offers exceptional versatility while maintaining an open, connected feel throughout the main living areas. A whole-house generator is on-site, providing added peace of mind during storm-related power outages. A brick paver driveway, tile roof and professional landscaping establish a polished arrival. Inside, wood-look tile flooring, recessed lighting and white plantation shutters carry a clean, cohesive aesthetic throughout the home. The living room is filled with natural light from five windows and anchored by a modern ceiling fan, while the adjacent dining area draws additional light through its windows and sliding glass door, creating an easy transition between indoor and outdoor spaces. Open to the living and dining areas, the kitchen serves as the center of the main level with white shaker-style cabinetry, quartz countertops and a designer marble tile backsplash. A three-seat island provides a natural gathering place, complemented by stainless steel gas cooking appliances and a pantry. Positioned just off the kitchen, the primary suite offers a private retreat with a tray ceiling, walk-in closet and well-appointed en-suite bath. A dual-sink white vanity provides generous preparation space, while the floor-to-ceiling tiled walk-in shower features a built-in bench. A dedicated linen closet adds further storage. Additional guest bedrooms and baths provide comfortable accommodations, while a downstairs den with French doors creates a quiet setting for work or study. Upstairs, the carpeted flex room expands the home’s versatility and can readily serve as a media room, fitness space, office, playroom or secondary lounge. The upstairs bedroom and full bath create a private retreat that is especially well suited for extended family or out-of-town guests, offering added separation and privacy from the main living areas. Outdoors, a covered living area with paver flooring overlooks the screened saltwater pool and spillover spa, both framed by brick pavers. Beyond the pool enclosure, the home backs to a preserve and small creek, providing a natural backdrop and an added sense of privacy. Residents of Winding Cypress enjoy access to a private clubhouse with year-round gatherings, live music, holiday events and community activities. Ideally between downtown Naples and beaches of Marco Island, this residence combines preserve-side privacy, substantial indoor-outdoor living, flexible accommodations and the added security of a whole-house generator in one of Southwest Florida’s well-established communities.

6825 Greenbriar Court, Naples

$1,295,000

PRICED TO SELL! Discover exceptional value in one of Naples’ most desirable lifestyle communities, Winding Cypress. Ideally situated on an oversized preserve lot with peaceful pond views, this beautifully maintained Pinnacle floor plan offers over 2,500 square feet of living space with 3 spacious bedrooms, 3 full bathrooms, and a versatile den. Built in 2020, this move-in-ready residence combines elegant finishes, thoughtful upgrades, and outstanding indoor-outdoor living. The expansive outdoor area features a large picture-window screened lanai, gas-heated saltwater pool and spa, custom outdoor kitchen, and generous brick-paver lanai with a covered entertaining area—perfect for enjoying the Naples lifestyle year-round. A newly installed electric hurricane screen provides additional protection and convenience. The home is equipped with whole-house hurricane shutters, a whole-house generator capable of supporting the pool and spa, and an oversized 3-car garage with epoxy flooring and hurricane-rated, insulated garage doors. Additional attic insulation and a separate garage A/C system provide the option for climate-controlled storage or workspace. The beautifully appointed kitchen features white quartz countertops, premium stainless steel appliances, a gas cooktop, and a beverage refrigerator. The spacious primary suite offers exceptional organization with a custom California Closets design, while the custom pantry provides additional storage and functionality. Beyond the residence, Winding Cypress offers an exceptional resort-style lifestyle. The impressive clubhouse features a heated resort pool and spa, poolside dining at The Shady Palm, state-of-the-art fitness center, library, and elegant gathering rooms. Residents also enjoy tennis and pickleball courts, bocce, dog parks, a community garden, and scenic walking and nature trails. Beautifully maintained grounds and a welcoming atmosphere create a true sense of community, all while being conveniently located near the best of Naples. Located in an X flood zone, with no flood insurance required, this exceptional home offers the perfect combination of luxury, privacy, recreation, and peace of mind. Priced to sell and offering tremendous value, this is an opportunity to own a beautifully upgraded home in one of Naples’ premier communities.

3 Beds ⋅ 3 Baths ⋅ 226027501 MLS

PRICED TO SELL! Discover exceptional value in one of Naples’ most desirable lifestyle communities, Winding Cypress. Ideally situated on an oversized preserve lot with peaceful pond views, this beautifully maintained Pinnacle floor plan offers over 2,500 square feet of living space with 3 spacious bedrooms, 3 full bathrooms, and a versatile den. Built in 2020, this move-in-ready residence combines elegant finishes, thoughtful upgrades, and outstanding indoor-outdoor living. The expansive outdoor area features a large picture-window screened lanai, gas-heated saltwater pool and spa, custom outdoor kitchen, and generous brick-paver lanai with a covered entertaining area—perfect for enjoying the Naples lifestyle year-round. A newly installed electric hurricane screen provides additional protection and convenience. The home is equipped with whole-house hurricane shutters, a whole-house generator capable of supporting the pool and spa, and an oversized 3-car garage with epoxy flooring and hurricane-rated, insulated garage doors. Additional attic insulation and a separate garage A/C system provide the option for climate-controlled storage or workspace. The beautifully appointed kitchen features white quartz countertops, premium stainless steel appliances, a gas cooktop, and a beverage refrigerator. The spacious primary suite offers exceptional organization with a custom California Closets design, while the custom pantry provides additional storage and functionality. Beyond the residence, Winding Cypress offers an exceptional resort-style lifestyle. The impressive clubhouse features a heated resort pool and spa, poolside dining at The Shady Palm, state-of-the-art fitness center, library, and elegant gathering rooms. Residents also enjoy tennis and pickleball courts, bocce, dog parks, a community garden, and scenic walking and nature trails. Beautifully maintained grounds and a welcoming atmosphere create a true sense of community, all while being conveniently located near the best of Naples. Located in an X flood zone, with no flood insurance required, this exceptional home offers the perfect combination of luxury, privacy, recreation, and peace of mind. Priced to sell and offering tremendous value, this is an opportunity to own a beautifully upgraded home in one of Naples’ premier communities.

6907 Cocoplum Street, Naples

$1,349,500

BRING OFFERS! Welcome to this highly upgraded Infinity Model, a rare offering in the prestigious Winding Cypress community of Naples. Built by renowned DiVosta Builders, this residence is one of only three Infinity Models within a community of more than 750 homes, making it an exceptionally unique opportunity. Featuring an extra-wide three-car garage with a dedicated third bay ideal for a golf cart, hobby vehicle, or additional storage, this home has been significantly enhanced with premium upgrades throughout and offers a level of quality rarely found in today's market. Designed for both luxury and everyday comfort, the expansive open-concept floor plan showcases soaring tray ceilings exceeding 11 feet, custom faux painting, extensive crown molding, and elegant designer finishes throughout. The spacious great room seamlessly connects to the gourmet kitchen, highlighted by a six-burner Thermador gas range and cooktop, premium Liebherr refrigerator, custom cabinetry, and a massive leather-finished quartzite island perfect for entertaining. The seller's extensive investment in upgrades is evident in every detail. Designer window treatments, custom bed coverlets, built-in features, and custom closets throughout create a refined, move-in-ready environment. The completely remodeled primary bath offers a spa-inspired retreat featuring a curbless walk-in shower, floating vanity, premium fixtures, designer tilework, and stunning 48-inch porcelain tile flooring throughout. Outdoor living is equally impressive. The expansive lanai with desirable western exposure captures spectacular Naples sunsets and provides ample space for a custom pool, spa, and additional outdoor living areas. Pool plans and contractor quotes are available, making it easy for the next owner to create their ideal backyard oasis. The fully equipped outdoor kitchen provides the perfect setting for entertaining family and friends while enjoying the privacy and tropical surroundings. Additional upgrades include hurricane-impact windows and doors, a dramatic zero-corner sliding glass door, whole-house generator, tankless water heater, Kinetico water filtration system, Sonos surround sound system, epoxy-coated garage floors, insulated garage doors, built-in garage storage, and a dedicated air-conditioning system for the garage. As one of Naples' premier natural gas communities, Winding Cypress offers an unmatched lifestyle with a residents-only restaurant, resort-style pool and spa, fitness center, pickleball, tennis and bocce courts, and over 800 acres of protected preserve. Ideally located just 10 minutes from Marco Island's white sand beaches and approximately 15 minutes from Olde Naples, this exceptional residence combines rarity, luxury, and location in one extraordinary offering. This is more than a home—it's a statement of quality, craftsmanship, and lifestyle. One or more photos have been virtually staged, AI-generated, or rendered.

3 Beds ⋅ 3 Baths ⋅ 226021460 MLS

BRING OFFERS! Welcome to this highly upgraded Infinity Model, a rare offering in the prestigious Winding Cypress community of Naples. Built by renowned DiVosta Builders, this residence is one of only three Infinity Models within a community of more than 750 homes, making it an exceptionally unique opportunity. Featuring an extra-wide three-car garage with a dedicated third bay ideal for a golf cart, hobby vehicle, or additional storage, this home has been significantly enhanced with premium upgrades throughout and offers a level of quality rarely found in today's market. Designed for both luxury and everyday comfort, the expansive open-concept floor plan showcases soaring tray ceilings exceeding 11 feet, custom faux painting, extensive crown molding, and elegant designer finishes throughout. The spacious great room seamlessly connects to the gourmet kitchen, highlighted by a six-burner Thermador gas range and cooktop, premium Liebherr refrigerator, custom cabinetry, and a massive leather-finished quartzite island perfect for entertaining. The seller's extensive investment in upgrades is evident in every detail. Designer window treatments, custom bed coverlets, built-in features, and custom closets throughout create a refined, move-in-ready environment. The completely remodeled primary bath offers a spa-inspired retreat featuring a curbless walk-in shower, floating vanity, premium fixtures, designer tilework, and stunning 48-inch porcelain tile flooring throughout. Outdoor living is equally impressive. The expansive lanai with desirable western exposure captures spectacular Naples sunsets and provides ample space for a custom pool, spa, and additional outdoor living areas. Pool plans and contractor quotes are available, making it easy for the next owner to create their ideal backyard oasis. The fully equipped outdoor kitchen provides the perfect setting for entertaining family and friends while enjoying the privacy and tropical surroundings. Additional upgrades include hurricane-impact windows and doors, a dramatic zero-corner sliding glass door, whole-house generator, tankless water heater, Kinetico water filtration system, Sonos surround sound system, epoxy-coated garage floors, insulated garage doors, built-in garage storage, and a dedicated air-conditioning system for the garage. As one of Naples' premier natural gas communities, Winding Cypress offers an unmatched lifestyle with a residents-only restaurant, resort-style pool and spa, fitness center, pickleball, tennis and bocce courts, and over 800 acres of protected preserve. Ideally located just 10 minutes from Marco Island's white sand beaches and approximately 15 minutes from Olde Naples, this exceptional residence combines rarity, luxury, and location in one extraordinary offering. This is more than a home—it's a statement of quality, craftsmanship, and lifestyle. One or more photos have been virtually staged, AI-generated, or rendered.

7478 Winding Cypress Drive, Naples

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