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$760,000
2 Beds ⋅ 2 Baths ⋅ 225023743 MLS
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 DR, Naples

Courtesy of Realty One Group MVP.

Selling Office: Horizons by the Sea Inc.

$855,000
3 Beds ⋅ 3 Baths ⋅ 225022390 MLS
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 DR, Naples

Courtesy of Berkshire Hathaway FL Realty.

Selling Office: eXp Realty LLC.

$537,000
2 Beds ⋅ 2 Baths ⋅ 225021743 MLS
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 LN, Naples

Courtesy of Keller Williams Marco Realty.

Selling Office: Keller Williams Marco Realty.

$620,000
2 Beds ⋅ 2 Baths ⋅ 225021309 MLS
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 LN, Naples

Courtesy of Coldwell Banker Realty.

Selling Office: John R Wood Properties.

$890,000
3 Beds ⋅ 2 Baths ⋅ 225018609 MLS
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 DR, Naples

Courtesy of Orchid Realty International.

Selling Office: Coldwell Banker Realty.

$1,475,000
3 Beds ⋅ 3.5 Baths ⋅ 225016804 MLS
3 bedroom and 3 bath Stonewater Model home in Winding Cypress

6912 Cocoplum ST, Naples

Courtesy of William Raveis Real Estate.

Selling Office: William Raveis Real Estate.

$453,000
2 Beds ⋅ 2 Baths ⋅ 225011172 MLS
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 LN, Naples

Courtesy of Realty One Group MVP.

Selling Office: Compass Florida LLC.

$860,000
3 Beds ⋅ 2 Baths ⋅ 225008365 MLS
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 DR, Naples

Courtesy of William Raveis Real Estate.

Selling Office: William Raveis Real Estate.

$635,000
2 Beds ⋅ 2 Baths ⋅ 225001830 MLS
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 DR, Naples

Courtesy of Premier Sotheby's Int'l Realty.

Selling Office: Naples Trust Real Estate Servi.

$850,000
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 DR, Naples

Courtesy of Premier Sotheby's Int'l Realty.

Selling Office: Premier Sotheby's Int'l Realty.

$1,255,000
3 Beds ⋅ 3 Baths ⋅ 225001834 MLS
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 DR, Naples

Courtesy of Premier Sotheby's Int'l Realty.

Selling Office: Premier Sotheby's Int'l Realty.

$645,000
2 Beds ⋅ 2 Baths ⋅ 224103914 MLS
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 CT, Naples

Courtesy of Compass Florida LLC.

Selling Office: William Raveis Real Estate.

$710,000
2 Beds ⋅ 2 Baths ⋅ 224101522 MLS
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 DR, Naples

Courtesy of Island Realty Marco.

Selling Office: KW Elevate Luxury.

$880,000
3 Beds ⋅ 2 Baths ⋅ 224091808 MLS
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 DR, Naples

Courtesy of Coldwell Banker Sunstar Realty.

Selling Office: Berkshire Hathaway FL Realty.

$775,000
2 Beds ⋅ 2 Baths ⋅ 224089763 MLS
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 DR, Naples

Courtesy of DomainRealty.com LLC. (239) 300-5260

Selling Office: Realty One Group MVP.

$992,500
2 Beds ⋅ 2 Baths ⋅ 224090027 MLS
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 DR, Naples

Courtesy of Premier Sotheby's Int'l Realty.

Selling Office: John R Wood Properties.

$975,000
3 Beds ⋅ 3 Baths ⋅ 224088928 MLS
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 DR, Naples

Courtesy of Royal Shell Real Estate, Inc..

Selling Office: Paradise Coast Property Team.

$830,000
3 Beds ⋅ 3 Baths ⋅ 224083667 MLS
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 DR, Naples

Courtesy of William Raveis Real Estate.

Selling Office: Premier Sotheby's Int'l Realty.

$1,495,000
3 Beds ⋅ 3 Baths ⋅ 224083615 MLS
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 with crown molding and custom detail wall, saltwater pool w/integral spa, whole house generator, hurricane impact windows, zero corner slider with impact glass, Storm Smart Kevlar screen across lanai, leaded glass front door, upgraded kitchen appliance package, upgraded kitchen & bath cabinet package, plantation shutters throughout, home security system, extended 3 car garage w/epoxy floor, additional refrigerator/freezer & built in cabinets, custom closet and pantry storage systems, upgraded laundry room w/built in cabinets and utility sink, den complete with built in desk & storage system, upgraded electrical include custom fixtures, ceiling fans and dimmer switches. The exterior has beautiful Bohemian shutters along with a paver walkaround. This gorgeous home sits on an oversized private lot at the end of a dead-end cul-de-sac. Winding Cypress boasts one of the most outstanding community amenities anywhere in Naples and at an incredible value. They include a private, residents only restaurant, spectacular resort pool, spa & beach cabana, expansive clubhouse w/an amazing fitness center w/men's/women's locker rooms, conference & meeting rooms, library, community kitchen, pickleball, tennis, & bocce courts, dog park, nature boardwalk, and a community garden. Winding Cypress is perfectly located 10 minutes from Marco Island & 15 minutes from downtown Olde Naples.

6883 Cocoplum ST, Naples

Courtesy of William Raveis Real Estate.

Selling Office: John R Wood Properties.

$935,000
3 Beds ⋅ 2 Baths ⋅ 224082513 MLS
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 DR, Naples

Courtesy of John R Wood Properties.

Selling Office: Premier Sotheby's Int'l Realty.

$470,000
2 Beds ⋅ 2 Baths ⋅ 224079403 MLS
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 LN, Naples

Courtesy of Premier Sotheby's Int'l Realty.

Selling Office: William Raveis Real Estate.

$530,000
2 Beds ⋅ 2 Baths ⋅ 224076682 MLS
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 LN, Naples

Courtesy of Berkshire Hathaway FL Realty.

Selling Office: Premier Sotheby's Int'l Realty.

$785,000
2 Beds ⋅ 2 Baths ⋅ 224074690 MLS
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 DR, Naples

Courtesy of John R Wood Properties. 410-207-8431

Selling Office: Alfred Robbins Realty Group.

$690,000
3 Beds ⋅ 2 Baths ⋅ 224074239 MLS
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 DR, Naples

Courtesy of John R Wood Properties.

Selling Office: John R Wood Properties.

$995,000
3 Beds ⋅ 3 Baths ⋅ 224055933 MLS
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 DR, Naples

Courtesy of Royal Shell Real Estate, Inc..

Selling Office: John R Wood Properties.

$775,000
2 Beds ⋅ 2 Baths ⋅ 224051672 MLS
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 DR, Naples

Courtesy of Premier Sotheby's Int'l Realty.

Selling Office: Premier Sotheby's Int'l Realty.

$945,000
4 Beds ⋅ 3 Baths ⋅ 224052264 MLS
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 CT, Naples

Courtesy of Realty One Group MVP.

Selling Office: RE/MAX Trend.

$1,450,000
4 Beds ⋅ 4 Baths ⋅ 224050943 MLS
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 ST, Naples

Courtesy of Realty One Group MVP.

Selling Office: Coldwell Banker Realty.

$1,175,000
3 Beds ⋅ 3 Baths ⋅ 224048727 MLS
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 DR, Naples

Courtesy of John R Wood Properties.

Selling Office: BERKSHIRE HATHAWAY FL REALTY.

$720,000
2 Beds ⋅ 2 Baths ⋅ 224041079 MLS
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 DR, Naples

Courtesy of Coldwell Banker Realty.

Selling Office: Coldwell Banker Realty.

The data relating to real estate for sale on this web site comes in part from the Broker Reciprocity Program (BR Program) of M.L.S. of Naples, Inc. Properties listed with brokerage firms other than this company are marked with the BR Program Icon or the BR House Icon and detailed information about them includes the name of the listing brokers. The properties displayed may not be all the properties available through the BR Program. The information provided is for consumers’ personal, non-commercial use and may not be used for any other purpose.