Sold in Winding Cypress, Naples, FL

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

7597 BLACKBERRY DR, Naples

$750,000

2 Beds ⋅ 2 Baths ⋅ 225031142 MLS

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

7128 Lily WAY, Naples

$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

$674,000

3 Beds ⋅ 2 Baths ⋅ 225050266 MLS

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

7445 Winding Cypress DR, Naples

$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

$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

$900,000

2 Beds ⋅ 2 Baths ⋅ 225053774 MLS

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

6848 Winding Cypress DR, Naples

$885,000

3 Beds ⋅ 2 Baths ⋅ 225034820 MLS

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

7451 Blackberry DR, Naples

$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

$510,000

2 Beds ⋅ 2 Baths ⋅ 225033541 MLS

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

7650 Jacaranda LN, Naples

$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

$975,000

3 Beds ⋅ 3 Baths ⋅ 225034039 MLS

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

7530 Geranium WAY, Naples

Recently Sold Listings in Winding Cypress, Naples, FL

Be the First to Know About New Winding Cypress Homes

Winding Cypress Real Estate Map Search

All Sold in Winding Cypress, Naples, FL

How much is your home worth?

How much is your home worth?

Fahey Team

Search

Resources

About