Winding Cypress Houses Sold

Premium
Premium
$300 - $400 per SqFt
Ratings
Reviews (
)
Results 29 of 54
Sold - May 13, 2026
Winding Cypress, 6912 Cocoplum St, Naples, Florida 34114, image 1
$1,475,000 $325K
  • 3 Beds
  • 31/2 Baths
  • 2,923 SqFt
  • $505/SqFt
Premium
House sold in Winding Cypress
6912 Cocoplum St, Naples, FL 34114
3 bedroom and 3 bath stonewater model home in winding cypress
Sold - May 8, 2026
Winding Cypress, 6754 Pennyroyal Dr, Naples, Florida 34114, image 1
$800,000 $30K
  • 3 Beds
  • 3 Baths
  • 2,158 SqFt
  • $371/SqFt
Premium
House sold in Winding Cypress
6754 Pennyroyal Dr, Naples, FL 34114
This gorgeous mystique floor plan features 3 bedrooms, a den, a rare 3 full bathrooms, heated pool, and a 2-car garage. Inside the home is loaded with upgrades, impact windows and doors, custom built-in cabinetry in the living & laundry room, crown molding, tray ceilings, recessed lighting, electric blinds, designer hardware and lighting, and abundant storage throughout. Embrace the florida lifestyle with the open-concept zero-corner slider connecting the indoor and outdoor living spaces. The pool deck offers a spacious covered lanai, a modern pool, added privacy, and highly desirable southwest exposure. No detail has been spared in the garage, which features a built-in workbench and storage, an electric screen garage door, epoxy flooring, and plenty of room for bikes and more. Winding cypress is a natural gas community with resort-style amenities. Dine at shady palm, the onsite restaurant, or enjoy pickleball, bocce, tennis, a state-of-the-art fitness center, a resort-style pool, a community garden, and even two dog parks for your furry friends. This pet-friendly community allows rentals, has low fees, and boasts a prime location—convenient to marco island, 5th avenue, and i-75.
Sold - May 5, 2026
Winding Cypress, 6902 Winding Cypress Dr, Naples, Florida 34114, image 1
$835,000 $25K
  • 3 Beds
  • 2 Baths
  • 2,084 SqFt
  • $401/SqFt
Premium
House sold in Winding Cypress
6902 Winding Cypress Dr, Naples, FL 34114
Stunning 3-bedroom + den home in sought-after winding cypress – welcome to your dream home in the prestigious, resort-style community of winding cypress in naples, fl. Built in 2022, this impeccably maintained 3-bedroom + den, 2-bathroom residence blends modern design with everyday comfort. Step inside to find an open-concept floor plan featuring, abundant natural light, and contemporary finishes throughout. The kitchen boasts quartz countertops, stainless steel appliances, a large center island, and a spacious pantry—perfect for entertaining or casual family meals. The flexible den space offers the ideal setup for a home office, media room, or guest overflow. The primary suite is a serene retreat with a large walk-in closet and a spa-like ensuite bathroom featuring dual vanities and a walk-in shower. Recently installed lights on the lanai make the area glow at night. Very private preserve views! Also recently installed are electric retractable hurricane screens for added safety. Enjoy florida living at its best with a screened lanai, ideal for relaxing or dining alfresco, with a large heated pool. The home also includes a 2-car garage, impact windows, and smart home features for added peace of mind. Residents of winding cypress enjoy resort-caliber amenities including a large clubhouse, fitness center, resort pool & spa, on-site restaurant, tennis & pickleball courts, fire pit, dog park, and over 800 acres of preserved natural space with walking/biking trails. Conveniently located just minutes from downtown naples, white sand beaches, shopping, and dining. Don’t miss this rare opportunity to own a move-in ready home in one of naples’ most desirable communities!

READY TO SELL?

We can help
Sell Faster
For Top Dollar
With The Best Terms
Sold - Apr 30, 2026
Winding Cypress, 7255 Live Oak Dr, Naples, Florida 34114, image 1
$599,900 $20K
  • 2 Beds
  • 2 Baths
  • 1,659 SqFt
  • $362/SqFt
Premium
House sold in Winding Cypress
7255 Live Oak Dr, Naples, FL 34114
This home has just been freshly painted inside and out. Professionally painted kitchen and bath cabinets, nice private south waterview , screened lanai able to enlarge or expand with a pool. Previous owner had a great workshop in garage with 8 overhead lights, addition dual media cat5/rg6 charging station for a tesla , framed peg boards for hanging tools , custom storage cabinets and a pull down staircase for added storage. Home features 2 bedrooms 2 baths plus den a whole house generator and attached manual and electric storm shutters. Remaining furniture in home is staying. Live oak is a beautiful mature tree lined street on cul de sac and just a short walk to the amenity center, dog park or community garden .Rarely will you find a single family home at this price in winding cypress . Great value ! Winding cypress amenity center offers so much within its gates, its own shady palm restaurant, resort pool , gym , bocci and pickleball courts, dog park , walking trails and so much more. Winding cypress is a gated community located just mins to 75, downtown and marco island. Photos to be uploaded on 1/24
Sold - Apr 23, 2026
Winding Cypress, 6698 Pennyroyal Dr, Naples, Florida 34114, image 1
$890,000 $53K
  • 3 Beds
  • 3 Baths
  • 2,150 SqFt
  • $414/SqFt
Premium
House sold in Winding Cypress
6698 Pennyroyal Dr, Naples, FL 34114
Discover resort-style living in this rare three-bedroom plus den, three-bath natural gas home in the highly sought-after community of winding cypress. Designed for privacy and effortless indoor–outdoor living, it features an oversized fully custom pool with integrated seamless spa and a panoramic barless screen lanai, integrated home theater sound, all overlooking lush, tranquil landscaping. The great room opens with a dramatic zero-corner disappearing slider, and the home is nearly brand new with 2022 construction still under the renowned divosta builder warranty. Located on a private cul-de-sac, this home offers peaceful living while keeping you close to world-class amenities. Winding cypress boasts private nature trails, community gardens, and an impressive 18, 000-square-foot resort clubhouse with a poolside restaurant, full-time activities director, lap lanes, zero-edge resort pool with waterfall, fire pit, pickleball, tennis, and more. The community now features two grand entrances/exits on both tamiami trail (u.S. 41) and collier boulevard (951), offering exceptional convenience.
Sold - Apr 14, 2026
Winding Cypress, 7057 Live Oak Dr, Naples, Florida 34114, image 1
$625,000 $20K
  • 3 Beds
  • 2 Baths
  • 2,230 SqFt
  • $280/SqFt
Premium
House sold in Winding Cypress
7057 Live Oak Dr, Naples, FL 34114
Winding cypress – price reduced to sell- property sits approximately 2+ feet above fema base flood elevation. Fema loma in process — flood insurance not required by lender. Rare opportunity to purchase in this community at this price point. Lowest priced 4 bedroom home in winding cypress. Welcome to your florida dream home in the sought-after gated community of winding cypress! This immaculate residence built in 2016, offers the perfect blend of modern luxury and relaxed coastal living. Featuring 2, 230’sq under air, 4 bedrooms. Two full baths, and an open-concept floor plan, this home is designed for comfort and entertaining. Step inside to find upgraded tile flooring, beautiful crown molding, a gourmet kitchen with granite countertops, stainless steel appliances, and a large center island ideal for gathering with friends and family. The spacious great room opens through sliding glass doors to a screened lanai, creating seamless indoor-outdoor living. This home also features a "sunroom" addition and an oversized garage. Enjoy peaceful views of the lush landscaping and lake—the perfect backdrop for morning coffee or sunset cocktails. The primary suite offers a spa-like bath with dual sinks, walk-in shower, and large walk-in closet. Additional features include plantation shutters, impact-resistant windows and doors, whole house water purification system, new electric hurricane screens, a "sunroom" addition not included in other floor plans, and an oversized garage and a 2-car extended garage with epoxy flooring. Located within minutes of downtown naples and the gulf beaches, winding cypress offers resort-style amenities including a lagoon-style pool, on-site restaurant, tennis, pickleball, fitness center, dog park, and miles of nature trails. Move-in ready, this is the best priced home of its size in winding cypress — this home combines style, value, and an unbeatable location.
Sold - Apr 9, 2026
Winding Cypress, 7717 Jacaranda Ln, Naples, Florida 34114, image 1
$635,000 $24K
  • 2 Beds
  • 2 Baths
  • 1,554 SqFt
  • $409/SqFt
Premium
Villa sold in Winding Cypress
7717 Jacaranda Ln, Naples, FL 34114
This gorgeous serenity villa features 2 bedrooms, a den, a pool, and a 2-car garage, and is being offered turnkey furnished. The pool deck showcases one of the best lake views in the community, complete with spectacular sunsets, a picture-window screen, a spacious covered lanai, and a pool heated by both electric and solar—helping keep energy costs down. Enjoy peace of mind with impact windows and doors throughout, a whole-home generator, and a hurricane screen for added lanai protection. Inside, the home is loaded with upgrades, including plantation shutters, under-cabinet lighting, a tray ceiling, custom shelving in the living room and den, and more. Winding cypress is a natural gas community with resort-style amenities. Dine at shady palm, the onsite restaurant, or enjoy pickleball, bocce, tennis, a state-of-the-art fitness center, a resort-style pool, a community garden, and even two dog parks for your furry friends. This pet-friendly community allows rentals, has low fees, and boasts a prime location—convenient to marco island, 5th avenue, and i-75.
Sold - Mar 30, 2026
Winding Cypress, 7785 Jacaranda Ln, Naples, Florida 34114, image 1
$550,000
  • 2 Beds
  • 2 Baths
  • 1,574 SqFt
  • $349/SqFt
Premium
Villa sold in Winding Cypress
7785 Jacaranda Ln, Naples, FL 34114
The one and only cressida villa plan with the unique front entrance and foyer layout in winding cypress with an expanded lanai and a sweeping, wide-water views that feels endless. This light-filled, impeccably maintained residence showcases all quartz countertops, premium cabinetry, porcelain tile, natural gas, and seamless indoor-outdoor living designed for entertaining or quiet sunset evenings. The oversized lanai captures panoramic water views, creating a private, tranquil backdrop rarely available. Move-in ready and in amazing condition, this home stands out for its scale, upgrades and setting. In the resort community of winding cypress, a low-fee, resort-style guard-gated community with 800 acres of preserve, full-time activities director, resort and lap pool, on-site restaurant, fitness center, pickleball and tennis courts, and miles of recreational, biking and nature trails.
Sold - Mar 23, 2026
Winding Cypress, 7167 Live Oak Dr, Naples, Florida 34114, image 1
$575,000 $25K
  • 3 Beds
  • 2 Baths
  • 1,554 SqFt
  • $370/SqFt
Premium
House sold in Winding Cypress
7167 Live Oak Dr, Naples, FL 34114
Rare villa opportunity in winding cypress! This turnkey, fully furnished villa sits on an extra-large, ultra-private lot with exceptional spacing between neighbors, creating a peaceful and open feel that is hard to find. The backyard is a retreat, featuring a saltwater private pool framed by mature cypress trees, colorful landscaping and wide natural preserve views. Inside, the home offers thoughtful upgrades including 8-foot interior doors, new bedroom flooring, refreshed landscaping and built-in garage storage that helps keep everything organized. As a natural gas home, it features gas cooking and provides flexibility for future enhancements, offering efficiency and convenience. Living in winding cypress means enjoying resort-style amenities without the high fees. Residents have access to an expansive resort pool with beach entry, a full-service restaurant and bar, a state-of-the-art fitness center, pickleball, tennis and bocce courts, a dog park, and miles of scenic walking and biking trails. The beautifully designed clubhouse includes a social hall, gathering spaces and a library, creating opportunities to connect and engage with neighbors. This home blends nature, privacy, comfort and community into one exceptional offering.
Sold - Mar 16, 2026
Winding Cypress, 7690 Jacaranda Ln, Naples, Florida 34114, image 1
$575,000 $64K
  • 2 Beds
  • 2 Baths
  • 1,554 SqFt
  • $370/SqFt
Premium
Villa sold in Winding Cypress
7690 Jacaranda Ln, Naples, FL 34114
Set against private garden views with tranquil eastern exposure, this beautifully appointed villa in winding cypress offers a peaceful retreat and effortless indoor-outdoor living. Featuring two bedrooms plus a den, two baths, and a two-car garage, this thoughtfully designed residence combines quiet luxury with meticulous updates in one of naples’ most dynamic lifestyle communities. The screened lanai is ideal for entertaining or unwinding, complete with brick paver flooring, a saltwater pool with waterfall feature, pool heater, and recent upgrades including a new salt generator and pool pump. A custom outdoor kitchen with a stainless steel gas grill with matching hood and sink further enhances the outdoor living experience. Electric hurricane shutters protect the lanai, while manual shutters cover the remainder of the home. Inside, tile flooring extends throughout, accented by crown molding, recessed lighting, and white plantation shutters. The living room opens to the lanai through expansive glass sliders, anchored by a modern ceiling fan. The kitchen features white shaker-style cabinetry, quartz countertops, a tile backsplash, pantry, and stainless steel appliances including a gas range, refrigerator with icemaker, microwave, and dishwasher. A modern chandelier defines the dining area, which flows easily into the main living space. The primary suite is a private haven with a tray ceiling, garden views, custom closet, and a spa-inspired bath featuring dual quartz vanities, full-width mirrors, and a frameless glass walk-in shower. The second bedroom includes a walk-in closet and an adjacent bath with a shower-tub combination. A den with french doors offers flexible space for a home office or reading room. Additional highlights include a mini-split air conditioning system in the garage, a brand-new water heater, and recent property updates including a full exterior repaint (approximately two years ago) and interior paint touch-ups. Residents of winding cypress enjoy access to resort-style amenities including a pool, an attended fitness center, an on-site restaurant, five tennis courts, four bocce ball courts, four pickleball courts, a community garden, and a dog park. With a vibrant social calendar, low hoa fees, rental-friendly policies, and a prime location near marco island, downtown naples, 5th avenue, and i-75, this villa offers elevated living in a premier naples community.
Sold - Mar 12, 2026
Winding Cypress, 7658 Jacaranda Ln, Naples, Florida 34114, image 1
$460,000 $39K
  • 2 Beds
  • 2 Baths
  • 1,554 SqFt
  • $296/SqFt
Premium
Villa sold in Winding Cypress
7658 Jacaranda Ln, Naples, FL 34114
This property is nestled in one of naples’ most desirable communities. This home features two spacious bedrooms, two elegant baths, and a flexible den—perfect for a home office, hobby room or additional guest area. The upgraded kitchen is equipped with stainless steel appliances, quartz counter tops in kitchen and both bathrooms, and bright 42” cabinetry with under lighting, creating an inviting space for entertaining. Enjoy the open-concept living and dining area with stylish tile flooring on the diagonal throughout, plantation shutters on all windows, and 2 interior pocket doors that provide privacy to the owners and guest suite areas. The sliding doors lead to a private covered screened lanai ideal for relaxing or dining outdoors. A large rear lot where you can design your own pool area if so desired. This property provides ample space for both relaxation and functionality as a vacation home or easy full-time florida living.
Sold - Mar 11, 2026
Winding Cypress, 7412 Winding Cypress Dr, Naples, Florida 34114, image 1
$1,495,000 $200K
  • 4 Beds
  • 4 Baths
  • 3,656 SqFt
  • $409/SqFt
Premium
House sold in Winding Cypress
7412 Winding Cypress Dr, Naples, FL 34114
Motivated seller! Luxurious lakeside living in winding cypress – rare one owner pinnacle model! Welcome to this stunning lake view home offering 3, 656 sq. Ft. Of modern elegance in the prestigious, amenity-rich community of winding cypress. With 4 bedrooms, 4 bathrooms, a den, bonus room, and 2, 5-car garage, this home is thoughtfully designed for both everyday living and entertaining on a grand scale. Step inside to discover a light-filled open floor plan accented with tile flooring in the main living areas, brand-new luxury vinyl plank flooring in all three downstairs bedrooms, and crown molding throughout the first floor. The chef’s kitchen is a showstopper, boasting quartz countertops, premium kitchenaid stainless steel appliances, a new natural gas cooktop, soft-close cabinetry, walk-in pantry, new dishwasher, and upgraded sink—all designed for style and function. Enjoy seamless indoor-outdoor living with zero-corner sliding doors that open to an expansive lanai featuring a picture screen enclosure, heated pool and spa, and a custom outdoor kitchen with built-in hub. With southwestern exposure overlooking the long lake and preserve, sunsets here are simply unforgettable. Retreat to the primary suite with a spa-like bathroom and custom walk-in closets, while guests enjoy privacy with an en suite bedroom on the main level. Upstairs, the bonus room offers endless flexibility for a game room, theater, or additional living space. This home is equipped with hurricane-impact windows, built-in sonos surround sound system, smart home features, and abundant storage—ensuring comfort, safety, and convenience. As a resident of winding cypress, you’ll enjoy world-class amenities, including:heated resort-style & lap pools, hot tub, and gas fire pit, covered outdoor restaurant bar & grill, expansive clubhouse with fitness center, library, and event space, pickle ball, bocce, and tennis courts, miles of scenic sidewalks & boardwalk trails, two dog parks for furry family members. Perfectly positioned on a premium lot, close to the community center and surrounded by excellent local infrastructure, this home is one of the rarely available larger homes in winding cypress—ideal for hosting family and friends in comfort and style. Experience the best of modern naples living in this extraordinary home.
Sold - Mar 6, 2026
Winding Cypress, 7211 Live Oak Dr, Naples, Florida 34114, image 1
$835,000 $15K
  • 3 Beds
  • 2 Baths
  • 2,230 SqFt
  • $374/SqFt
Premium
House sold in Winding Cypress
7211 Live Oak Dr, Naples, FL 34114
Check out this impeccably maintained residence offers an exceptional living experience. The open floor plan features three spacious bedrooms, a versatile den or flex room, and two full bathroom. Elegant details include crown molding, tray ceilings, plantation shutters, hunter douglas blinds, and updated flooring provides a tranquil space for relaxation or entertaining. The custom gourmet kitchen equipped with under-cabinet lighting, granite countertops, a wall oven with microwave, gas cooktop, matching range hood, soft-close drawers with pull outs, and a walk-in pantry for more than ample storge. This property sits on an oversized private lot with tropical landscaping, a newly screened lanai, and a large pool.
Sold - Mar 6, 2026
Winding Cypress, 7176 Live Oak Dr, Naples, Florida 34114, image 1
$520,000 $30K
  • 3 Beds
  • 2 Baths
  • 1,554 SqFt
  • $335/SqFt
Premium
Villa sold in Winding Cypress
7176 Live Oak Dr, Naples, FL 34114
Welcome to effortless, refined living in the highly desirable winding cypress community. Set on the largest homesite in the neighborhood, this impeccably upgraded 3-bedroom, 2-bath villa offers exceptional privacy, expansive outdoor space, and a true lock-and-leave lifestyle. Furnishings are negotiable, making this a flexible opportunity for both full-time and seasonal residents. Designed for relaxed everyday living and easy entertaining, the open floor plan feels light, inviting, and polished without being formal. Thoughtful designer touches throughout create a warm, comfortable atmosphere that flows naturally from indoors to outdoors. The extended screened lanai becomes an everyday retreat, ideal for morning coffee, sunset unwinding, or hosting friends, while the outdoor summer kitchen makes casual gatherings effortless. Peace of mind is a defining feature of this home, with over $100, 000 in safety and security upgrades already in place. A whole-house backup generator, advanced security system, hurricane protection, and smart access features allow you to travel or entertain with confidence, knowing everything is covered. Living in winding cypress means enjoying a resort-style lifestyle every day. Residents have access to a beautifully appointed clubhouse with on-site dining, resort and lap pools, a jacuzzi, fitness center, tennis, pickleball, bocce courts, and a dog park. The community is surrounded by natural preserves and lakes, creating a serene setting while remaining minutes from shopping, dining, and daily conveniences. This is a rare opportunity to own a premier villa in one of southeast naples’ most sought-after gated communities. Priced competitively and offering flexibility on furnishings, this home delivers comfort, security, and lifestyle in one exceptional package.
Sold - Mar 3, 2026
Winding Cypress, 7520 Blackberry Dr, Naples, Florida 34114, image 1
$1,100,000 $50K
  • 3 Beds
  • 3 Baths
  • 2,496 SqFt
  • $441/SqFt
Premium
House sold in Winding Cypress
7520 Blackberry Dr, Naples, FL 34114
Introducing a luxury estate with landscaped privacy corner lot home in winding cypress with pool and spa. Step into elegance with this stunning pinnacle model estate home, set in the prestigious, gated community of winding cypress. This home stands out with its soaring raised tray ceilings, rare privacy and spacious yard, impact glass for peace of mind, and an expansive open layout filled with natural light and outstanding upgrades. Designed for those who love to entertain, the chef-inspired gourmet kitchen features top-tier finishes, premium appliances, and a spacious expanded island, the ideal gathering space for family and friends. With three bedrooms, three baths, a versatile den and an upgraded oversized three-car garage, this home offers flexibility and space to suit your lifestyle. Outside, a private backyard oasis awaits, complete with lush landscaping, a serene water view and a sprawling grassy yard, a rare find in this community. Take a refreshing dip in your sparkling pool and spa, designed for ultimate relaxation in a peaceful setting. Beyond your doorstep, winding cypress offers resort-style living like no other. The nearly 18, 000-square-foot clubhouse boasts a zero-entry infinity pool with a lap section, a poolside restaurant, beach cabanas and even a sandy beach. Stay active with numerous pickleball courts, clay tennis courts, bocce, an outdoor yoga movement studio, and a vibrant community hall managed by a full-time activity director. Winding cypress is a resort gated community at the midpoint between marco island and downtown naples, and this home delivers the ultimate combination of luxury, convenience and an unmatched lifestyle. Don’t miss your chance to own one of the desirable and private estate homes in winding cypress of naples.
Sold - Feb 27, 2026
Winding Cypress, 6779 Winding Cypress Dr, Naples, Florida 34114, image 1
$910,000 $15K
  • 3 Beds
  • 2 Baths
  • 2,003 SqFt
  • $454/SqFt
Premium
House sold in Winding Cypress
6779 Winding Cypress Dr, Naples, FL 34114
This summerwood floorplan is situated on a gorgeous lake and features 3 bedrooms, a den, 2 bathrooms, a gas heated pool and spa, and an extended 2-car garage. The home includes valuable storm-ready features such as a whole-home generator, impact-resistant windows and doors, and electric hurricane screens for added protection. Inside, the home is loaded with upgrades such as a custom built-in bar, tv stand and vanity, custom cabinetry in the primary closet, pantry, and laundry room, crown molding, tray ceiling, and a modern curated accent wall. Upgraded kitchen appliances and abundant storage complete the space. Embrace the florida lifestyle with the open-concept layout seamlessly connecting indoor and outdoor living spaces. The pool deck features a spacious covered lanai overlooking the lake with a highly desirable southwest exposure, along with an outdoor kitchen and a custom saltwater pool and spa complete with a sun ledge. No detail has been spared in the garage as well, it features a mini split, insulated door, and an extra 4 feet of length, allowing room for tools, bikes and more! Winding cypress is a natural gas community with resort-style amenities! Dine at shady palm, the onsite restaurant, or enjoy pickleball, bocce, tennis, a state-of-the-art fitness center, a resort-style pool, a community garden, and even 2 dog parks for your furry friend. This pet-friendly community allows rentals, has low fees, and boasts a prime location—convenient to marco island, 5th avenue, and i-75.
Sold - Feb 10, 2026
Winding Cypress, 6699 Pennyroyal Dr, Naples, Florida 34114, image 1
$850,000 $75K
  • 3 Beds
  • 2 Baths
  • 2,094 SqFt
  • $406/SqFt
Premium
House sold in Winding Cypress
6699 Pennyroyal Dr, Naples, FL 34114
Perfection is the only way to describe this home! It shows like a model as it has been rarely lived in since built barely three years ago. Welcome to the desirable pulte/divosta mystique model located in the popular amenity rich community of winding cypress. This waterfront property sits on a dead-end cul-de-sac and is loaded with owner and builder upgrades. It's impeccably decorated and furnished and could come turnkey providing the new owner with everything you'll ever need to begin living in paradise! The mystique’s footprint, a 3 bed, 2 bath plus optional den offers the sought after open kitchen, great room, and dining area concept with split bedrooms to ensure comfort and privacy. All the bedrooms are large with the primary suite being expansive. This home's upgrades include a whole-house generator, a hurricane impact zero-corner sliding glass door that provides a spectacular indoor/outdoor living area combining an expansive great room to the under roof lanai dining and and separate sitting section. That's just part of the lighted lanai. There's an extended paver area for you to soak in the sun while you admire the custom pool with a soothing water feature. Looking out over the beautiful lake is made easy with the option "picture window" lanai screen. Electric stormsmart metal shutters enclose the lanai providing additional peace of mind, safety and security. Additional enhancements include a chef's kitchen layout with quartz counters, a natural gas cooktop and range, upgraded cabinets with above and under lighting, expansive island with an overhang to sit three, an upgraded backsplash and a large walk-in pantry. This home also boasts upgraded tile plank flooring, custom 8' doors throughout, high-end interior plantation shutters on all windows, an expanded laundry area with cabinets, counters, a utility sink, and extra storage. The 2 car garage has an insulated overhead door. Winding cypress is optimally located just 15 minutes to olde naples, 10 minutes to both marco island and i75, and 30 minutes to rsw airport. For this price point, the amenities at winding cypress are second to none. A resident's only full service restaurant, resort pool with spa that rivals a las vegas hotel, pickleball, tennis, and bocce courts, the best fitness center around, an vibrant community center with onsite management and activities director, a dog park, community garden, and a boardwalk nature trail are just a few of the things that make winding cypress so special. With only 766 single-family homes spread out over 1250 total acres that includes 850+ acres of spectacular preserve and lakes, enjoy the peace, serenity and beautiful wildlife that few communities are able to offer.
Sold - Feb 3, 2026
Winding Cypress, 7716 Winding Cypress Dr, Naples, Florida 34114, image 1
$1,150,000 $50K
  • 3 Beds
  • 31/2 Baths
  • 2,923 SqFt
  • $393/SqFt
Premium
House sold in Winding Cypress
7716 Winding Cypress Dr, Naples, FL 34114
This home is an amazing value for winding cypress!! Once you compare, you'll agree. The stonewater model is the largest one floor living within the community. The sought after "open area concept" footprint boasts 3 expansive bedrooms including a most impressive owner's suite, 3 full baths plus and additional pool bath , a large den-flex room with glass french doors, desirable 3 car garage with additional storage racks overhead. Upgrades include an executive waterfront and private preserve view lot, pool with integral spa.
Sold - Jan 27, 2026
Winding Cypress, 7659 Jacaranda Ln, Naples, Florida 34114, image 1
$575,000 $50K
  • 2 Beds
  • 2 Baths
  • 1,544 SqFt
  • $372/SqFt
Premium
Villa sold in Winding Cypress
7659 Jacaranda Ln, Naples, FL 34114
Welcome to this charming 2-bedroom plus den, 2-bath beautiful villa in the highly desirable community of winding cypress. Built in 2017, this residence offers 1, 544 square feet of thoughtfully designed living space. The interior is light and bright, featuring easy-care tile floors in the main living areas, a breakfast bar for casual dining, and carpet in the bedrooms for added comfort. The den with french doors provides the perfect space for a home office or flex room, while the primary suite offers a private retreat with dual sinks and a walk-in shower. For added peace of mind, the home is equipped with a built-in taexx pest control system. Step outside to your private backyard oasis, complete with a sparkling inground pool — new pentair 1.5 hp superflo variable speed pool pump installed september 2025 — perfect for relaxing or entertaining guests year-round. Winding cypress is known for its resort-style amenities, including a large clubhouse, community pool with cabanas, fitness center, tennis, pickleball, and bocce courts, plus walking and biking trails surrounded by natural preserves. Ideally located in east naples, you’re just a short drive from marco island, downtown naples, shopping, dining, and world-famous gulf beaches. This home is the perfect combination of comfort, convenience, and community living.
Sold - Jan 27, 2026
Winding Cypress, 7815 Jacaranda Ln, Naples, Florida 34114, image 1
$620,000 $10K
  • 2 Beds
  • 2 Baths
  • 1,574 SqFt
  • $394/SqFt
Premium
Villa sold in Winding Cypress
7815 Jacaranda Ln, Naples, FL 34114
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.
Sold - Jan 16, 2026
Winding Cypress, 6856 Winding Cypress Dr, Naples, Florida 34114, image 1
$858,500 $41K
  • 3 Beds
  • 2 Baths
  • 2,084 SqFt
  • $412/SqFt
Premium
House sold in Winding Cypress
6856 Winding Cypress Dr, Naples, FL 34114
Sense the comfort and beauty of this magnificent home the minute you enter the foyer and see the view out to the inviting pool and spa. This 3 bedroom, plus separate den, great room floor-plan is perfect for entertaining or just a lovely place to call home. These original owners have impeccably maintained the home making it feel brand new. Built in 2021 it boasts a chef's delight kitchen with stainless steel appliances, center island and breakfast bar, natural gas cooktop/range, pull-out drawers, quartz counter-tops, recessed and pendant lighting, and more! The cook of the house will love it! The great room and dining area are adjacent to the kitchen. An extra plus is the den with double raised paneled doors and a window for natural light. The main bedroom is approx 14' x 16' and sits on its own separate wing from the other bedrooms. You will love the main bathroom with its 9' x 3'3" tiled shower with multiple shower heads, dual sinks, quartz counter-tops, walk-in closet and separate toilet closet. It is very spacious! Another plus to this home is the zero corner doors off the great room extending your great room out to your covered lanai. The extended lanai is all plumbed for the outdoor kitchen of your liking. Enjoy the florida sunshine in your pool and spa in the privacy of your own backyard which backs up to a preserve. Some of the other features of this lovely home are a 9' x 7' laundry room with cabinets, folding counters, sink, and storage closet, 2 car garage with a 4 foot extension and epoxy flooring, and impact resistant windows and sliders. The home boasts beautiful tile and light colors throughout. The white plantation shutters in many of the rooms add to the character of the home. Winding cypress is a newer, well maintained community offering an abundance of amenities. You will find a resort-style pool and separate spa, cabanas, shady palm cafe, pickleball, bocce, tennis, state-of-the-art fitness center, community garden and a dog park for your fur babies. Winding cypress sits in a great location in collier county, less than 30 minutes from beautiful 5th avenue in naples, and the white sand beaches of marco island. This home is a must see!
Sold - Dec 15, 2025
Winding Cypress, 7355 Mockingbird Ct, Naples, Florida 34114, image 1
$875,000 $25K
  • 3 Beds
  • 2 Baths
  • 2,198 SqFt
  • $398/SqFt
Premium
House sold in Winding Cypress
7355 Mockingbird Ct, Naples, FL 34114
This extended summerwood floorplan is situated on a private street and features 3 bedrooms, a den, 2 bathrooms, a gas heated pool and spa, and an extended 2-car garage. The home includes valuable storm-ready features such as a whole-home generator, impact-resistant windows and doors, and electric hurricane screens for added protection. The open-concept layout seamlessly connects indoor and outdoor living spaces. The pool deck features a large covered lanai ideal for enjoying sunset views over the lake and preplumb of electric, gas, and water providing the option to add a built-in outdoor kitchen. Additional upgrades include tile flooring throughout, plantation shutters, trey ceiling, custom screened entryway, widened walkway & driveway and generous storage space. Turnkey furnishings are available with the sale, some exclusions. Winding cypress is a natural gas community with resort-style amenities! Dine at shady palm, the onsite restaurant, or enjoy pickleball, bocce, tennis, a state-of-the-art fitness center, a resort-style pool, a community garden, and even 2 dog parks for your furry friend. This pet-friendly community allows rentals, has low fees, and boasts a prime location—convenient to marco island, 5th avenue, and i-75.
Sold - Dec 5, 2025
Winding Cypress, 7370 Mockingbird Ct, Naples, Florida 34114, image 1
$645,000 $31K
  • 2 Beds
  • 2 Baths
  • 1,805 SqFt
  • $357/SqFt
Premium
House sold in Winding Cypress
7370 Mockingbird Ct, Naples, FL 34114
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!
Sold - Nov 21, 2025
Winding Cypress, 6839 Winding Cypress Dr, Naples, Florida 34114, image 1
$1,260,000 $90K
  • 3 Beds
  • 3 Baths
  • 2,515 SqFt
  • $501/SqFt
Premium
House sold in Winding Cypress
6839 Winding Cypress Dr, Naples, FL 34114
This pinnacle floorplan is situated on the largest lake in the neighborhood and features 3 bedrooms, a den, 3 bathrooms, a pool and spa, and a 3-car garage. The open-concept layout includes a dramatic zero-corner slider that seamlessly connects indoor and outdoor living spaces. Peace of mind comes with a whole-home generator and impact-resistant windows and doors. Inside, you'll find extensive upgrades throughout. The kitchen boasts built-in appliances and a spacious island—perfect for entertaining. Additional highlights include soaring tray ceilings, crown molding in the den and entry, and tile flooring throughout. The air-conditioned 3-car (extended by 4 ft) garage offers ample storage with custom shelving and a built-in workbench. Outdoors, the heated pool and spa are powered by both gas and solar, a smart, energy-efficient combination. The expansive outdoor kitchen, hurricane screens for added protection, and generous deck space create an ideal setting for sunset views. Other exterior features include lush landscaping with low-voltage lighting, an extra-wide driveway (recently sealed), a custom designed screened-in entryway, and panoramic wide lake views. Winding cypress is a natural gas community with resort-style amenities! Dine at shady palm, the onsite restaurant, or enjoy pickleball, bocce, tennis, a state-of-the-art fitness center, a resort-style pool, a community garden, and even 2 dog parks for your furry friend. This pet-friendly community allows rentals, has low fees, and boasts a prime location—convenient to marco island, 5th avenue, and i-75.
Sold - Nov 17, 2025
Winding Cypress, 6767 Pennyroyal Dr, Naples, Florida 34114, image 1
$990,000 $109K
  • 3 Beds
  • 2 Baths
  • 2,185 SqFt
  • $453/SqFt
Premium
House sold in Winding Cypress
6767 Pennyroyal Dr, Naples, FL 34114
Wow! This beautifully designed and meticulously maintained home checks all the right boxes. Featuring the highly desirable summerwood floor plan with great room extension, it is perfect for entertaining or simply relaxing at home after a nice day out in beautiful naples, fl. The kitchen features upgraded appliances, quartz countertops, an oversized island and walk-in pantry. The two guest bedrooms provide enough room for guests. The office/den can easily serve as a 4th bedroom if desired. Other interior features include high-grade porcelain tile throughout, a laundry/utility room with plenty of storage and natural gas for cooking, heated water and clothes drying. Exterior upgrades abound with a one-of-a-kind extended lanai with custom pavers and a built-in outdoor kitchen. There is plenty of space for outdoor gatherings, cookouts, an afternoon nap, a dip in the pool or just taking in some florida sunshine. Looking through the huge portrait "no-see" lanai screen is one of the very best long water views in the entire community. The view is simply gorgeous, inspiring "wows" from all. The driveway and side walkway are extended. There is over $100k in upgrades to this magnificent home. Just pack your bags and head on down to enjoy our very special slice of tropical paradise. Worried about maintenance and insurance costs, and/or storms? Newer construction (2021) negates a large future roof replacement cost for some time. And a newer a/c system should provide many more years of solid service. Hurricane impact doors and windows are throughout providing for great energy efficiency and home protection. Also, the lot of this property is elevated. It is not in a mandatory flood insurance zone. And there is a whole home gas generator too should the need ever arise. All aforementioned should assist in obtaining lower insurance premiums and keep maintenance costs down. This home offers easy peasy and worry-free living by any measure. To top it all off, this sensational home resides in the highly prized community of winding cypress. An onsite restaurant, modern fitness center, community pool and a full calendar of social gatherings with some of the best naples residents around are a nice walk, bike or golf cart ride away. Also, located conveniently between downtown naples and marco island, opportunities to visit some of our finest beaches, shopping and dining locations are just minutes away. Great home. (check.) great view. (check.) great community. (check.) great location. (check.) this property checks all the right boxes for the time of your life in beautiful naples, fl.
Sold - Nov 17, 2025
Winding Cypress, 7642 Jacaranda Ln, Naples, Florida 34114, image 1
$455,000 $82K
  • 2 Beds
  • 2 Baths
  • 1,554 SqFt
  • $293/SqFt
Premium
Villa sold in Winding Cypress
7642 Jacaranda Ln, Naples, FL 34114
Tucked away treasure in winding cypress- step into a slice of serenity with this charming attached villa, nestled in one of the most peaceful corners of naples. Unlike the typical coastal designs so common in the area, this home offers a more rustic warmth—perfect for those who appreciate natural textures, cozy finishes, and a relaxed, grounded lifestyle. With 2 bedrooms, a versatile den, 2 full bathrooms, and a 2-car garage, this villa checks all the boxes for comfort and functionality. The open layout is inviting yet intimate, ideal for both quiet evenings and casual entertaining. The kitchen is equipped with natural gas—a rare find that’s perfect for those who love to cook and value energy efficiency. Step outside to the screened-in lanai where mornings are best spent with coffee in hand, surrounded by the sounds of nature and a view of your private backyard oasis. An extended outdoor patio provides the perfect space to unwind under the stars. Located within the gated, master-planned community of winding cypress, this home offers so much more than just a beautiful space—it’s part of a vibrant lifestyle. Developed by divosta homes and surrounded by over 800 acres of natural preserves and 80 acres of lakes, winding cypress is a nature lover’s dream, tucked beside the picayune strand forest. Residents enjoy top-tier amenities including the shady palm café, a stunning resort-style waterfall pool, clubhouse, fitness center, tennis, bocce, and pickleball courts, and scenic walking trails. Plus, you’re just minutes from shopping and dining at tamiami crossing and freedom square. If you’ve been waiting for a home that feels like a true escape—but still close to it all—7642 jacaranda ln is calling.
Sold - Nov 14, 2025
Winding Cypress, 7049 Live Oak Dr, Naples, Florida 34114, image 1
$800,000 $25K
  • 3 Beds
  • 2 Baths
  • 2,230 SqFt
  • $359/SqFt
Premium
House sold in Winding Cypress
7049 Live Oak Dr, Naples, FL 34114
Enjoy resort-style living in this winding cypress community near 5th avenue and marco island. This home features a private pool, sunroom and the community’s largest covered lanai. Designed for year-round comfort, it offers a new air-conditioning system with additional cooling in the primary suite, impact glass throughout, and natural gas for efficiency and gourmet cooking. Inside, the oversized primary shower, upgraded tile and premium counters elevate everyday living. Set on a quiet street just a short distance to the club at winding cypress, you’ll have dining, pickleball, tennis, bocce and a resort pool at your fingertips. Mature landscaping and preserve views ensure privacy while the open layout makes entertaining effortless. With nearly 2, 300 square feet of living space, this residence blends comfort, convenience and the best of the florida lifestyle with resort living just around the corner.
Sold - Nov 6, 2025
Winding Cypress, 6787 Winding Cypress Dr, Naples, Florida 34114, image 1
$710,000 $10K
  • 2 Beds
  • 2 Baths
  • 1,654 SqFt
  • $429/SqFt
Premium
House sold in Winding Cypress
6787 Winding Cypress Dr, Naples, FL 34114
Step inside through a welcoming entryway and discover an open-concept floor plan. The heart of the home is the great room with tray ceiling and crown moldings, the modern kitchen, beautifully appointed with granite countertops, sleek stainless-steel appliances, and a generous center island suited for both everyday living and effortless entertaining. The primary suite offers a peaceful retreat with a walk-in closet, double vanity, walk-in shower. This beautifully cared-for home offers a rare opportunity to enjoy an elevated lifestyle in a sought-after winding cypress community—
Sold - Oct 30, 2025
Winding Cypress, 7235 W Clamshell Ln, Naples, Florida 34114, image 1
$1,000,000
  • 3 Beds
  • 3 Baths
  • 2,512 SqFt
  • $398/SqFt
Premium
House sold in Winding Cypress
7235 W Clamshell Ln, Naples, FL 34114
Location, location! This meticulously maintained and decorated pinnacle model located on a corner lot with privacy on both sides including a lake and wooded area view is unique! Conveniently located within walking distance to clubhouse! The home features 3 bedrooms plus a den, 3 full baths and 3 car garage in this highly sought after natural gas community of winding cypress! This large lanai features a custom gas outdoor kitchen and a beautiful custom pool and spa! A must see to be appreciated! Home protection includes impact windows, sliders and electric shutters winding cypress offers a beautiful clubhouse, resort style pool and spa and waterfall feature! In addition to pickleball, tennis, bocce, state of the art fitness center and on-site director for classes! A dog park, community garden and plenty of biking and walking trails to enjoy!
1 - 29 of 54 Results

Similar Communities & Listings

Results 3 of 27
Esplanade At Hacienda Lakes, 8209 W Lucello Ter, Naples, Florida 34114, image 1
$650,000
  • 2 Beds
  • 2 Baths
  • 1,558 SqFt
  • $417/SqFt
House for sale in Esplanade At Hacienda Lakes
8209 W Lucello Ter, Naples, FL 34114
Private, peaceful setting at the end of cul-de sac sits this brand new furnished villa with screened-in lania over looking the preserve. One story living, hassle free lifestyle, with 2 bedrooms, den/office, 2 baths, and 2- car garage. The decor is sleek with tones of grey and white contemporary lighting and fixtures gives a high energy “vibe”. Enjoy the resort lifestyle here at esplanade of hacienda lakes which includes 6, 500 sq. Ft. Club house, 24/7 fitness gym, circular resistance pool and spectacular lap pool, hot tub, fire-pit , umbrellas by the pool, and music, pickleball, tennis, bocce courts , playground dog park. Fun social events social & card room plus billiards. Everyone is raving about the amazing “over the top events “ the club put on.
Esplanade At Hacienda Lakes, 8438 Volaro Way, Naples, Florida 34114, image 1
$675,000
  • 2 Beds
  • 2 Baths
  • 1,680 SqFt
  • $402/SqFt
House for sale in Esplanade At Hacienda Lakes
8438 Volaro Way, Naples, FL 34114
Thoughtfully upgraded and offered turnkey furnished, this move-in ready 2-bedroom plus den, 2-bath home delivers the easy, low-maintenance lifestyle buyers are looking for in esplanade at hacienda lakes. Tucked at the end of a quiet cul-de-sac with peaceful lake views and southern exposure, the setting is just as appealing as the home itself. Designed with both style and practicality in mind, the residence features hurricane impact glass windows and doors for year-round protection and peace of mind. Inside, architectural details like wood coffered and tray ceilings add warmth and character, while plantation shutters and plank-style flooring create a clean, cohesive look throughout. The open-concept layout flows comfortably for everyday living and entertaining. The kitchen is well equipped with ge café appliances, quartz countertops, a built-in wine fridge, and generous cabinet space. The adjoining living area feels open yet inviting, with custom ceiling detail adding visual interest without overwhelming the space. The den offers flexibility for a home office or guest overflow, while the owner’s suite provides a quiet retreat with a bay window sitting area, tray ceiling, and a spacious ensuite bath. Outdoor living is where this home really shines. The screened lanai features a summer kitchen and looks out over the lake, creating the perfect backdrop for relaxing evenings and entertaining. Additional highlights include an extended two-car garage with extra storage space. Residents of esplanade at hacienda lakes enjoy a true resort-style lifestyle with a clubhouse, pool, fitness center, tennis, pickleball, and an active social calendar—all just minutes from naples beaches, dining, and shopping. A well-maintained home, a private setting, and a community that offers it all—this is naples living made simple.
Azure At Hacienda Lakes, 9209 N Cayman Dr, Naples, Florida 34114, image 1
$599,000
  • 2 Beds
  • 22/2 Baths
  • 1,573 SqFt
  • $381/SqFt
Villa for sale in Azure At Hacienda Lakes
9209 N Cayman Dr, Naples, FL 34114
Welcome to 9209 cayman drive — effortless living in azure at hacienda lakes this charming 2-bedroom plus den villa offers breathtaking water views and an open, airy layout bathed in natural light. Plantation shutters throughout lend a classic florida elegance, while the living area’s electric fireplace adds a cozy, inviting touch. The well-appointed kitchen features a gas cooktop and quartz countertops , and the cozy lanai is the perfect spot to unwind with tranquil water views or entertain friends. As a resident of azure at hacienda lakes, you’ll enjoy access to a clubhouse, fitness center, tennis and pickleball courts, a resort-style pool and spa, and so much more. And the location couldn’t be better — just minutes from 5th avenue’s world-renowned restaurants and boutique shops, naples’ white sandy beaches, the naples botanical gardens, hamilton harbor yacht club, and the vibrant bayshore arts district.
1 - 3 of 27 Results

Subdivision Amenities

Bike And Jog Path
Bocce Court
Business Center
Cabana
Clubhouse
Community Room
Dog Park
Fitness Center
Hobby Room
Internet Access
Library
Park
Pickleball
Play Area
Pool
Private Membership
Restaurant
Shuffleboard Court
Sidewalk
Spa/Hot Tub
Streetlight
Tennis Court(s)
Underground Utility
Barbecue
Bike And Jog Path
Bocce Court
Clubhouse

Frequently Asked Questions

Comparable & Nearby Subdivisions

ComparableNearby

Schools

Scores

Walk Score®
Car-Dependent. Almost all errands require a car.
0

100
Transit Score®
Minimal Transit. It is possible to get on a bus.
0

100
Bike Score®
Somewhat Bikeable. Minimal bike infrastructure.
29

100
Sound Score®
Very loud.
0

100

Naples
Premium
Premium Homes & Condos

Related Searches in Naples, FL

Map
Filters
HomeSearchHome ValueProfile