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$700,000
3 Beds ⋅ 2 Baths ⋅ 2026015957 MLS
Welcome to your beautiful Summerwood floor plan home ... Enjoy Florida living in this IMPECCABLY maintained STUNNING home featuring 3 bedrooms, den/sitting room, 2 full bathrooms. Enjoy a spacious living room which is open to the gourmet kitchen featuring a NATURAL GAS range, a large pantry and an island, with ample prep space, for gathering with friends and family. There is tile flooring throughout! Step outside to the a very sought after outdoor living life with the EXTENDED LANAI!! On the Lanai is a built in kitchen for all of your entertaining needs! The home has a FULL HOUSE GENERATOR & IMPACT RESISTENCE WINDOWS. The window and sliding door to the Lanai are storm protected with a STORM SMART SCREEN!! The primary suite is a private retreat with a walk-in closet, dual-sink vanity, and a large step in with glass shower. The dining room offers tranquil views of the expansive lanai. A 2 car garage has a huge extra space for storage. The brick-paver driveway provides ample parking. Set on a beautiful homesite, this residence blends privacy with proximity to the best of South Naples. The subdivision hosts an amazing club, with all residents enjoying access to the community’s restaurant, resort style pool, exercise room/gym, tennis, bocce, and pickleball courts. Experience unparalleled luxury, comfort, and location here, an absolute must-see!

7022 Live Oak DR, Naples
$692,500
2 Beds ⋅ 2 Baths ⋅ 223069737 MLS
Nestled within Naples' scenic Winding Cypress community, this 2-bedroom plus den, 2-bathroom home, built in 2016, embodies the quintessential Florida lifestyle. The interior boasts coffered ceilings, impact-resistant windows and doors, and an extended kitchen island - a chef's dream! Natural gas availability enhances cooking and heating efficiency, while the primary bedroom features a charming beadboard accent wall. Crown molding adds an elegant finish throughout, and the master bath boasts double sinks for added luxury. Tile floors! Practical features include a golf cart parking area in the garage and a 13KW Generac generator, ensuring uninterrupted comfort during power outages. Step into the backyard oasis, where a heated pool beckons beneath a vast screen enclosure, ideal for year-round enjoyment. Winding Cypress offers an array of amenities, including a community restaurant, pool, scenic walking trails, pickleball and tennis courts, all enhancing your quality of life. It is time to enjoy all that SWFL has to offer!

7244 Live Oak DR, Naples
$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
$690,000
2 Beds ⋅ 2 Baths ⋅ 224041080 MLS
Rare opportunity to own the crème de la crème villa in Winding Cypress. This pool home features 2 bedrooms, plus den, 2 bathrooms and a 2 car garage and is being offered turnkey furnished! The property boasts exceptional upgrades, including impact windows, a whole-house generator, crown molding, tile throughout, electric hurricane screens, upgraded appliances, closet systems throughout and so much more. The outdoor oasis features a gorgeous outdoor kitchen, remote control awning for additional shade, and arguably one of the best lake views in all of Winding Cypress! Winding Cypress has amenities galore! Enjoy dining at Shady Palm, the onsite restaurant, play pickleball, bocce, tennis, workout in the state of the art fitness center or lounge by the resort style pool, garden at the community garden, or take fido to the dog park! Winding Cypress is pet friendly, allows rentals, has low fees and is centrally located between Marco Island, 5th Ave, & I75 making it an ideal location!

7793 Jacaranda LN, Naples
$675,000
2 Beds ⋅ 2 Baths ⋅ 225025806 MLS
This move in ready furnished Winding Cypress Serenity 2 bedroom plus den Attached Villa with POOL & SPA is a unique quality find. This Serenity floor plan with the kitchen conveniently tucked away behind peninsula island allows for optimal entertaining space. Kitchen features Quartz countertops, natural gas range & SS appliances. Other high quality highlights include, plantation shutters, crown molding, Lutron shades at slider, recessed & under cabinet lighting, upgraded lighted mirrors in both baths, laundry room cabinets & sink, privacy door for guest suite, pull down attic stairs in garage, wide, driveway, pest control piping in the walls, Storm Smart electric hurricane shades on lanai and landscaped lighting around lanai. Slight pie shape lot and lush landscaping offers extra privacy for lanai and pool area. Located in sought after Winding Cypress Community with it's rich amenities including a resort style pool, restaurant/bar, fire pit, fitness center, outdoor yoga deck, pickle-ball, tennis, bocce ball, community garden, dog park, and a nature trail boardwalk that wanders through protected natural preserves. Centrally located between Marco Island and 5th Ave allows easy access to the surrounding areas beautiful beaches, restaurants and entertainment.

7742 Jacaranda LN, Naples
$675,000
2 Beds ⋅ 2 Baths ⋅ 224016819 MLS
This stunning lake view villa pool home with 2 car garage in the low fee community of Winding Cypress offers a luxurious lifestyle with its serene lake views and exceptional amenities. Home features include: Premium Wide Lake View: Step out onto your patio and soak in the breathtaking vistas of the tranquil lake. Whether it’s morning coffee or evening sunsets, this view will captivate you. Tile on the Diagonal: The elegant diagonal tile flooring flows seamlessly throughout the home, adding a touch of sophistication. Recessed and Cabinet Lighting: Illuminate your living spaces with style. Whether you’re hosting a dinner party or enjoying a quiet evening, the lighting sets the mood just right. Heated Pool: Take a refreshing dip in the heated pool year-round. Imagine relaxing by the water, surrounded by lush greenery and the soothing sounds of nature. Trey Ceiling: The main living area features a trey ceiling, adding architectural interest and a sense of spaciousness. White Cabinetry Throughout: The timeless white cabinetry complements any decor and keeps the home bright and airy. Gorgeous Sunsets: As the day winds down, enjoy spectacular sunsets from your own backyard oasis. New Quartz Countertops: The kitchen, master bath, and guest bath have been upgraded with beautiful quartz countertops. The sinks and faucets are also new. New Tile Plank: The master bedroom, master bath, and guest bedroom now feature stylish tile plank flooring. LED Lanai Lights: Illuminate your pool area for evening gatherings and relaxation. Custom Garage Shelving: Organize your garage space efficiently. New Dishwasher and Clothes Washer: Modern appliances for your convenience. New Pool Cage Screens: Fresh screens enhance the pool area. Motorized Sunscreen for Lanai: Control sunlight and create a comfortable outdoor space. Whole House Water Filter System: Enjoy pure filtered throughout your home. Winding cypress features include: Shady Palm Restaurant: Onsite dining for residents. Treat yourself to delicious meals without leaving the community. Pickleball, Bocce, Tennis: Stay active and social. Engage in friendly matches with neighbors and friends. State-of-the-Art Fitness Center: Achieve your fitness goals. Whether it’s cardio, strength training, or yoga, the fitness center has you covered. Resort-Style Pool: Lounge by the pool, soak up the sun, and enjoy the Florida weather. Community Garden: Green thumbs welcome! If you love gardening, this is the place to nurture your plants. Dog Park: Fido-approved fun! Let your furry friend run and play in the designated dog park. Location: Centrally situated between Marco Island, 5th Ave, and I75, this home offers convenience and easy access to all that Naples, Florida, has to offer. Don’t miss out on this exceptional opportunity! Contact your agent today to schedule a viewing.

7627 Jacaranda LN, 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
$650,000
3 Beds ⋅ 2 Baths ⋅ 224004192 MLS
Best-Valued Single-Family Home with Quality Finishes and Resort-Style Amenities in Winding Cypress! This beautifully crafted 3-bedroom, 2-bathroom home, complete with a private office, is the best-valued single-family residence in the desirable Winding Cypress community. Thoughtfully designed with quality finishes, this home features tile flooring throughout, plantation shutters, crown molding, high-end granite countertops and stainless-steel appliances with huge island/breakfast bar in a gourmet kitchen, equipped with natural gas cooking. The separate dining area offers an inviting space for meals and entertaining. Outside, enjoy the private, screened-in lanai surrounded by lush tropical gardens and a raised herb garden. This home is equipped with full hurricane protection on all windows and doors, including Storm Smart hurricane screens on the lanai, ensuring peace of mind in stormy weather. The Sellers have shared that their home has never incurred damage from any of the recent storms. Pre-inspected and move-in ready, with low HOA fees, this home is a true value. Winding Cypress is an amenity-rich, pet-friendly community, featuring a resort-style pool and spa, outdoor bar and grill, tennis, pickleball, bocce courts, and two gated, off-leash dog parks. With a vibrant social calendar, there are endless ways to connect and enjoy the neighborhood. Conveniently located near downtown Naples, with its beautiful beaches, dining, and entertainment, as well as the scenic Marco Island coastline, this home blends luxury, security, and community lifestyle. Don’t miss your chance to make this tropical retreat your own!

7267 Live Oak DR, Naples
$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
$640,000
3 Beds ⋅ 2 Baths ⋅ 224023172 MLS
This beautiful Winding Cypress Villa home offers 1,554 sq. ft. of comfort has 3 bedrooms, 2 full bathrooms, Screened in lanai, salt water pool and spa and a 2-car garage also has lots of upgrades. The list is attached in the Supplements section. Located just minutes to Marco Island and downtown Naples, the community features a clubhouse with a resort style pool, spa, state of the art fitness center, very nice restaurant, tennis, bocce and Pickle Ball of course. Shopping and restaurants are nearby. The 800+ acre preserve with a boardwalk adds to the outdoor appeal. Ideal for those seeking a stylish home in a prime location. Upgrades include: Hurricane windows and doors through out including Lanai sliders, automated Hurricane shutter's on lanai,A.C Unit in garage, Framed mirror's in bathrooms,new pool heater in 2/24, plantation shutter's thru out,full storm door with screen on front door,keyless entry on front door,UV lights in HVAC.

7175 Live Oak DR, Naples
$635,000
2 Beds ⋅ 2 Baths ⋅ 226009024 MLS
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.

7717 Jacaranda LN, Naples
$635,000
2 Beds ⋅ 2 Baths ⋅ 225059100 MLS
On a premium oversized lot, this beautifully upgraded villa offers one of the most stunning sunset water views in all of Winding Cypress. The extended screened lanai features a panoramic no-see-um screen, heated saltwater pool, and a fully equipped outdoor kitchen with a five-burner Bull Grill, stainless steel sink, premium refrigerator, and a 42-inch lighted vent hood, an entertainer’s dream and the ultimate space to relax and take in the view. Hurricane-impact windows and doors throughout the home provide peace of mind, while a stylish glass entry door, two ceiling-mounted garage storage racks, and attic access in the garage and primary closet add smart functionality. Inside, the open floor plan is elegant and inviting with diagonal tile flooring, plantation shutters and upgraded LED recessed lighting. The home includes two furnished bedrooms plus a flexible den with 8-foot French doors and a new Murphy bed, ideal for guests or a home office. The gourmet kitchen features granite countertops, a tasteful tiled backsplash, staggered cabinetry with under- and over-cabinet lighting, and bar seating. California Closets have been added to the primary suite and kitchen pantry for optimal organization. This smart home includes a Nest thermostat, video doorbell, cameras at garage and lanai, Nest Protect smoke and CO2 detectors and Leviton Wi-Fi lighting switches. Gently lived in as a pet-free, smoke-free seasonal home, it shows like new. Winding Cypress offers over 800 acres of natural preserves, a resort-style clubhouse with a heated pool, restaurant, fitness center, white sand beach, tennis and pickleball courts, dog park and scenic nature trails. With low HOA fees and a natural gas community, all just 25 minutes to 5th Avenue, 20 minutes to Marco Island and five minutes to major shopping, this home blends luxury, peace of mind and lifestyle in one incredible package.

7773 Jacaranda LN, Naples
$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
$625,000
3 Beds ⋅ 2 Baths ⋅ 225074768 MLS
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.

7057 Live Oak DR, Naples
$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
$615,000
2 Beds ⋅ 2 Baths ⋅ 226005934 MLS
Sunset water views stretch across a sparkling long lake from your private pool and spa, creating a breathtaking backdrop for everyday living and entertaining from the fully equipped natural gas outdoor kitchen. This beautifully maintained home stands out with major recent upgrades including a brand new AC system (2026), new washer and dryer, new hot water heater, and new carpet, offering peace of mind and allowing the home to live comfortably and effortlessly from day one. The open floor plan feels light, bright, and inviting with updated flooring and elegant quartz and granite surfaces throughout. The thoughtfully designed layout offers two spacious bedrooms plus a flexible den with an alcove ideal for adding a closet, making it perfect for guests, a home office, or additional sleeping space. The gourmet kitchen blends style and function with granite countertops, a tasteful tiled backsplash, staggered cabinetry, and bar seating for casual gatherings, while natural gas service and ceiling-mounted garage storage racks add everyday convenience. Gently lived in as a pet-free, smoke-free seasonal residence, the property shows like new. Located in the resort-style community of Winding Cypress, residents enjoy more than 800 acres of preserved natural landscape and exceptional amenities including a clubhouse with a heated pool, on-site restaurant, fitness center, white sand beach, tennis and pickleball courts, dog park, and scenic nature trails, all with low HOA fees and an ideal location just 25 minutes to Fifth Avenue South, 20 minutes to Marco Island, and minutes to major shopping and dining, creating a lifestyle that blends luxury, convenience, and unforgettable views.

7639 Jacaranda LN, Naples
$615,000
2 Beds ⋅ 2 Baths ⋅ 224025546 MLS
BIG PRICE REDUCTION! THIS IS ONE OF THE LOWEST PRICED VILLA POOL HOME! Discover this stunning 3-bedroom, 2-bathroom villa with a 2-car garage and a luxurious gas heated pool that is ideally situated on a premium pie-shaped lot adjacent to nature preserve and near to the vibrant Winding Cypress Amenity Center is the perfect place to make your own paradise. The flex room offers endless possibilities as a third bedroom or as a home office/den. The Serenity Model offers the perfect blend of charm and sophistication, whether you seek a year-round haven or a seasonal escape to enjoy Florida's renowned lifestyle. Indulge in effortless entertaining as the seamless open floor plan leads you to a covered lanai and expansive brick paver pool deck that gazes out onto a serene nature preserve. Witness breathtaking sunsets that paint the sky in hues of warmth while serenaded by the harmonious symphony of nature within your private screened enclosure in the prestigious Winding Cypress community. This home has features including stainless-steel appliances, elegant granite countertops, a beautifully tiled backsplash in the kitchen, and 20" ceramic tile flooring throughout the main living spaces. Noteworthy accents such as plantation shutters, rich wood flooring in the den, accordion hurricane shutters, an electric rolldown hurricane shutter at the lanai, and a host of other upscale finishes. Nestled within a secure, amenity-rich enclave, residents enjoy access to a lavish Community Center, overseen by a full-time activities’ director, offering an array of recreational facilities from card/game rooms and a library to a poolside bar and restaurant. Stay active with a state-of-the-art gym, outdoor Yoga and movement studios, group exercise classes, a resort-style pool with a dedicated lap lane, inviting fire pits, dog parks for both large and small dogs, illuminated tennis courts, pickleball and bocce courts, and sprawling lakes and nature preserves spanning nearly 800 acres, providing boundless walking and riding trails for outdoor enthusiasts. Perfectly positioned in proximity to upscale shopping, dining venues, the sandy beaches of Naples and nearby Marco Island, the ambiance of downtown Naples along 5th Avenue & 3rd Street, as well as convenient access to medical facilities, educational institutions, places of worship, I-75, RSW International Airport, and the breathtaking wonders of the Florida Everglades.

7113 Live Oak DR, Naples
$610,000
2 Beds ⋅ 2 Baths ⋅ 224001602 MLS
Fully furnished and ready to move in. Built in 2019, this light, bright, fresh villa is ideal for seasonal or permanent Florida living. Upgraded cabinets, countertops and flooring. Bright, light cabinets, paint and flooring for more contemporary design. Lush, tropical landscaping with a private and peaceful backyard just off the screened lanai. Split bedroom plan for privacy when you have family visiting. Large walk-in shower in primary bath. Great clubhouse with restaurant and community pool for gracious in-community living. Close to Marco Island and a short drive to Naples beaches provides the best of all worlds, private, quiet living and quick access to all the fun, sun and amenities Southwest Florida is known for.

7694 Jacaranda LN, Naples
$605,000
2 Beds ⋅ 2 Baths ⋅ 224015477 MLS
Beautiful, like-new furnished single family attached villa with long lake view. Built in 2019, this move-in ready Serenity floor plan includes two bedrooms plus den, two bathrooms, upgraded tile floors, extended lanai with Storm Smart hurricane screens, hurricane impact windows/doors throughout. Southern exposure. Natural gas community. Quartz countertops, stainless appliances, plantation shutters. A highly sought after community, Winding Cypress has over 800 acres of lakes and preserves, resort-style pool and spa, restaurant, tennis, bocce & pickleball, fire pit, state-of-the-art fitness center, nature boardwalk, small & large dog parks. Restaurants and shopping nearby. Enjoy resort-style living at its best in this lovely home.

7790 Jacaranda LN, Naples
$605,000
2 Beds ⋅ 2 Baths ⋅ 223044659 MLS
Stunning Serenity villa in Winding Cypress for sale! This home features 2 bedrooms plus a den, 2 bathrooms, with a 2 car garage - and some of the furniture is negotiable. This light an airy villa features tile floor throughout, recessed lighting, upgraded cabinets and counters in all areas, 8 foot doors, gorgeous landscaping, room for a pool and so much more! Winding Cypress has amenities galore! Enjoy dining at Shady Palm, the onsite restaurant, play pickleball, bocce, tennis, workout in the state of the art fitness center or lounge by the resort style pool, garden at the community garden, or take fido to the dog park! Winding Cypress is pet friendly, allows rentals, has low fees and is centrally located between Marco Island, 5th Ave, & I75 making it an ideal location!

7646 Jacaranda LN, Naples
$600,000
2 Beds ⋅ 2 Baths ⋅ 224008394 MLS
Villa w/ PEACEFUL view! Attached villa Serenity floor plan that lives like a single family home w/ luxury features throughout- tray ceilings, 18" tile flooring, quartz countertops, custom tile backsplash in kitchen, convection double oven, designer light fixtures, high-end cabinetry, crown molding, French door entry to den, frameless glass enclosure in master shower, custom built heated pool, & a built-in Generac generator system & transferrable home warranty. The outdoor living space is the GEM of the home- massive pool deck, solar & gas heated pool, large covered area w/ enough room for dining set & lounging area, & having a serene lake view. Meticulously maintained & updated w/ new accordion hurricane shutters, whole home water filtration system for optimum water quality, & freshly painted exterior. The roof was just power washed this past summer. This natural gas community has over 800 acres of lakes & preserve, resort- style pool, fire pit, community rm, restaurant, tennis, bocce ball, pickleball, cabanas, yoga deck, fitness facility, locker rooms, full time activities director, catering room, catering kitchen, activity room, nature board walk, garden, small & large dog parks.

7574 Jacaranda LN, Naples
$600,000
2 Beds ⋅ 2 Baths ⋅ 223074303 MLS
PRISTINE LIKE NEW CONDITION! This two bedroom, two bath plus den and two car garage attached villa home built in 2017 is offered FULLY FURNISHED and features a roomy 1,542 air conditioned living space, kitchen with quartz counter tops, tile back-splash, breakfast bar, stainless steel appliances, 42" upper cabinets, natural gas range, plantation shutters, large block tile in the main living areas and baths, plush carpeted bedrooms, recessed lighting, modern ceiling fans and light fixtures, tray ceiling in the primary bedroom with frameless shower door and double sink vanity in it's en suite bath, laundry room with wash basin, manual shutters, a private screened lanai and brick paver driveway. Awesome casual living at Winding Cypress offers an impressive clubhouse, resort-style pool, spa, fitness center, tennis, pickleball, bocce and pool-side full service restaurant. The community is comprised of 1,100 acres with 800 acres of preserve and lakes. Residents enjoy an untouched natural setting, from the boardwalk, pavilion and bird wading overlook, to the linear park and community garden. Just minutes to Naples and Marco Island beaches, 5th Ave and RSW Airport!

7630 Jacaranda LN, Naples
$599,900
2 Beds ⋅ 2 Baths ⋅ 226002887 MLS
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

7255 Live Oak DR, Naples
$595,000
2 Beds ⋅ 2 Baths ⋅ 225072028 MLS
This charming model is the perfect fit featuring an inviting open-floor concept where natural light streams through the windows. The kitchen boasts granite counters, stainless appliances and a center island and extra storage for everyday use and easy entertaining. The pantry closet has plenty of space for all of your staple goods. Tile floors are throughout much of the space. There's a den/flex room with french doors that can be used as an additional bedroom when needed or office, hobby or quiet sitting room. Additional guest bedroom and bathroom with combined tub and shower and granite topped vanity offers privacy for your family and guests. The laundry room features a spacious storage area with shelving for your all your supplies. There are storage racks in the two car garage to house your coolers for the beach. Be sure to take time to relax and enjoy your morning beverage and the beautiful sunsets on the screened lanai that overlooks the OVERSIZED lot with mature landscaping complete with an outdoor kitchen with grill, sink, and fridge for your convenience. Winding Cypress is a sought after, gated community and is appreciated for its active, social lifestyle and world class amenities. It’s nestled within 800 acres of natural preserve and 80 acres of serene lakes teeming with migratory wildlife. Head over to the clubhouse with state-of-the-art fitness center, locker rooms with showers, movement room for classes, internet café, event room, catering kitchen, resort-style pool with spa and cabanas, restaurant with bar, firepit, pickleball, tennis and bocce courts. Take the pups to play in the dog park. Walk or ride your bike on the many paths including the peaceful preserve boardwalk. If gardening is your passion, there is a community garden to grow your favorite vegetables. HOA management and friendly staff are onsite to assist and coordinate regular events for all to enjoy. Minutes from beaches, golfing, fishing, boating, shopping, and cultural activities. It's time to enjoy the Florida lifestyle!

7248 Live Oak DR, Naples
$590,000
2 Beds ⋅ 2 Baths ⋅ 223029622 MLS
Presenting resort living at its best with the extremely popular DiVosta Serenity model in Winding Cypress of Naples. This home is set on a tremendous private, pie-shaped lot with a large, covered lanai. The extra space surrounding the home makes it unique to the neighborhood. The home includes a modern, fully upgraded kitchen and breakfast bar setup alongside an open dining area. This nearly new home includes an immense amount of builder-installed upgrades as well. The split layout inside allows guests privacy and features a large owners' suite, guest bedroom suite and two full baths. The Club at Winding Cypress is a must-see and boasts a massive resort pool, sunset sand cabanas, bocce ball, pickleball, clay tennis courts, yoga deck, large gym workout facility, fire pits, nature trail, locker rooms, a full-time activities director, sandbar restaurant and much more. Winding Cypress is one of Naples most unique resort-style, non-golf communities ever built. It includes over 800 acres of pristine preserve, insulating the ideal location. It is perfectly situated in the heart of Marco Island and close to 5th Avenue in downtown Naples.

7594 Jacaranda LN, Naples
$580,000
2 Beds ⋅ 2 Baths ⋅ 226006762 MLS
Nestled within the gated, amenity-rich community of Winding Cypress, this thoughtfully designed turnkey furnished two-bedroom plus den, two-bath residence offers an exceptional blend of comfort, quality, and relaxed Florida living. The open floor plan is enhanced by wood flooring throughout the main living areas, along with crown molding, and a distinctive coffered ceiling in the living and dining area, creating a refined yet inviting atmosphere. The kitchen is both elegant and functional, featuring 42" white cabinetry, granite countertops, tile backsplash, undercabinet lighting, and stainless-steel appliances—ideal for everyday living and entertaining alike. A flexible den with French doors provides the option for a private home office, media room, or additional guest space. Seamless indoor-outdoor living is achieved through the expansive custom lanai, designed for entertaining with an outdoor kitchen complete with gas grill, refrigerator, and sink, an above-ground HotSprings hot tub with beautiful outdoor furnishings including a dining table for six, over-sized parasol umbrellas that provide shade, and picture-frame lanai screens that showcase peaceful preserve surroundings. Additional highlights include a whole-house gas generator, two-car garage, and plantation shutters. Winding Cypress is a natural gas community thoughtfully designed around preserved natural beauty and an active, social lifestyle. At its heart is an impressive clubhouse with a heated resort-style pool and spa, poolside dining at The Shady Palm, state-of-the-art fitness center, library, and community gathering rooms. Other amenities include pickleball and tennis courts, bocce courts, dog parks, a community garden, and scenic walking and nature trails. Known for its welcoming atmosphere and beautifully maintained grounds, Winding Cypress offers a true sense of community while remaining conveniently close to everything Naples has to offer. A six-passenger well-maintained golf cart is included for effortless access throughout the neighborhood.

7121 Live Oak DR, Naples
$575,000
3 Beds ⋅ 2 Baths ⋅ 225079293 MLS
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.

7167 Live Oak DR, Naples
$575,000
2 Beds ⋅ 2 Baths ⋅ 225069223 MLS
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.

7659 Jacaranda LN, Naples
$575,000
2 Beds ⋅ 2 Baths ⋅ 225056443 MLS
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.

7690 Jacaranda LN, Naples
$565,000
2 Beds ⋅ 2 Baths ⋅ 226006913 MLS
Discover effortless luxury in this lovely villa—your private oasis in a premier gated Naples community, Winding Cypress. This inviting 2-bedroom + den, 2-bath home delivers exceptional comfort and versatility with a bright, open layout designed for effortless living and entertaining. Step into the expansive Great Room with high ceilings, creating an open, airy vibe—perfect for gathering with friends or unwinding after a day out in Naples. The chef's kitchen impresses with premium quartz countertops, solid wood soft-close cabinets, and natural gas cooking. High-traffic porcelain tile flooring flows seamlessly throughout the entire villa, paired with smooth-finish walls for a clean, modern, low-maintenance aesthetic. The flexible den, enclosed by beautiful glass panel doors, adapts effortlessly as a home office or third bedroom. Both bedrooms feature generous walk-in closets, and the bathrooms showcase floor-to-ceiling porcelain tile, glass showers, and spa-like sophistication. The master bath elevates your routine with a dramatic full-wall custom mirror and elegant drop-down designer lighting. Outside, this premium lot offers generous spacing between villas and captivating views over the community's second-largest lake—where serene water vistas create an unparalleled sense of tranquility and timeless appeal. The west-facing orientation captures breathtaking sunsets reflecting off the shimmering waters, while the south-facing exposure floods the interior with natural light. Plenty of space awaits an extended lanai or private pool, all enhanced by the soothing backdrop of the lake. Built for peace of mind: impact windows and doors boost energy efficiency, reduce noise, and lower insurance premiums—no flood insurance required in FEMA Zone X. Appliances, A/C, and water heater have performed flawlessly since new. Fiber optic connectivity ensures ultra-fast internet and seamless 4K streaming. Natural gas powers cooking, drying, hot water, and preps for a whole-home generator. Nestled in gated Winding Cypress—praised as Naples' best lifestyle value with remarkably low HOA fees that cover comprehensive maintenance (lawn care, irrigation, community upkeep) plus full access to extensive high-end amenities—you'll embrace the pet-friendly lifestyle with two dedicated dog parks, miles of scenic walking/biking trails across 800+ acres of preserved natural land, and a vibrant social calendar with events curated by the on-site activities director. Resort-style perks include the on-site Shady Palm Café for casual dining and drinks, state-of-the-art fitness center with movement/yoga room, sparkling resort pool and spa, lighted tennis and pickleball courts, bocce courts, community garden, fire pit, and more—all accessible by foot, bike, or golf cart. Conveniently located between downtown Naples and Marco Island, you're minutes from pristine beaches, upscale shopping, and fine dining. Paradise is calling.

7733 Jacaranda LN, Naples

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