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Winding Cypress Houses for Sale

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  • /49

    $774,000

    • 3 Beds
    • 2 Baths
    • 2,198 Sq Ft

    7445 Winding Cypress Dr, Naples, FL 34114

    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

    Agent Photo

    Drayton Herold

    KW Elevate Luxury

    (239) 439-4013

    7445 Winding Cypress Dr, Naples, FL 34114
  • /46

    $1,250,000 Open Sun 1PM - 4PM

    • 3 Beds
    • 3 Baths
    • 2,496 Sq Ft

    7788 Winding Cypress Dr, Naples, FL 34114

    Nestled within an exclusive gated community and surrounded by a serene nature preserve, this elegant 3-bedroom, 3-bathroom home with a spacious den/office is the epitome of refined Florida living. The open, airy floor plan flows seamlessly, with high ceilings and large windows that capture abundant natural light and offer unobstructed views of the lush preserve behind the home. This home has

    Justine Hine Royal Shell Real Estate, Inc

    7788 Winding Cypress Dr, Naples, FL 34114
  • /48

    $925,000

    • 3 Beds
    • 2 Baths
    • 2,084 Sq Ft

    6870 Winding Cypress Dr, Naples, FL 34114

    This turnkey furnished Mystique home feels like a model — impeccably maintained, thoughtfully laid out, and filled with cozy, stylish touches throughout! The floorplan features 3 bedrooms + den, 2 baths, pool and spa, and an oversized car garage. The open-concept layout features a dramatic zero-corner slider, seamlessly connecting indoor and outdoor spaces, while the whole home generator,

    Kendra Hoefs Realty One Group MVP

    6870 Winding Cypress Dr, Naples, FL 34114
  • /34

    $979,900 Open Sun 1PM - 3PM

    • 3 Beds
    • 2 Baths
    • 2,100 Sq Ft

    6787 Pennyroyal Dr, Naples, FL 34114

    Beautiful like new mystique contemporary home.with lots of privacy gorgeous marble look tile floor, custom wood moldings featuring beams in trey ceiling in gathering room, upgraded kitchen back splash and faucet , custom hallway, decorative wall design in master bedroom , oversized shower and upgraded shower heads, custom master closet and laundry room with plenty of cabinets and storage

    Linda Covino Royal Shell Real Estate, Inc.

    6787 Pennyroyal Dr, Naples, FL 34114
  • /46

    $1,099,000

    • 3 Beds
    • 2 Baths
    • 2,185 Sq Ft

    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

    Jeff Waldman Premiere Plus Realty Company

    6767 Pennyroyal Dr, Naples, FL 34114
  • /48

    $1,195,000

    • 3 Beds
    • 3 Baths
    • 2,496 Sq Ft

    7520 Blackberry Dr, Naples, FL 34114

    Introducing a luxury estate site 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

    Taylor Smith Premier Sotheby's Int'l Realty

    7520 Blackberry Dr, Naples, FL 34114
  • /46

    $950,000 Open Sun 1PM - 4PM

    • 3 Beds
    • 2 Baths
    • 2,186 Sq Ft

    7679 Winding Cypress Dr, Naples, FL 34114

    Imagine waking up every morning in your dream home, nestled in one of Naples’ most sought-after gated communities. This isn’t just a place to live—it’s a lifestyle defined by comfort, elegance, and convenience. As you step through the front door, you’re welcomed by a bright, open-concept floor plan that immediately feels like home. The heart of the house—your chef-inspired kitchen—boasts granite

    Joseph Bartos Premiere Plus Realty Company

    7679 Winding Cypress Dr, Naples, FL 34114
  • /46

    $975,000

    • 3 Beds
    • 2 Baths
    • 2,094 Sq Ft

    6699 Pennyroyal Dr, Naples, FL 34114

    Welcome to this Winding Cypress beauty! Why wait months to build and spend twice as much to get less in a home and amenities. This 2022 built classic Mystique Model has everything you'll ever need in a home and is located in Naples best hidden secret.....Winding Cypress! Located on a private, quiet, dead-end cul-de-sac, this home has many builder upgrades. The home is impeccably decorated and

    Theresa Bocka William Raveis Real Estate

    6699 Pennyroyal Dr, Naples, FL 34114
  • /46

    $999,900

    • 3 Beds
    • 2 Baths
    • 2,198 Sq Ft

    7355 Mockingbird Ct, Naples, FL 34114

    Welcome to your new home in Winding Cypress, a vibrant community in the heart of Southeast Naples. Surrounded by 800 acres of lush preserves and 80 acres of peaceful lakes, this is the ideal setting to enjoy a serene, nature-filled lifestyle. Yet, with Downtown Naples and the iconic 5th Avenue—one of America’s most beautiful streets—just 20 minutes away, you’ll always be close to the best of city

    Mike Zecchino The Agency Naples

    7355 Mockingbird Ct, Naples, FL 34114
  • /50

    $1,350,000

    • 3 Beds
    • 3 Baths
    • 2,515 Sq Ft

    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

    Kendra Hoefs Realty One Group MVP

    6839 Winding Cypress Dr, Naples, FL 34114
  • /48

    $1,497,500

    • 3 Beds
    • 3 Baths
    • 2,634 Sq Ft

    7478 Winding Cypress Dr, Naples, FL 34114

    Welcome to this exceptional Infinity Model home, a rare find in the prestigious Winding Cypress community of Naples, Florida. Built by the esteemed DiVosta Builders, this residence is one of only three Infinity Models in a community of over 750 homes—making it a truly exclusive opportunity. Designed with elegance and comfort in mind, this home showcases a sprawling open-concept layout, top-tier

    Austin Kellam Coldwell Banker Realty

    7478 Winding Cypress Dr, Naples, FL 34114
  • /35

    $720,000 Open Sun 1PM - 4PM

    • 2 Beds
    • 2 Baths
    • 1,654 Sq Ft

    6787 Winding Cypress Dr, Naples, FL 34114

    Sophisticated living with serene views in this rarely available Abbeyville model built in 2021. This home provides a shining example of comfort, style, and thoughtful design. Ideally positioned to offer peaceful water and sunset views, has been meticulously maintained and invites you to enjoy the absolute best in a Florida lifestyle.Step inside through a welcoming entryway and discover an

    Theresa Bocka William Raveis Real Estate

    6787 Winding Cypress Dr, Naples, FL 34114
  • /50

    $639,000

    • 2 Beds
    • 2 Baths
    • 1,554 Sq Ft

    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

    Michelle Thomas Premier Sotheby's International Realty

    7690 Jacaranda Ln, Naples, FL 34114
  • /43

    $900,000

    • 3 Beds
    • 2 Baths
    • 2,230 Sq Ft

    7211 Live Oak Dr, Naples, FL 34114

    Welcome to your personal retreat in Winding Cypress, where resort-style living meets sophisticated comfort! This magnificent Summerville Extended model by Pulte is move-in ready and offers an unparalleled blend of privacy, elegance, and stunning lake views. Perfectly positioned on an oversized, pie-shaped lot with no homes behind, you’ll enjoy serene tranquility and an open

    Felicia Saraceno eXp Realty LLC

    7211 Live Oak Dr, Naples, FL 34114
  • /33

    $799,000

    • 2 Beds
    • 2 Baths
    • 1,685 Sq Ft

    7128 Lily Way, Naples, FL 34114

    Thoughtful price improvements, upgraded finishes throughout, an expanded kitchen island & a rare 4-foot extension in the garage sets this home apart - topped off by a stunning private pool overlooking the lake. This property offers exceptional appeal. This is a stunning Abbeyville home in Winding Cypress, a move-in ready! This immaculate residence is a must-see, featuring a fresh neutral palette,

    Kate Pentelow Premiere Plus Realty Company

    7128 Lily Way, Naples, FL 34114
  • /27

    $695,000

    • 2 Beds
    • 2 Baths
    • 1,805 Sq Ft

    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

    Joseph Scott Compass Florida LLC

    7370 Mockingbird Ct, Naples, FL 34114

Why Live in Winding Cypress

Winding Cypress in Naples is a gated community featuring around 800 homes and villas, predominantly in Coastal Contemporary and Mediterranean Revival styles. Residents enjoy professionally landscaped properties with trimmed lawns and flower-filled gardens. The neighborhood boasts a crime score significantly lower than the national average, providing a safer living environment. Amenities include a clubhouse, pool, dog park, community garden, and courts for tennis, bocce, and pickleball. The community is adjacent to Picayune Strand Forest, offering a boardwalk and picnic area. Golf enthusiasts will find several courses within 4 miles, such as Eagle Creek Golf and Country Club. Boating facilities are available at Tarpon Club Marina and Naples Cruise Club, less than 10 miles away. The Shady Palm Café, located in the clubhouse, is a popular spot for residents, serving food and drinks and hosting neighborhood events. Shopping options are conveniently located 2 miles away at Tamiami Crossing and Shops at Eagle Creek, featuring stores like Walmart, Aldi, and Publix. Highway 41 provides access to Naples, 10 miles away, and Marco Island, 11 miles to the south, with public transit available via Collier Area Transit. The nearest healthcare facility is Physicians Regional on Collier Boulevard, 3 miles away. Schools in the Collier County School District, including Lely Elementary, Manatee Middle, and Lely High, have high ratings. Florida SouthWestern State College - Collier Campus is also nearby, just 4 miles from the community.
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