15

Winding Cypress Houses for Sale

Section Image Section Image
  • /50

    $825,000

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

    7049 Live Oak Dr, Naples, FL 34114

    Enjoy resort-style living in this Winding Cypress community near 5th Ave 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 brand-new AC system with additional cooling in the primary suite, impact glass throughout, and natural gas for efficiency and gourmet cooking. Inside, the oversized primary

    Agent Photo

    Taylor Smith

    Premier Sotheby's Int'l Realty

    (239) 392-1442

    7049 Live Oak 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

    Agent Photo

    Taylor Smith

    Premier Sotheby's Int'l Realty

    (239) 396-4003

    7520 Blackberry Dr, Naples, FL 34114
  • /25

    $1,099,000

    • 3 Beds
    • 3 Baths
    • 2,512 Sq Ft

    7235 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

    Tommy Ogiba Downing Frye Realty Inc.

    7235 Clamshell Ln, Naples, FL 34114
  • /36

    $950,000

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

    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

    Elliot Barton Waterfront Realty Group Inc

    6902 Winding Cypress Dr, Naples, FL 34114
  • /39

    $899,000

    • 3 Beds
    • 3 Baths
    • 2,128 Sq Ft

    6770 Pennyroyal Dr, Naples, FL 34114

    Discover your dream home in the prestigious Winding Cypress community! This newly constructed, pet-friendly residence boasts 3 spacious bedrooms plus a versatile den, perfect for guests or a home office. Designed for seamless entertaining, the open-concept floor plan flows effortlessly, with zero-corner sliders merging the indoor living area with a stylish outdoor kitchen and bar—ideal for

    Ryan Buchalter William Raveis Real Estate

    6770 Pennyroyal Dr, Naples, FL 34114
  • /34

    $979,900

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

    6787 Pennyroyal Dr, Naples, FL 34114

    Beautiful like new mystique contemporary home.with lots of privacy with beautiful long lake view on one of the largest lakes in WC . gorgeous marble design tile floor, custom wood moldings , beams in trey ceiling in gathering room, upgraded kitchen back splash and faucet , custom molding in foyer , Custom wall design in master bedroom , oversized shower and upgraded shower heads, custom

    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
  • /49

    $950,000

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

    7679 Winding Cypress Dr, Naples, FL 34114

    Welcome to this beautifully designed home located in one of Naples’ most desirable gated communities. The open-concept floor plan features a spacious kitchen with granite countertops, a gas stove, and a wall oven, making it both functional and inviting. Impact-resistant doors and windows provide peace of mind while showcasing stunning lake views.The large covered lanai with a summer kitchen

    Joseph Bartos Premiere Plus Realty Company

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

    $925,000

    • 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. You can't tell this rarely lived in home from a new built. 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

    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
  • /35

    $720,000 Open House 9/14

    • 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

    $895,000

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

    7211 Live Oak Dr, Naples, FL 34114

    Experience Your Best Life at Winding Cypress! Ready to live like you're on vacation every single day? This isn't just a home; it's your personal retreat in the highly sought-after Winding Cypress community. This spectacular Summerville Extended model is meticulously designed for those who crave the perfect blend of resort-style luxury and sophisticated comfort.Imagine waking up to

    Felicia Saraceno eXp Realty LLC

    7211 Live Oak Dr, 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.

Home Trends in Winding Cypress, FL

Housing Trends

Median Sale Price
$850,000
Median Single Family Sale Price
$945,000
Median Townhouse Sale Price
$643,500
Median 2 Bedroom Sale Price
$539,500
Average Price Per Sq Ft
$448
Number of Homes for Sale
23
Last 12 months Home Sales
83
Months of Supply
3.30
Median List Price
$899,000
Median Change From 1st List Price
9%
Median Home Sale Price YoY Change
-1%
How to Buy a Home How to Finance a Home How to Sell a Home