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Winding Cypress Homes for Sale

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  • /48

    $1,190,000

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

    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

    Agent Photo

    Taylor Smith

    Premier Sotheby's Int'l Realty

    (239) 396-4003

    7520 Blackberry Dr, Naples, FL 34114
  • /48

    $529,000

    • 2 Beds
    • 2 Baths
    • 1,574 Sq Ft

    7638 Jacaranda Ln, Naples, FL 34114

    Introducing the incredibly rare Winding Cypress model, the Cressida villa, now available with expansive private yard and lanai space. This unique villa features a dedicated private front entrance and an expanded foyer, complemented by an open yet defined living concept. The home boasts a wealth of builder-installed upgrades, including granite finishes, high-end porcelain floors, a glass-tiled

    Agent Photo

    Taylor Smith

    Premier Sotheby's Int'l Realty

    (239) 539-4020

    7638 Jacaranda Ln, Naples, FL 34114
  • /43

    $819,000 Open Sun 1PM - 4PM

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

    7507 Live Oak Dr, Naples, FL 34114

    Winding Cypress – Resort-Style Living in Naples - Priced to sell!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, 3 bedrooms plus a den, 2 full baths, and an open-concept floor plan, this home is designed for

    Craig Jerabeck Premiere Plus Realty Company

    7507 Live Oak Dr, Naples, FL 34114
  • /49

    $925,000

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

    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

    Theresa Bocka William Raveis Real Estate

    6699 Pennyroyal Dr, Naples, FL 34114
  • /49

    $899,000 Open Sun 1PM - 4PM

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

    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

    Brian Stolliker Berkshire Hathaway FL Realty

    6856 Winding Cypress Dr, 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
  • /37

    $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
  • /40

    $959,900

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

    6787 Pennyroyal Dr, Naples, FL 34114

    Beautiful 2022 mystique model contemporary home.long corner private lot , beautiful long lake view on one of the largest lakes in WC. Ready for imediate occupancy most furniture has been removed. 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 ,

    Linda Covino Royal Shell Real Estate, Inc.

    6787 Pennyroyal Dr, Naples, FL 34114
  • /44

    $870,000

    • 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
  • /21

    $1,188,000 Open House 11/09

    • 3 Beds
    • 2 Baths
    • 2,166 Sq Ft

    7457 Winding Cypress Dr, Naples, FL 34114

    PRIVACY-PRIVACY-PRIVACY An exceptional model styled home on a premium lot withrare, unobstructed views of the lake with State and Federally protected preserves that willnever be built on. This residence offers unmatched privacy and outdoor living, with twostandout features: an expansive screened lanai with custom accent lighting, saltwater, heatedpool, plus an outdoor dry bar with

    Beth M Abraham Gulf Coast International Prop

    7457 Winding Cypress Dr, Naples, FL 34114
  • /45

    $649,900 Open Sun 1PM - 4PM

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

    7248 Live Oak Dr, Naples, FL 34114

    Welcome home to this charming Abbeyville model featuring its inviting open-floor concept where natural light streams through the windows. The kitchen boasts granite counters, stainless appliances and a center island with pendant lights and extra storage for everyday use and easy entertaining. The pantry closet has plenty of space for all of your staple goods. Low maintenance tile floors are

    Theresa Bocka William Raveis Real Estate

    7248 Live Oak Dr, Naples, FL 34114
  • /37

    $1,695,000

    • 4 Beds
    • 4 Baths
    • 3,656 Sq Ft

    7412 Winding Cypress Dr, Naples, FL 34114

    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 3-car garage, this home is thoughtfully designed for both everyday living and entertaining on a grand

    Manuela Schinagl Manuela Realty

    7412 Winding Cypress Dr, Naples, FL 34114
  • /45

    $599,900

    • 2 Beds
    • 2 Baths
    • 1,544 Sq Ft

    7659 Jacaranda Ln, Naples, FL 34114

    Welcome to this charming 2-bedroom plus den, 2-bath single-family home 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

    Stanley Whitcomb III Premiere Plus Realty Company

    7659 Jacaranda Ln, Naples, FL 34114
  • /41

    $749,900

    • 3 Beds
    • 2 Baths
    • 1,594 Sq Ft

    7670 Jacaranda Ln, Naples, FL 34114

    Discover refined living with this beautifully appointed villa in Winding Cypress, where luxury and comfort meet in perfect balance. Designed for those who appreciate both elegance and ease, this home offers an unparalleled lifestyle inside and out.Arriving fully furnished and enhanced by the sellers’ two-seater Club Car golf cart, this property delivers a true move-in ready experience. Every

    Sean Smuk Coldwell Banker Realty

    7670 Jacaranda Ln, Naples, FL 34114
  • /44

    $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
  • /16

    $539,000

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

    7602 Jacaranda Ln, Naples, FL 34114

    Welcome to this meticulous light and bright two bedroom plus den, two bathroom property located in the preserve style, amenity rich community of Winding Cypress. Featuring stainless steel appliances, roomy kitchen, in residence laundry room with newer washer and dryer, screened in lanai, and open floor plan this home has multiple indoor and outdoor spaces for entertaining guests and hosting

    Taylor Miller Coldwell Banker Realty

    7602 Jacaranda Ln, Naples, FL 34114
  • /33

    $579,900

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

    7176 Live Oak Dr, Naples, FL 34114

    Sophisticated Villa Living in Winding Cypress – Priced to Sell/Fully Furnished. An extraordinary opportunity awaits in the highly sought-after Winding Cypress community—this impeccably upgraded 3-bedroom, 2-bathroom villa is set on the largest homesite in the neighborhood, offering both privacy and an expansive outdoor retreat. Thoughtfully enhanced with luxury upgrades and high-end finishes,

    Samantha Krol Coldwell Banker Realty

    7176 Live Oak Dr, Naples, FL 34114
  • /41

    $534,500

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

    7658 Jacaranda Ln, Naples, FL 34114

    This beautiful Winding Cypress Serenity Villa home offers 1,554 sq. ft. of comfort with 2 bedroom plus den, 2 bathrooms, screened lanai, and a 2-car garage. It features multiple quality upgrades including stainless appliances with both gas and electric connectivity for the stove, 22" porcelain tile on the diagonal throughout, plantation shutters, Quartz countertops in kitchen and bathrooms, den

    Bob Lashenka Downing Frye Realty Inc.

    7658 Jacaranda Ln, Naples, FL 34114
  • /41

    $615,000

    • 3 Beds
    • 2 Baths
    • 1,544 Sq Ft

    7167 Live Oak Dr, Naples, FL 34114

    Don't miss your chance to own a Serenity Turnkey Pool Villa in the highly sought-after Winding Cypress community! This meticulously designed residence boasts 3 bedrooms, 2 bathrooms, and a 2-car garage, offering both comfort and style.Step outside to your private outdoor oasis, complete with a tranquil waterfall feature, electrically heated salt pool, built-in speakers, and serene

    Kendra Hoefs Realty One Group MVP

    7167 Live Oak Dr, Naples, FL 34114
  • /32

    $640,000

    • 2 Beds
    • 2 Baths
    • 1,574 Sq Ft

    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

    Kati Bepko Coldwell Banker Realty

    7815 Jacaranda Ln, Naples, FL 34114
  • /28

    $665,000

    • 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

    Joseph Scott Compass Florida LLC

    7370 Mockingbird Ct, Naples, FL 34114
  • /46

    $900,000

    • 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

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.

Frequently Asked Questions

Is Winding Cypress a good place to live?
Winding Cypress is a good place to live. Winding Cypress is considered very car-dependent and somewhat bikeable. Winding Cypress is a neighborhood with a crime score of 1, making it safer than the average neighborhood in the U.S. It has a median age of 69. The average household income is $115,017 which is above the national average. College graduates make up 43.4% of residents. A majority of residents in Winding Cypress are home owners, with 12.5% of residents renting and 87.5% of residents owning their home. A local real estate agent serving Winding Cypress can help you decide if this neighborhood is the right one for you. Learn more on our Winding Cypress neighborhood guide.
Is Winding Cypress, FL a safe neighborhood?
Winding Cypress, FL is safer than the average neighborhood in the United States. It received a crime score of 1 out of 10.
How much do you need to make to afford a house in Winding Cypress?
The median home price in Winding Cypress is $899,000. If you put a 20% down payment of $179,800 and had a 30-year fixed mortgage with an interest rate of 6.27%, your estimated principal and interest payment would be $4,440 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $190K a year to afford the median home price in Winding Cypress. The average household income in Winding Cypress is $115K.
What are the best public schools in Winding Cypress?
The best public schools that serve Winding Cypress are:
What are the most popular zip codes in Winding Cypress, Naples, FL?
The most popular zip codes in Winding Cypress, Naples, FL include 34114, 34110, 34113, 34102 and 34109.
What are the most popular neighborhoods near Winding Cypress, Naples, FL?
The most popular neighborhoods near Winding Cypress, Naples, FL are Belle Meade, Naples Reserve, Reflection Lakes, South Naples and Imperial Wilderness.
Are home prices dropping in Winding Cypress?
Yes, home prices in Winding Cypress are down 14% in the last 12 months.

Home Trends in Winding Cypress, FL

Housing Trends

Median Sale Price
$850,000
Median Single Family Sale Price
$890,000
Median Townhouse Sale Price
$599,900
Median 2 Bedroom Sale Price
$537,000
Average Price Per Sq Ft
$416
Number of Homes for Sale
22
Last 12 months Home Sales
73
Months of Supply
3.60
Median List Price
$899,000
Median Change From 1st List Price
8%
Median Home Sale Price YoY Change
0%
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