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Winding Cypress Homes for Sale

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  • 6825 Greenbriar Ct, Naples, FL 34114
    6825 Greenbriar Ct, Naples, FL 34114
    6825 Greenbriar Ct, Naples, FL 34114
    /45

    $998,000

    $152K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 3,036 Sq Ft

    6825 Greenbriar Ct, Naples, FL 34114

    Spacious & Immaculate accurately describe this outstanding retreat in the sought-after community of Winding Cypress. This rare, two-story Mystique footprint boasts 4 bedrooms, 3 full baths, a large den/office, and over 3160 square feet of adjusted living space, 3036 square feet under air. This residence was one of the last built in the community, 3 years new, and shows like a model home. Located

    Agent Photo

    Theresa Bocka

    William Raveis Real Estate

    (239) 488-2755

    6825 Greenbriar Ct, Naples, FL 34114
  • 6844 Winding Cypress Dr, Naples, FL 34114
    6844 Winding Cypress Dr, Naples, FL 34114
    6844 Winding Cypress Dr, Naples, FL 34114
    /47

    $949,900

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

    6844 Winding Cypress Dr, Naples, FL 34114

    Welcome to newest and last phase of homes built in 2020 in the vibrant well maintained community of Winding Cypress. Located just off Collier and 41 and minutes to 75 , Marco Island and downtown NaplesThis summer wood model is sure to please with 3 bdrms den and 2 baths with full showers , primary bath with custom mirrors. custom closet , plantation shutters mini a/c in garage, whole house

    Linda Covino Royal Shell Real Estate, Inc.

    6844 Winding Cypress Dr, Naples, FL 34114
  • 6787 Pennyroyal Dr, Naples, FL 34114
    6787 Pennyroyal Dr, Naples, FL 34114
    6787 Pennyroyal Dr, Naples, FL 34114
    /47

    $935,000

    • 3 Beds
    • 2 Baths
    • 2,076 Sq Ft

    6787 Pennyroyal Dr, Naples, FL 34114

    Set on a private corner homesite with breathtaking long lake views, this like-new contemporary residence built in 2022 offers an exceptional blend of style, comfort and modern functionality within the sought-after community of Winding Cypress. Designed with a great room and split-bedroom floor plan, this three-bedroom plus den, two-bath home with a two-car garage showcases light-filled interiors,

    Michelle Thomas Premier Sotheby's International Realty

    6787 Pennyroyal Dr, Naples, FL 34114
  • 7679 Winding Cypress Dr, Naples, FL 34114
    7679 Winding Cypress Dr, Naples, FL 34114
    7679 Winding Cypress Dr, Naples, FL 34114
    /53

    $875,000

    $74K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 2,186 Sq Ft

    7679 Winding Cypress Dr, Naples, FL 34114

    Welcome to this beautifully designed residence located within one of Naples' most desirable gated communities. The open-concept floor plan is enhanced by volume and tray ceilings, crown molding, plantation shutters throughout, and an extended driveway, adding both elegance and curb appeal. The spacious kitchen features granite countertops, a gas cooktop, wall oven, and ample cabinetry—making it

    Joseph Bartos Premiere Plus Realty Company

    7679 Winding Cypress Dr, Naples, FL 34114
  • 7460 Blackberry Dr, Naples, FL 34114
    7460 Blackberry Dr, Naples, FL 34114
    7460 Blackberry Dr, Naples, FL 34114
    /50

    $850,000

    $49K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 2,188 Sq Ft

    7460 Blackberry Dr, Naples, FL 34114

    Paradise at your fingertips. This modern three-bedroom plus den residence in the prestigious resort style living gated community of Winding Cypress, offers a bright, expansive open floor plan, breathtaking lake views, ceramic tile throughout and a gorgeous and functional updated kitchen featuring solid maple shaker cabinetry, premium hardware, and spacious pantry. This residence is also equipped

    Angelica Andrews Premier Sotheby's Int'l Realty

    7460 Blackberry Dr, Naples, FL 34114
  • 7022 Live Oak Dr, Naples, FL 34114
    7022 Live Oak Dr, Naples, FL 34114
    7022 Live Oak Dr, Naples, FL 34114
    /39

    $750,000

    $50K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 2,078 Sq Ft

    7022 Live Oak Dr, Naples, FL 34114

    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

    Kathy Friedle John R. Wood Properties

    7022 Live Oak Dr, Naples, FL 34114
  • 7670 Jacaranda Ln, Naples, FL 34114
    7670 Jacaranda Ln, Naples, FL 34114
    7670 Jacaranda Ln, Naples, FL 34114
    /41

    $698,500

    $62K PRICE DROP
    • 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
  • 7247 Clamshell Ln, Naples, FL 34114
    7247 Clamshell Ln, Naples, FL 34114
    7247 Clamshell Ln, Naples, FL 34114
    /34

    $1,645,000

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

    7247 Clamshell Ln, Naples, FL 34114

    A must-see opportunity—spacious, stunning views, showpiece home and resort style Florida living. A rare opportunity to own a 4 bedroom estate home with breathtaking views in the sought-after community of Winding Cypress, offering top-tier amenities at surprisingly low HOA fees. This award-winning Pinnacle model boasts numerous upgrades and interiors like the builder’s model home and is on one of

    Sheila Kumar Real Broker, LLC

    7247 Clamshell Ln, Naples, FL 34114
  • 6770 Pennyroyal Dr, Naples, FL 34114
    6770 Pennyroyal Dr, Naples, FL 34114
    6770 Pennyroyal Dr, Naples, FL 34114
    /37

    $825,000

    $74K PRICE DROP
    • 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
  • 7229 Wiregrass Ct, Naples, FL 34114
    7229 Wiregrass Ct, Naples, FL 34114
    7229 Wiregrass Ct, Naples, FL 34114
    /52

    $1,750,000

    • 4 Beds
    • 4.5 Baths
    • 3,965 Sq Ft

    7229 Wiregrass Ct, Naples, FL 34114

    Rare to find, this light-filled 2-story Stonewater model offering 4 bedrooms, den and 4.5 baths on a pie shaped waterfront lot in the highly desirable gated community of Winding Cypress in Naples. This home has been upgraded to include all available options totaling over $650,000 including 2nd floor loft, hurricane windows and doors, upgraded finishes throughout including smooth drywall, seamless

    Manuela Schinagl Manuela Realty, Inc

    7229 Wiregrass Ct, Naples, FL 34114
  • 7666 Jacaranda Ln, Naples, FL 34114
    7666 Jacaranda Ln, Naples, FL 34114
    /2

    $575,000

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

    7666 Jacaranda Ln, Naples, FL 34114

    Experience elevated resort-style living in the highly desirable community of Winding Cypress. This impeccably maintained and tastefully updated 2-bedroom plus den, 2-bath villa offers soaring 9’4” ceilings and an attached two-car garage, delivering both comfort and functionality in a truly move-in-ready residence. Thoughtful upgrades include a newer refrigerator and hot water heater, upgraded

    Susan Heller EXP Realty LLC

    7666 Jacaranda Ln, Naples, FL 34114
Florida Collier County Naples Winding Cypress

Real Estate & Homes for Sale in Winding Cypress, Naples

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.
Learn more about living in Winding Cypress

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 with minimal transit options. 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 3 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 $899,900. If you put a 20% down payment of $180,000 and had a 30-year fixed mortgage with an interest rate of 6.51%, your estimated principal and interest payment would be $4,550 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $195K a year to afford the median home price in Winding Cypress. Learn how much home you can afford with our Home Affordability Calculator. 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, 34102, 34113, 34110 and 34103.
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 Fiddler's Creek.
Are home prices dropping in Winding Cypress?
Yes, home prices in Winding Cypress are down 11% in the last 12 months.

Home Trends in Winding Cypress, FL

On average, homes in Winding Cypress, Naples sell after 138 days on the market compared to the national average of 58 days. The median sale price for homes in Winding Cypress, Naples over the last 12 months is $835,000, down 3% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$835,000
Median Single Family Sale Price
$856,500
Median Townhouse Sale Price
$575,000
Median 2 Bedroom Sale Price
$550,000
Average Price Per Sq Ft
$410
Number of Homes for Sale
11
Last 12 months Home Sales
100
Months of Supply
1.30
Median List Price
$899,900
Median Change From 1st List Price
9%
Median Home Sale Price YoY Change
-3%
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