Winding Cypress Homes for Sale

Q: What are the best public schools in Winding Cypress?

The best public schools that serve Winding Cypress are:Manatee Elementary School has a B+ Niche grade and a student teacher ratio of 13:1.Manatee Middle School has a B Niche grade, a student teacher ratio of 19:1 and an average review score of 4.0.Lely High School has a B Niche grade, a student teacher ratio of 21:1 and an average review score of 4.0.

/45
$940,000

$210K 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

Theresa Bocka

William Raveis Real Estate

6825 Greenbriar Ct, Naples, FL 34114
Explore Winding Cypress
/50
$1,400,000
- 4 Beds
- 4.5 Baths
- 3,464 Sq Ft
7759 Winding Cypress Dr, Naples, FL 34114

Welcome to one of the most prestigious, stately, and expansive offerings throughout the entire, always-desirable community of Winding Cypress. This exclusive Stonewater Model, with a full 2nd floor of living space, is a DiVosta Builder's flagship luxury home and a very rare find. This property sits on the most exceptional 1/4 acre lot with a spectacular large lake view and full preserve backdrop

Theresa Bocka

William Raveis Real Estate

7759 Winding Cypress Dr, Naples, FL 34114
/31
$599,900
- 3 Beds
- 2 Baths
- 1,554 Sq Ft
7156 Live Oak Dr, Naples, FL 34114

Welcome to your private paradise in the highly sought-after, resort-style community of Winding Cypress! This TURNKEY FURNISHED true 3-bedroom, 2-bathroom villa offers the ultimate blend of luxury, comfort, and effortless living is move-in ready for your immediate enjoyment.The 2-car attached garage—complete with convenient overhead storage racks and additional utility sink—offer great

Theresa Bocka

William Raveis Real Estate

7156 Live Oak 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
/42
$940,000

$20K PRICE DROP
- 3 Beds
- 2 Baths
- 2,076 Sq Ft
6727 Pennyroyal Dr, Naples, FL 34114

This meticulously maintained Mystique features 3 bedrooms + den, 2 bathrooms, 2 car garage with a pool and spa overlooking a lake! This home is situated on a spacious corner lot making it ideal for privacy while maintaining a stunning lake view. The turnkey designer furnishings have hardly been used and it's a pet free home. Outside the private oasis features a spa with waterfall, plenty of

Kendra Hoefs Realty One Group MVP

6727 Pennyroyal Dr, Naples, FL 34114
/50
$1,349,500
- 3 Beds
- 3 Baths
- 2,634 Sq Ft
7478 Winding Cypress Dr, Naples, FL 34114

BRING OFFERS! Welcome to this highly upgraded Infinity Model, a rare offering in the prestigious Winding Cypress community of Naples. Built by renowned DiVosta Builders, this residence is one of only three Infinity Models within a community of more than 750 homes, making it an exceptionally unique opportunity. Featuring an extra-wide three-car garage with a dedicated third bay ideal for a golf

Austin Kellam Coldwell Banker Realty

7478 Winding Cypress Dr, 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

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

Winding Cypress Home Prices vs. Nearby Naples, FL Neighborhoods

	Winding Cypress	Naples Reserve	Fiddler's Creek	Lely Resort
Median Home Price	$900,000	$999,000	$849,000	$725,000
Median Sale Price	$835,000 -2% YoY	$875,000 +9% YoY	$799,000 -16% YoY	$700,000 +9% YoY
Median Single Family Price	$875,000	$948,900	$1,025,500	$910,000
Median Townhouse Price	$577,500	$460,000	$535,900	$450,000
Median Condo Price	--	$522,000	$568,950	$410,000
Total Active Listings	14	53	302	229
Market Conditions	1 Months of Supply Seller's Market	2 Months of Supply Seller's Market	2 Months of Supply Seller's Market	3 Months of Supply Seller's Market

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. 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% of residents renting and 88% 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 $900,000. If you put a 20% down payment of $180,000 and had a 30-year fixed mortgage with an interest rate of 6.58%, your estimated principal and interest payment would be $4,590 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $197K 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:

Manatee Elementary School has a B+ Niche grade and a student teacher ratio of 13:1.
Manatee Middle School has a B Niche grade, a student teacher ratio of 19:1 and an average review score of 4.0.
Lely High School has a B Niche grade, a student teacher ratio of 21:1 and an average review score of 4.0.

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, 34103 and 34145.

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 6% in the last 12 months.

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