10

Winding Cypress Homes for Sale

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  • /31

    $599,900

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

    7156 Live Oak Dr, Naples, FL 34114

    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. LOWEST 3 BEDROOM WITH A POOL IN THIS COMMUNITY. The 2-car attached garage—complete with convenient overhead storage racks and additional utility sink—offer great convenience. Discover a bright, open-concept living space

    Agent Photo

    Theresa Bocka

    William Raveis Real Estate

    7156 Live Oak Dr, Naples, FL 34114
  • /50

    $1,300,000

    $100K PRICE DROP
    • 4 Beds
    • 4.5 Baths
    • 3,464 Sq Ft

    7759 Winding Cypress Dr, Naples, FL 34114

    PRICE IMPROVEMENT _Ready for New Owners- Look at all the upgrades in this prestigious, stately, and expansive Stonewater offering everything option possible located in the highly-desirable natural gas community of Winding Cypress. The open concept main living area plus a 2nd floor for guest, media, home office, craft or game room of your choice. This is DiVosta Builder's flagship luxury home and

    Agent Photo

    Theresa Bocka

    William Raveis Real Estate

    7759 Winding Cypress Dr, Naples, FL 34114
  • /50

    $1,195,000

    Open Sun 1PM - 3PM
    • 3 Beds
    • 3 Baths
    • 2,500 Sq Ft

    7230 Live Oak Dr, Naples, FL 34114

    Beautiful home inside and out Pinnacle style home in Winding Cypress. This home features 3 generous size bedrooms, 3 full bath , 2 car plus golf cart garage . Custom oversized salt water heated pool with stairs , sunshelf, 3 waterfall features and oversized hot tub all surrounded by beautiful landscaping on an oversized lot with plenty of privacy. All impact resistance doors and windows, zero

    Linda Covino Royal Shell Real Estate, Inc.

    7230 Live Oak Dr, Naples, FL 34114
  • /46

    $1,250,000

    • 54 Beds
    • 3 Baths
    • 2,950 Sq Ft

    7700 Winding Cypress Dr, Naples, FL 34114

    BEAUTIFUL AND METICULOUSLY MAINTAINED 5 BEDROOM, 3 BATH HOME IN DIVOSTA'S GATED WINDING CYPRESS COMMUNITY, ONE OF NAPLES MOST DESIRABLE LOCATIONS CONVENIENT TO DOWNTOWN NAPLES, MARCO ISLAND'S PRISTINE BEACHES AS WELL AS NEARBY SHOPPING AND RESTAURANTS. THIS SUMMERWOOD FLOORPLAN FEATURES A MASTER ON MAIN LIVING FLOOR WITH LARGE BATH AND WALK-IN CLOSET, A LARGE LOFT SPACE UPSTAIRS WITH A SEPARATE

    Tim Sykes Anchor Real Estate

    7700 Winding Cypress Dr, Naples, FL 34114
  • /40

    $920,000

    $40K 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
  • /55

    $1,060,000

    Open Sun 1PM - 4PM
    • 4 Beds
    • 2 Baths
    • 2,230 Sq Ft

    7564 Winding Cypress Dr, Naples, FL 34114

    Most lake lots give you water. This one gives you the sunset. The western exposure at 7564 Winding Cypress Drive turns the back of the house into the best seat in the community every evening, and the extended lanai is built with no-see-um mesh in picture-window construction, so the horizon comes through without a frame across it.Behind that view is a one-owner 2018 DiVosta Summerwood,

    Alex Ollila Gordon Pass Realty LLC

    7564 Winding Cypress Dr, Naples, FL 34114
  • /50

    $965,000

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

    6825 Greenbriar Ct, Naples, FL 34114

    Preserve views on a quiet cul-de-sac street define this two-story Mystique residence in Winding Cypress, where a saltwater pool with spillover spa, expansive outdoor living and flexible interior spaces create a home designed for both relaxation and entertaining. With four bedrooms, a den, an upstairs flex room, three baths and a two-car garage, the floor plan offers exceptional versatility while

    Michelle Thomas Premier Sotheby's International Realty

    6825 Greenbriar Ct, Naples, FL 34114
  • /43

    $1,295,000

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

    6907 Cocoplum St, Naples, FL 34114

    PRICED TO SELL! Discover exceptional value in one of Naples’ most desirable lifestyle communities, Winding Cypress. Ideally situated on an oversized preserve lot with peaceful pond views, this beautifully maintained Pinnacle floor plan offers over 2,500 square feet of living space with 3 spacious bedrooms, 3 full bathrooms, and a versatile den.Built in 2020, this move-in-ready residence

    Michael Dorobanti Compass Florida LLC

    6907 Cocoplum St, 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,

    Susan Heller EXP Realty LLC

    7666 Jacaranda Ln, 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.

Winding Cypress, Naples, FL Home Prices vs. Nearby Neighborhoods

Winding Cypress Fiddler's Creek Naples Lakes Country Club Lely Resort
Median Home Price
$900,000
$800,000
$655,000
$725,000
Median Sale Price
$835,000
-1% YoY
$760,000
-24% YoY
$570,000
-5% YoY
$725,000
+12% YoY
Avg. Price per Square Foot
$412
$357
$323
$351
Median Single Family Price
$858,500
$1,015,293
$1,155,444
$915,000
Median Townhouse Price
$575,000
$535,900
--
$460,000
Median Condo Price
--
$560,000
$465,000
$415,000
Total Active Listings
10 listings
290 listings
22 listings
227 listings
Market Conditions
1 Month of Supply
Seller's Market
2 Months of Supply
Seller's Market
1 Month 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.
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 6.31%, your estimated principal and interest payment would be $4,460 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $191K 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, 34109 and 34112.
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 3% in the last 12 months.
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