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Winding Cypress Condos for Sale

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  • /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 Int'l Realty

    7690 Jacaranda Ln, Naples, FL 34114
  • /42

    $499,900

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

    7642 Jacaranda Ln, Naples, FL 34114

    Tucked Away Treasure in Winding Cypress- Step into a slice of serenity with this charming attached villa, nestled in one of the most peaceful corners of Naples. Unlike the typical coastal designs so common in the area, this home offers a more rustic warmth—perfect for those who appreciate natural textures, cozy finishes, and a relaxed, grounded lifestyle. With 2 bedrooms, a versatile den, 2

    Scott Bertha Downing Frye Realty Inc.

    7642 Jacaranda Ln, Naples, FL 34114
  • /33

    $585,000

    • 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 Marzucco Real Estate

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

    $539,500

    • 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

    Anne Lashenka Downing Frye Realty Inc.

    7658 Jacaranda Ln, Naples, FL 34114
  • /41

    $615,000 Open Sun 1PM - 3PM

    • 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

    $665,000 Open Sun 1PM - 4PM

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

    7815 Jacaranda Ln, Naples, FL 34114

    PRICE DRASTICALLY REDUCED FOR QUICK SALE!! This beautiful villa in highly sought-after Winding Cypress offers two bedrooms, two baths plus a den along with a two-car air-conditioned garage. Step onto your lanai with the largest pool and hot tub available in a villa. Couple that with a spectacular long lake view and you truly have a one-of-a-kind home. Winding Cypress offers resort-style

    Kati Bepko Coldwell Banker Realty

    7815 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.
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