8

Winding Cypress Condos for Sale

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  • /42

    $537,000

    • 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
  • /49

    $549,000

    • 2 Beds
    • 2 Baths
    • 1,579 Sq Ft

    7650 Jacaranda Ln, Naples, FL 34114

    Welcome to your dream home in the heart of one of Naples' most sought-after communities! This stunning FRONT entrance Cressida villa offers the perfect blend of comfort, style, and convenience. Featuring two spacious bedrooms, two full baths, and a versatile den/flex room that can be used as an in-home office or guest area, this home is designed to meet all your needs.The updated kitchen

    Theresa Bocka William Raveis Real Estate

    7650 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

    $579,500

    • 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
  • /32

    $675,000

    • 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 living

    Kati Bepko Coldwell Banker Realty

    7815 Jacaranda Ln, Naples, FL 34114
  • /41

    $640,000

    • 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
  • /46

    $475,000

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

    7686 Jacaranda Ln, Naples, FL 34114

    Don’t miss this exceptional opportunity to own an upgraded Cressida villa in the sought-after community of Winding Cypress! This front-entry home lives like a single-family residence, offering 2 bedrooms + den, 2 bathrooms, a 2-car garage, and a stunning expanded patio with extra covered space—more than most villas.Inside, enjoy luxury upgrades including white cabinetry, quartz countertops, crown

    Kendra Hoefs Realty One Group MVP

    7686 Jacaranda Ln, Naples, FL 34114
  • /27

    $559,000

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

    7702 Jacaranda Ln, Naples, FL 34114

    Absolutely the best deal on a 2 bedroom plus den with French doors, 2 baths, 2 car garage attached villa with your own POOL in Winding Cypress. You better Hurry. Furniture negotiable too, move right in for season, nicely furnished.What's Special: *Open floor plan *Epoxy garage floor *Granite countertops*3 ft. bathroom countertops *Remote controlled garage screen*Remote controlled hurricane

    Mike Miller Berkshire Hathaway FL Realty

    7702 Jacaranda Ln, Naples, FL 34114

About 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.

Home Trends in Winding Cypress, FL

Home Trends

Median Price (12 Mo)
$850,000
Median Single Family Price
$995,000
Median Townhouse Price
$662,500
Median 2 Bedroom Price
$579,500
Average Price Per Sq Ft
$460
Number of Homes for Sale
35
Last 12 months Home Sales
82
Months of Supply
5.10
Median List Price
$959,500
Median Discount From 1st List Price
9%
Median Home Sale Price YoY Change
-6%
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