The community of Winding Cypress is found in Naples. Superbly situated for access to all of the Naples region amenities and comforts has to offer.

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19 listings match your search criteria.
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Active
7072 Live Oak Dr   Naples
  • 4Bedrooms
  • 4Bathrooms
  • 3350Sq Ft
  • 2015Year Built
$1,599,900

Welcome to this stunning Tangerly Oak model home, thoughtfully designed with space, style, and Florida living in mind. This expansive 4-bedroom residence with a generous loft offers a flexible floor plan ideal for both everyday living and hosting guests, all enhanced by beautiful designer upgrades throughout. Step outside to an exceptional outdoor living space featuring a…

Active
7412 Winding Cypress Dr   Naples
  • 4Bedrooms
  • 4Bathrooms
  • 3656Sq Ft
  • 2017Year Built
$1,595,000

Motivated Seller! Luxurious Lakeside Living in Winding Cypress – Rare One Owner Pinnacle Model! Welcome to this stunning lake view home offering 3,656 sq. ft. of modern elegance in the prestigious, amenity-rich community of Winding Cypress. With 4 bedrooms, 4 bathrooms, a den, bonus room, and 2,5-car garage, this home is thoughtfully designed for both…

Active
7520 Blackberry Dr   Naples
  • 3Bedrooms
  • 3Bathrooms
  • 2496Sq Ft
  • 2017Year Built
$1,160,000

Introducing a luxury estate with landscaped privacy corner lot home in Winding Cypress with pool and spa. Step into elegance with this stunning Pinnacle model estate home, set in the prestigious, gated community of Winding Cypress. This home stands out with its soaring raised tray ceilings, rare privacy and spacious yard, impact glass for peace…

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7457 Winding Cypress Dr   Naples
  • 3Bedrooms
  • 2Bathrooms
  • 2166Sq Ft
  • 2017Year Built
$1,155,000

The Martin Ray Floor Plan is PRIVACY-PRIVACY-a REAL Piece of Florida Paradise. An exceptional model styled home on a premium lot with rare, unobstructed views of the lake and the Preserve. This residence offers unmatched privacy and outdoor living, with two standout features: an expansive screened lanai with custom accent lighting, saltwater, heated pool, plus an outdoor dry…

Active
6825 Greenbriar Ct   Naples
  • 4Bedrooms
  • 3Bathrooms
  • 3036Sq Ft
  • 2022Year Built
$1,150,000

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…

Active
6787 Pennyroyal Dr   Naples
  • 3Bedrooms
  • 2Bathrooms
  • 2186Sq Ft
  • 2022Year Built
$949,900

Move in Ready 3 year old 3 bdrm den 2bath Mystic model at Winding Cypress. Here are some of the reasons we are we different from the rest . widened paved driveway comfortablly fitting 2 cars side by side, corner lot for privacy, beautiful long lake view…

Active
7679 Winding Cypress Dr   Naples
  • 3Bedrooms
  • 2Bathrooms
  • 2186Sq Ft
  • 2019Year Built
$949,000

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, 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 both…

Active
6698 Pennyroyal Dr   Naples
  • 3Bedrooms
  • 3Bathrooms
  • 2150Sq Ft
  • 2022Year Built
$943,000

Discover resort-style living in this rare three-bedroom plus den, three-bath natural gas home in the highly sought-after community of Winding Cypress. Designed for privacy and effortless indoor–outdoor living, it features an oversized fully custom pool with integrated seamless spa and a panoramic barless screen lanai, integrated home theater sound, all overlooking lush, tranquil landscaping. The…

Active
6902 Winding Cypress Dr   Naples
  • 3Bedrooms
  • 2Bathrooms
  • 2084Sq Ft
  • 2022Year Built
$925,000

Stunning 3-Bedroom + Den Home in Sought-After Winding Cypress – Welcome to your dream home in the prestigious, resort-style community of Winding Cypress in Naples, FL. Built in 2022, this impeccably maintained 3-bedroom + den, 2-bathroom residence blends modern design with everyday comfort. Step inside to find an open-concept floor plan featuring, abundant natural light,…

Active
7211 Live Oak Dr   Naples
  • 3Bedrooms
  • 2Bathrooms
  • 2230Sq Ft
  • 2015Year Built
$849,900

This impeccably maintained residence offers an exceptional living experience. The open floor plan features three spacious bedrooms, a versatile den or flex room, and two full bathrooms. Elegant details include crown molding, tray ceilings, plantation shutters, Hunter Douglas blinds, and updated flooring. The added sunroom provides a tranquil space for relaxation or entertaining. The custom designed…

Active
6770 Pennyroyal Dr   Naples
  • 3Bedrooms
  • 3Bathrooms
  • 2128Sq Ft
  • 2023Year Built
$825,000

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…

Active
7057 Live Oak Dr   Naples
  • 3Bedrooms
  • 2Bathrooms
  • 2230Sq Ft
  • 2016Year Built
$799,900

Winding Cypress – Resort-Style Living in Naples - Priced to sell! Welcome to your Florida dream home in the sought-after gated community of Winding Cypress! This immaculate residence built in 2016, offers the perfect blend of modern luxury and relaxed coastal living. Featuring 2,230’sq under air, 3 bedrooms plus a den, 2 full baths, and an…

Active
7670 Jacaranda Ln   Naples
  • 3Bedrooms
  • 2Bathrooms
  • 1594Sq Ft
  • 2018Year Built
$739,900

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…

Active
7248 Live Oak Dr   Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1685Sq Ft
  • 2016Year Built
$639,900

Single Family home in Winding Cypress -Ready for the season!! This charming model is the perfect fit featuring an inviting open-floor concept where natural light streams through the windows. The kitchen boasts granite counters, stainless appliances and a center island and extra storage for everyday use and easy entertaining. The pantry closet has plenty…

Active
7690 Jacaranda Ln   Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1554Sq Ft
  • 2018Year Built
$610,000

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…

Active
7167 Live Oak Dr   Naples
  • 3Bedrooms
  • 2Bathrooms
  • 1554Sq Ft
  • 2015Year Built
$600,000

Rare villa opportunity in Winding Cypress! This turnkey, fully furnished villa sits on an extra-large, ultra-private lot with exceptional spacing between neighbors, creating a peaceful and open feel that is hard to find. The backyard is a retreat, featuring a saltwater private pool framed by mature cypress trees, colorful landscaping and wide natural preserve views.…

Active
7176 Live Oak Dr   Naples
  • 3Bedrooms
  • 2Bathrooms
  • 1554Sq Ft
  • 2015Year Built
$550,000

Welcome to effortless, refined living in the highly desirable Winding Cypress community. Set on the largest homesite in the neighborhood, this impeccably upgraded 3-bedroom, 2-bath villa offers exceptional privacy, expansive outdoor space, and a true lock-and-leave lifestyle. Furnishings are negotiable, making this a flexible opportunity for both full-time and seasonal residents. Designed for relaxed everyday living…

Active
7658 Jacaranda Ln   Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1554Sq Ft
  • 2018Year Built
$534,500

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…

Active
7602 Jacaranda Ln   Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1554Sq Ft
  • 2017Year Built
$529,000

Welcome to this meticulous light and bright two bedroom plus den, two bathroom property located in the preserve style, amenity rich community of Winding Cypress. Featuring stainless steel appliances, roomy kitchen, in residence laundry room with newer washer and dryer, screened in lanai, and open floor plan this home has multiple indoor and outdoor spaces…

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