The community of Winding Cypress is located in Naples. Ideally situated for access to all of the Naples region attractions and advantages has to offer.

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15 listings match your search criteria.
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Active
6678 Pennyroyal Dr   Naples
$1,050,000
  • 3Bedrooms
  • 3Bathrooms
  • 3196Sq Ft
  • 2022Year Built
$1,050,000

This 2 Story Mystique Model, located in the desireable community of Winding Cypress, absolutely has to be seen to appreciate all that it offers. Instead of using AI to draft a lofty, fluffy, low information description of this home, we are just going to just list a few of the features and upgrades of this…

Active
7022 Live Oak Dr   Naples
$799,900
  • 3Bedrooms
  • 2Bathrooms
  • 2078Sq Ft
  • 2016Year Built
$799,900

Welcome to your beautiful Summerwood floor plan home ... Enjoy Florida living in this IMPECCABLY maintained STUNNING home featuring 3 bedrooms, den/sitting room, 2 full bathrooms. Enjoy a spacious living room which is open to the gourmet kitchen featuring a NATURAL GAS range, a large pantry and an island, with ample prep space, for…

Active
7631 Winding Cypress Dr   Naples
$1,099,000
  • 4Bedrooms
  • 2Bathrooms
  • 2186Sq Ft
  • 2018Year Built
$1,099,000

This beautifully designed and impeccably maintained home offers the perfect blend of elegance and comfortable Naples living. Featuring the highly sought-after Summerwood floor plan with a spacious Great Room extension, the open layout creates an impressive, light-filled space perfect for entertaining guests or relaxing with family after a day exploring beautiful Naples, FL. The gourmet kitchen…

Active
7229 Wiregrass Ct   Naples
$1,750,000
  • 4Bedrooms
  • 4 + 1 HalfBathrooms
  • 3965Sq Ft
  • 2023Year Built
$1,750,000

Rare to find, this light-filled 2-story Stonewater model offering 4 bedrooms, den and 4.5 baths on a pie shaped waterfront lot in the highly desirable gated community of Winding Cypress in Naples. This home has been upgraded to include all available options totaling over $650,000 including 2nd floor loft, hurricane windows and doors, upgraded finishes…

Active
7247 Clamshell Ln   Naples
$1,645,000
  • 4Bedrooms
  • 4Bathrooms
  • 3656Sq Ft
  • 2016Year Built
$1,645,000

A must-see opportunity—spacious, stunning views, showpiece home and resort style Florida living. A rare opportunity to own a 4 bedroom estate home with breathtaking views in the sought-after community of Winding Cypress, offering top-tier amenities at surprisingly low HOA fees. This award-winning Pinnacle model boasts numerous upgrades and interiors like the builder’s model home and…

Active
7670 Jacaranda Ln   Naples
$698,500
  • 3Bedrooms
  • 2Bathrooms
  • 1594Sq Ft
  • 2018Year Built
$698,500

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
7666 Jacaranda Ln   Naples
$575,000
  • 2Bedrooms
  • 2Bathrooms
  • 1574Sq Ft
  • 2018Year Built
$575,000

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 pavers, plantation shutters,…

Active
7460 Blackberry Dr   Naples
$850,000
  • 3Bedrooms
  • 2Bathrooms
  • 2188Sq Ft
  • 2016Year Built
$850,000

Paradise at your fingertips. This modern three-bedroom plus den residence in the prestigious resort style living gated community of Winding Cypress, offers a bright, expansive open floor plan, breathtaking lake views, ceramic tile throughout and a gorgeous and functional updated kitchen featuring solid maple shaker cabinetry, premium hardware, and spacious pantry. This residence is also…

Active
7733 Jacaranda Ln   Naples
$585,000
  • 2Bedrooms
  • 2Bathrooms
  • 1554Sq Ft
  • 2018Year Built
$585,000

Discover effortless luxury in this lovely villa—your private oasis in a premier gated Naples community, Winding Cypress. This inviting 2-bedroom + den, 2-bath home delivers exceptional comfort and versatility with a bright, open layout designed for effortless living and entertaining. Step into the expansive Great Room with high ceilings, creating an open, airy vibe—perfect for gathering…

Active
6770 Pennyroyal Dr   Naples
$825,000
  • 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
7638 Jacaranda Ln   Naples
$499,900
  • 2Bedrooms
  • 2Bathrooms
  • 1574Sq Ft
  • 2017Year Built
$499,900

OPPORTUNITY AWAITS – LOWEST PRICE AVAILABLE! Welcome to the largest villa model in Winding Cypress, featuring a rare private front entrance and expanded foyer that sets the tone for this thoughtfully designed home. This spacious 2-bedrooms and massive den offers an open yet defined living concept with abundant natural light and seamless indoor-outdoor flow. Enjoy…

Active
7679 Winding Cypress Dr   Naples
$900,000
  • 3Bedrooms
  • 2Bathrooms
  • 2186Sq Ft
  • 2019Year Built
$900,000

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, crown molding, 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…

Active
7072 Live Oak Dr   Naples
$1,499,900
  • 4Bedrooms
  • 4Bathrooms
  • 3350Sq Ft
  • 2015Year Built
$1,499,900

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
7457 Winding Cypress Dr   Naples
$1,098,000
  • 3Bedrooms
  • 2Bathrooms
  • 2166Sq Ft
  • 2017Year Built
$1,098,000

Rare opportunity in Winding Cypress this Marten Ray Model Home, Turnkey home fully upgraded, move-in ready home on a premium lot with unobstructed lake and protected preserve views. Experience complete privacy and a resort-style outdoor setting in one of Naples’ most desirable communities. Experience one of the most desirable homes in Winding Cypress, offering a…

Active
6825 Greenbriar Ct   Naples
$998,000
  • 4Bedrooms
  • 3Bathrooms
  • 3036Sq Ft
  • 2022Year Built
$998,000

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…

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