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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3Bedrooms
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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…
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3Bedrooms
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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…
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3Bedrooms
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2Bathrooms
- 2186Sq Ft
- 2018Year Built
$1,099,000
This beautifully designed and impeccably maintained home offers the perfect blend of elegance and comfortable Florida living in Naples. 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.
The gourmet…
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4Bedrooms
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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…
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4Bedrooms
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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…
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3Bedrooms
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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…
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2Bedrooms
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2Bathrooms
- 2036Sq Ft
- 2018Year Built
$989,000
Experience refined Naples living in this impeccably maintained, fully furnished residence in the prestigious gated community of Winding Cypress. Featuring two bedrooms plus a den, two baths, plus an extended additional den leading to the waterfront pool area, and an extended 2-car garage; this home has been thoughtfully designed and is move-in ready - blending…
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2Bedrooms
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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,…
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3Bedrooms
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2Bathrooms
- 2188Sq Ft
- 2016Year Built
$850,000
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 equipped with gas stove,…
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3Bedrooms
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2Bathrooms
- 2186Sq Ft
- 2022Year Built
$919,000
The View !!!!!!!! built in 2022 Move in Ready ! Like new Contemporary style mystique model 3 bdrm den 2bath in Winding Cypress. Location Location with this breathtaking long lake view , last home on street on long landscaped corner affords plenty of privacy.Some of…
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2Bedrooms
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2Bathrooms
- 1554Sq Ft
- 2018Year Built
$585,000
Discover effortless luxury in this impeccably maintained villa—your private oasis in Naples' premier gated community, Winding Cypress. This inviting 2-bedroom + den, 2-bath home delivers exceptional comfort and versatility.
Both bedrooms feature generous walk-in closets. The guest suite offers true privacy with a hallway pocket door that creates a secluded en-suite retreat. Bathrooms showcase floor-to-ceiling porcelain…
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2Bedrooms
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2Bathrooms
- 1554Sq Ft
- 2016Year Built
$599,000
Nestled within the gated, amenity-rich community of Winding Cypress, this thoughtfully designed turnkey furnished two-bedroom plus den, two-bath residence offers an exceptional blend of comfort, quality, and relaxed Florida living. The open floor plan is enhanced by wood flooring throughout the main living areas, along with crown molding, and a distinctive coffered ceiling in the…
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3Bedrooms
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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…
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3Bedrooms
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2Bathrooms
- 2100Sq Ft
- 2021Year Built
$949,900
Welcome to newest and last phase of homes built in 2020 in the vibrant well maintained community of Winding Cypress. Located just off Collier and 41 and minutes to 75 , Marco Island and downtown Naples
This summer wood model is sure to please with 3 bdrms 2 baths with full showers ,…
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2Bedrooms
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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…
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3Bedrooms
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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…
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4Bedrooms
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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…
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3Bedrooms
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2Bathrooms
- 2166Sq Ft
- 2017Year Built
$1,098,000
Rare opportunity in Winding Cypress—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 rare combination of premium lot, complete upgrades, and…
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4Bedrooms
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3Bathrooms
- 3036Sq Ft
- 2022Year Built
$1,050,000
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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