Luxury homes for sale & real estate in Winding Cypress, FL

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ABOUT THIS HOME
Luxury Home for sale in Winding Cypress, FL:
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 great room opens with a dramatic zero-corner disappearing slider, and the home is nearly brand new with 2022 construction still under the renowned DiVosta builder warranty. Located on a private cul-de-sac, this home offers peaceful living while keeping you close to world-class amenities. Windi

$943,000

3 beds3 baths2,150 sq ft

6698 Pennyroyal Dr, Naples, FL 34114

Community gardens • 6,969 sq ft lot • 2 garage spots

OPEN JAN 11, 1PM TO 4PM

ABOUT THIS HOME
Luxury Home for sale in Winding Cypress, FL:
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 years new, and shows like a model home. Located on a very private lot on a cul-de-sac, this salt water pool home with private spa is meticulously one-owner maintained, beautifully decorated, and loaded with builder upgrades. For peace of mind, the owners added a whole house generator as well. The expansive, upstairs addition includes a huge

$1,150,000

4 beds3 baths3,036 sq ft

6825 Greenbriar Ct, Naples, FL 34114

Private spa • Private lot • Cul de sac

OPEN JAN 4, 1PM TO 4PM

ABOUT THIS HOME
Luxury Home for sale in Winding Cypress, FL:
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 bar with refrigerator and cabinetry—all designed to create your own private resort overlooking nature. Inside, every detail reflects model-quality craftsmanship. The home showcases a chef’s kitchen with Alexa-linked gas 5 Burner stove/oven, upgraded cabinetry with pull-out drawers, upgraded appliances.

$1,188,000

3 beds2 baths2,166 sq ft

7457 Winding Cypress Dr, Naples, FL 34114

Screened lanai • Unobstructed views • Butler's wine bar

ABOUT THIS HOME
Luxury Home for sale in Winding Cypress, FL:
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 of mind, and an expansive open layout filled with natural light and outstanding upgrades. Designed for those who love to entertain, the chef-inspired gourmet kitchen features top-tier finishes, premium appliances, and a spacious expanded island, the ideal gathering space for family and friends. With three bedrooms, three baths, a versatile den and an

$1,160,000

3 beds3 baths2,496 sq ft

7520 Blackberry Dr, Naples, FL 34114

Gated community • Serene water view • 8,712 sq ft lot

ABOUT THIS HOME
Luxury Home for sale in Winding Cypress, FL:
Perfection is the only way to describe this home! It shows like a model as it has been rarely lived in since built barely three years ago. Welcome to the desirable Pulte/DiVosta Mystique Model located in the popular amenity rich community of Winding Cypress. This waterfront property sits on a dead-end cul-de-sac and is loaded with owner and builder upgrades. It's impeccably decorated and furnished and could come turnkey providing the new owner with everything you'll ever need to begin living in paradise! The Mystique’s footprint, a 3 bed, 2 bath plus optional den offers the sought after open kitchen, great room, and dining area concept with split bedrooms to ensure comfort and privacy

$925,000

3 beds2 baths2,094 sq ft

6699 Pennyroyal Dr, Naples, FL 34114

Natural gas cooktop • Custom pool • Epoxy painted floor

Property at 7412 Winding Cypress Dr, Naples, FL 34114, 4 beds, 4 baths

$1,595,000

4 beds4 baths3,656 sq ft

7412 Winding Cypress Dr, Naples, FL 34114

Property at 6902 Winding Cypress Dr, Naples, FL 34114, 3 beds, 2 baths

$925,000

3 beds2 baths2,084 sq ft

6902 Winding Cypress Dr, Naples, FL 34114

Property at 6787 Pennyroyal Dr, Naples, FL 34114, 3 beds, 2 baths

$959,900

3 beds2 baths2,186 sq ft

6787 Pennyroyal Dr, Naples, FL 34114

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ABOUT THIS HOME
Luxury Home for sale in Winding Cypress, FL:
Spectacular new Stock Homes Madison model on one of the best lots in Naples Reserve, offering panoramic lake views across from the natural beauty of the Picayune Strand State Forest. This pristine home offers the finest finish details and architectural detail including coffered ceiling detail, impact windows & doors, 14-16-foot ceilings, 10-foot sliders, sparkling tile flooring, shiplap walls, decorative shutters and more. State-of-the-art cook’s kitchen offers 42-inch white shaker cabinetry, massive island with quartz countertops, wine refrigerator, lovely hood over six-burner gas stove and more. The sprawling outdoor space is dramatic with picture frame cage enhancing soothing

$2,300,000

4 beds4.5 baths2,947 sq ft

14362 Laguna Springs Ln, Naples, FL 34114

Massive island • Quartz countertops • Panoramic lake views

ABOUT THIS HOME
Luxury Home for sale in Winding Cypress, FL:
Discover unparalleled luxury and privacy in this exquisite residence crafted by renowned builder Aston Woods. Nestled on a tranquil cul-de-sac, this home boasts breathtaking long water views, offering a serene escape from the everyday hustle. Experience the allure of the Corfu model, boasting four lavish bedroom ensuites, the fifth bedroom was converted to a built-in office with ensuite. The interior impresses with its meticulous design, introducing a grand great room that features a gourmet kitchen. Here, a gas range, generous island, and ample pantry space create the perfect culinary setting. This culinary haven seamlessly transitions into a spacious dining area and an elegant living room

$1,450,000

4 beds5 baths3,447 sq ft

14785 Leeward Dr, Naples, FL 34114

Community boat ramp • Saltwater pool • Spa added in 2022

3D WALKTHROUGH

ABOUT THIS HOME
Luxury Home for sale in Winding Cypress, FL:
Beautiful, updated Naples golf course Lely Resort home with 2,934 sf on a single level. A three bedroom, three bath split plan with separate home office and private saltwater pool and spa. 12-foot ceilings with tray detailing and accent lighting add to the flow of the main living areas and office. 10-foot ceilings are found in the bedrooms and oversized garage. The main living areas have 18" tile on a diagonal, hardwood flooring in the home office and newer carpeting in the bedrooms. Very private and quiet on a lot just under 12,000 sf with double fairway views of the meticulously maintained Flamingo Golf Course from the family room, living room, master bedroom and lanai/pool area. Thi

$1,549,000

3 beds3 baths2,935 sq ft

7984 Tiger Lily Dr, Naples, FL 34113

17th tee box • Saltwater pool • Spa

ABOUT THIS HOME
Luxury Home for sale in Winding Cypress, FL:
Gorgeous 4 bedroom, 3.5 bath FURNISHED Carlyle home with a heated POOL on a lake in Verona Walk. The great room flows seamlessly into the dining area and a well-appointed kitchen, complete with solid cabinetry, stainless steel appliances, and granite countertops. The kitchen offers generous counter space and a layout perfect for entertaining. Large sliders open to a private lanai where you can enjoy serene views and the gentle Florida breeze—ideal for morning coffee or sunset relaxation. The living room has a fireplace for quiet relaxation and window plantation shutters are throughout the home. The home has a central vacuum system, whole house surge protection, and a generator plug in

$875,000

4 beds3.5 baths2,487 sq ft

8008 Wilfredo Ct, Naples, FL 34114

Lake in verona walk • Private lanai • Fireplace

ABOUT THIS HOME
Luxury Home for sale in Winding Cypress, FL:
Welcome to Verona Walk, a premier resort-style community offering luxury, comfort, lakeside tranquility, and convenience! X-Flood Zone - no flood insurance required. This beautifully updated ONE-OWNER, 3-bedroom + Den, 2-bathroom home with a 2-car garage and 2,188 sq. ft. of living space showcases elegant upgrades and thoughtful details throughout. Enjoy Southern exposure and a private backyard oasis featuring a lake view, and heated chlorine pool & spa, perfect for year-round relaxation. Step inside to find a bright, open-concept floor plan with fresh interior paint (2022), crown molding, Bermuda shutters, and all-new light fixtures and fans for a refined coastal feel. The 2022 kitch

$850,000

3 beds2 baths2,188 sq ft

8516 Benelli Ct, Naples, FL 34114

Heated chlorine pool • Accordion shutters • Shiplap accent walls

ABOUT THIS HOME
Luxury Home for sale in Winding Cypress, FL:
Like new, Custom Built 3323 sq ft home in Tiger Island Estates at Lely Resort, featuring 4 bedrooms, den/office, 4 full baths, and oversized two car garage. Lots of crown molding and tray ceilings, two zone AC, 2 ton replaced in 2017 and 5 ton in 2023. Newly Updated master bath in 2025. All appliances, including washer and dryer, replaced in 2013. New paint in all areas inside and outside in 2013. New Alarm System and surround sound in 2015. New roof and rescreened pool cage in 2019. Full hurricane protection on all windows and doors as well as electric Hurricane Screens to enclose the Lanai. New pavers on driveway and pool deck. Beautiful negative edge Salt Water Pool and Spa completely re

$1,650,000

4 beds4 baths3,323 sq ft

8007 Tiger Lily Dr, Naples, FL 34113

New alarm system • Rescreened pool cage • Custom built

Property at 14391 Laguna Springs Ln, Naples, FL 34114, 3 beds, 3 baths

$1,499,000

3 beds3 baths2,591 sq ft

14391 Laguna Springs Ln, Naples, FL 34114

Property at 14386 Laguna Springs Ln, Naples, FL 34114, 4 beds, 3.5 baths

$2,135,000

4 beds3.5 baths3,122 sq ft

14386 Laguna Springs Ln, Naples, FL 34114

Property at 14878 Windward Ln, Naples, FL 34114, 3 beds, 2.5 baths

$1,150,000

3 beds2.5 baths2,344 sq ft

14878 Windward Ln, Naples, FL 34114

Property at 14338 Laguna Springs Ln, Naples, FL 34114, 4 beds, 4.5 baths

$2,395,000

4 beds4.5 baths2,971 sq ft

14338 Laguna Springs Ln, Naples, FL 34114

Property at 14394 Laguna Springs Ln, Naples, FL 34114, 4 beds, 3 baths

$2,270,000

4 beds3 baths2,467 sq ft

14394 Laguna Springs Ln, Naples, FL 34114

Property at 14372 Neptune Ave, Naples, FL 34114, 3 beds, 3.5 baths

$1,889,999

3 beds3.5 baths2,749 sq ft

14372 Neptune Ave, Naples, FL 34114

Property at 14238 Galley Ct, Naples, FL 34114, 3 beds, 3 baths

$1,799,000

3 beds3 baths2,704 sq ft

14238 Galley Ct, Naples, FL 34114

Property at 8650 Palermo Ct, Naples, FL 34114, 3 beds, 2.5 baths

$925,000

3 beds2.5 baths2,250 sq ft

8650 Palermo Ct, Naples, FL 34114

Property at 14211 Charthouse Cir, Naples, FL 34114, 4 beds, 4.5 baths

$2,650,000

4 beds4.5 baths4,134 sq ft

14211 Charthouse Cir, Naples, FL 34114

Property at 14362 Charthouse Cir, Naples, FL 34114, 3 beds, 3.5 baths

$1,595,000

3 beds3.5 baths2,743 sq ft

14362 Charthouse Cir, Naples, FL 34114

Property at 14226 Charthouse Cir, Naples, FL 34114, 4 beds, 3.5 baths

$2,195,000

4 beds3.5 baths3,255 sq ft

14226 Charthouse Cir, Naples, FL 34114

Property at 14302 Charthouse Cir, Naples, FL 34114, 4 beds, 3.5 baths

$1,949,888

4 beds3.5 baths3,011 sq ft

14302 Charthouse Cir, Naples, FL 34114

Property at 14282 Charthouse Cir, Naples, FL 34114, 3 beds, 3.5 baths

$2,275,000

3 beds3.5 baths3,050 sq ft

14282 Charthouse Cir, Naples, FL 34114

Property at 13407 Snook Cir, Naples, FL 34114

$1,100,000

— beds— baths— sq ft

13407 Snook Cir, Naples, FL 34114

Luxury Homes for Sale in Winding Cypress

There are currently 8 luxury homes for sale in Winding Cypress at a median listing price of $784K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Winding Cypress stay on the market for 144 days. Popular neighborhoods include Winding Cypress, Naples Reserve, Falling Waters Beach Resort, Fiddler's Creek, and South Naples. This map is refreshed with the newest listings in Winding Cypress every 15 minutes.

In the past month, 5 homes have been sold in Winding Cypress. In addition to houses in Winding Cypress, there were also 0 condos, 1 townhouse, and 0 multi-family units for sale in Winding Cypress last month. Find your dream home in Winding Cypress using the tools above. Use filters to narrow your search by price, square feet, beds, and baths to find homes that fit your criteria. Our top-rated real estate agents in Winding Cypress are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Winding Cypress. Our Winding Cypress real estate stats and trends will give you more information about home buying and selling trends in Winding Cypress. If you're looking to sell your home in the Winding Cypress area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Winding Cypress with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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