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:
The Martin Ray Floor Plan is PRIVACY-PRIVACY-PRIVACY. 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. A butler’s wine ba

$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:
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

ABOUT THIS HOME
Luxury Home for sale in Winding Cypress, FL:
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 everyday living and entertaining on a grand scale. Step inside to discover a light-filled open floor plan accented with tile flooring in the main living areas, brand-new luxury vinyl plank flooring in all three downstairs bedrooms, and crown molding throughout the first floor. The chef’s kitchen is a showstopper, boasting quart

$1,595,000

4 beds4 baths3,656 sq ft

7412 Winding Cypress Dr, Naples, FL 34114

Chef's kitchen • Lake view home • Smart home features

ABOUT THIS HOME
Luxury Home for sale in Winding Cypress, FL:
Sense the comfort and beauty of this magnificent home the minute you enter the foyer and see the view out to the inviting pool and spa. This 3 bedroom, plus separate den, great room floor-plan is perfect for entertaining or just a lovely place to call home. These original owners have impeccably maintained the home making it feel brand new. Built in 2021 it boasts a chef's delight kitchen with stainless steel appliances, center island and breakfast bar, natural gas cooktop/range, pull-out drawers, quartz counter-tops, recessed and pendant lighting, and more! The cook of the house will love it! The great room and dining area are adjacent to the kitchen. An extra plus is the den with double r

$899,000

3 beds2 baths2,084 sq ft

6856 Winding Cypress Dr, Naples, FL 34114

Zero corner doors • Extended lanai • 2 garage spots

ABOUT THIS HOME
Luxury Home for sale in Winding Cypress, FL:
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, and contemporary finishes throughout. The kitchen boasts quartz countertops, stainless steel appliances, a large center island, and a spacious pantry—perfect for entertaining or casual family meals. The flexible den space offers the ideal setup for a home office, media room, or guest overflow. The primary suite

$950,000

3 beds2 baths2,084 sq ft

6902 Winding Cypress Dr, Naples, FL 34114

Quartz countertops • Large center island • Spacious pantry

Property at 7520 Blackberry Dr, Naples, FL 34114, 3 beds, 3 baths

$1,160,000

3 beds3 baths2,496 sq ft

7520 Blackberry 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:
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

$1,750,000

4 beds4 baths3,323 sq ft

8007 Tiger Lily Dr, Naples, FL 34113

New alarm system • Rescreened pool cage • Custom built

OPEN DEC 14, 1PM TO 3PM3D WALKTHROUGH

ABOUT THIS HOME
Luxury Home for sale in Winding Cypress, FL:
This stunning Stock Development-built, three-bedroom plus den Siesta III residence captures the essence of refined coastal living with elegant finishes, thoughtful upgrades, and serene indoor-outdoor flow. In the prestigious Crane Point neighborhood of Naples Reserve, this home blends architectural excellence with a contemporary sense of comfort. Upon entry, volume ceilings, abundant natural light, and new interior and exterior paint create a bright and inviting ambiance. The open-concept great room features a custom feature wall that becomes the visual centerpiece of the space, while designer lighting, new fans, and Hunter Douglas window treatments enhance both style and functionality. The

$1,499,000

3 beds3 baths2,591 sq ft

14391 Laguna Springs Ln, Naples, FL 34114

Infinity-edge spa • Impact glass windows • Gourmet kitchen

ABOUT THIS HOME
Luxury Home for sale in Winding Cypress, FL:
Welcome to a rare opportunity in the boutique community of Naples Reserve, where sophistication blends seamlessly with relaxed coastal living. Crafted by Stock Development, and showcasing the distinctive touches of Linda Burke Interiors, this beautiful home sits on an oversized lakefront lot, offering panoramic water views and direct access to two large lakes. For those dreaming of water recreation, a private boat dock may be built, elevating your Florida lifestyle to new heights. From interior luxury living, to the spacious lanai and pool area, this home is designed for discerning buyers who want both style and quality. Featuring 12-foot tray ceilings, expansive impact-rated windows and do

$2,135,000

4 beds3.5 baths3,122 sq ft

14386 Laguna Springs Ln, Naples, FL 34114

Lakefront lot • Private boat dock • Spa

ABOUT THIS HOME
Luxury Home for sale in Winding Cypress, FL:
In Naples Reserve, this coastal-style ranch residence offers 3,368 square feet of thoughtfully designed living space on an oversized corner homesite. Built in 2018 and lightly used as a vacation home, the residence provides exceptional privacy and expanded views of beautifully maintained landscaping. The open-concept floor plan includes three bedrooms plus a den, two full baths, and one half bath. The spacious primary suite features direct access to the lanai, dual walk-in closets, and an en-suite bath. The island kitchen is outfitted with white cabinetry, stone countertops, a walk-in pantry and an adjacent dining area ideal for entertaining. Tile flooring extends through all main living ar

$1,150,000

3 beds2.5 baths2,344 sq ft

14878 Windward Ln, Naples, FL 34114

Island kitchen • Screened lanai • Walk in pantry

ABOUT THIS HOME
Luxury Home for sale in Winding Cypress, FL:
Welcome to Crane Point at Naples Reserve! One of Naples’ most popular communities where luxury and laid-back living meets vacation-style amenities. This custom Stock Development "Madison" model captures the best of Florida living with peaceful lake and private preserve views on "rowing Lane". Designed for both family comfort and versatility, this 2971 sqft-4-bedroom plus den, 4.5-bath home, offers a spacious retreat for everyone. From the moment you step inside the foyer, you will notice statement designer lighting, dramatic 16-foot ceilings with custom wood tray accents and expansive glass sliders with a bee-line to SPECTACULAR VIEWS. Wood-look tile dresses the ma

$2,395,000

4 beds4.5 baths2,971 sq ft

14338 Laguna Springs Ln, Naples, FL 34114

Lake views • Spa • Custom pool

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

$2,750,000

4 beds4.5 baths4,134 sq ft

14211 Charthouse Cir, Naples, FL 34114

Property at 14362 Charthouse Cir, Naples, FL 34114, 4 beds, 3.5 baths

$1,650,000

4 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

$2,295,000

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 14286 Charthouse Cir, Naples, FL 34114, 3 beds, 3.5 baths

$2,075,000

3 beds3.5 baths3,077 sq ft

14286 Charthouse Cir, Naples, FL 34114

Property at 14224 Laguna Springs Ln, Naples, FL 34114, 4 beds, 3 baths

$1,699,000

4 beds3 baths2,445 sq ft

14224 Laguna Springs Ln, Naples, FL 34114

Property at 13407 Snook Cir, Naples, FL 34114

$1,100,000

— beds— baths— sq ft

13407 Snook Cir, Naples, FL 34114

Property at 13379 Snook Cir, Naples, FL 34114

$925,000

— beds— baths— sq ft

13379 Snook Cir, Naples, FL 34114

Property at 13613 Snapper Ln, Naples, FL 34114

$1,750,000

— beds— baths— sq ft

13613 Snapper Ln, Naples, FL 34114

Luxury Homes for Sale in Winding Cypress

There are currently 7 luxury homes for sale in Winding Cypress at a median listing price of $750K. 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 136 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, 2 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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