MLS Listings for Sale in Winding Cypress, FL

19 homes

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NEW 12 HRS AGO

ABOUT THIS HOME
MLS Listings for Sale in Winding Cypress, FL
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 true retreat, featuring a saltwater private pool framed by mature cypress trees, colorful landscaping, and wide natural preserve views. Inside, the home offers thoughtful upgrades including 8-foot interior doors, new bedroom flooring, refreshed landscaping, and built-in garage storage that helps keep everything organized. As a true natural gas home, it features gas cooking and provides flexibility for future enhancements, offering both efficiency and conve

$600,000

3 beds2 baths1,554 sq ft

7167 Live Oak Dr, Naples, FL 34114

Extra-large lot • New bedroom flooring • 6,098 sq ft lot

OPEN DEC 7, 1PM TO 4PM

ABOUT THIS HOME
MLS Listings 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 4 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
MLS Listings 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

OPEN SUN, 1PM TO 4PM

ABOUT THIS HOME
MLS Listings 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
MLS Listings for Sale in Winding Cypress, FL
The finest in resort style living! You do not want to miss this opportunity to own a find like this in the community of Winding Cypress. This beautifully updated 2+den/2 bath jem has 9'4" ceilings with a two car garage is move-in ready and it has everything you need to call the sought after Villa your home. Newer refrigerator + hot water tank, pavers, plantation shutters and much more. Almost 2/3 of this amazing community is set aside just for a tranquil preserve and wooded area. Only 8 miles to downtown Naples and 9 miles to Marco Island. Just a few amenities include pickle ball, bocce court, clubhouse, community park, community pool/spa/hot tub, community room and much more. What are

$539,000

2 beds2 baths1,574 sq ft

7666 Jacaranda Ln, Naples, FL 34114

Pickle ball • Bocce court • Community pool

Property at 7057 Live Oak Dr, Naples, FL 34114, 3 beds, 2 baths

$819,000

3 beds2 baths2,230 sq ft

7057 Live Oak Dr, Naples, FL 34114

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

$1,695,000

4 beds4 baths3,656 sq ft

7412 Winding Cypress Dr, Naples, FL 34114

Property at 7248 Live Oak Dr, Naples, FL 34114, 2 beds, 2 baths

$649,900

2 beds2 baths1,685 sq ft

7248 Live Oak Dr, Naples, FL 34114

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

$950,000

3 beds2 baths2,084 sq ft

6902 Winding Cypress Dr, Naples, FL 34114

Property at 7176 Live Oak Dr, Naples, FL 34114, 3 beds, 2 baths

$579,900

3 beds2 baths1,554 sq ft

7176 Live Oak Dr, Naples, FL 34114

Property at 7659 Jacaranda Ln, Naples, FL 34114, 2 beds, 2 baths

$599,900

2 beds2 baths1,544 sq ft

7659 Jacaranda Ln, Naples, FL 34114

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

$1,185,000

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

Property at 7602 Jacaranda Ln, Naples, FL 34114, 2 beds, 2 baths

$539,000

2 beds2 baths1,554 sq ft

7602 Jacaranda Ln, Naples, FL 34114

Property at 7670 Jacaranda Ln, Naples, FL 34114, 3 beds, 2 baths

$749,900

3 beds2 baths1,594 sq ft

7670 Jacaranda Ln, Naples, FL 34114

Property at 7690 Jacaranda Ln, Naples, FL 34114, 2 beds, 2 baths

$639,000

2 beds2 baths1,554 sq ft

7690 Jacaranda Ln, Naples, FL 34114

Property at 6770 Pennyroyal Dr, Naples, FL 34114, 3 beds, 3 baths

$899,000

3 beds3 baths2,128 sq ft

6770 Pennyroyal Dr, Naples, FL 34114

Property at 7658 Jacaranda Ln, Naples, FL 34114, 2 beds, 2 baths

$534,500

2 beds2 baths1,554 sq ft

7658 Jacaranda Ln, Naples, FL 34114

Property at 7638 Jacaranda Ln, Naples, FL 34114, 2 beds, 2 baths

$529,000

2 beds2 baths1,574 sq ft

7638 Jacaranda Ln, Naples, FL 34114

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ABOUT THIS HOME
MLS Listings for Sale in Winding Cypress, FL
The J. W. Marriott golf membership is available with this charming luxury condominium. In newly upgraded Laguna at Fiddler's Creek, this superior location has an exceptional lake view and is close to the Laguna neighborhood pool. The attached two-car garage and delightful courtyard provide a welcoming entry into an open foyer. The charming interior includes 10-foot ceilings, 8-foot doors and impact glass throughout. Ceramic tile flooring and the ideally designed floor plan add to this environment of gracious living. Granite counters, new appliances and open space throughout create a theme of luxury living with three bedrooms and three full baths. Walk-in closets and the exceptionally spacio

$605,000

3 beds3 baths2,100 sq ft

9243 Tesoro Ln #102, Naples, FL 34114

$1,072 HOA • 2 garage spots • Community pool

ABOUT THIS HOME
MLS Listings for Sale in Winding Cypress, FL
Searching for a waterfront home in Naples with room to grow and personalize? This 4-bedroom, 3-bath residence offers just that! Built in 2012 on a quarter-acre lot, this 2,032 sq ft home features an open, light-filled layout designed for comfortable Florida living. The spacious living area flows to a screened lanai overlooking a backyard lagoon, perfect for morning coffee or evening sunsets. Inside, a split-bedroom design provides privacy and flexibility for family, guests, or a home office space. The kitchen opens to the great room, creating a natural gathering area for entertaining. With a few thoughtful updates, this property could easily reflect your personal style while increasing long

$629,000

4 beds3 baths2,067 sq ft

14654 Fern Lake Ct, Naples, FL 34114

7,840 sq ft lot • $368 HOA • 2 garage spots

ABOUT THIS HOME
MLS Listings 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

7,405 sq ft lot • $466 HOA • 2 garage spots

ABOUT THIS HOME
MLS Listings for Sale in Winding Cypress, FL
Located in the highly coveted Reflection Lakes community, this stunning lakefront 3-bed, 2-bath villa perfectly blends style and functionality. Step inside to discover an open floor plan, highlighted by elegant crown molding and neutral tile flooring—a perfect blank slate ready for your personal touch. The highlight of this home is the spacious screened lanai, complete with a private pool installed in 2022, offering the perfect backdrop for outdoor relaxation or entertaining. Move right in as this home comes fully furnished with new, modern furniture, allowing you to embrace the relaxed Florida lifestyle from the moment you arrive. The chef-inspired kitchen is equipped with stainless

$459,000

3 beds2 baths1,391 sq ft

14598 Grapevine Dr, Naples, FL 34114

4,791 sq ft lot • $338 HOA • 2 garage spots

ABOUT THIS HOME
MLS Listings for Sale in Winding Cypress, FL
Goregous Coastal Luxury & Resort-Style 3 bed 2 bath Single Family luxury home with FULL SIZE Solar Pool, and LOW HOA! Offering the ideal blend of elegance, wellness & relaxation, a true private-retreat where every day feels like a vacation! Nestled on tranquil LAKE with WESTERN EXPOSURE! Enjoy breathtaking SUNSETS that paint the sky each evening. A true Southwest Florida lifestyle experience! LOW HOA, Move-In Ready & designer touches for the Discriminating Buyer. Beautiful Double Door Front Entry, NEW AC, Manual HURRICANE SHUTTERS providing peace of mind, NEW Professional Landscaping. Large Kitchen for the Gourmet Chef in your life, new stainless appliances, a separate For

$719,000

3 beds2 baths2,116 sq ft

14291 Manchester Dr, Naples, FL 34114

7,405 sq ft lot • $368 HOA • 2 garage spots

ABOUT THIS HOME
MLS Listings for Sale in Winding Cypress, FL
Immaculate and freshly painted this versatile home is ready for you to make it your own. Within the last two years everything has been upgraded or remodeled including the washer, dryer, gas stove, refrigerator/freezer, microwave and the mini split a/c in familyroom. All of the light fixtures and ceiling fans have been updated and new front and rear doors installed. The interior is completely and tastefully painted while the exterior flaunts beautiful landscaping as well as a cement patio affording some privacy in the back yard. This home is located in Enchanting Shores 55 plus coop and offers a multitude of amenities and activities and is extremely well managed, maintained and affordable. C

$119,000

1 bed1.5 baths845 sq ft

26 Garnet Dr Unit 26G, Naples, FL 34114

$162 HOA • Garage • Community pool

Property at 14331 Neptune Ave, Naples, FL 34114, 4 beds, 3 baths

$1,495,000

4 beds3 baths2,467 sq ft

14331 Neptune Ave, Naples, FL 34114

Property at 9081 Albion Ln S #6508, Naples, FL 34113, 3 beds, 2.5 baths

$525,000

3 beds2.5 baths1,800 sq ft

9081 Albion Ln S #6508, Naples, FL 34113

Property at 45 Aquamarine Ave Unit 45Q, Naples, FL 34114, 2 beds, 2 baths

$275,000

2 beds2 baths1,500 sq ft

45 Aquamarine Ave Unit 45Q, Naples, FL 34114

Property at 2191 Yellowfin Cir, Naples, FL 34114, 2 beds, 2 baths

$679,000

2 beds2 baths1,405 sq ft

2191 Yellowfin Cir, Naples, FL 34114

Property at 159 Cheetah Dr #159, Naples, FL 34114, 2 beds, 2 baths

$149,000

2 beds2 baths1,000 sq ft

159 Cheetah Dr #159, Naples, FL 34114

Property at 1144 Enbrook Loop, Naples, FL 34114, 2 beds, 2 baths

$447,900

2 beds2 baths1,503 sq ft

1144 Enbrook Loop, Naples, FL 34114

Property at 8089 Xenia Ln, Naples, FL 34114, 2 beds, 2 baths

$449,000

2 beds2 baths1,540 sq ft

8089 Xenia Ln, Naples, FL 34114

Property at 8007 Tiger Lily Dr, Naples, FL 34113, 4 beds, 4 baths

$1,750,000

4 beds4 baths3,323 sq ft

8007 Tiger Lily Dr, Naples, FL 34113

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 14134 Nautica Ct, Naples, FL 34114, 3 beds, 2.5 baths

$625,000

3 beds2.5 baths1,841 sq ft

14134 Nautica Ct, Naples, FL 34114

Property at 8407 Benelli Ct, Naples, FL 34114, 3 beds, 2 baths

$749,000

3 beds2 baths2,188 sq ft

8407 Benelli Ct, Naples, FL 34114

Property at 9066 Albion Ln N #5104, Naples, FL 34113, 3 beds, 2 baths

$475,000

3 beds2 baths1,771 sq ft

9066 Albion Ln N #5104, Naples, FL 34113

Property at 13371 Snook Cir, Naples, FL 34114

$525,000

— beds— baths— sq ft

13371 Snook Cir, Naples, FL 34114

Property at 13461 Ladyfish Ln, Naples, FL 34114

$560,000

— beds— baths— sq ft

13461 Ladyfish Ln, Naples, FL 34114

MLS Listings for Sale in Winding Cypress

There are currently 19 mls listings for sale in Winding Cypress at a median listing price of $720K. 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 108 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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