Winding Cypress, FL homes for sale & real estate

17 homes

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ABOUT THIS HOME
Winding Cypress, FL Homes for Sale
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 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 natural gas home, it features gas cooking and provides flexibility for future enhancements, offering efficiency and convenience. Living in

$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
Winding Cypress, FL Homes for Sale
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
Winding Cypress, FL Homes for Sale
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
Winding Cypress, FL Homes for Sale
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
Winding Cypress, FL Homes for Sale
Winding Cypress – Resort-Style Living in Naples - Priced to sell! Welcome to your Florida dream home in the sought-after gated community of Winding Cypress! This immaculate residence built in 2016, offers the perfect blend of modern luxury and relaxed coastal living. Featuring 2,230’sq under air, 3 bedrooms plus a den, 2 full baths, and an open-concept floor plan, this home is designed for comfort and entertaining. Step inside to find upgraded tile flooring, a gourmet kitchen with granite countertops, stainless steel appliances, and a large center island ideal for gathering with friends and family. The spacious great room opens through sliding glass doors to a screened lanai, c

$819,000

3 beds2 baths2,230 sq ft

7057 Live Oak Dr, Naples, FL 34114

Gated community • Lagoon-style pool • Gourmet kitchen

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

$569,000

3 beds2 baths1,554 sq ft

7176 Live Oak Dr, Naples, FL 34114

Property at 7666 Jacaranda Ln, Naples, FL 34114, 2 beds, 2 baths

$539,000

2 beds2 baths1,574 sq ft

7666 Jacaranda Ln, Naples, FL 34114

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

$950,000

3 beds2 baths2,084 sq ft

6902 Winding Cypress Dr, Naples, FL 34114

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

$825,000

3 beds3 baths2,128 sq ft

6770 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 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 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 7658 Jacaranda Ln, Naples, FL 34114, 2 beds, 2 baths

$534,500

2 beds2 baths1,554 sq ft

7658 Jacaranda Ln, Naples, FL 34114

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NEW 32 HRS AGO

ABOUT THIS HOME
Winding Cypress, FL Homes for Sale
Tucked on a quiet cul-de-sac on one of the best lakefront lots in Verona Walk, this immaculate Oakmont is the one you’ve been waiting for. Southern exposure bathes the home in sunshine and delivers sweeping water views from the moment you open the front door. Through the covered entry discover an open concept layout with soaring volume ceilings flooded with abundant natural light throughout. The chef’s kitchen offers white wood cabinetry, granite counters, and a center island with breakfast bar open to the dining area and great room. The three spacious bedrooms include a luxurious primary suite with dual vanities, a soaking tub, separate shower, and two expansive walk-in closets

$779,000

3 beds3 baths1,983 sq ft

8596 Alessandria Ct, Naples, FL 34114

8,712 sq ft lot • $466 HOA • 2 garage spots

ABOUT THIS HOME
Winding Cypress, FL Homes for Sale
Welcome to 2085 Yellowfin Circle – the perfect blend of luxury, comfort, and Florida living! This stunning 5-bedroom, 3-bath home is located in the desirable gated community of Manatee Cove, offering low HOA fees, no CDD, and natural gas throughout. The spacious open floor plan features a 3-car garage with insulated doors, a tankless gas water heater, and numerous upgrades inside and out. Step outside to your private oasis—an extended screened lanai with a heated pool, outdoor kitchen, and tranquil lake views. Perfect for entertaining or relaxing year-round! Additional highlights include location within Flood Zone X, meaning flood insurance is not required by mortgage lenders, a

$738,000

5 beds3 baths2,615 sq ft

2085 Yellowfin Cir, Naples, FL 34114

6,969 sq ft lot • $295 HOA • 3 garage spots

ABOUT THIS HOME
Winding Cypress, FL Homes for Sale
SPACIOOUS, READY TO MOVE IN, TURNKEY, 2 BEDROOM, 2 BATHROOM MANUFACTURED HOME IN HIGHLY DESIRABLE ENCHANTING SHORES 55 PLUS COMMUNITY. BOTH BEDROOMS BOAST QUEEN SIZE BEDS AND WALK IN CLOSETS. THE MASTER BEDROOM HAS ITS OWN BATHROOM WITH NEW COMODE AND WALK IN SHOWER WHILE MAIN HAS NEW COMODE AND A TUB/SHOWER UNIT AND WASHER/DRYER IN CLOSET. THE LARGE HORSESHOE KITCHEN FEATURES AN ABUNDANCE OF COUNTERSPACE AND CABINTRY AS WELL AS A BREAKFAST BAR. THE DININGROOM IS LARGE ENOUGH TO ACCOMODATE MULTIPLE DINNER GUESTS. THE FORMAL LIVINGROOM IS FULLY FURNISHED AND OPENS TO AN ENORMOUS FAMILYROOM WITH BEAUTIFUL WINDOWS INCLUDING ROLLER SHADES. WALK OUTSIDE TO ENCLOSED LANAI AND SHED/WORKSHOP WHICH

$152,000

2 beds2 baths1,100 sq ft

38 Turquoise Ave Unit 38T, Naples, FL 34114

$162 HOA • Garage • Community pool

ABOUT THIS HOME
Winding Cypress, FL Homes for Sale
LOCATION, LOCATION, LOCATION. .1 1/2 BUILDINGS TO THE LAZY RIVER!. .. THIS FIRST FLOOR 2BR/2B CONDO IS BEING SOLD TURNKEY AS SHOWN! BEAUTIFUL WOOD-LOOK FLOORING, VOLUMN CEILINGS & COASTAL FEELING FROM THE SECOND YOU WALK IN. .. LANAI ENCLOSURES FOR DAYS YOU WANT THE LANAI AIR CONDITIONED & SLIDE THEM OPEN ON A BEAUTIFUL DAY FOR A TROPICAL BREEZE. THIS SPECTACULAR TROPICAL VIEW WILL MAKE THIS YOUR FAVORITE ROOM IN THE HOUSE!! STORM PROTECTION WILL ALSO GIVE YOU PEACE OF MIND WHEN AWAY. LARGE PRIMARY BEDROOM WITH SPACEOUS BATH, WALK IN CLOSET & A MAGNIFICENT LAKE & FOUNTAIN VIEW. SPLIT BEDROOMS WILL ALLOW YOUR GUESTS PRIVACY. 1 CAR OVER-SIZED GARAGE. .. HOME OF THE FAM

$374,900

2 beds2 baths1,351 sq ft

6760 Beach Resort Dr #9, Naples, FL 34114

$642 HOA • Garage • Community pool

ABOUT THIS HOME
Winding Cypress, FL Homes for Sale
SELLER SAYS SELL NOW. BEST PRICE 2 BEDROOM IN OLE RESORT. Move-In Ready 2-Bedroom Home This inviting 2-bedroom, 2-bathroom home with a 2-car garage is ready for its new owner! Fully furnished, it allows for an effortless move-in—just get approved and start enjoying life at Ole in Lely Resort. The master bedroom features a walk-in closet and a spacious shower, while the second bedroom, located on the opposite side of the home for added privacy, also includes a walk-in closet and a tub/shower combo. A separate laundry room adds extra convenience. The current owner, who resides outside the country, has only used the property for a few weeks in recent years. Easy to show—call for mo

$350,000

2 beds2 baths— sq ft

9064 Capistrano St N #5004, Naples, FL 34113

$964 HOA • 2 garage spots • Community pool

(855) 450-0442

OPEN SUN, 1PM TO 4PM

ABOUT THIS HOME
Winding Cypress, FL Homes for Sale
This stunning villa has been fully remodeled from top to bottom and is completely move-in ready. The interior has been entirely gutted and rebuilt with luxury plank vinyl flooring, fresh paint, new lighting throughout, ceiling fans, and custom closets for beautifully organized storage. A large family room with vaulted ceilings creates an open, airy gathering space. The den offers flexible use — ideal as a dining area, or a secondary family room. The brand-new kitchen features white shaker cabinetry, quartz countertops, stainless steel appliances, and a stylish subway tile backsplash. The laundry room offers new matching cabinetry and its own coordinating backsplash for a clean, cohesi

$574,900

2 beds2 baths1,540 sq ft

8205 Xenia Ln, Naples, FL 34114

5,227 sq ft lot • $436 HOA • 2 garage spots

Property at 9 Garnet Dr Unit 9G, Naples, FL 34114, 2 beds, 2 baths

$79,900

2 beds2 baths810 sq ft

9 Garnet Dr Unit 9G, Naples, FL 34114

Property at 9110 Capistrano St S #8402, Naples, FL 34113, 3 beds, 2 baths

$479,000

3 beds2 baths1,771 sq ft

9110 Capistrano St S #8402, Naples, FL 34113

Property at 9271 Museo Cir #204, Naples, FL 34114, 3 beds, 3.5 baths

$674,900

3 beds3.5 baths2,599 sq ft

9271 Museo Cir #204, Naples, FL 34114

Property at 932 Palm Dr #274, Naples, FL 34114, 2 beds, 2 baths

$167,000

2 beds2 baths859 sq ft

932 Palm Dr #274, Naples, FL 34114

Property at 9063 Capistrano St N #4408, Naples, FL 34113, 3 beds, 2.5 baths

$449,900

3 beds2.5 baths1,800 sq ft

9063 Capistrano St N #4408, Naples, FL 34113

Property at 14558 Manchester Dr, Naples, FL 34114, 3 beds, 2 baths

$605,000

3 beds2 baths1,760 sq ft

14558 Manchester Dr, Naples, FL 34114

Property at 14654 Fern Lake Ct, Naples, FL 34114, 4 beds, 3 baths

$629,000

4 beds3 baths2,067 sq ft

14654 Fern Lake Ct, Naples, FL 34114

Property at 8516 Benelli Ct, Naples, FL 34114, 3 beds, 2 baths

$850,000

3 beds2 baths2,188 sq ft

8516 Benelli Ct, Naples, FL 34114

Property at 14598 Grapevine Dr, Naples, FL 34114, 3 beds, 2 baths

$459,000

3 beds2 baths1,391 sq ft

14598 Grapevine Dr, Naples, FL 34114

Property at 14291 Manchester Dr, Naples, FL 34114, 3 beds, 2 baths

$719,000

3 beds2 baths2,116 sq ft

14291 Manchester Dr, Naples, FL 34114

Property at 26 Garnet Dr Unit 26G, Naples, FL 34114, 1 bed, 1.5 baths

$115,000

1 bed1.5 baths845 sq ft

26 Garnet Dr Unit 26G, 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 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

Average home prices near Winding Cypress, FL

Cities

Neighborhoods
Zip Codes

Winding Cypress homes for sale
$822,000
Naples Reserve Golf Club homes for sale
$1,362,000
Naples Reserve homes for sale
$1,362,000
Falling Waters Beach Resort homes for sale
$379,000
Fiddler's Creek homes for sale
$795,000
Royal Fakapalm homes for sale
$699,000
South Naples homes for sale
$449,000

Winding Cypress, FL real estate trends

All Home Types trends in Winding Cypress, FL

Median Sale Price
# of Homes Sold
Median Days on Market

All Home Types

Median Sale Price (All Home Types)

$930,000

-18.1% YoY | Oct 2025

1 year
3 year
5 year

Based on Redfin calculations of home data from MLS and/or public records.

Location

Data

Oct 2025

Growth

% YoY

Winding Cypress, FL

$930,000

-18.1%

See more Winding Cypress, FL market insights

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