Homes with Pools for Sale in Winding Cypress, FL

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OPEN SUN, 1PM TO 4PM

ABOUT THIS HOME
Home with a Pool for sale in Winding Cypress, FL:
Exceptional southern exposure, breathtaking preserve and water views, and one of the most desirable homesites in Winding Cypress set the stage for this highly upgraded Pinnacle residence. Originally selected with a $125,000 lot premium, this exceptional property is tucked away on a quiet cul-de-sac street and offers a rare combination of privacy, natural beauty, and refined Naples living. Far beyond the standard Pinnacle floor plan, the home features soaring ceilings, expansive living spaces, abundant storage, and a sophisticated kitchen designed for entertaining with an oversized island, wine cooler, natural gas cooking, and impressive walk-in pantry. The private owner’s wing offers

$1,575,000

3 beds3 baths2,496 sq ft

6932 Cocoplum St, Naples, FL 34114

Water views • Wine cooler • Natural gas cooking

NEW 34 HRS AGO

ABOUT THIS HOME
Home with a Pool for sale in Winding Cypress, FL:
Situated on a private . 29 acre, end lot in the highly sought-after gated community of Winding Cypress, this home offers 3,696 square feet of refined Naples living space. Built in 2016, this two-story Pinnacle floor plan features 4 bedrooms, 4 full bathrooms, a versatile den and a spacious 3 car garage. The extended lanai with a premium long lake water view features a custom-built saltwater pool and spa combo plus a fully equipped built-in outdoor gas kitchen, a wonderful place to entertain family and friends. Step inside to discover wood-look tile flooring leading to a gourmet chef’s kitchen, stainless-steel appliances, natural gas cook top, a walk-in pantry and an expansive center i

$1,550,000

4 beds4 baths3,696 sq ft

7383 Mockingbird Ct, Naples, FL 34114

Gated community • Private end lot • Outdoor gas kitchen

OPEN SUN, 1PM TO 4PMFLOOR PLAN

ABOUT THIS HOME
Home with a Pool for sale in Winding Cypress, FL:
Thank you for taking a look at the best value in sought after Winding Cypress! This pristine, 2-Story Summerwood Model, is loaded with options and is located on one of the nicest, private, and quiet lots in the entire community. This amazing home is perfectly situated on a lake's edge with a preserve backdrop. It's on a cul-de-sac with no thru traffic, and miles off of major roadways so it's incredibly quiet, private, with no road noise. If you are looking for a luxurious and functional space to entertain guests, or have them spend some overnights visiting, this is the property for you. Pride of original ownership is clear. With over 3200 square feet there's incredible room to entertain whi

$990,000

4 beds3 baths3,206 sq ft

7775 Winding Cypress Dr, Naples, FL 34114

Private quiet lot • Cul-de-sac • Lake's edge

3D WALKTHROUGH

ABOUT THIS HOME
Home with a Pool for sale in Winding Cypress, FL:
Western sunset views, peaceful pond vistas, and added privacy, this Winding Cypress villa offers a setting that’s truly special! Beautifully upgraded, this unfurnished 2 Bedroom + Den residence enjoys desirable western exposure overlooking a picturesque pond, complemented by private green space adjacent to the property, creating a serene and tranquil retreat. Inside, an inviting open floor plan showcases builder-installed upgrades, elegant porcelain tile, granite countertops, and a stylish kitchen featuring stainless steel appliances and decorative backsplash. The spacious den offers flexibility as a third bedroom or home office. Additional highlights include California Closets throug

$539,000

2 beds2 baths1,554 sq ft

7591 Jacaranda Ln, Naples, FL 34114

Private green space • Granite countertops • 2 garage spots

ABOUT THIS HOME
Home with a Pool for sale in Winding Cypress, FL:
This home has had a complete refresh with a lot of new improvements, new heat/ac units on both floors new pool pump and heater, new roof vents, new lanai screen, pavers on front and side with a refresh landscaping with sitting area, new epoxy garage flooring in extended garage to add a golf cart or storage, interior freshly painted, . this home is a martin ray style 2 story home features 2 split bedrooms on the first floor 2 full baths and office/ den , expanded kitchen with extended coffee /wine station and full pantry and new refridgerator. 2nd floor features a great room , private bedroom and full bath, great for guests or a needed private suite , The pool has a beautiful expanded

$925,000

3 beds3 baths2,300 sq ft

7235 Live Oak Dr, Naples, FL 34114

New lanai screen • Pavers on front • New pool pump

Property at 7098 Live Oak Dr, Naples, FL 34114, 3 beds, 2 baths

$520,000

3 beds2 baths1,554 sq ft

7098 Live Oak Dr, Naples, FL 34114

Property at 7247 Clamshell Ln, Naples, FL 34114, 4 beds, 4 baths

$1,549,000

4 beds4 baths3,656 sq ft

7247 Clamshell Ln, Naples, FL 34114

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

$548,000

2 beds2 baths1,554 sq ft

7602 Jacaranda Ln, Naples, FL 34114

Property at 7230 Live Oak Dr, Naples, FL 34114, 3 beds, 3 baths

$1,100,000

3 beds3 baths2,500 sq ft

7230 Live Oak Dr, Naples, FL 34114

Property at 6825 Greenbriar Ct, Naples, FL 34114, 4 beds, 3 baths

$945,000

4 beds3 baths3,036 sq ft

6825 Greenbriar Ct, Naples, FL 34114

Property at 7072 Live Oak Dr, Naples, FL 34114, 4 beds, 4 baths

$1,350,000

4 beds4 baths3,350 sq ft

7072 Live Oak Dr, Naples, FL 34114

Property at 7156 Live Oak Dr, Naples, FL 34114, 3 beds, 2 baths

$590,000

3 beds2 baths1,554 sq ft

7156 Live Oak Dr, Naples, FL 34114

Property at 6907 Cocoplum St, Naples, FL 34114, 3 beds, 3 baths

$1,295,000

3 beds3 baths2,515 sq ft

6907 Cocoplum St, Naples, FL 34114

Property at 7700 Winding Cypress Dr, Naples, FL 34114, 5 beds, 3 baths

$1,250,000

5 beds3 baths2,950 sq ft

7700 Winding Cypress Dr, Naples, FL 34114

Property at 7478 Winding Cypress Dr, Naples, FL 34114, 3 beds, 3 baths

$1,349,500

3 beds3 baths2,634 sq ft

7478 Winding Cypress Dr, Naples, FL 34114

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NEW 30 HRS AGO

ABOUT THIS HOME
Home with a Pool for sale in Winding Cypress, FL:
Experience refined Florida living in this beautifully appointed three-bedroom plus den, three full baths, Stock Development Siesta III residence, ideally situated within the sought-after gated community of Naples Reserve. Thoughtfully enhanced with impact glass throughout, designer lighting, upgraded landscaping and exceptional outdoor living features, this home offers an inviting blend of sophistication, comfort and effortless entertaining. The beautifully designed outdoor living area serves as private retreat, featuring a sparkling pool and spa, a custom outdoor kitchen and electric storm screens for added comfort and protection. Lush, upgraded landscaping enhances the tropical ambiance,

$1,810,000

3 beds3 baths2,591 sq ft

14212 Laguna Springs Ln, Naples, FL 34114

Upgraded landscaping • Outdoor living area • Impact glass

OPEN SAT, 10AM TO 11AMVIDEO TOUR

ABOUT THIS HOME
Home with a Pool for sale in Winding Cypress, FL:
Convenient location for a 2Br/1Ba home in Naples, Florida! Welcome to 200 Cheetah Drive! This delightful residence would work perfectly for a seasonal retreat, full-time home, or investment property. The main bedroom is very spacious and accommodates a king-size bed. The second bedroom features a queen-size bed. The kitchen boasts a recently added center island with seats. Throughout the home you will appreciate the vinyl plank flooring that was installed in 2025. Other notable updates in 2024 & 2025 include several windows, drywall, rear patio pavers, vinyl siding, and furniture. This home is being sold furnished and also features a roof-over. In addition to these great qualities, YO

$139,000

2 beds1 bath888 sq ft

200 Cheetah Dr #200, Naples, FL 34114

Gated community • Own your own land • Roof-over

3D WALKTHROUGH

ABOUT THIS HOME
Home with a Pool for sale in Winding Cypress, FL:
This furnished two-bedroom, 2.5-bath townhouse in Ole at Lely Resort comes with income already in place. Seasonal tenants are booked through the end of April, so the next owner starts collecting rent right away. The buyer will need to honor the existing rental agreements. The open floor plan connects the kitchen to the main living areas. Major updates are already done, with a new roof and new air conditioning, both installed in 2024. The primary suite has a king bed and the guest bedroom has a queen, and the furnishings and housewares stay, so the unit is ready for guests or for you. Right behind the property is a semi-private pool and grilling area shared only with the other units in the q

$299,000

2 beds2.5 baths1,441 sq ft

9055 Capistrano St N #4206, Naples, FL 34113

New air conditioning • Open floor plan • Lagoon-style pool

OPEN SUN, 1PM TO 4PM

ABOUT THIS HOME
Home with a Pool for sale in Winding Cypress, FL:
Looking for the perfect place to call home? This furnished 2014 Carrington model home with attached 2 car garage and pool located in the beautiful resort style Verona Walk gated community is waiting for you! This beautiful home features a master bedroom suite, guest bedroom, 2 full baths plus a den office with french doors. The open concept floor plan has vaulted ceilings with lots of natural lighting perfect for entertaining or just relaxing. The upgraded Kitchen cabinetry, accent lighting, subway tile backsplash, granite counter tops, with breakfast bar and newer high-end appliances including a double oven, create a great cooking experience. The dining area has a large window offering a

$529,000

2 beds2 baths1,554 sq ft

8494 Karina Ct, Naples, FL 34114

Attached car garage • Master bedroom suite • 6,098 sq ft lot

OPEN SUN, 1PM TO 3PM

ABOUT THIS HOME
Home with a Pool for sale in Winding Cypress, FL:
Enjoy resort-style living at 8992 Cambria Cir #1603 in Olé at Lely Resort. This rarely available, fully furnished Santa Monica townhome offers 2 bedrooms, 2.5 baths, and 1,509 square feet with a distinctive split-level layout featuring an elevated dining room and sunken living room. Highlights include an eat-in kitchen with abundant cabinetry, tile and wood finishes, an oversized front porch, and an attached one-car garage. Upstairs, two en-suite bedrooms include a primary suite with dual vanities and two custom walk-in closets, plus a convenient laundry area and office/flex space with built-ins. Steps away, enjoy a semi-private pool, barbecue stations, and lounge areas. Walk to Ol&e

$360,000

2 beds2.5 baths1,509 sq ft

8992 Cambria Cir #1603, Naples, FL 34113

Eat in kitchen • Fully furnished • Semi private pool

OPEN SUN, 1PM TO 4PM

ABOUT THIS HOME
Home with a Pool for sale in Winding Cypress, FL:
One or more photo(s) has been virtually staged, AI generated or rendered. The Ultimate Florida Escape in VeronaWalk! This popular DiVosta-built Capri model attached villa is constructed with solid poured concrete, is not in a flood zone, and offers a bright, open split-bedroom floor plan designed for comfortable Florida living. Meticulously maintained and recently upgraded from top to bottom, this move-in-ready home features 2 bedrooms plus a versatile den, 2 beautifully updated bathrooms, and an attached 2-car garage. Enjoy a fresh feel throughout with newly installed luxury vinyl plank flooring, fresh interior paint, new lighting fixtures, and ceiling fans. Soaring vaulted ceilings and a

$450,000

2 beds2 baths1,540 sq ft

8311 Yasmina Way, Naples, FL 34114

Not in a flood zone • Recently upgraded • 4,356 sq ft lot

Property at 8003 Panther Trl #704, Naples, FL 34113, 2 beds, 2 baths

$354,900

2 beds2 baths1,460 sq ft

8003 Panther Trl #704, Naples, FL 34113

Property at 151 Cheetah Dr #151, Naples, FL 34114, 1 bed, 1 bath

$89,000

1 bed1 bath408 sq ft

151 Cheetah Dr #151, Naples, FL 34114

Property at 158 Cheetah Dr #158, Naples, FL 34114, 1 bed, 1 bath

$95,000

1 bed1 bath700 sq ft

158 Cheetah Dr #158, Naples, FL 34114

Property at 17 Jade Dr Unit 17J, Naples, FL 34114, 2 beds, 2 baths

$79,500

2 beds2 baths600 sq ft

17 Jade Dr Unit 17J, Naples, FL 34114

Property at 561 Cattleya Refuge #561, Naples, FL 34114, 1 bed, 2 baths

$174,000

1 bed2 baths960 sq ft

561 Cattleya Refuge #561, Naples, FL 34114

Property at 9093 Capistrano St S #7501, Naples, FL 34113, 2 beds, 2.5 baths

$375,000

2 beds2.5 baths1,487 sq ft

9093 Capistrano St S #7501, Naples, FL 34113

Property at 1220 Enbrook Loop, Naples, FL 34114, 2 beds, 2 baths

$469,900

2 beds2 baths1,503 sq ft

1220 Enbrook Loop, Naples, FL 34114

Property at 558 Cattleya Refuge #558, Naples, FL 34114, 2 beds, 2 baths

$230,000

2 beds2 baths960 sq ft

558 Cattleya Refuge #558, Naples, FL 34114

Property at 14727 Nautilus Pl, Naples, FL 34114, 4 beds, 3 baths

$925,000

4 beds3 baths2,350 sq ft

14727 Nautilus Pl, Naples, FL 34114

Property at 206 Cheetah Dr #206, Naples, FL 34114, 1 bed, 1.5 baths

$129,000

1 bed1.5 baths840 sq ft

206 Cheetah Dr #206, Naples, FL 34114

Property at 8181 Xenia Ln, Naples, FL 34114, 2 beds, 2 baths

$539,900

2 beds2 baths1,540 sq ft

8181 Xenia Ln, Naples, FL 34114

Property at 8957 Malibu St #502, Naples, FL 34113, 2 beds, 2.5 baths

$389,000

2 beds2.5 baths1,531 sq ft

8957 Malibu St #502, Naples, FL 34113

Property at 535 Cheetah Dr, Naples, FL 34114

$110,000

Land2,613 sq ft (lot)

535 Cheetah Dr, Naples, FL 34114

Property at 13431 Snook Cir, Naples, FL 34114

$550,000

Land3,049 sq ft (lot)

13431 Snook Cir, Naples, FL 34114

Homes with Pools for Sale in Winding Cypress

There are currently 15 homes with pools for sale in Winding Cypress at a median listing price of $978K. 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 30 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, 1 home has 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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