Homes with Parking for Sale in Winding Cypress, FL

18 homes

Sort:

Recommended

ABOUT THIS HOME
Home with Parking for sale in Winding Cypress, FL:
Discover resort-style living in this rare 3-bedroom + den, 3-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 theatre 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. Winding Cypress

$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 TODAY, 1PM TO 4PM

ABOUT THIS HOME
Home with Parking 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

ABOUT THIS HOME
Home with Parking 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 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 TODAY, 1PM TO 4PM

ABOUT THIS HOME
Home with Parking 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

OPEN DEC 14, 1PM TO 4PM

ABOUT THIS HOME
Home with Parking for sale in Winding Cypress, FL:
PRICE ADJUSTMENT- Ready for the season This charming model is the perfect fit featuring an inviting open-floor concept where natural light streams through the windows. The kitchen boasts granite counters, stainless appliances and a center island and extra storage for everyday use and easy entertaining. The pantry closet has plenty of space for all of your staple goods. Tile floors are throughout much of the space. There's a den/flex room with french doors that can be used as an additional bedroom when needed or office, hobby or quiet sitting room. Additional guest bedroom and bathroom with combined tub and shower and granite topped vanity offers privacy for your family and guests. The laun

$639,900

2 beds2 baths1,685 sq ft

7248 Live Oak Dr, Naples, FL 34114

Stainless appliances • Pantry closet • Open-floor concept

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 6699 Pennyroyal Dr, Naples, FL 34114, 3 beds, 2 baths

$925,000

3 beds2 baths2,094 sq ft

6699 Pennyroyal Dr, 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 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 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 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 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 6856 Winding Cypress Dr, Naples, FL 34114, 3 beds, 2 baths

$899,000

3 beds2 baths2,084 sq ft

6856 Winding Cypress Dr, Naples, FL 34114

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

$529,000

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

Viewing page 1 of 1

End of results

Nearby homes that match your criteria

ABOUT THIS HOME
Home with Parking for sale in Winding Cypress, FL:
Carrington Model , Original Owner , Built in 2012 , This Open floor plan with 3bdrms and 2 full baths . ALSO HAS AN OVERSIZED LOT with Easy access to install a custom pool. There is also Extra Hurricane Protection with custom Accordion shutter's . Upgraded Stainless steel and granite counter tops, extended tile , freshly painted epoxy garage floor . Verona Walk offers 24 hr. guarded gated entry, lighted tennis, bocce ball, basketball and pickle ball courts, resort-size community Lagoon pool, lap pool, tot lot, over 20 miles trails, 24/7 gym, post office, café/restaurant, ice cream Shoppe, hair salon, gas station, library, computer center, ballroom, card rooms, and a full-time activit

$439,000

3 beds2 baths1,540 sq ft

8379 Karina Ct, Naples, FL 34114

Extended tile • Granite counter tops • Oversized lot

ABOUT THIS HOME
Home with Parking for sale in Winding Cypress, FL:
Gorgeous 4 bedroom, 3.5 bath FURNISHED Carlyle heated POOL home on a lake in Verona Walk. A spacious 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

3D WALKTHROUGH

ABOUT THIS HOME
Home with Parking for sale in Winding Cypress, FL:
Experience bright southern exposure and stunning expansive lake views surrounded by lush, tropical landscaping in this beautifully maintained second-floor residence in the popular Laguna neighborhood in desirable Fiddler's Creek community. Filled with natural light and designed for effortless indoor-outdoor living, this spacious three-bedroom, three-full-bath home offers a generous layout with soaring ceilings, impact doors and windows, and an expansive lanai that creates a serene retreat overlooking peaceful water views and palm trees. An attached two-car garage enhances everyday convenience, while the home's elevated position provides exceptional privacy, sunlight and an inviting sense of

$588,000

3 beds3 baths2,361 sq ft

9271 Museo Cir #203, Naples, FL 34114

Expansive lake views • Soaring ceilings • Expansive lanai

3D WALKTHROUGH

ABOUT THIS HOME
Home with Parking for sale in Winding Cypress, FL:
Experience refined luxury living in this stunning 3-bedroom, 3-bath residence in Tiger Island Estates, complete with a versatile den and ideally positioned along the 17th tee box of the prestigious Flamingo Golf Course at Lely Resort. Designed with both elegance and comfort in mind, this exquisite home offers spacious interiors, sophisticated finishes, and an effortless indoor–outdoor flow perfect for today’s lifestyle. The open-concept main living area is defined by soaring 12-foot ceilings, tray detailing, arched entryways, abundant natural light, and seamless access to the home’s private outdoor retreat complete with a stunning saltwater pool and spa, space for entertai

$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
Home with Parking for sale in Winding Cypress, FL:
Spectacular sunsets every day! This western exposure 3 bedroom, 3 bath first floor coach home provides coffee table book worthy images that are unforgettable. Fresh and inviting, with a coastal vibe you will love, in the village of Laguna in Fiddler’s Creek. Newer roofs, all impact windows, 3 year old AC unit, light colored tile accented by wood flooring in kitchen, spacious primary suite with shower, soaking tub, 2 vanities, water closet, 2 walk in closets, and access to private lanai. Warm welcoming kitchen with stainless appliances, loads of cherry cabinetry, plus casual dining area leads into the family room which oozes relaxation and comfort. The living and dining area separates

$575,000

3 beds3 baths2,100 sq ft

9255 Museo Cir #102, Naples, FL 34114

Resort pools • Newer roofs • Stainless appliances

3D WALKTHROUGH

ABOUT THIS HOME
Home with Parking for sale in Winding Cypress, FL:
LOCK IN YOUR NAPLES FUTURE! LEASED TOWNHOME WITH RESORT AMENITIES. Why wait for prices to rise? Secure your piece of paradise today and let the rental income offset your costs. This stunning townhome in Ole at Lely Resort is the perfect "Buy and Hold" opportunity, currently leased at $2,500/mo until May 2027. This is your chance to purchase a future vacation home or retirement haven now, while generating guaranteed revenue. This asset is mechanically sound and offers stress-free ownership, featuring a brand new roof (2024) and a newer 2-stage AC (2023). The two-story townhouse provides a spacious 2-bedroom, 2.5-bath layout with an open-concept living area and a sleek kitchen. It i

$345,000

2 beds2.5 baths1,520 sq ft

9067 Capistrano St N #4503, Naples, FL 34113

Fitness center • Semi-private pool • Brand new roof

Property at 8700 Querce Ct, Naples, FL 34114, 3 beds, 2 baths

$489,000

3 beds2 baths1,437 sq ft

8700 Querce Ct, Naples, FL 34114

Property at 8941 Malibu St #1, Naples, FL 34113, 3 beds, 2 baths

$399,900

3 beds2 baths1,770 sq ft

8941 Malibu St #1, Naples, FL 34113

Property at 7063 Toscana Ct, Naples, FL 34114, 3 beds, 2.5 baths

$849,000

3 beds2.5 baths2,000 sq ft

7063 Toscana Ct, Naples, FL 34114

Property at 9235 Tesoro Ln #101, Naples, FL 34114, 3 beds, 3 baths

$549,000

3 beds3 baths2,300 sq ft

9235 Tesoro Ln #101, Naples, FL 34114

Property at 8596 Alessandria Ct, Naples, FL 34114, 3 beds, 3 baths

$779,000

3 beds3 baths1,983 sq ft

8596 Alessandria Ct, Naples, FL 34114

Property at 2085 Yellowfin Cir, Naples, FL 34114, 5 beds, 3 baths

$738,000

5 beds3 baths2,615 sq ft

2085 Yellowfin Cir, Naples, FL 34114

Property at 6760 Beach Resort Dr #9, Naples, FL 34114, 2 beds, 2 baths

$374,900

2 beds2 baths1,351 sq ft

6760 Beach Resort Dr #9, Naples, FL 34114

Property at 9064 Capistrano St N #5004, Naples, FL 34113, 2 beds, 2 baths

$350,000

2 beds2 baths— sq ft

9064 Capistrano St N #5004, Naples, FL 34113

(855) 450-0442

Property at 8205 Xenia Ln, Naples, FL 34114, 2 beds, 2 baths

$574,900

2 beds2 baths1,540 sq ft

8205 Xenia Ln, 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 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

Homes with Parking for Sale in Winding Cypress

There are currently 18 homes with parking 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.

More real estate resources for Winding Cypress, FL

Neighborhoods

Nearby Cities

Zip Codes

Nearby Cities with Homes with Parking

Nearby Neighborhoods with Homes with Parking

More to explore in Winding Cypress, FL

How to buy a house in Winding Cypress, FL

How much house can I afford?

How to buy a house in 10 steps

First-time homebuyer's guide

See more home buying guides

Popular Markets in Florida

Download the Redfin App on the Apple App Store

Download the Redfin App from the Google Play Store

Join us

Become an Agent

Get referrals

Careers

Find homes faster

About us

Why Redfin?

Community Impact

Diversity & Inclusion

Find us

Subsidiaries

Affiliated Business

Countries

United States

Canada

Updated September 2025: By searching, you agree to the Terms of Use, and Privacy Policy.

Do not sell or share my personal information.

REDFIN and all REDFIN variants, WALK SCORE, and the R logos, are trademarks of Redfin Corporation, registered or pending in the USPTO.

California DRE #01521930

Redfin is licensed to do business in New York as Redfin Real Estate. NY Standard Operating Procedures

New Mexico Real Estate Licenses

TREC: Info About Brokerage Services, Consumer Protection Notice

All mortgage lending products and information are provided by Rocket Mortgage, LLC | NMLS #3030; www.NMLSConsumerAccess.org. Licensed in 50 states. This site is not authorized by the New York State Department of Financial Services for mortgage solicitation or loan applications activities related to properties located in the State of New York.

Redfin Corporation is an affiliated business of Rocket Limited Partnership. Each company, and their subsidiaries, are separate legal entities operated and managed through its own management and governance structures.

If you are using a screen reader, or having trouble reading this website, please call Redfin Customer Support for help at 1-844-759-7732.

REDFIN IS COMMITTED TO AND ABIDES BY THE FAIR HOUSING ACT AND EQUAL OPPORTUNITY ACT. READ REDFIN'S FAIR HOUSING POLICY AND THE NEW YORK STATE FAIR HOUSING NOTICE.