Winding Cypress, FL homes for sale & real estate

8 homes

Sort:

Recommended

ABOUT THIS HOME
Winding Cypress, FL Homes for Sale
Attached villa in the highly sought after community of Winding Cypress. This home boasts 2 bedrooms plus a den which can be used as a 3rd bedroom, 2 full bathrooms and a 2 car garage. Well maintained! The community is situated off of Collier Blvd close to US41 (Tamiami Trl) which is a 15 minute drive to either downtown Naples or Marco Island. You get the best of both worlds and short drive to I-75 takes you to the airport within 40 minutes. This 2019 home is equipped with a full gas kitchen indoors and out. Enjoy a relaxing evening in your own heated pool/spa. This neighborhood is sure to cure boredom with it's miles and miles of hiking/biking/walking paths, nature trails and overlooks, do

$599,900

2 beds2 baths1,554 sq ft

Dog park • Fitness center • Full gas kitchen

7674 Jacaranda Ln, Naples, FL 34114

ABOUT THIS HOME
Winding Cypress, FL Homes for Sale
PRICED TO SELL! Discover exceptional value in one of Naples’ most desirable lifestyle communities, Winding Cypress. Ideally situated on an oversized preserve lot with peaceful pond views, this beautifully maintained Pinnacle floor plan offers over 2,500 square feet of living space with 3 spacious bedrooms, 3 full bathrooms, and a versatile den. Built in 2020, this move-in-ready residence combines elegant finishes, thoughtful upgrades, and outstanding indoor-outdoor living. The expansive outdoor area features a large picture-window screened lanai, gas-heated saltwater pool and spa, custom outdoor kitchen, and generous brick-paver lanai with a covered entertaining area—perfect for

$1,295,000

3 beds3 baths2,515 sq ft

Peaceful pond views • Brick-paver lanai • 0.26 acre lot

6907 Cocoplum St, Naples, FL 34114

FLOOR PLAN

ABOUT THIS HOME
Winding Cypress, FL Homes for Sale
Welcome to one of the most prestigious, stately, and expansive offerings throughout the entire, always-desirable community of Winding Cypress. This exclusive Stonewater Model, with a full 2nd floor of living space, is a DiVosta Builder's flagship luxury home and a very rare find. This property sits on the most exceptional 1/4 acre lot with a spectacular large lake view and full preserve backdrop across the water. Quiet, serene privacy is what you should expect all day long, especially as you witness the incredible early morning sunrises. As soon as you enter the home's grand 2 story foyer via the front double doors, you can't help but notice the opulent main gathering area highlighted by so

$1,400,000

4 beds4.5 baths3,464 sq ft

Quartz countertops • Lake view • Heated built-in pool

7759 Winding Cypress Dr, Naples, FL 34114

FLOOR PLAN

ABOUT THIS HOME
Winding Cypress, FL Homes for Sale
Welcome to your private paradise in the highly sought-after, resort-style community of Winding Cypress! This TURNKEY FURNISHED true 3-bedroom, 2-bathroom villa offers the ultimate blend of luxury, comfort, and effortless living is move-in ready for your immediate enjoyment. The 2-car attached garage—complete with convenient overhead storage racks and additional utility sink—offer great convenience. Discover a bright, open-concept living space featuring seamless tile flooring throughout. The spacious great room flows effortlessly into your own private outdoor oasis. The enlarged screened lanai offers you enjoyment of a private pool and outdoor grill kitchen, located on a excepti

$599,900

3 beds2 baths1,554 sq ft

Brand new hvac unit • Private pool • Accordian shutters

7156 Live Oak Dr, Naples, FL 34114

ABOUT THIS HOME
Winding Cypress, FL Homes for Sale
This meticulously maintained Mystique features 3 bedrooms + den, 2 bathrooms, 2 car garage with a pool and spa overlooking a lake! This home is situated on a spacious corner lot making it ideal for privacy while maintaining a stunning lake view. The turnkey designer furnishings have hardly been used and it's a pet free home. Outside the private oasis features a spa with waterfall, plenty of covered seating areas, and a top of the line outdoor kitchen. Recent updates include an upgraded 400 BTU pool heater (heats up pool quicker), new pool pump, and updated outdoor grill components. While located in the newest section of Winding Cypress - it is in a quiet location with convenient access to b

$940,000

3 beds2 baths2,076 sq ft

Upgraded pool heater • Lake view • Private oasis

6727 Pennyroyal Dr, Naples, FL 34114

Property at 6844 Winding Cypress Dr, Naples, FL 34114, 3 beds, 2 baths

$949,900

3 beds2 baths2,100 sq ft

6844 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

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

$575,000

2 beds2 baths1,574 sq ft

7666 Jacaranda Ln, Naples, FL 34114

Viewing page 1 of 1

End of results

Nearby homes that match your criteria

NEW 4 HRS AGO3D WALKTHROUGH

ABOUT THIS HOME
Winding Cypress, FL Homes for Sale
ELEGANCE meets effortless Florida living in Naples Florida. This beautifully maintained 4 bedroom, 3 FULL bath home features an open concept design and quality upgrades throughout. The stylish kitchen offers stainless steel appliances, under counter lighting, custom wood pantry and shelving in the walk in pantry. Plantation shutters, tile, clean carpet in the guest bedrooms, luxury vinyl flooring in the primary, and eight ceiling fans (one in the kitchen) to add comfort and sophistication. Outside, enjoy a solar-heated pool and private lanai with motorized shutters—perfect for year-round entertaining and relaxation. Additional highlights include 2023 interior paint, updated landscapin

$649,000

4 beds3 baths2,006 sq ft

Motorized shutters • Custom wood pantry • Open concept design

14631 Fern Lake Ct, Naples, FL 34114

NEW 9 HRS AGO3D WALKTHROUGH

ABOUT THIS HOME
Winding Cypress, FL Homes for Sale
One or more photo(s) has been virtually staged, AI generated or rendered. A unique 3 bedroom opportunity in Enbrook! Completed in 2023, this beautifully designed residence blends timeless style with thoughtful functionality, offering an exceptional opportunity to enjoy like-new construction without the wait. This house has been filled with custom upgrades that elevate both everyday living and entertaining. The open, light-filled interior showcases porcelain plank flooring throughout, elegant marble backsplashes, frameless glass shower enclosures, plantation shutters, and motorized window shades that provide both beauty and convenience. The spacious primary suite is enhanced by a custom Cali

$470,000

3 beds2 baths1,503 sq ft

Plantation shutters • Marble backsplashes • 3,920 sq ft lot

1108 Enbrook Loop, Naples, FL 34114

NEW 13 HRS AGOFLOOR PLAN

ABOUT THIS HOME
Winding Cypress, FL Homes for Sale
Shows like a model-Lake Views-Private Pool and Spa! Welcome to a standout opportunity in the desirable Reflection Lakes at Naples, where beautiful lake view, inviting indoor -outdoor living and thoughtful updates come together in one exceptional SWFL home! This 3-bedroom plus den, 2 bath residence offers a spacious, open layout designed for both comfortable everyday living and entertaining. The main living area flows easily into the dining area and breakfast nook, creating a bright and welcoming gathering place. Plantation shutters add timeless style and character throughout the home while the versatile den provides the perfect space for a home office, sitting room, or additional guest

$699,500

3 beds2 baths2,151 sq ft

Private pool • Lake views • Spa

14024 Mirror Dr, Naples, FL 34114

NEW 14 HRS AGO

ABOUT THIS HOME
Winding Cypress, FL Homes for Sale
* * RARE OPPORTUNITY — THE ONLY CARRINGTON VILLA CURRENTLY AVAILABLE IN VERONAWALK! * * One of the community’s most desirable villa floor plans, this spacious 3-bedroom, 2-bath attached villa offers an open and inviting layout with beautiful water views with SOUTHERN exposure. The light-filled living and dining areas feature vaulted ceilings and tile flooring, creating an easy flow for both everyday living and entertaining. The kitchen offers abundant cabinetry, granite countertops, stainless steel appliances, recessed lighting, and a generous breakfast bar with additional seating. Sliding glass doors open the main living area to the covered, screened lanai, where you can rel

$499,900

3 beds2 baths1,554 sq ft

Water views • Southern exposure • Tile flooring

8664 Genova Ct, Naples, FL 34114

ABOUT THIS HOME
Winding Cypress, FL Homes for Sale
One or more photo(s) has been virtually staged, AI generated or rendered. Welcome to easy Naples living in Reflection Lakes! This beautifully prepared 3-bedroom, 2-bath attached villa offers 1,560 square feet of comfortable living space and is truly move-in ready. Thoughtfully prepared for sale, the home features fresh interior paint, professionally deep-cleaned and sealed tile flooring throughout, and all-new light fixtures and ceiling fans. A professional pre-listing inspection was also completed, with necessary repairs addressed in advance—providing added confidence and peace of mind for the next owner. Offered almost fully furnished, this villa makes an ideal Naples residence, sea

$400,000

3 beds2 baths1,560 sq ft

Gated community • Fitness center • Clubhouse

14135 Fall Creek Ct, Naples, FL 34114

OPEN SUN, 1PM TO 4PM

ABOUT THIS HOME
Winding Cypress, FL Homes for Sale
Freshly reintroduced with an entirely new presentation, this expansive Stock-built lakefront residence combines exceptional scale with an impressive collection of thoughtful upgrades. Highlights include a whole-house generator, impact-resistant windows and doors, electric storm shutters, a buried 500-gallon propane tank supplying the gas cooktop, pool heater, outdoor grill and generator, an expanded outdoor kitchen, saltwater pool and spa, and panoramic views across one of Naples Reserve’s largest lakes. The insulated three-car garage is equally well equipped with a mini-split air-conditioning system and electric overhead storage platforms that conveniently lower to the floor—el

$1,814,935

4 beds3.5 baths3,122 sq ft

Saltwater pool • Buried propane tank • 0.25 acre lot

14386 Laguna Springs Ln, Naples, FL 34114

Property at 8556 Alessandria Ct, Naples, FL 34114, 3 beds, 3 baths

$769,000

3 beds3 baths1,983 sq ft

8556 Alessandria Ct, Naples, FL 34114

Property at 14487 Manchester Dr, Naples, FL 34114, 3 beds, 2.5 baths

$729,000

3 beds2.5 baths1,980 sq ft

14487 Manchester Dr, Naples, FL 34114

Property at 9108 Capistrano St S #7405, Naples, FL 34113, 3 beds, 2.5 baths

$449,000

3 beds2.5 baths1,730 sq ft

9108 Capistrano St S #7405, Naples, FL 34113

Property at 8075 Tiger Cv #1711, Naples, FL 34113, 2 beds, 2 baths

$319,000

2 beds2 baths1,203 sq ft

8075 Tiger Cv #1711, Naples, FL 34113

Property at 9092 Capistrano St S #6401, Naples, FL 34113, 3 beds, 2.5 baths

$419,000

3 beds2.5 baths1,715 sq ft

9092 Capistrano St S #6401, Naples, FL 34113

Property at 9110 Capistrano St S #8401, Naples, FL 34113, 3 beds, 2.5 baths

$449,000

3 beds2.5 baths2,086 sq ft

9110 Capistrano St S #8401, Naples, FL 34113

Property at 14686 Sonoma Blvd, Naples, FL 34114, 3 beds, 2 baths

$519,000

3 beds2 baths1,772 sq ft

14686 Sonoma Blvd, Naples, FL 34114

Property at 6760 Beach Resort Dr #5, Naples, FL 34114, 2 beds, 2 baths

$429,900

2 beds2 baths1,351 sq ft

6760 Beach Resort Dr #5, Naples, FL 34114

Property at 6720 Beach Resort Dr #10, Naples, FL 34114, 2 beds, 2 baths

$399,000

2 beds2 baths1,351 sq ft

6720 Beach Resort Dr #10, Naples, FL 34114

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

$293,900

2 beds2 baths— sq ft

9064 N Capistrano St #5004, Naples, FL 34113

(954) 477-7335

Property at 14105 Winchester Ct #504, Naples, FL 34114, 3 beds, 2 baths

$439,000

3 beds2 baths1,368 sq ft

14105 Winchester Ct #504, Naples, FL 34114

Property at 8732 Querce Ct, Naples, FL 34114, 3 beds, 2 baths

$519,000

3 beds2 baths1,437 sq ft

8732 Querce Ct, Naples, FL 34114

Property at 13440 Snook Cir, Naples, FL 34114

$990,000

Land4,356 sq ft (lot)

13440 Snook Cir, Naples, FL 34114

Property at 12 Pearl Dr, Naples, FL 34114

$69,000

Land

12 Pearl Dr, Naples, FL 34114

Average home prices near Winding Cypress, FL

Cities

Neighborhoods
Zip Codes

Winding Cypress homes for sale
$944,950
Naples Reserve Golf Club homes for sale
$1,214,500
Naples Reserve homes for sale
$1,214,500
Falling Waters Beach Resort homes for sale
$399,000
Fiddler's Creek homes for sale
$699,000
Royal Fakapalm homes for sale
$641,842
South Naples homes for sale
$415,000

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)

$867,066

+14.1% YoY | Jul 2026

1 year
3 year
5 year

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

Location

Data

Jul 2026

Growth

% YoY

Winding Cypress, FL

$867,066

+14.1%

See more Winding Cypress, FL market insights

More to explore in Winding Cypress, FL

Featured
Price
Bedroom

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

Buy the right home at the right price near Winding Cypress with a local Redfin real estate agent.

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

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.