Date
Details
Price
Change
Source
10/25/2026
Listed
$990,000
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
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Property Description
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 while also providing privacy for visitors. This home boasts 4 bedrooms, 3 full baths, and a large office or flex room that can be used as the new owner desires. The upstairs area is expansive with a huge gathering space that can be used as a theater room, craft area, media room, or office. The upstairs has it's own large bedroom and full bathroom. The 2nd floor also has it's own zoned climate control with a dedicated additional HVAC unit. The upgrades and amenities that this property offers are impressive. These features include: an upgraded kitchen package that adds optional cabinets, quartz counters & premium appliances, plank tile flooring, an incredible extended great room gathering space, built-in saltwater pool w/integral spa, a whole house generator, easy-use accordion shutters, hurricane rated electric shades enclosing the lanai, an outdoor summer kitchen, surround sound ceiling speakers, an upgraded, private owner's suite, built-in closet organizers, convenient interior plantation shutters, and a deep 2 car garage with epoxy flooring and a must have 2nd refrigerator. Winding Cypress is an amenity rich, natural gas community and a hidden gem of Naples. Meet friends and neighbors at the resident's only, full-service restaurant and bar that's conveniently located at the edge of the incredible resort pool. Play pickleball, tennis, or bocce on the premium lighted courts. Take advantage of the world-class fitness center. Enjoy the nature trail boardwalk, dog parks, and community garden. Participate in any of the huge selection of activities that the community and HOA offers. Speaking of the HOA, you will not find a better value for cost anywhere in Naples. It's not even close. The HOA General Manager, Assistant Manager, Activities Director, and Support Staff are all full-time and on site to better assist the residents. Winding Cypress is conveniently located just 10 minutes to the beaches and entertainment on Marco Island, 15 minutes to all that downtown Olde Naples has to offer, 10 minutes to I75, and just 35 minutes to RSW Airport.
Full Property Details
Full Property Details for 7775 Winding Cypress Dr
General
- Price: $990,000
- HOA FEE: $514/month
- HOA FEE FREQ.: Quarterly
- Taxes: (2025)
- Status: Active
- Type: Single Family
- Source: Bonita_Springs
- MLS ID: 226037594
- Updated: 10/26/2026
- Added to Site: 11 day(s) ago
Rental Information
- Lease/Rent Term: 30
- Min. Lease (Days): 30
Interior
- Interior Features: Split Bedrooms, Great Room, Den - Study, Guest Bath, Guest Room, Home Office, Media Room, Built-In Cabinets, Pantry, Wired for Sound, Walk-In Closet(s)
- Appliances: Gas Cooktop, Dishwasher, Disposal, Double Oven, Dryer, Microwave, Range, Refrigerator with Icemaker, Self-Cleaning Oven, Wall Oven, Washer
- Furnishings: Unfurnished
- Flooring: Carpet, Tile
Rooms
Bathrooms
- Total Bathrooms: 3
- Full Bathrooms: 3
- Primary Bathroom: Dual Sinks, Shower Only
Bedrooms
- Total Bedrooms: 4
- Primary Bedroom: Master BR Ground
Other Rooms
- Kitchen: Kitchen Island, Pantry
- Dining Room: Breakfast Bar, Dining - Family, Eat-in Kitchen
- Laundry: Inside
Additional Information
- Shared Amenities: Bike And Jog Path, Bocce Court, Clubhouse, Pool, Community Room, Dog Park, Fitness Center Attended, Internet Access, Library, Pickleball, Restaurant, Sidewalks, Street Lights, Tennis Court(s), Gated
- Pool: Yes
- Private Pool: Yes
- Pool Description: Community Lap Pool, In Ground, Concrete, Gas Heat, Salt Water
- Spa: Yes
- Spa Description: In Ground
- Tennis: Yes
- Security/Safety: Smoke Detector(s), Smoke Detectors
- Equipment: Generator, Satellite Dish
Exterior
- Exterior Features: Outdoor Kitchen, Automatic Sprinkler, Water Display
- Porch/Patio/Deck: Screened Lanai/Porch, Patio
Parking
- Garage: Yes
- Attached garage: Yes
- Garage Spaces: 2
- Covered Spaces: 2
- Parking Features: Driveway Paved, Garage Door Opener, Attached
Location
- Area: NA37 - East Collier S/O 75 E/O 9
- County: Collier
- Subdivision: WINDING CYPRESS
- Building Name: WINDING CYPRESS
- Driving Directions: Please use the Main Gate Entrance off of Collier Blvd. One inside turn Right and follow down Winding Cypress Dr property will be on the Left . The US41 gate that is for resident's only.
- Direction Faces: Southwest
Community
- Association: Yes
- Assoc. Fees Include: Cable TV, Insurance, Internet, Irrigation Water, Maintenance Grounds, Legal/Accounting, Manager, Rec Facilities, Repairs, Reserve, Security, Street Lights, Street Maintenance
- Units Assoc/Comm: 766
- Pets Allowed: Yes
- Number of Pets: 3
- Management Type: Professional
Heating & Cooling
- Air Conditioning: Yes
- Cooling Type: Ceiling Fan(s), Central Electric
- Heating Type: Central Electric, Natural Gas, Zoned
Utilities
- Gas: Natural
- Sewer: Central
- Water: Central
- Cable Available: Yes
- Utility Description: Underground Utilities, Natural Gas Connected, Cable Available, Natural Gas Available
Structural Information
- Description/Design: Single Family Residence
- Exterior Const.: Concrete Block, Stucco
- Roof: Tile
- Windows: Single Hung, Shutters Electric, Shutters - Manual, Shutters - Screens/Fabric, Window Coverings
- Doors: French Doors
- Stories/Levels: 2
- Stories in Building: 2
- Square Feet: 3,206
- Sq. Ft. Source: Property Appraiser Office
- Living Area: 3,206 Sq. Ft.
- Year Built: 2019
Lot Features
- Property View: Lake, Landscaped Area, Preserve
- Lot Size (Acres): 0.2
- Lot Size (Sq. Ft.): 8,712
- Lot Size Source: Property Appraiser Office
- Lot Dimensions: 58 x 58 x 135 x 135
- Frontage: Cul-De-Sac, Dead End, Private Road
- Frontage Feet: 58
- Street/Road Desc.: Paved
- Irrigation System: Central
- Lot Features: Across From Waterfront, Cul-De-Sac
- Lot Description: Across From Waterfront, Cul-De-Sac
Water Features
- Water Front: Yes
- Water Front Desc.: Lake Front
- Lake Front: Yes
Financial Considerations
- Association Fee: $1,543
- Assoc Fee Freq.: Quarterly
- Application Fee: $280
- Tax Year: 2025
- Terms: Buyer Finance/Cash
Disclosures and Reports
- Ownership: Single Family
- Legal Description: WINDING CYPRESS PHASE 2 REPLAT LOT 409
- Property ID: 82679019822
- Section: 2
- Lot Number: 409
Listed by William Raveis Real Estate
We Value Your Privacy
We Value Your Privacy
We Value Your Privacy
Listing agents
— 7775 Winding Cypress Dr —
William Raveis Real Estate
William Raveis Real Estate
NMLS#: 1598647Get Pre-Approved Today
Schools
Schools serving 7775 Winding Cypress Dr
School District:Collier County School District
| Name | Grades | Distance |
|---|---|---|
Lely Elementary School 8125 Lely Cultural Parkway, Naples, FL 34113 | PK-5 | 3.6 mi |
Manatee Middle School 1920 Manatee Road, Naples, FL 34114 | 6-8 | 0.8 mi |
Lely High School 1 Lely High School Boulevard, Naples, FL 34113 | 9-12 | 3.6 mi |
Disclaimer:
School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.
Price & Sales History for 7775 Winding Cypress Dr
Tax History
Tax History for 7775 Winding Cypress Dr
Year
Property Taxes
Change
Tax Assessment
Change
2025
$8,560
—
$635,200
3%
2025
$8,560
5%
$618,500
3%
2024
$8,137
1%
$601,069
3%
2023
$8,082
5%
$583,562
6%
2021
$7,719
1%
$550,063
-3%
2022
$7,667
-1%
$566,565
4%
2021
$7,719
248%
$542,468
1448%
2019
$2,220
321%
$35,035
10%
2018
$527
-64%
$31,850
5%
2017
$1,453
—
$30,466
—
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
Estimate the Cost
Estimate the Cost for 7775 Winding Cypress Dr
7775 Winding Cypress Dr, Naples, FL 34114 (MLS# 226037594) is a Single Family property with 4 bedrooms and 3 full bathrooms. 7775 Winding Cypress Dr is currently listed for $990,000 and was received on October 25, 2026. Want to learn more about 7775 Winding Cypress Dr? Do you have questions about finding other Single Family real estate for sale in Naples? You can browse all Naples real estate or contact a Coldwell Banker agent to request more information.