7775 Winding Cypress DR NAPLES FL 34114 | MLS #226037594

7775 Winding Cypress DR
NAPLES, FL, 34114
$990,000
4 Beds
3 Baths
3,206 SqFt
0.2 Acres
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MLS #226037594 image #0
Listing Provided Courtesy of William Raveis Real Estate
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.

Property Details

Price:
$990,000
MLS #:
226037594
Status:
Active
Beds:
4
Baths:
3
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
WINDING CYPRESS
Neighborhood:
windingcypress
Listed Date:
Oct 25, 2026
Finished Sq Ft:
3,206
Total Sq Ft:
3,206
Lot Size:
8,712 sqft / 0.20 acres (approx)
Year Built:
2019
WaterfrontLakefrontPoolTennisCommunity PoolCommunity GatedCommunity Club HouseWinding CypressWindingcypressWinding CypressWith Approval

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Schools

Interior

Appliances
Gas Cooktop, Dishwasher, Disposal, Double Oven, Dryer, Microwave, Range, Refrigerator/Icemaker, Self Cleaning Oven, Wall Oven, Washer
Bathrooms
3 Full Bathrooms
Cooling
Ceiling Fan(s), Central Electric
Flooring
Carpet, Tile
Heating
Central Electric, Natural Gas, Zoned
Interior Features
Built-In Cabinets, French Doors, Pantry, Smoke Detectors, Wired for Sound, Walk-In Closet(s), Window Coverings
Laundry Features
Laundry in Residence
Levels
2

Exterior

Architectural Style
Two Story, Single Family
Association Amenities
Bike And Jog Path, Bocce Court, Clubhouse, Pool, Community Room, Dog Park, Fitness Center, Internet Access, Library, Pickleball, Restaurant, Sidewalk, Streetlight, Tennis Court(s), Underground Utility
Attached Garage YN
1
Community Features
Clubhouse, Pool, Dog Park, Fitness Center, Restaurant, Sidewalks, Street Lights, Tennis Court(s), Gated
Construction Materials
Concrete Block, Stucco
Covered Spaces
2
Exterior Features
Screened Lanai/Porch, Outdoor Kitchen
Garage Spaces
2
Lot Features
Across From Waterfront, Cul-De-Sac
Other Structures
Tennis Court(s), Outdoor Kitchen
Parking Features
Driveway Paved, Attached
Parking Spots
2
Parking Total
2
Patio And Porch Features
Patio
Roof
Tile
Security Features
Smoke Detector(s), Gated Community
Spa Features
Community, Below Ground
View
Lake, Landscaped Area, Preserve
Waterfront Features
Lake
Window Features
Window Coverings

Financial

HOA Fee
$6,656
Tax Year
2025
Taxes
$8,560

Map

Community

Subdivisions in NAPLES

Market Summary

Current real estate data for Single Family in NAPLES as of Oct 25, 2026
2,412
Single Family Listed
135
Avg DOM
712
Avg $ / SqFt
$2,426,120
Avg List Price

Property Summary

    Located in the WINDING CYPRESS subdivision, 7775 Winding Cypress DR NAPLES FL is a Single Family for sale in NAPLES, FL, 34114. It is listed for $990,000 and features 4 beds, 3 baths, and has approximately 3,206 square feet of living space, and was originally constructed in 2019. The current price per square foot is $309. The average price per square foot for Single Family listings in NAPLES is $712. The average listing price for Single Family in NAPLES is $2,426,120. To schedule a showing of MLS#226037594 at 7775 Winding Cypress DR in NAPLES, FL, contact your Century 21 Carioti agent at 2392986550.

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